I continue to be grateful for this space to share these reflections and conversations with you and to have this very orderly record of the very disorderly life I’ve been living.

I hope your own money dates can offer you the same satisfaction! Remember, this is way more about the life your money supports than it is about how you move money around. I love these check-ins for helping me see the joyful ways I use money and for constantly reminding me of the values I want my money to support.

💡 A money date is an exercise I crafted for You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

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I’ve always known I’d let my hair turn gray without hiding it. I was afraid it’d be difficult to do and I’d give into the temptation to dye it, but it’s been pretty smooth sailing so far.

My mom’s hair has been naturally gray for as long as I can remember, and I can remember her as far back as her 20s. I don’t know exactly when the gray started for her, because she’s also been dying it for as long as I can remember. For years when I was a kid, she bought boxes of hair color from Walmart and dyed her hair at home every couple of months.

(Actually, she “colored” it; she’d be upset to hear me say she “dyed” her hair, because that meant something much less classy to her. But to me the words mean the same thing, and I like the word dyed better, so I use that.)

She eventually graduated to having her hair done at the salon and went in for an appointment every six weeks for nearly two decades. She might have been touching up roots in the meantime; I was a teenager by then and not paying attention. I do know at one point around her late 30s she told me her hair was completely gray under the brown dye I was used to, and I couldn’t believe it. I’d never seen her with anything but brown hair, and it seemed wild to me that she might naturally look so different.

What I remember most about my mom’s hair was how much of a burden it seemed to be to her. The cost of dying must have made her feel guilty in our working class household. Spending hours immersed in salon gossip wasn’t her favorite pastime. For years, she lamented choosing to dye her hair, because she felt like she couldn’t get away from it.

She finally decided to go gray in her 50s, after almost 30 years of hiding under the hair dye. The decision began a years-long process to avoid the shock of going directly from brunette to blue-hair too suddenly. There’s a whole system to this that her stylist worked through with her, so she could help her hair transition comfortably out of constant dye jobs and into its natural color.

By the time she let it all go, her hair wasn’t just fully gray; it was white. She’s in her 60s now, and she seems to have embraced her natural hair color. She has beautiful, full, wavy hair I’ve always been jealous of, and it looks lovely in white with its smooth gray lowlights.

Like a lot of lessons I learned from my mom, I heard her regrets and vowed to avoid them for myself. I committed at a young age to letting my hair turn gray naturally and never spend my time, money or energy covering it up.

I did wonder, though… What if my hair is fully gray by my late 20s? Will I really be able to live with that? With the pressure against aging in our culture, I didn’t know if I’d be up for the test.

My hair didn’t gray as fast as my mom’s had, though. I spotted a few novel gray strands by my late 20s, but my hair didn’t read as “graying” for years after that. Around age 33, I was headed into a restaurant with friends, who caught a glimpse of my hair highlighted by the Florida sun and complimented me for letting it gray naturally. That was the first time I knew my hair was graying.

(I probably didn’t notice it myself sooner because it was happening near the back of my head, and whatever’s going on back there is frankly none of my business.)

My hair has continued to gray slowly, but it’s still mostly brown — I think? If you asked me to describe my mom, I’d probably still say she has brown hair, which is a weird trick the mind plays on us. My mother-in-law had a full head of gray hair when I met her 16 years ago, and my partner referred to her as blond for years until I finally broke the news to him. I know my gray hairs are not a sneaky thing I spot once in a while in the bathroom mirror, because people my age and older point them out all the time. But would a younger person look at me and see a gray-haired old lady? I’m so curious to ask, but that has to be the uncoolest thing a middle-aged person can possibly do, right?

From the moment my friends noticed my gray streak in that restaurant parking lot, I’ve had to choose over and over again to stick with my commitment not to dye my hair. It hasn’t been extremely difficult so far, but I’ve definitely had to think about it. I’ve had a lot going for me: slowly spreading, well-placed gray highlights in my otherwise flat brown hair. My mom’s voice in my head lamenting 30 years of dye jobs. Remote work that keeps colleagues from seeing me in full detail. Thin privilege that lends me a pass on other judgeable beauty choices. A cool woman I once worked with who was a few years older than me and gray at her temples but who exuded youthful energy and cheerfulness; her demeanor, for me, broke the association between gray hair and being old.

I’ve also grown into adulthood among millennials who are ostensibly fine with gray hair. There was even a period where the youths were dying their hair gray and silver, apparently, and someone briefly declared gray hair very stylish and cool. But I haven’t met many people my age who aren’t covering gray hair. Throughout my 30s, I listened to the chorus of support for gray hair and looked around at nary a gray head in sight, and I assumed my hair must have been aging earlier than everyone else’s. Turns out, gray hair is one of those things we love to support for others but can’t quite participate in ourselves. Like vacation days or public schools.

When another millennial woman compliments my graying hair, I kind of hear her saying, You’re so brave for allowing yourself to be this ugly in public.

Maybe I am. Mostly, I don’t think about it much. I wouldn’t say I love my graying hair, as much as I can’t say I love any part of my body. I’ve been generally happy with it over the years as a charming part of myself — but mostly as an insignificant detail that goes mostly unnoticed.

But now the rest of me is visibly aging, too. I see more and more of my mother and my grandmother in the mirror every day. I have my grandma’s hands and feet and stomach. My lips are losing color. My eyes are always tired. My gray hair seemed charming when it surrounded a cherubic face. But on this old lady? It’s just another thing about me that’s old.

I’m not upset to be aging. It’s a privilege to grow old; we all know that inherently. I knew many people who died in their 20s, and I had a sister who died when she was 39 — I’m very happy to celebrate turning 40. We should welcome the signs of aging that remind us of our good fortune.

I guess I’m upset that it’s so normalized for people to hide their aging. I don’t want to spend my time, money or energy dying my hair or getting botox or lip fillers or any of that stuff I’ve just recently learned is a thing now. I want to feel good in my body as it is naturally, and I don’t want to feel bad about myself for looking my age. But when I see my frumpy self in a Zoom frame next to a bunch of people around my age who have smooth faces, bright lips and gleaming hair, it’s hard not to judge (or feel judged). That’s not to say any of this is your fault if you’re into any of this beauty stuff; you know how I feel about individual responsibility. This is just how it feels to be a middle-aged woman in our culture, and I’m experiencing it for the first time.

I’m also not upset enough by this feeling to start dying my hair. I appreciate the freedom of never having that task on my to-do list.

On a 2024 episode of Office Ladies, Jenna Fischer said this about aging that had me in tears:

“One morning [in my mid-40s], I looked down at my hands and I got immediately emotional because my hands looked just like my mother’s hands. And I thought, one day she’s not going to be here anymore, but she’s always going to be in my hands. I’m going to see her…when I look at my hands.”

Even though she wasn’t able to enjoy the same liberation at my age, I’m so grateful to my mom for teaching me how much freer I could live by eschewing the expectation to defy aging.

One day, she won’t be here anymore, but I’ll be able to see her gray hair and her laugh lines every day in the mirror — and what a privilege.

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It’s not a life I want to live — I don’t want to dedicate that much time to growing, storing and preparing food — but it can certainly look appealing. I like that my partner dedicates his time to growing food in our garden and helps us live more simply, at least for a few months each year.

If you follow other personal finance content, you’ve probably been encouraged at some point to grow your own food to save money, but I wouldn’t suggest that. Gardening enough to feed yourself is a lifestyle, not a little hack. And in my part of the world, the growing season is just a few months long with one harvest at the end. It would be a full-time job to grow enough in those few months, then preserve it somehow for the winter, to feed my family sufficiently to cut our grocery bill. I’m happy to pay for others to do the bulk of that work for me. Don’t feel bad if the gardening bandwagon isn’t for you!

My life has been pretty simple and uneventful as I’ve settled into my new job, so I have little else to report. I had to work hard to avoid once again giving thanks for sunshine and our slow crawl toward summer, and this gardening check in is basically a sneaky way of doing that, after all.

Let’s move on to my money date :)

💡 A money date is an exercise I crafted for You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

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If you don’t want to be notified about essays in this project, you can unsubscribe from just this section by unchecking “Hi, I’m 40” under notifications in your account settings.

I’ve been in my new job about three months as you read this. Taking this job after a destabilizing layoff has had me thinking a lot about what I value in work right now — how life has shaped those values, how I feel about my choices and what work means for me personally, professionally and financially in this moment.

In short: It’s really f*cking complicated.

I’m a millennial who was too poor and too aimless in my 20s to notice the impact the last time our economy and job market felt like it does now. I didn’t absorb my generation’s hustle mentality to protect against these market forces; I only took in half of the message, the part about forging your own path and doing work you’re passionate about.

For nearly two decades, doing something I love has been my north star for work.

I idolized bloggers who were building online businesses, publishing books and forging viable paths doing work they loved. I missed the part where Recession-era corporate layoffs were the catalyst for almost every one of those journeys.

Now I’ve intentionally and enthusiastically taken a job in corporate marketing, the most selling out of all selling out a writer can do. And I’m not sad about it.

I have this job because I reached out to an old colleague after I was laid off. He was still with the startup where I’d started my career in 2015, except it’d been acquired by a multi-national marketing conglomerate during my absence. I knew the company I had loved then no longer existed, but I was excited for an opportunity to work with some old pals and to tread on familiar ground again.

I asked about writing or editing work, and he surprised me by pitching a new position they were designing in content strategy, one he thought I’d be uniquely qualified to take on even though it involved a lot of data analysis I had no experience with. That challenge and that faith in me were exciting, so I took it on.

I’m certainly not doing the creative writing work I thought I’d earn my way into by my 40s, and I’m not even doing service journalism in personal finance anymore. I work in content marketing for personal finance companies — a reality I was desperate to avoid when I started in this industry.

But more than 10 years later, I’m happy to accept this fate — and I’m actually quite proud that I’ve earned this position.

So how do I quiet the little nag in my brain that says I should be ashamed of how I make money?

How I gave up on everything that used to matter to me

I took my last job because I was in the midst of burnout, freelance work in my industry had dried up and the promise Substack had made to small creators was quickly fading. A former client reached out with a surprise job offer, and I jumped at the promise of a stable paycheck and a company to pay for my health insurance. They made me end my freelance work because of perceived conflicts of interest, and I eased up on newsletter work to avoid perpetuating my burnout. After six months, they laid me off.

Left to start from scratch, eat away savings and build up debt, I couldn’t imagine launching into the hustle again. I’d been singing for my dinner as a freelancer for six years, three with a newsletter piled on and two with a book project piled on top of that. I’d taken a full-time job to consolidate my responsibilities and ease the burden of constantly wondering where my income would come from. I’d just caught my breath for the first time in years when they pulled the rug out from under me.

That was the second time I’d been laid off from a job I’d been recruited into only months before, and it was the third time I witnessed layoffs at a company. (Being spared isn’t as devastating, but it still leaves a scar.) Also fun: A year earlier, I’d made it through weeks of interviews at one job and got on a call to receive my official job offer, only to find out the company had been acquired that day and they were on a hiring freeze. With headlines proclaiming historic job market volatility and record layoffs, I don’t think I’ll ever feel safe in a job again.

I couldn’t imagine scrounging for freelance work, and I couldn’t imagine the indignity of performing through more interviews. But I’m the breadwinner in my house, and I could only dip into my savings so far before hitting a complete panic. I had to find work somehow, and I wanted to wade through the least bullshit possible to do it.

That’s how I got to the job I have now.

To be clear: It doesn’t feel like a last resort or a compromise or a disappointment! It offers challenging work I enjoy with people I quite like for pay I think is fair. But it doesn’t spark what my 20-something self would call “passion”; it’s clear 20 years of struggling in this economic system has whittled my brain into a point that makes me grateful for a job I would have scoffed at when I had the privilege of imagining the life I wanted to live.

I’m not here to say that’s reality and we have to suck it up. It absolutely sucks that this is what work in the American economy does to people. A nation of our wealth where middle age is inevitably filled with regret and despondence is ridiculous. I’m just here to say: This is how I’m getting by these days.

What I value in work right now

The most honest thing I can say is that, right now, I work for the paycheck. The most important thing a job can offer me is a direct deposit that doesn’t stop coming until I’m ready to leave. And I really mean that. The only reason I didn’t apply for jobs at Starbucks or McDonald’s is that they don’t pay enough; I’m no longer deterred by unfulfilling work or detestable corporate brand names.

But let’s not be so bleak.

I also revisited my criteria for good work, and the job I have now checks all the boxes in unexpected ways. Of all the jobs I half-heartedly applied for after my layoff, this is the only one that comes close.

I’m certain you’ve consumed my book, You Don’t Need a Budget, cover-to-cover multiple times, but just in case — here’s how I define good work along three dimensions of financial wellness:

• Head: It serves financial goals with a solid salary and opportunities for advancement.

• Health: It operates in your best interest through quality-of-life features like health insurance, inclusivity and work-life balance.

• Heart: It’s aligned with your values, where you want to make an impact and how you want to care for people.

My job pays me a great salary — the highest I’ve ever earned and, notably, the amount I asked for. It offers health insurance (by mandate, a protection I don’t have as a freelancer), a better-than-average 401(k) match, fully remote work with actually optional offices in two states, and they haven’t shied away from DEI initiatives in the wake of Trump 2.0. Plus, they haven’t had layoffs there in more than two years, so, you know, yay.

Does this job serve my heart?

20-something me would laugh out loud at that question. She 100% would have called me a corporate sellout and berated me for saddling myself with a mortgage and an iPhone. Then she’d roll over and sleep soundly on the futon she found on the side of the street.

40-year-old me needs a memory-foam mattress and an annual mammogram. I’m no longer willing or able to make the financial sacrifices I made in my 20s, so I can’t hold work to my 20-year-old standards anymore.

But, beyond the money, the job serves my heart in ways I wouldn’t have thought to look for in my 20s.

First, the people I work with value my contribution. The person who hired me was eager to get me in the door. They see my ragged work history and my forays into self-employment and authorship, and they love me for all of it. Having just dipped my toe into the job market these past couple of years, I know it’s exceedingly rare to be valued for the person you actually are.

Second, I have the opportunity to bring joy to people I work with. I might not be a nurse at a nonprofit clinic in an impoverished immigrant neighborhood; the work I produce isn’t providing even a necessary public service or entertainment. But there are real people in front of me every day who show up because their paycheck keeps their families alive, and I can put my energy toward giving them a good day.

I’ve been frequently revisiting my favorite takeaway from Bree Groff’s book Today Was Fun:

“All I want is to spend my days with funny, creative, inspiring people who are lovely to hang around. And while we’re hanging out, a fun thing to do is create value for others and money for ourselves.”

Reading Groff’s book broke open the meaning of good work for me. She doesn’t wax poetic about finding meaning and passion in your work; she just says wherever you go for a paycheck should and can be fun most days.

There’s some capitalist nihilism in this concession. I’d really rather tell you being laid off set me free from the hamster wheel of corporate America and let me finally chase my creative dreams. But that story was never true for the people who told it to us in the 2010s. Many of those bloggers I adored quietly went back to work after 2020. Anyone still in business for themselves depends on corporate America for contracts or sponsorship, or worse, on private equity for investment. Everyone is staring down the barrel of AI.

The high hopes of my 20s have been dashed. But instead of letting that turn me into the hopeless middle-aged crank I hated encountering back then, I can adjust my barometer and find happiness where it’s available to me.

What I’ll take from (and give to) this job

I appreciate the security of the paycheck from this job. But I’ve done work for money for the past six years, and that alone leaves me hollow. I can find more in this job, like I did the first time I worked for the company. I found a new version of myself in that era, and it has defined everything I’ve done over the past decade — the work I’ve pursued, the things I’ve created, the living I’ve been able to maintain, the ideas I’ve contributed to the ether. It strengthened me in a way I’ll never lose.

After leaving for new horizons six years ago, why does it make sense to go back now?

I returned to this (new version of the) company, because it felt like the right time for me and for them. New leadership had taken over shortly before I was hired, and they explicitly value quality in media, not just marketing dollars. The team I joined is eager to reinforce the foundation of the brand I helped build a decade ago — a quality I staunchly defended early in my career. This makes an environment that feels like the right place for me to develop and grow in creative and strategic thinking, not just another corporate job to collect a paycheck and use half of my brain.

It’s the right time for me, because I’m ready to work for a company again, and I want to do meaningful work for good pay.

Working for a startup in a booming niche, I saw the interesting and creative work that can be done with the resources of a multi-million-dollar company. It’s frustrating to try to build in the scrappy way I’ve done over the past six years. I can continue to do “meaningful work” through my book and this newsletter, and I’m proud of what I create here. But working solo only lets me scratch the surface of what can be done with content.

Plus, earning very little money makes me vulnerable and unfocused in my work. Working inside a company with a good paycheck gives the stability I need to do satisfying work I’m proud of.

And, one of the most important things I’ve been missing: It lets me work with a team toward a shared goal. I love the freedom to create what I want, when I want, through my own projects, and I appreciate messages from readers about how this work impacts real lives. But I’m always strongest when I have a team to bolster me; I thrive under accountability, feedback, idea sharing and cooperative problem-solving. I once thought I might eventually build out a company with a team of my own to create that environment on my own terms — but my dalliances in business building have let me know that’s not the right path for me.

Instead, I can apply my entrepreneurial spirit to spinning up projects and building processes that make days easier and more enjoyable for my coworkers. It’s satisfying that I can suggest a shift that’ll make it easier for them to work and help the company earn an additional $2,000 a day, securing our jobs for the foreseeable future.

In my creative work, I can set up creative systems all day (and I do! And I love it!), but I can’t give jobs to dozens of people fighting for their lives just like I was a few months ago.

Again — I don’t find this state of things acceptable. I’d prefer to put all of my skills into building a cooperative that helps raise money to elect socialists who enact public benefits and dismantle corporate power. In fact, I tried that. It didn’t keep my family fed.

So I’m going with the corporate sellout option.

Finding a new balance

In this latest chapter, I’m finding a new balance. I previously oscillated between starving artist and corporate shill, and I’ve been spending the past several years trying to find who I am along that spectrum. It’s certainly not 100% of either.

Now, I feel comfortable throwing myself into this job without losing myself in service of the corporation. I can distinguish between doing good by my coworkers and blind obedience to company goals. I can be grateful for the support the company offers without believing they care about me. I can get comfortable with my paycheck while holding onto my nest egg and freelance contacts for the day someone moves my name to the wrong column in a spreadsheet.

It’s not unlikely that I’ll tire of corporate work another five years down the road, maybe under a more favorable economy, and swing back toward something creative and independent. But for now, I’m glad I’m good at this work, and I’m going to stop being mad at myself for enjoying it.

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The newsletter is about money psychology — why we do what we do with money, and the invisible forces that make it so hard to stop. But following Hanna also teaches me a lesson about how to work. She sets a high bar in this space with content that’s thoughtful, well-researched and thorough without feeling dense or intimidating. Hanna is a New York City based Certified Financial Planner and financial journalist who’s been writing about money for more than a decade, and her expertise shines through in her writing.

Hanna has her thumb on the pulse of our culture of money and offers insight into the latest trends and questions weighing on your mind — from the horrors of life admin to the depravity of gambling on war like it’s the Super Bowl.

I’m so excited to chat with Hanna about her own experiences with money and get to know the person behind the brilliant advice and analysis she shares every week.

I love the way you frame the three forces shaping your financial life: internal, social and structural. I’ll encourage folks to read your full article on the topic, but can you briefly explain these forces? How does traditional financial advice address them (or not)?

So the basic idea is that your financial behavior isn’t just about you. There are three main forces constantly shaping what you do with money:

• Internal forces are the psychological stuff — unconscious beliefs you have about money, often formed and developed in childhood and absorbed through interactions with your family, peers and the world around you. These beliefs form “scripts” that run in the background of your thoughts and drive a lot of your financial behavior. Like, maybe you grew up watching your parents fight about money, and now you avoid looking at your bank account. That’s an internal force.

• Social forces are everything coming from the people around you and the culture you live in — particularly what your reference group (your friends, your neighbors, your coworkers) considers to be “normal” financially. Social media has massively distorted this, expanding the pool of people we compare ourselves to.

• Structural forces are the systems, products and policies that are literally designed to make it harder (or easier!) to make good financial decisions. Buy now, pay later embedded in every checkout screen. Subscription models that are easy to sign up for and impossible to cancel. The economy itself.

Most traditional financial advice basically only addresses the first one — and even then, just barely. They’ll offer up prescriptive advice like, just make a budget, cut out all “unnecessary” spending and be more disciplined. All of which puts all the responsibility on you. It completely ignores the fact that you’re making financial decisions inside a system that’s been engineered to exploit your psychology. I firmly believe that once you can see all three forces at work, you stop blaming yourself so much and start making decisions with a lot more clarity.

What’s the most joyful thing you’ve done with money in the past six(ish) months?

I booked a very last-minute trip to New Zealand to watch one of my closest friends perform — he’s a dancer. It was completely spur of the moment — he invited me two weeks before we were supposed to leave, and I booked my tickets the very next day.

At the time, I’d been feeling burned out and honestly kind of seasonally depressed with the New York winter, and something in me just said: Go.

It was not a “responsible” financial decision by any traditional metric. But I would argue that it restored me in a way that no amount of staying home and being sensible would have. I rented a car and drove around the North Island for a couple of days, soaking in the summer sun and taking in the most incredible views. Also, as an avid Lord of the Rings fan, the trip to Hobbiton was worth every penny.

I came back feeling like a person again.

That trip is a good example of what I actually believe about money, which is that its best use is buying you flexibility and autonomy (if that’s what you value, of course). Not stuff — the ability to say yes to the things that make your life feel like yours.

What messages did you get about money growing up? Which have you held onto and which have you let go?

I grew up in a very high-achieving, Type A family. My parents talked very directly and regularly about money, about what things cost, what they could and couldn’t afford, how they were thinking about big financial decisions. They were also really clear about boundaries. I knew early on that after college, I was financially on my own.

The main message I got from all of that was: Money is something you need to understand, and no one is going to handle it for you.

I also grew up in a really high-performing, academic environment, where success was tangibly measured through grades, schools, job titles, salaries, etc. I internalized this idea that your worth is what you can measure. And for a long time, money became one of the primary ways I kept score with myself, through my income or my net worth.

That led to a lot of anxiety. Because when your sense of security is tied to a number, no number is ever enough. I kept thinking I’d feel settled at the next milestone, whatever that was, and then I’d get there and the goalpost would move.

What I’ve definitely held onto from this is the work ethic. I’m not mad at the part of me that’s driven and ambitious — that energy built my career and my newsletter and everything I care about professionally.

What I’ve let go of (or I’m trying to let go of) is the idea that my income or net worth is a reflection of how successful I am. Money is a tool. That’s a deceptively simple thing to say and a much harder thing to believe. I’m still working on it.

How do various facets of your identity impact your work and finances?

I’m an anxious person. I’m very self-critical. I carry a lot of self-doubt, even when the evidence doesn’t support it. And all of that shows up in my financial life.

For example, take my scarcity mindset. When it comes to work, I’m terrible at saying no. I want to be the person who can do it all, which really means I want to be the person who never has to turn down money. That’s a form of ambition, I suppose, but it’s ultimately not beneficial.

Being the person I am and also living in an environment like New York City can give you this “hustler” like mentality, the belief that you just have to keep striving and making more money. Which sounds empowering, and sometimes it is. But it also means I don’t always stop to ask whether I should do something. I’ve hit money milestones I thought would make me feel secure, and the feeling never came. One realization I’ve come to in my money relationship journey is that financial security isn’t a set number. It’s really your relationship with “enough”.

My definition of “enough” is ever changing, but right now it’s the ability to give myself options, especially with just how much uncertainty it feels like there is out in the world. But I’m also working to accept that I’m someone who gets a lot of pleasure and identity from work, and that’s OK, too.

What’s one financial decision that frequently causes you stress? How do you work through it?

Being a freelancer in New York City. That’s the decision, really — because it’s a decision, every single day. I am choosing to live in one of the most expensive cities in the world without a steady paycheck, and that math doesn’t always math.

There’s a running calculation I can never fully turn off: Is this sustainable? Can I afford to turn down that project to protect my time for my own work? I left a more stable path to build something more self-directed, and I believe in it. But bills inherently will pop up, and I’ll get anxious again.

The way I’ve worked through it — and “worked through” is generous, it’s more like “am actively working through” — is by getting clear on why I made this decision. I stay in New York because of the people. My community is here. The creative energy, the friendships, the collisions with interesting humans that make my work better — that’s all here. And I’ve decided that’s worth more to me than the stability I’d get by moving somewhere cheaper or taking a salaried job I don’t love.

Essentially, I’m choosing community and autonomy over predictability. Some months that feels like freedom. Other months it feels like a very expensive gamble. But I think that’s what it actually looks like to align your money with your values — it’s just yours.

Besides yours, what personal finance newsletter(s) do you most recommend and why? Who is it best for?

• (Katie Gatti Tassin) — Sharp, funny, and very structurally aware. Katie’s great at taking a cultural moment and showing you the economic forces underneath it.

• — She makes macroeconomics feel human, which is genuinely hard to do. If you want to understand what’s happening in the economy without your eyes glazing over, Kyla’s your person.

• Anne Helen Petersen (Culture Study) — Not technically a money newsletter, but she writes about work, class and American life in a way that’s deeply connected to everything I think about.

Instead of talking about the weather, what do you wish strangers would ask you about when you meet on the street?

I wish people would ask me what I’m reading — I go through about 70 books a year and I always have a recommendation loaded. Either that, or I wish someone would let me talk to them about urbanism and why American cities are designed for cars instead of people. I’m a big fan, which is maybe a niche thing to bring up on the street, but honestly I think the way a city is built tells you everything about what a society actually values. And that connects to my money work more than you’d think.

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A seventh-grade classmate caught me by surprise outside of the band room one day. She was one of the popular girls, and I was not, so it was thrilling to have her attention out of the blue. Until that weird question came out of her mouth.

It was too harsh and rude and specific. But it wasn’t unusual.

I laughed awkwardly and truthfully told her, no, I didn’t “puke or something,” and ducked into my next class to escape her scrutiny.

This comment stands out in my memory now. But I barely processed its weight at the time, because it was one of such a slew of everyday jokes and jabs from people who felt entitled to comment on the size of my body throughout my entire childhood.

I was a skinny child in the 1990s and 2000s, when skinniness was a particularly potent currency. Around ages 12 and 13, kids and adults frequently told me I looked like the TV character Ally McBeal, despite truly looking nothing like the actress who played her, Collista Flockhart. All we had in common was brown hair and bodies people felt entitled to judge. Classmates referred to me as “anorexic” like it was a synonym for “skinny,” without concern for whether or not I might be struggling with an eating disorder (I wasn’t). People regularly felt the need to tell me to eat something, usually a hamburger. (I did. I ate a lot, like many growing kids! I ate with the abandon of someone who never worried about anti-fat bias.)

I wasn’t a particularly remarkable child. I didn’t fit in a lot of places, but I didn’t stand out, either. I wasn’t strange enough to forge my own path, and I wasn’t extraordinary enough to inspire awe. I wasn’t beautiful or fashionable, but I wasn’t hideous or gaudy. I was forgettable. People didn’t have much to say about me.

But they always had something to say about my body.

They commented on how much I “could” eat at every meal, like it was a superpower. They told me to eat more no matter how much I ate. They commented on my body in a bathing suit. They guessed my pants size. They compared me to adult celebrities. They accused me of having an eating disorder.

These were never compliments. But they weren’t exactly insults? It was clear to me early on that thinness is valued in our culture and that I had the privilege of holding that value. But the comments didn’t make me feel valuable. They made me feel like everyone hated me. Like my thinness made them uncomfortable, so I should “eat a hamburger” to change it. Or my thinness wasn’t fair, so I had to apologize for enjoying food without the shame they attached to it. Or let them believe I was “achieving” thinness because of extreme discipline or disordered eating.

Our culture sugarcoats thin-shaming in a veneer of jealousy, the way we protect ignorance through anti-intellectualism. In both cases, being “against” an elusive ideal is a defense mechanism against not being able to achieve it.

“The reason people are angry at the thin woman is because they hate fat,” said anti-diet, fat positive journalist Virginia Sole-Smith in a 2022 episode of her Burnt Toast podcast. “When those jokes get made, they are actually anti-fat jokes; they’re not anti-thin jokes.”

I’ve always been irritated by thin-shaming jokes, and I should be, because people should just stop talking about my GD body. But the comments also confused me. In a culture that demands thinness, why would everyone fight so hard against mine? It’s clarifying to understand these comments as a symptom of anti-fat bias, where people attribute my thinness to being over-disciplined. Mocking a thin person for caring too much, for being so self-obsessed that they’re that thin, reinforces our cultural belief that people have fat1 bodies because of a lack of self-control.

I’ve never faced the kind of bias, discrimination or lack of access that people in bigger bodies face in our culture. I’ve never worried about airplane seats, the weight-limit of chairs, getting a job, enjoying a meal in public, or wearing the same uniform as teammates or co-workers. I’ve always had hangups about my body size and shape, hated buying clothes, been uncomfortable in photos — all standard fare for girls in our culture. But I know my thinness brings me a great deal of privilege, even with its own weird flavor of scrutiny.

Constant commentary about my thinness throughout my childhood taught me anti-fatness without ever using the word “fat,” and it taught me to internalize all of our culture’s body shaming. Comments about my thinness were an ongoing reminder that:

1. People are looking at my body.

2. Being thin makes me remarkable.

The first point isn’t unique. Girls learn early that our bodies are being monitored and evaluated at every turn. That happens no matter your body size or shape — someone will comment about something on your body. Your size, shape, height, skin color, eye color, hair color, hair texture, shoe size, the shape of your hands, the curve of your nose, the width of your mouth, the length of your eyelashes — people are obsessed with children’s bodies. I happened to learn this lesson from people telling me to eat a hamburger when they saw me in a bathing suit.

I didn’t realize I’d internalized the second point until just a few years ago.

Feeling otherwise unremarkable and knowing that the size of my body left an impression on people taught me that being thin was a key part of my identity. Without this quality, I would be completely forgettable.

I didn’t notice this belief for a long time, because my young body was skinny regardless of what I ate or how I moved. But I started to think about it more when my adult body began to respond to inputs.

I started hormonal birth control at 17 but quickly stopped because I was uncomfortable with the weight gain it caused. (I convinced myself I quit because of mood swings.)

When I started earning a living wage for the first time, I indulged in all the rich foods, the restaurant meals, the appetizers and desserts, that I’d restricted when I was broke. Unlike the indulgences that were put to work by my growing body as a kid, my body turned these into extra mass that padded my skinniness. I’d never been trained to “watch my weight,” so I didn’t note that change at first.

Then I got my first Apple Watch in my early 30s. It let me count my steps, and it offered, unsolicited, how many calories my activity was burning. So I started counting calories-in a few months later. Apps didn’t make it easy to count calories without setting a weight goal, so I went ahead and did that for the first time, too — while continuing to tell myself I wasn’t the kind of person who did diets or intentional weight loss.

By the time the pandemic hit in 2020, I had the pieces in place for restriction and discipline, and my body became something I could control in the midst of utter chaos and uncertainty.

I’d always stayed thin as an adult, including through weight fluctuations and the natural adjustments that happen with age. But hitting my mid-30s, I was broaching the new territory of being an invisible old lady. Years into it now, I find it to be a blessing, but it was disorienting at first. After a lifetime of being ogled, it’s weird to suddenly be aging and shapeshifting and seemingly unworthy of attention (creepy as that attention can be).

With this new ability to control levers I’d never thought about before, I could make myself skinny again, like I’d been in my early 20s, as a teenager, as the little girl adults weirdly resented. I could reclaim that thing that made me remarkable — and it felt like a triumph.

Of course, it wasn’t. I skirted way too close to actual anorexic and bulimic behaviors. I felt dizzy and dehydrated all the time. I was never not thinking about the food I’d eaten or what I’d eat next (how fucking boring). I started policing a body people had finally stopped noticing — and all the comments came right back. I’d made myself remarkable again.

And, of course, I still never felt good in my body. I welcomed the comments a little more as an adult than I had as a kid, because I felt like I’d earned them. And because they’d been conspicuously absent during the years I’d simply let my body grow.

This was how I realized thinness had become part of my identity.

When I was remarkably skinny, I was worthy of attention. Controlling my body and forcing it back into skinniness gave me a couple more years of head turns and Instagram likes, just a little bit more of the respect and awe the world allots for the effort it believes we devote to being thin, just a little less of the judgment reserved for those of us who “let ourselves go.”

I’m still thin. This is the body I have. But I’ve been able to stop trying to force it to be remarkable. The weight and the pants sizes fluctuate, the padding around my bones comes and goes, my body parts morph into different shapes, my relationship with gummy bears ebbs and flows, my enjoyment of movement starts and stops.

Our culture never stops expecting women to control our bodies and force them into some elusive ideal shape. But as a 40-year-old woman who’s not a particularly public figure, I can attest that the attention and the expectations do slow down. People sort of expect my body to be uninteresting now, and it’s been nice to let it settle into its uninterestingness.

It’s been much more interesting to work toward being remarkable in other areas. All the things I can do with the resources I used to pour into counting calories!

“Women are starving themselves. They’re spending more time thinking about their calorie intake than how to change the world,” screenwriter and author Vanessa Garcia wrote for The Washington Post in a 2014 essay about her experiences with anorexia and bulimia.

Garcia continued, “What a waste of life. I think about the missed opportunities and the unmet goals I sacrificed because of the time and energy I wasted on cutting my weight. If I could talk to my 25-year-old self, I’d tell her, ‘Your time is precious. Get help. Do it now. You have too many important things to do.’”

Since I stopped hyperfocusing on my body, I published a book. I launched a successful newsletter. I managed a political campaign. I was the treasurer for my county Democrats in 2024. I bought my first house. I started a scholarship for my local high school graduates.

I’ve been plenty remarkable. And no one talking about my book is trying to get me to eat a damn hamburger.

Your turn

This is a tough subject to wade into, so I’ll start by asking you to please be kind! I’d love to hear about the ways our culture has impacted your relationship with your body, and how that’s impacted your experience overall. Please be mindful of how talk about bodies, weight loss, disordered eating and exercise might effect other readers, and avoid details about weight, clothing sizes, diet or weight-loss plans, etc.

Leave a comment

I’ve been off the juice since 2016 and happy about it. But a few weeks ago (watch out; this story gets a bit wild…), I had a Smart Water that I later realized contained some caffeine. 🤪 I was surprised by my good mood all afternoon and realized it was the stimulant. At such a low dose, it let me focus and get through work but didn’t trigger the jitters, anxiety or dependence I used to get from coffee.

So I’m bringing caffeine back. Just a little, only every once in a while. I’ve tried it as an antidote to light depression, and that’s been nice. And it’s wonderful for a Sunday when I’m facing a long list of writing and business tasks I really want to do but couldn’t otherwise focus on.

This is no revelation, obviously! But it doesn’t have to be. I’m not here to give advice.1 This is a snapshot of my experience, and reintroducing a drug I’ve been off of for 10 years is having a significant impact on my mindset today. Also to say: After some recent mental health challenges, it’s nice to have this little tool to help steer the ship in the right direction once in a while.

💡 A money date is an exercise I crafted for You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

Read more

I didn’t grow up with civic pride for Wisconsin. The state was just a background fact of my life. Now I observe people from other backgrounds showing such pride in where they’re from, staunchly defending it from the encroachment of monoculture or imperialism — I wonder what about Wisconsin I’d defend on the world stage.

It’s a tough question to answer in general, but especially in this moment. I’ve spent the past three years living near my hometown in central Wisconsin after nearly two decades of living in other cities and states. I haven’t been happy here. I get sad when I think about what Wisconsin means to me right now. Returning to my rural roots means I’m now surrounded by aging boomers who voted for Trump, who spew outright bigotry about immigrants, who look at me weird because I once dared to leave this place, who desperately want for nothing to change — including their own lot in life, because they don’t believe they deserve better and they don’t know who they are without their struggle.

And, yet, this place is somehow part of me.

I didn’t think of myself as “from Wisconsin” for the first 25 years of my life. I was born and raised in a rural, central-Wisconsin town just south of the Fox Valley, and my extended family all lived in that same town. My mom and dad had met in high school in that town, my mom and stepdad worked at a factory there, my cousins and I attended elementary school there, we celebrated Christmas at my grandparents’ house on the edge of town. In fourth grade, my best friend’s family moved to a different town, and I was crushed because we’d never see each other again. They moved 27 miles away.

Wisconsin culture isn’t legible to most people outside of the state. There are just 6 million of us here, and most of us keep to ourselves and never leave. Wisconsin culture isn’t shipped the way many other states’ cultures are — California and New York are widely exported through entertainment and media. The Southeast and Texas have deep historical significance we study in school. Folks from the South and Northeast are immediately outed by their accents. The Mountain West, even though its miniscule population is often dismissed, shoulders the cowboy mystique that undergirds American individualism. The Southwest is associated with Native nations that influence its signature motifs. Wisconsin isn’t unique among low-population states that most Americans can’t find on a map; it’s not that easy for folks outside of the state to name exactly what makes Wisconsin, Wisconsin.

But my state stands out among other small states in a few things that keep it in the national consciousness: our small-market championship NFL team, our Big-10 university and our enduring political significance.

Green Bay Packers

Growing up, I had no idea Green Bay was a tiny city. The Green Bay Packers loom large everywhere in Wisconsin, of course. But they also have an unusual nationwide following — sitting side-by-side in lists with the Cowboys, Steelers and Patriots, all hailing from way more populated regions.

Growing up, I wore Brett Favre jerseys on Packer game days and celebrated the Super Bowl XXXI win, despite not caring about football one bit and never watching the games. My grandma had an entire spare room decked out in Packers memorabilia, including a framed certificate declaring her ownership of what she referred to as “a piece of Lambeau Field,” which was a few shares of stock in our community-owned team.

University of Wisconsin

Education is one place Wisconsin punches way above its weight. Though we’re a middling No. 21 in the nation for population and No. 26 for income, Wisconsin ranks No. 7 in K-12 education and No. 10 in higher education.

I attended (but didn’t graduate from) the school that everyone else calls the University of Wisconsin, but to those of us in the state, it’s UW-Madison. (Because every college in our public university system is a “University of Wisconsin”; I still can’t make sense of state systems that don’t work this way.) I didn’t choose it because I was seeking a particular quality of education; I chose it because I wanted to live in Madison.

Only after barely getting accepted into the most competitive school in our state did I learn just how prestigious it is — and not only to Wisconsinites. UW-Madison is a public research institution and a NCAA Division 1 school, which means it does a lot more than teach communications to undergrads. Wikipedia says the school claims 20 Nobel laureates and 41 Pulitzer Prize winners and a slew of Fulbright Scholars and MacArthur Fellows. In sports, it competes in the Big Ten Conference, has won 31 national championships and produced dozens of Olympic medalists.

While I was living in Florida, I told a friend with a Ph.D. that I’d gone to UW-Madison and dropped out, and he was aghast. To have the opportunity to attend that school and give it up?! But it didn’t feel that way to me. I chose the UW system because my social class fed me into the public university pipeline, and I chose Madison because the city is the only place in Wisconsin where I feel like I belong.

Madison and Milwaukee

Wisconsin has two sorta real cities: Milwaukee and Madison. Milwaukee is an industrial and economic center, a mini-Chicago a couple hours further up the Lake Michigan shore. (Don’t come for me, Milwaukeeans, for comparing you to Chicago. I’m not wrong.)

A metro area of 1.3 million people, Milwaukee is a city most outsiders know from Wayne’s World and not much else. (Maybe the Bucks, now that they’re good? Even Wisconsinites weren’t Bucks fans when I was young.)

To rural Wisconsinites, Milwaukee is the epitome of a big, scary city that they tend to disown. Actually, its crime rate is pretty typical of comparable cities; but folks who never leave small towns don’t know what that means. They just see a lot of traffic and a lot of non-white faces, and they get scared. I’m sure it has nothing to do with the fact that we live in one of the most segregated states in the nation — 59% of Wisconsin’s Black people live in Milwaukee County, a total of 90% when you include its neighboring counties and Madison. That leaves a lot of land we rural folks can travel without ever seeing a Black face.

Even though I grew up among these folks in the conservative rural center of the state, the place in Wisconsin I most identify as “home” is Madison — the liberal enclave conservatives here refer to as “77 square miles surrounded by reality.” That’s a little rude, but it’s not inaccurate…

Madison is a city, so it produces economic value, of course, but unlike Milwaukee, the city’s main allure isn’t work opportunities. What Madison holds for those of us weirdos raised elsewhere in the state is the possibility of becoming. You go to Madison to attend college, or work in politics or government, or simply to suspend your adolescence well into middle age while you try your hand at being a sound engineer, videographer, muralist, poet or stand-up comedian.

Madison is the place young Wisconsin weirdos go to do all the things our rural communities told us we could never do. To be all the things they never allowed us to be. Like a gay, autistic, atheist, child-free author (hi!).

And the rest

My experience of Wisconsin is specifically rural and working class, which isn’t all the state is. 22% of our population lives in urban and suburban Milwaukee, another 7.5% in and around Madison, and the culture of those cities seeps into the rest of the state — albeit slowly and against great resistance.

But, that leaves more than 70% of Wisconsinites living in small cities and rural areas.

The majority of the Wisconsin experience is existing in places no one has ever heard of and doing things no one will ever acknowledge.

We’re a state you almost never have to drive through or even fly over. Concert tours tend to skip us. Major films rarely shoot here. Our tourist attraction is… the woods. Wisconsin isn’t on many bucket lists.

Those are my roots.

This is why my people are taught to embrace strife. To resist change. To fear difference. There’s an inbred nihilism here, an understanding that nothing we do matters. And yet, a desperate striving to make meaning wherever possible. For most of the people around me, that means clinging to tradition, savoring the tiniest claims to power, elbowing out any influence that questions those traditions or that power.

Wisconsin politics

Compare Wisconsin’s rural-to-city ratio to neighboring Illinois, where 74% of residents live in the Chicago metro area; or Minnesota, where 63% of residents live in the Minneapolis-St. Paul area.

That’s what makes our state a contradictory purple mass in contrast with our seemingly comparable neighbors. Something like 75% of Madisonians and 68% of Milwaukeeans are Democrats, but those blue dots are too small to carry the state like Minneapolis and Chicago carry theirs.

Some combination of geniality and historical union membership convinces rural Wisconsinites to vote for Democrats seemingly at random. We’re not just a purple state on the presidential election map every four years; living in the state is truly a mixed bag politically.

Our legislature has been in the hands of Republicans since the post-2010 gerrymandering sweep, but it’s been stymied by a Democratic governor for the past seven years. Our current U.S. senators are Ron Johnson, an old businessman swept in by the Tea Party movement; and Tammy Baldwin, a Madison liberal, Smith graduate and our country’s first openly gay senator.

Wisconsin is known for both Joe McCarthy, the leader of the 1950s Red Scare; and Bob LaFollete, a socialist governor, U.S. senator and breakout third-party candidate in the 1924 presidential election. We’re the only state in the upper Midwest that hasn’t legalized cannabis. The most recent additions to our state supreme court have been liberal women from Milwaukee and Madison who won by respective margins of 11% and 20%. It surprised no one that both Tammy Baldwin and Donald Trump won the state in 2024.

Beer and cheese

I truly have nothing to say about beer or cheese. But I know this is what Wisconsin means to most people outside of the state.

That’s on us, I guess. Our MLB team is called the Brewers, and our NFL fans wear foam hats that look like cheese.

Being so embedded in this Wisconsinness all my life, I don’t see it as all that notable. I grew up eating dinner at taverns, because that’s where the best Wisconsin food is — especially fish fries, which take over the menu every Friday night. I didn’t realize how much we normalize drinking here until I moved away. I was proud of that culture when I was young; now I’ve been sober for 11 years, and I’m glad I escaped it.

I’m still surprised when people have become full adults and have never seen a cheese curd (neither fried nor squeaky) — but it’s not like our economy runs on cheese shops. (Now that I’m thinking about it, though, I did go to high school down the road from a cheese factory, so…)

Contrary to our simplistic reputation, though, Wisconsin is an oddly diverse state. Some glaciers gracing our region some millennia ago left us a landscape dotted with lakes, mountains, forests, prairie, farmland, rivers, a delightful hand-shaped plot of land bordering two Great Lakes.

And, while we are about as white as we’re perceived (about 80%), Wisconsin is home to strong Native, Asian, Hispanic, Latino and Black populations. I’m really proud that our education standards require both Native American and Asian history, which adds rich texture to the “Wisconsin” identity.

Forward!

When I decided to write about being from Wisconsin, I thought I’d have very little to say. It’s not an identity people often ask about, so I don’t even know what might interest you.

But I feel Wisconsin so deeply.

I’ve worked for weeks on this essay, and even though I’ve pulled a ton out, it’s still the longest in this series so far. Many of the pieces I’ve left out will fit into essays about other parts of my identity — because my Wisconsinness permeates so much of who I am, what I’ve done and how I’ve done it.

It’s tough for me to be proud of my home state right now — but I continue to have hope. Democrats and socialists gained a lot of ground in our legislature two years ago, and they’re poised to take control after this year’s election. Plus, a lot about how we function is already worthy of pride: our education system, environmental conservation and public health care are pretty cool. I’m really proud of the work ethic I learned here. I love our accent (no it’s not the one you’re thinking of).

I’m glad my nieces and nephews get to travel outside of the state, and I hope they chase curiosity and opportunity wherever it takes them when they’re older — but I’m also glad they get to grow up here like I did. Wisconsin breeds smart, scrappy people with a lot of grit, and I’m proud they’ll take that with them.

I guess I found some pride in the end! My feelings about this place are definitely complicated. But it’ll always be my home, no matter where I’m living. And those contradictions are what make Wisconsin what it is, after all.

Your turn!

Where are you from? Do you identify strongly with any one place, or a lot of them? What do you love about your roots? What do you not love about them? What are the myths people believe about where you’re from? What’s something you wish more people knew about where you’re from?

Leave a comment

All this is to say: I should be very proud and very impressed with myself. As a girl from a rural, working-class Wisconsin town, I’m punching way above my weight.

But I’m constantly questioning my right to be in this position and hoping no one looks too closely at my greatest blemish: I don’t have a college degree.

None. Nadda. Zippo.

Every time I log into LinkedIn and see the prompt to “finish filling out your education details,” I want to scream at the screen, “I have! That’s it, that’s all I’ve got to say about that!”

Every time I have to check that box on some survey: What’s the highest level of education you’ve completed? It’s “high school.” Sometimes I have the option to say “some college.”

Every time you read a report about how “uneducated white people” impact our politics? That’s my demo.

I don’t think “uneducated” is a fair way to describe me (especially if you’re going to be so rude about it). Even “non-college-educated” is inaccurate; I attended the most prestigious public university in my state for nearly four years and learned a ton while I was there. I’ve since developed a strong expertise — enough to write that book, get those bylines, earn that money.

I just happen to be degree-less.

I’m an auto-didact. Depending on who you talk to, that might be highly respected or highly suspect. My feelings about it change from week to week.

Punching above my class as I do, I’m surrounded by people who didn’t just graduate from college. They have master’s degrees and PhDs. Many from prestigious private and Ivy League schools, or respected places like the Walter Cronkite School of Journalism and the Wharton School of Business. And they were straight-A students and high school valedictorians who entered college with a pile of AP credits.

I got a D in AP History and dropped out of AP Calculus after barely getting a C- with extra tutoring from the teacher in the first semester. (I did wear an “honor cord” at graduation for having over a 3.0 GPA, but I was also late to the ceremony.)

I was waitlisted at the University of Wisconsin and let in at the last minute. I think my GPA over my years there was two-point-something.

I don’t take to formal education. That’s not surprising to me now that I know I’m autistic; I’ve heard the same from countless other neurodivergent auto-didacts. But I didn’t know that when I was in high school and college. I sailed through elementary and middle school with all this “potential,” but I hit a wall once I had opportunities to take classes that actually challenged that potential.

I loved what I learned in AP U.S. History, but on test day, all I could remember were subjects’ first names and some cool things they did. Or maybe the name of their wives who were mentioned once. That wasn’t enough to pass a test that asked for details and dates. (Wish we’d have had Hamilton then, because I’m a GD whiz in U.S. history now!) I did great with algebra, because it’s basically math grammar, and I’m obsessed with language; but calculus was all formulas that required a special calculator that had no place in the real world, and I couldn’t wrap my head around it. Even my English classes were tough to get through, because everything we read was at least a century old and the daily reading load was more than I could keep up with. As much as I loved writing, I hated writing analysis essays of those terrible old novels I couldn’t read.

A teacher once asked us to write an essay about what Machiavelli meant by “the ends justify the means,” and I hadn’t read a word of The Prince.1 I wrote 500 words about how the meaning of life is revealed just before its end, and the teacher found it so beautifully written yet profoundly wrong that he was compelled to read it in front of the whole class. (They rallied to make him raise my grade on the assignment, so it was kind of a shining moment despite the humiliation.)

I assumed I’d make it through college, because that was the next step and I’d made it through the rest so far. Maybe I’d have earned a degree if I’d stayed at the diverse community college I’d adored for a year. But the standards I faced at the University of Wisconsin were too high to skate by on a moving-but-incorrect interpretation of Machiavelli. And the work of it didn’t always jibe with me. Consistently showing up to class regardless of wildly inconsistent energy. Participation points that expected me to form thoughts immediately and to speak up in front of the entire class. Group projects. Multiple-choice exams. Five-paragraph essays.

I loved the lectures. I loved earning credit for internships and community service. And I had one amazing Community Journalism class where we interviewed real people in the city and wrote blog posts. That one changed my life — I dropped out after that semester to go work as a writer.

That was 16 years ago, and I have, in fact, been working professionally as a writer ever since. I could have stayed and tried to earn a journalism degree first, but, honestly, I’d probably still be there.

Over four years in college, I bounced from major to major trying to find something that fit and never pieced together a real speciality. Five years into being a writer, I found personal finance, and over the next four years, I finally developed the expertise I could never hone through formal education.

In 2021, after six years of writing about money, I did get certified as a financial educator, so now I have a credential to prove my expertise. But everything I needed to know to pass that test I learned through my work as a writer, not through the required course.

While my agent and I were writing my book proposal, he took to calling my experience as a personal finance journalist a “masterclass” in personal finance, and nothing could be more perfect. That’s exactly what my work has been. As a service journalist, it’s been my job to distill information for readers. That forced me to learn and understand a ton of topics I’d otherwise know nothing about. I’ve interviewed financial planners, mortgage brokers, debt negotiators, lenders, fintech founders and, once, a local plumber who told me whether you could save money by peeing in the shower (tl;dr: maybe, not much). I’ve read bankruptcy laws, lending agreements and the fine print on bank accounts. Then I write everything down with the goal of answering specific reader questions.

If only all of my education had been structured this way.

I was an artistic girl with her head in the clouds, and I ended up becoming an expert in finance. Of all things. Because I got to learn about this topic in the ways that worked for me.

I know I’m not stupid. Despite how I show up in statistics, I don’t believe I’m uneducated, either. But sometimes, I do wonder whether all the ways I’ve failed in life are tied to never earning that degree. I see anecdotally and statistically the ways people with college degrees are better off, and I think, Yep. You should have just tried harder.

Would I have learned to be more disciplined if I’d persevered through a degree program?

Would I be a better researcher if I’d gone to grad school?

Would I have more opportunities if I could tap into an alumni network?

Would I get more job interviews or make more money if my resume listed a degree?

Would I know more if I’d figured out how to pass tests?

Would I, in fact, be smarter if I had just been able to stick it out through school?

The people around me are all so smart, and that’s such a privilege. I’m usually the dumbest person in the room. Sometimes I treasure that distinction, because it means I’ve somehow gotten somewhere no one expected me to belong. And that I get to learn from incredible people. But it’s a lonely status.

It’s not like anyone is asking about my degree in normal conversations. I didn’t have to present a resume to get a book deal. My decade in personal finance media is much more important to my career now than a degree I might have gotten 16 years ago. Probably no one is thinking about my college education day to day. I think people generally assume I’ve got a degree, actually.

But it crops up for me in subtle ways that feed my insecurity.

When someone mentions how many books they read on their week-long vacation, I wonder if they learned to digest information that quickly in grad school. When I can’t recall a name or year or location from history, I wonder if it’s because I didn’t study enough. When I see someone rising through a career I’d love to have, I wonder if they landed just the right job out of college after a prestigious internship.

I can never know the difference a college degree might have had on my trajectory. Realistically, I’m guessing it wouldn’t be much. The successes and failures I’ve experienced all track with the way my brain works and the things that interest me; powering through a degree program wasn’t going to change any of that.

But it’ll always be a little tough to resist comparing myself to all the smarter people in the room.

Your turn!

How does education fit into your life today? What does your history with education mean to you? Most importantly, please let me know: Do you think I’m stupid because I don’t have a college degree??

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Onto my money date…

I’m looking back on my week and see a calendar filled with meetings and tasks — which feels pretty good! It’s been satisfying, about eight weeks into my new job, to get into a groove and dig into challenging tasks. After a stint in a job that was just about getting a paycheck, I’m happy to be in one that stretches my brain, connects me with cool people and fills my days with purpose.

Warmer, sunnier and longer days are helping a lot, too. Cheers for spring!

💡 A money date is an exercise I crafted for You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

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Ren is a writer and artist from Northern England. They started their newsletter Wavy Thoughts in 2024, a day after a doctor told them they were experiencing autistic burnout. Substack surfaced the posts for me as I was most certainly in the midst of my own collapse. I devoured Ren’s writing about burnout and unmasking neurodivergence, queerness, sobriety and creativity.

What I love most is that Ren’s essays are not only validating and comforting — as so much writing about neurodivergence is when we’re out here diagnosing and treating ourselves — but it is also utterly entertaining. They write with a delightful sense of humor and wit that cut through the treacle and naval-gazing that can weigh down personal essays.

Ren also frequently illustrates their newsletter, which is a fun touch; and they recently released their first poetry zine on their Etsy shop.

I got to chat with Ren about neurodivergence and money, creating art without judgment and — something so very British and so very autistic at once — potatoes! Catch our conversation below.

Something we don’t talk about enough in the personal finance space (that we emphasize at Healthy Rich) is the intersection of money with various parts of our identities. At Wavy Thoughts, you write about your experience as autistic and ADHD (AuDHD) as well as things like sobriety and queerness. How do these various facets of your identity, and others, impact your work and finances?

I think my neurodivergence makes the most obvious impact on my work and finances. I’m an extremely all-or-nothing person. It can translate into being the world’s best saver of money and penny-pincher extraordinaire, or it can mean going through a period where I’m having a dopamine-heavy time buying things I like but don’t necessarily need. Striking a balance can be tricky, though I feel I’ve got a lot better at it in the last few years.

Same with my creative work. I go through peaks and troughs in my creativity, and also in the way I “run” my (very) small business as a content creator. Sometimes it is just not the center of my focus, and I neglect it for a bit until it becomes appealing to me again. I do sometimes wish for a bit more consistency in my own focus, but then I wouldn’t be me if I were any other way!

What’s the most joyful thing you’ve done with money in the past six(ish) months?

Nothing extravagant, but this was very meaningful to me. When I gave myself permission to create artwork, I went into my local bargain store and bought one of every single art supply they had. I came out with a basketful of amazing things, including pencils, a sketchbook, acrylic paints, charcoal, pastels and pens. I’d never owned paints as an adult, and giving myself permission to make any old art and not class it as “good” or “bad” art has been so freeing.

What messages did you get about money growing up? Which have you held onto and which have you let go?

I grew up in a low income household and I think I still hold some trauma relating to financial insecurity. It’s made me quite scared of both having and not having money. I’ve tried my best to unlearn a lot of those reactions and fears, but it’s been a slow process — I’m getting there!

What’s one financial decision that frequently causes you stress? How do you work through it?

As the old meme goes, the rent is too damn high. There’s no real way to work through it other than grinning through the pain and hope one day things will change. They’re bringing in a whole new set of rent regulations to the U.K. soon, maybe we’ll see rent control in England in my lifetime.

Besides yours, what newsletter do you most recommend and why? Who is it best for?

The one I always go back to is ’s.

His “10 things worth sharing” newsletters never fail to brighten my day and introduce me to something new. I also find him generally inspiring as another writer who likes to draw. If you like creating stuff, he is definitely worth subscribing to.

Instead of talking about the weather, what do you wish strangers would ask you about when you meet on the street?

Rank the best use of potatoes from first to last. This is very important to me as a person from Northern England — we are at pains to remind people that we do in fact eat vegetables as potatoes are a vegetable, actually.

My ranking, if you’re interested, is:

1. Chips (fries to my American friends)

2. Crisps (Chips to my American friends)

3. Mash

4. Roasts

5. Literally any other type of potato

6. Literally anything else

7. …

8. Boiled

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Like millions of behind-the-times Americans, I’ve been listening to the album DeBí TiRAR MáS FOTos by Benito Antonio Martínez Ocasio a.k.a. Bad Bunny since the day after the Super Bowl. I was aware of the artist over the past few years, but I’m an old white lady who generally ignores hip hop music unless it becomes unignorable. I caught Bad Bunny’s “Tiny Desk Concert” last year (how many ways can I say I’m an old white lady?) — loved it, pulled up his top tracks on Apple Music, and walked away because I clocked it as party music that I wouldn’t enjoy.

Thankfully, this year’s Super Bowl Halftime performance put him in front of me again, made me cry, and I’ve been listening to this album and devouring half a decade of Spanglish press appearances ever since.

It’s the latest reminder that I love Spanish. And Puerto Rico.

I visited San Juan, Puerto Rico, for the first time in 2017, and I truly did fall in love with la isla del encanto. Just a few days there brought out the Spanish I’ve been studying in some way since seventh grade. It’s not conversational, but as a sober, shy tourist, I didn’t have much occasion to have conversations with anyone in Spanish, anyway. (Any locals interested in making conversation used it as an opportunity to practice their English, which eclipsed my Spanish.) But I could read a menu, order a meal, direct a cab and let a drug-store cashier know no necesito una bolsa, gracias. I visited again in 2023 for a conference, and I had the opportunity to network with Puerto Rican colleagues in Spanish and to watch entire presentations about personal finance in Spanish.

A few days living in Spanish in Puerto Rico always leaves me longing for more.

While writing my book, I found an exercise called “Your Ideal Day,” asking you to discover the life you want to live by imagining your ideal day. The first question asks you to imagine where you’re living, and the image that rose out of my gut was Puerto Rico. I hadn’t thought about the island in ages. This longing surprised me, and I haven’t been able to let it go since.

I know I’m only a tourist in Puerto Rico. I understand I’m not the first Midwesterner to fall in love with a tropical island on vacation. But in my defense: I was living on the gulf coast of Florida at the time, so the Caribbean wasn’t that novel. And I get the oppressiveness of tropical summers, the anxiety of hurricane season and the demeaning experience of living in a place designed around vacations for people richer than you.

I wasn’t dazzled by white-sand beaches and gem-toned waters.

I was dazzled, because Puerto Rico was the first time I was immersed in a Spanish-speaking world.

I started learning Spanish in school in seventh grade, and I took classes every year through my first semester in college. I loved learning a language; I loved how it made me think about my native language, and I loved how my teachers used the language as a portal to teach us about countries and cultures my other classes ignored. I loved, as the years went on, how much more mainstream Spanish was becoming in the United States, and that I was learning something that let me be part of that.

I’ve kept the language in my life after those seven years of formal education. I’d chat with people online in Spanish, pick up a copy of La Casa en Mango Street from the library, listen to the Spanish versions of familiar Ricky Martin or Shakira tracks, pick up a tutor through iTalki, run some streaks on Duolingo.

I’m a huge nerd for language and communication. I could spend hours in any conversation about the origins of words, regional accents, linguistic differences between countries, you name it. For years, this was where my relationship with Spanish lived. I learned the technical structure of the language, enjoyed drawing conjugation charts and desparately tried to decipher the nuances of ser versus estar. But in 27 years of studying the language, I never learned how to communicate in Spanish. Putting that number on the page is pretty embarrassing, actually. Spanish has been in my life for well over half of it, and I still have to use a translation app to order a turkey sandwich with confidence?

Visiting Puerto Rico and existing in a Spanish-speakers’ world began to unlock a new relationship with the language. It began to feel like a part of me; the language attached to my soul the way the island did, and I couldn’t shake it. It feels odd, because the language isn’t mine. But I finally understand why it feels like part of me.

Bad Bunny’s current seat at the helm of pop culture is the culmination of decades of Latin Americans forging a path into mainstream culture in the United States. Booking an almost-all-Spanish show in front of Middle America’s biggest audience of the year lets us know definitively: This is American culture.

In my lifetime, Spanish has made its way into American popular media assertively and unapologetically —Ugly Betty lines flying by without subtitles, “Despacito” hitting the Billboard Hot 100, In the Heights, AOC, Coco, so much more that I don’t have my finger on the pulse of. These successes send an undeniable message that this language is part of America — not a minority or a novelty or a niche concern, but an integral piece of what it means to be American in the United States and to live on the American continent.

What Bad Bunny’s foregrounding of the language has clarified for me — and, simultaneously, tons of others — is that Spanish feels like part of me because it’s part of what it means to be American.

I love Spanish, and I want to speak Spanish better (and more often), because I’m American.

I feel just as bashful saying this as I do proclaiming my love for Puerto Rico. Just as I am on the island, I’m a tourist in the Spanish language. No matter how much I love sunshine, saltwater and maduros, I’ll always be able to return to the mainland to escape a hurricane, flush toilet paper and work on reliable wifi. No matter how much my language skills improve, I’ll still have the privilege of a world that has been forced to run on English.

I’m a colonizer in love with the land my people have colonized.

The U.S. took over Puerto Rico colonization from Spain in 1898 and has been effectively re-colonizing the island for more than a century, most recently after some modern laws gave stupid tax breaks to stupid rich people if they pretend to live there. Gentrification is causing Manhattan-level housing costs and forcing locals out of homes that are being turned into short-term rentals for tourists like me who’ve just “discovered” the island. Or worse, being plowed down and replaced by skyscraping hotel-and-conference-centers that hide the Caribbean beaches from anyone who doesn’t pay for access.

I stayed in an Airbnb on my first trip to San Juan, and my conference was in one of those hotels on my second trip. (Hated the latter, for the record; there’s a reason shorelines should be protected as public domain.) When I’m there, I eat from local businesses, walk the public beaches and speak the local language. As a visitor, I attempt respect and deference — and, certainly, I do better than any tech bro stomping on the culture for a tax break — but I know I’m too ignorant and too foreign to the island to get it just right.

That distance is the same thing that’s kept me from learning Spanish the way I would have liked to all these years.

I can blame my rural, white, Midwestern upbringing for keeping me estranged from Spanish-speaking America — but I have to admit I’ve been surrounded by Spanish-speaking people my entire life. Not only as an adult living for stints in California and Florida, but my whole childhood in rural Wisconsin.

The tiniest, most conservative towns in my state are home to large swaths of Spanish-speaking immigrant families from Mexico and Central America, attracted here originally for work on Wisconsin farms. I attended public school with immigrant and first-generation kids who spoke Spanish at home. But I was separated from these families by a Midwestern kind of segregation I didn’t recognize until well into adulthood. More than 7% of the 25,000 people in my county are Hispanic or Latino. That’s a third of the 20% across the whole U.S., but it’s substantial for a place that thinks of itself as only white. I was so disconnected from these members of my community that it never occurred to me to consider Latino culture part of my town.

Now I see it. Second- and third-generation kids at my niblings’ schools are still speaking Spanish at home, but their families are more integrated into the community. They don’t disappear for half the year for farm work in Texas like the kids of my generation. My niece has friends preparing for quinceañeras. The high school soccer team is majority Latino. The grocery store down my street is a Mexican tienda.

Still, I don’t speak Spanish with the woman who runs the store. I get out a few phrases. I always open with hola and como estas. I request no bolsa when I check out. We’ve acknowledged that I speak un poquito español, and she seems happy about it.

But she only speaks to me in English that’s about as fluent as my Spanish. Maybe it’s a commentary on my language skills. Maybe it’s like the Puertorriqueños using me to practice their English. Maybe it’s rude of me to practice my Spanish on unconsenting service workers. I’m not sure. But I’m a tourist in her language; she’s trying to survive in mine. So I’m following her lead.

I wish I would’ve understood Latino culture and Spanish language as part of my culture growing up. I wish our public schools would have incorporated Spanish into the classrooms instead of separating immigrant kids into their own ESL cohort. I wish our parents would have encouraged us to play with the Mexican kids after school — I could’ve learned Spanish phrases at a young age from some friend’s Mexican tia?! I wish I weren’t an ignorant white lady playing catch up at age 40, trying to figure out whether it’s offensive to say hola to the Guatemalan lady at the grocery store.

I wish it hadn’t taken Bad Bunny in 2026 to make me feel the Spanish in my soul.

But I should be grateful it happened at all. It’s never too late to learn a little more. I’m already planning my next visit to Puerto Rico and eyeing winters in Mexico. My Bad Bunny binges have trained my YouTube algorithm toward Mexican educational channels and Telemundo Puerto Rico. I’ve got 40 years ahead of me to do better than my first 40. So I’ll take them.

Sin remordimientos.

Your turn

What role does language play in your life? If you’re in the United States, what is your relationship with Spanish? If you’re in another country, which languages permeate your culture, and what do they mean to you?

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To-dos and expectations weigh on me so heavily. And that weight becomes worse in the winter, when it’s a slog to get anything done and those to-dos pile even higher. With spring settling in around me and my new job bringing order back into my life, I’ve felt more focused and productive in the past couple of weeks than I’ve felt for months. I’m writing to-do lists and checking things off! It’s incredible!

This is the most mundane success, but it feels enormous. I know I’m not alone in experiencing this past winter as tougher to survive than most. Any regular seasonal depression was compounded by January’s especially oppressive weather and a political environment that keeps us in anxiety and despair.

Walking into the light at the end of that bleak tunnel has been an absolute salvation.

💡 A money date is an exercise from my book, You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

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That’s an odd thing to have to announce. But at my age, people tend to assume the opposite (and have opinions when they learn the truth).

I’ve accepted the label childfree for its positive embrace of not being a parent, but it doesn’t do a great job of describing my life or my relationship with children. As my friend writes at , you can have a “childful” life without being a parent — and that’s exactly what many non-parents want.

There was a time when I was annoyed by that argument. Women who were childfree-by-choice would rush to assure you, “I don’t want to be a parent, but I love children!” They weren’t mothers, but they were everyone’s weird auntie — delighted to babysit, buy birthday gifts, make funny faces at kids at the park, hold a coworker’s baby.

I didn’t feel that way. I didn’t want to be a mother, but I also didn’t want to hang out with other people’s children.

As a younger adult, I didn’t like being around children. They’re unpredictable, often loud, quite needy (if for no other reason than being too short to reach anything themselves), and everything they touch becomes permanently sticky for some reason.

This is all still true of children, but I’ve developed a tolerance that’s blossomed into, dare I say, appreciation for all of this childishness. My sister had her first child in 2011, I fell in love with her and she taught me how to love other children.

My desire to be a mother never emerged. But now I adore my nieces and nephews, I care deeply about the wellbeing of strangers’ children and I don’t freak out when a baby stares at me for 90 minutes on an airplane. (I also cry if I ever see a child crying or scared in a movie; if anyone can tell me what that is and how to make it stop, much appreciated, k thx!)

No, I won’t change my mind one day

I’ve never been pregnant or tried to be, and I realized pretty early into adulthood that I wasn’t going to want children of my own. It’s a deliberate decision a woman has to make in our culture. That’s odd, isn’t it? Shouldn’t we put those standards on the decision to become a parent? But — at least where I grew up in conservative, rural Wisconsin — becoming a parent is not a decision, it’s a default. Defying that default is a decision that requires much deliberation and is met with much critique.

(Which is weird, right? Like, if I say “I’m not so sure about having kids,” why would your first response be to think I absolutely need to be responsible for a child’s upbringing? That lack of interest should be a quick disqualifier.)

I grew up with parents who loved us dearly, but didn’t want to be parents. Both my mom and my stepdad, the parents I lived with most of the time, had had children because they were expected to as adults in a conservative Christian community. They didn’t like the way kids behaved or engaged with the world, and they didn’t have the resources or encouragement that many parents have today to learn about our development and relationships and psychology. We were not a child-centered household; kids were expected to be quiet, be clean and do as we were told. Childishness was met with irritation.

What I learned from the way I was raised is that having kids is difficult for parents.

I think that’s true for most parents, even if it’s not difficult for them for the same reasons it was difficult for my parents. But some parents also pass on the impression that having children brings them joy. I learned to see parenting only as something that terribly inconveniences adults, and I felt the ache of being a child of parents who seemed irritated by my hanging around. I took the lesson that a person shouldn’t willingly have children unless they were all-in on being a parent. Some people are super enthusiastic about becoming parents and having kids, and I’m happy to leave family life to them.

For almost two decades as a non-parent adult, people around me quietly assumed I’d eventually have kids. Even if I told someone outright I didn’t want kids, they seemed to assume that would change eventually. They’d hear, “I don’t want kids right now.” I’m a working class woman from the Midwest; parenthood was bound to happen as long as it was possible. It took me years to even believe myself when I said I didn’t want kids!

At this age, though, that assumption has faded. When I was around 35 years old, my mom finally asked — instead of another round of “Are you sure you don’t want kids?” — “Do you regret not having kids?” And I was so relieved, because I knew the pressure had passed.

What I love (and don’t) about not having kids

I love the life I’ve built without meeting any of the right milestones.

I love my house; it’s very small and cost relatively little money, and I couldn’t comfortably raise a family here. My partner and I get to make the space exactly what we want all the time, because it’s just for us. Nothing has to be child-proof or censored. I chose bold colors for every room — a purple dining room inspired by the TV show Friends, aqua walls in the den with retro 70s patterns on the curtains, 1950s-era olive green in my office with chrome details, and a deep, quiet burgundy in my bedroom. Nothing in my house is decorated with Spiderman or Disney princesses, and no space is dedicated to storing toys or stinky hockey uniforms.

I love spending my time on work, writing and travel. Not having kids means I can shape my days and weeks however I want. There’s no extra cost to traveling. I don’t have to arrange child care during the day. I don’t have to meet a child’s insatiable appetite for attention or occupation. I can sit at my computer as much or as little as I want throughout the day without guilt, and watch what I want to watch on TV at night (if that happens to be a Disney movie, it happens to be a Disney movie…).

I love that I’m not responsible for keeping children fed and housed, so my income can ebb and flow. I’m the breadwinner in my house, so I am responsible for the livelihood of another adult. But he’s much more flexible to and understanding of changes in income than a kid might be. He’s totally onboard if I say I want to stop working for a year to write a book — I wouldn’t want to ask a kid to absorb that kind of sacrifice by giving up ski club or something.

The argument that a woman in this day and age has the right to not become a parent is well-trodden ground. Yet, in practice, this still feels like an outlandish choice. We’re made to feel like unuseful weirdos in a world that’s not built for the lives we live.

Not having kids is one more thing about me that doesn’t fit the world I’m forced to live in. Nearly everyone my age in my area has kids, and their lives are arranged around children’s activities. That means my local social options are limited to retirees. There aren’t book clubs or writing circles or maker’s spaces filled with millennials with a bunch of free time. The millennials around here have kids and probably work two jobs to support them. Being social with retirees is fine — intergenerational relationships are good! — but it leaves me longing for people I can relate to more explicitly. I have connections with people my age who don’t have kids, but they’re scattered geographically, so we can’t grab coffee on Friday mornings. Finding a solid community of people my age who live a life anything like mine, even in a more populated city, would be difficult, because having kids is so culturally ingrained.

It’s particularly tough being a person without kids in my family, because plans are made around the people with kids. I’m often not consulted about when something will happen; the siblings with kids figure out what works for their schedule and then tell me about it. If I happen to have something going on, I just miss out on stuff; whatever is on my calendar isn’t treated with as much concern as kids’ recitals, basketball games and camps. This isn’t to downplay how hectic a family’s schedule is; I see what they’re dealing with. It’s just weird to assume my calendar — i.e. my life — is so much emptier because I don’t have kids filling it.

A childful life without kids of my own

In my 20s and early 30s, I loved not having kids because I loved the freedom to roam and be completely free from obligation to anyone. Now I’ve settled into a much more routine life, where I do a day job and spend my evenings writing and my weekends puttering around my house or yard. I don’t have the same kind of reckless abandon I had when I was younger; I accept responsibility now for showing up for the kids in my life.

This is why childfree no longer feels like the right label. My life is full of children I love, and I make so many decisions and plans around them. I live where I do in rural Wisconsin because it’s just four miles from where my sister lives with my nieces and nephews. I’m a short walk down the road from their school, so I’m very available for band concerts, games, plays and holiday programs, and I prioritize those in my (sometimes busy, TYVM!) calendar. Plus, I’m here in a pinch for missed-the-bus days!

I most love being a non-parent auntie, because I get to model this option for the kids in my life.

I want them to see me living the life I’ve chosen. I’m not an evangelist for not having kids, but I am an evangelist for thinking for yourself, knowing what you want life to be and doing everything you can to live that life. Coming from this small-town culture, I know how hard it is to imagine yourself doing anything other than what everyone around you is doing — which is usually getting a mediocre job, marrying someone of the opposite gender, having children and buying a home within 100 miles of where you grew up.

I want younger people around me to see that I imagined what I wanted in life and designed my life to make it happen. That they can do that, too. I am the weird auntie so they know being the weird auntie is an option — if they want it.

Your turn

What is your relationship to parenthood? What did you learn about parenthood from the way you were raised? How does your relationship to children impact how you’re perceived in the world around you?

Note: Let me reiterate that I don’t have an opinion about whether or not someone else should have children! (I would like everyone to feel the same about my choice.) Also acknowledging that some people want to be parents but can’t be for all kinds of shitty reasons. That’s a totally different experience that I would never claim to represent, but also an important part of this conversation in our culture that assumes parenting is a normal and easy choice.

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I’d been married to my (male) high school sweetheart for about a year, and we were at a strip club with friends. This was the era of Katy Perry’s “I Kissed a Girl,” and we assumed most women my age would go through a college “bicurious” phase before settling down with the right guy. The woman in the couple we were with was in that phase, and I was very… intrigued by her. I thought I was probably going through that phase, too.

At the strip club, my husband won a lap dance in a raffle. (We were too broke to ever buy one, but it was a week night, and we got a raffle ticket for like $5. Is this a Wisconsin thing??) The dancer invited me to join them, which seemed exciting and, in retrospect, probably made her feel safer. I’ll spare the details; I thought it was cool at the time, but it’s pretty rude, in retrospect, to have a stranger dance at you in their underwear for tips. I left, like every dumb guy I’ve ever heard talk about strip clubs, thinking she probably uniquely liked dancing for me. I’m sure it was just as stupid to dance for me as it was for any guy, but I do hope she felt safe. I didn’t touch her.

I was attracted to her, though. Not in a lasting way. But it struck me that there was no distinction between the desire I felt for this woman and the desire I felt for my husband. That’s how I knew.

It feels silly to describe this today. I get the sense that young people today would be unsurprised to be attracted to people of all genders. That many of them grow up knowing gender and sexuality are fluid and varied and not at all binary. The celebrities they follow are pansexual and gender-fluid and polyamorous and don’t find it pertinent to use any of those labels, least of all in the press. They just exist as they are and they date who they want to date.

But when I was 20 in 2006, my world was a wildly different place for a queer kid. (We weren’t using the word “queer” in a positive way most of the time, first of all.) Until that intriguing friend of mine starting musing she might be bisexual, I hadn’t considered that was a thing a person could be.

I might have heard the word bisexual once or twice. I think there was a girl in our high school who was out as bi, but no one believed her when she said it. That’s a lasting problem for us; people assume we’re either lying to attract straight men or denying being gay. Teenagers in the early aughts were real jerks about that. There was no bisexual representation on TV or in the movies we watched. On Friends, Carol left Ross and became a lesbian. In Chasing Amy, the lesbian Alyssa was accused of being a fraud when it was revealed she’d had sex with men. My small-town high school had two out gay kids — a femme gay boy and an androgynous lesbian who were best friends and band geeks. My conservative family members weren’t explicitly anti-LGBTQ+; they just didn’t acknowledge queerness at all. As far as I could tell, being gay was fine, but not something that was going to happen to me.

I had crushes on boys just like my other friends did, so I figured I was straight and didn’t question my identity throughout my entire adolescence. I definitely had a crush on my best friend in middle school, but I didn’t know that’s what it was. I was always uncomfortable with (read: jealous of) her boyfriends. She came out as bisexual herself during our senior year of high school, long after we’d drifted apart. I’ll always be sad for us; we could have been little 12-year-old girlfriends learning to be ourselves at the age when you learn to be yourself. But we spent those years learning to be something else and had to start over when we were older.

It didn’t sink in for me that a person could be bisexual until I was 20, and my intriguing friend told us she was. I don’t know why then. Maybe we’d just made it far enough as a culture, with “I Kissed a Girl” and But I’m a Cheerleader and David Bowie and a lot of tumblr blogs. Maybe the water I swam in had just shifted enough that I finally understood bisexuality as an identity and not a party trick. She told me she was bisexual, I believed her, and I immediately thought I might be, too.

Bisexuality remained sort of a party trick for me throughout my early 20s, though. In my marriage, what I thought was acceptance was, in retrospect, fetishization. I became a party trick, a novelty for my mostly male friend group to gawk over. I didn’t fully integrate bisexuality as an identity; it was a sexual quirk. Not something to share in polite company.

My marriage ended when I was 25, and I started hanging around people who affirmed my identity. I was finally able to internalize that affirmation, too. A few years later, Obergefell at the Supreme Court made marriage equality the law of the land in the U.S., and suddenly (briefly), an LGBTQ+ identity no longer relegated you to second-class citizenship. I wasn’t anywhere near wanting to marry the women I’d dated to that point, and I’ve been in a long-term relationship with a man ever since, so I can only understand a fraction of what that decision meant for LGBTQ+ folks at large. For me, it meant my identity was simply — miraculously — something a person could be. That was pretty earth-shattering.

If I were to come out fresh today, I’d probably call myself pansexual or maybe queer or, like the crystal-cool Gen Z celebrities, not claim any label at all. Calling myself “bisexual” in leftist queer circles can feel like being the old lady who still says “colored people” and doesn’t notice everyone looking at her funny. I know there are more than two genders, and my attraction doesn’t exclude trans and nonbinary people. The “bi” in bisexual irks people, and I understand why, linguistically. And I do appreciate an opportunity to learn from people younger than me whose worldviews aren’t fogged by the baggage I’ve had to overcome.

But I still hold onto the “bisexual” label, along with a broader “queer” identity. Because it took me 20 years to claim that label in the first place. It was another 10 years before I said the word to my mother. Another five before I could comfortably say it out loud in mixed company — and still not just anywhere. Erasure and biphobia have made me feel like a fraud, a slut, a liar and a tease, and I’ve only in recent years begun to feel belonging in the LGBTQ+ community. I’ve spent my second 20 years understanding what “bisexual” means to me — so I’m not giving up the label too easily.

Your turn!

How is your identity impacted by the era and culture you grew up in? How might you see yourself differently if you’d grown up in a different time?

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I’m writing from the cocoon of a winter storm in Wisconsin. Outside, it’s on-and-off blizzard conditions, something like 12 to 18 inches of snow falling… and absolute peaceful bliss.

We’ve known this storm was coming for about a week, so everyone canceled their plans and stocked up on food. Nonessential businesses are closed, Sunday church services were canceled. Traffic is down to nothing, and no one is revving up machines for yard work. My neighborhood is silent and blanketed in untouched, glittering white snow. I took a walk with my partner this morning in the snow, and it was beautiful. We tossed snowballs around the yard and hopped through the snow like puppies, and it was wonderful.

This storm — a typical late-winter sneak attack following a snap of warmer weather — could have felt unbearable. That last instance of cold and ice and snow removal after enduring nearly five months of winter. But my respite in New Mexico a couple of weeks ago gave me the refresh I needed to get through this final stretch. Instead of more cabin fever, I’m enjoying the day inside, and I delighted in a romp in the snow.

I worried a little before the trip about spending the money, but it was the right choice. Even when life throws me a layoff and a bunch of debt to manage, reducing my spending isn’t necessarily the right answer. The money spent on that trip was the necessary salve to get me through the rest of this winter with the strength to keep making progress on recovering my finances (and my life).

💡 Inspired by a Healthy Rich contributor, a money date is an exercise I crafted for You Don’t Need a Budget. Subscribers can follow along in a private space after the paywall, and I encourage you to steal my questions to guide your own reflections!

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In my whole life, I’ve never been in a room that felt full of people like me. I’ve gotten close. I’ve found rooms of editors who share my obsession with language and communication. I’ve found pockets of Democrats in my small, conservative town. I surrounded myself with stand-up comedians for years because it felt nice to be among misfits.

But something in me has always been off. I’m not doing the right kind of work, I’m not from the right kind of family, I didn’t have the right kind of education, I don’t have the right kind of ambition. Something’s always kept me apart from the people around me, no matter what connects us.

I know most people feel this way sometimes. Or some people feel this way a lot of the time. Or, I don’t know, maybe I assume this is how everyone feels because I can’t imagine feeling any other way. I pushed the feeling off for years, because I didn’t think it meant anything. I’d felt this alienation my whole life, so it just seemed like part of being human.

Then people started naming things about me I’d never paid attention to before.

On TikTok, on podcasts, in newsletters — people were naming traits I shared, isolating the characteristics that had always made me feel odd, offering labels and explanations (and praise!) for things I’d been reflexively suppressing.

How I have to concentrate so hard to maintain eye contact.

My visceral need to propose a solution to a problem when all you want to do is vent.

The way I understand new subjects by recognizing patterns they share with unrelated things.

How I take in every detail of a person’s hair, teeth, smile, jewelry, clothes, shoes and hand gestures, but can never remember their name or pick their face out of a line up later.

My tendency to blurt secrets because no one told me not to tell.

The fact that all of my friendships start with shared work.

My intolerance for small talk.

The way I work best when I’m in a room next to others who are working on their own thing.

How my favorite dates looked more like interviewing someone for a research paper.

The way I’ve always said, “I don’t necessarily care what someone’s into, I’m just attracted to people who are passionate about something.”

My comfort with hierarchy.

The way people think I’m questioning authority because I ask “why” a lot, but actually I just want to know… why.

How my face responds to things even when I try not to.

How I worried about getting too into the Spice Girls when I was 12, because I was a Hanson fan, and I thought liking other groups made me disloyal.

The act of changing my clothes at least three times every day to adjust to changing temperatures and activities.

How I can bring any conversation back around to writing, language or communication.

The way I’m always asking, “Does this smell weird to you?” and no one ever smells what I smell.

How I did basically nothing but read from age 3 to 18 but got C’s in English.

My tendency to pass out in crowded rooms.

The way “networking” exhausts me, but I can have a conversation with one person for four hours straight.

These, I learned, are autistic traits.

I took my first online autism test around 2018, when I was 32 years old. I took it on a lark, not because I thought I could actually be autistic. I scored just below the “you might be autistic” range, laughed a little, and didn’t think about it again for a couple of years.

Then I got on TikTok in 2020.

Creators identified as autistic and described their traits and experiences, and they were so familiar. (Remember how the early TikTok algorithm knew you better than you knew yourself?)

I took another online test. And another. And another. I tried several tests, and I took them over and over again. A couple of years older and more fully attuned to my inner life in the midst of pandemic-spurred isolation, I got higher scores. The same results, again and again. I was solidly inside the “you might be autistic” window now.

I started to jokingly adopt the identity with my partner, and he quickly noticed how much it wasn’t a joke. Autism explained so much about our experience together, our communication styles and challenges, the quirks and idiosyncrasies that enamored or irked him. With his validation, I adopted the identity with less trepidation — but only around our house.

Like many late-diagnosed folks, autism became one of my special interests. I read Unmasking Autism by Devon Price. I listened to the Autistic Culture podcast. I watched Love on the Spectrum on Netflix. I followed autism influencers on social media. What really tipped the scale for me was reading the manuscript of my friend Marian Schembari’s memoir, A Little Less Broken, in 2023.

By that time, I was venturing out and self-identifying as “neurospicy” online and fully settled into the truth of my autism with my partner. But I was still taking the tests periodically to convince myself I wasn’t being dramatic (drama being a cardinal sin for this midwestern gal). Marian’s memoir about an autism diagnosis in her 30s reached a part of me that had been afraid to show itself. As different as Marian’s personality is from mine, as distinct as her life experience is, I found myself in her stories. (It doesn’t hurt that her writing is enviably beautiful. See? I made this conversation about writing!) I devoured her manuscript and cried with joy and recognition — of myself, of a world unlocked, of a room I belonged in.

I’ve never gotten a formal diagnosis, and that’ll always leave me with some imposter syndrome. (As does being asked, “Don’t you think that’s offensive to real autistic people?” when I self-identify to people who see my years of masking as evidence that I couldn’t possibly be autistic.) I did go through the self-diagnosis process from Dr. Angela Kingdon’s book Am I Actually Autistic, which speaks directly to late diagnosis and autism in adults. I’m considering that, finally, definitive, and I’ve stopped taking the online tests for validation.

Stories of formal diagnosis terrify me — it often sounds invalidating and traumatizing. I don’t know if I’d even pass clinical tests mostly designed for young boys. I’ve heard too many stories of women my age seeking a diagnosis and being turned down because they made eye contact and small talk (because we’ve been doing this our entire lives for survival in a world that would not only emotionally reject but physically abuse and degrade us if we didn’t hide and capitulate!). I’m not a student and I work from home in a flexible industry, so I don’t currently have a need for accommodations that require my autism to be certified.

I’m rationalizing this because I feel like I have to — like you won’t take my identity seriously if I don’t explain to you exactly why I haven’t gotten it rubber-stamped by a licensed professional.

But that shouldn’t matter to me.

Identifying as autistic has helped me recognize and celebrate so many parts of myself I’ve always misunderstood. I’m not an introvert or socially anxious or lazy or weird. I’m autistic.

Claiming this identity over the past six years has helped me slowly build a life and an environment that supports the best version of me.

To appreciate the kinds of friendships I develop rather than lament the ones I don’t.

To seize on bursts of attention and energy, and rest when my body calls for it.

To enjoy watching The Office over and over and over and not feel weird about it. (Nor about listening to three distinct podcasts about the show and reading books about it and reading Jenna Fischer’s memoir and cooking Angela Kinsey’s recipes and hanging Pam’s painting on my wall and…)

To delight in an annual Apple Music Replay that shows the world I’ve been listening to almost nothing but the Hamilton soundtrack for five years. (Update for 2026: Nothing but Bad Bunny since the Super Bowl.)

To tell people in my household that cluttered surfaces make me physically ill instead of quietly hoping the tables will clear themselves.

To order takeout instead of sitting on display in a crowded restaurant.

To ask clients about money without shame.

To wear soft pants every day, all year, for the rest of my life.

To bring fidget toys into meetings.

To stretch my body anytime, anywhere.

To avert my eyes when you’re talking so I can hear what you’re saying.

Late diagnosis and self-diagnosis are tricky subjects in autistic medicine, because they’re only recently being considered carefully. Autistic culture, on the other hand, tends to accept them without question, because we recognize people with autistic traits as autistic, full stop.

We don’t need neurotypical-coded checklists to confirm what we innately know about ourselves. I’m so appreciative of the late-diagnosed autistic folks, especially women and queer folks who are underrepresented in the science, who’ve put their stories and experiences out in public to help the rest of us see ourselves more clearly.1

Recognizing my autism in my personality, strengths, desires and behaviors has changed my life. It’s helped me live a life that’s right for me without the shame or striving I suffered for my first 35 years. I don’t need to find a room full of people exactly like me, because I can be myself anywhere I go. I don’t need to choose exactly the right kind of work or the perfect path or the ideal hobbies, because I’ll find my special interest in anything I do — and in that, I’ll find myself.

I no longer need to be understood, because I understand myself.

Your turn!

Have you experienced a late-in-life diagnosis of neurodivergence? What did that explain about your experiences growing up? How has this self-recognition affected your life now?

Leave a comment

It was a morbid way to acknowledge a milestone birthday, but that’s how people felt about middle age in the late 90s. 40 meant you were “over the hill,” which, I guess, means peaked? On your way down? Heading toward death?

Now that I’m 40, that sounds ridiculous.

By the time my mom turned 40, Gen X was already shifting the narrative. They’d started to move the black-balloon, over-the-hill commemoration to age 50. Not because people en masse were living to 100 years old, but because 40 was beginning to feel so young, regardless of how much time you had left after it. Now a big chunk of my millennial cohort are in our 40s, and “millennial” still has a ring of youth to it (to my ears…).

No one got me black balloons this year. No one is calling me “over the hill.” It would be absurd, because, look at me; I’m basically still a child. 💁

I’ve been referring to myself as “nearly 40” for about five years already, so actually turning 40 — and, for the next 10 years, being in my 40s — doesn’t carry the kind of weight I expected it to. But, as I’ve started an entire project around it, this age apparently means something to me.

Statistically, I’m nearly halfway through my life. Psychologically, that makes 40 a big deal. Physiologically, my body seems to be in cahoots with the over-the-hill narrative; my joints are achier, my periods are lighter, my sex drive has finally got the memo that I don’t want to be impregnated and I get tired just from the amount of thinking I do in a day.

Women a few years older than me are talking about perimenopause, but I’m not there yet. I’m grateful to have this information out in the open so I don’t have to figure everything out on my own when I get there. But at 40, more than navigating a drastic bodily renaissance, I’m crossing a new portal in the labyrinth of my identity. I’ve gained enough distance from the person I discovered in my 20s and enough experience living as various versions of her to see what I might want to leave behind and what I might want to take into my next 40 years.

I likely have at least twice as much adulthood in front of me as behind me. When I look at what I’ve done and learned in my past 20 years, that makes me very excited for my next 40. I continue to accumulate knowledge, understanding and wisdom as I go, and to shed insecurities and, as we millennials say, give fewer f*cks. I accept that the world no longer expects me to be hot, so I don’t have to worry about projecting hotness ever again — what freedom! I’m getting better and better, so how exciting is it to think what I might do with this remaining time?

That’s how I’m feeling as I turn 40.

I feel like I’ve earned this optimism with the work I’ve put in the past 20 years. I truly feel like I’ve earned a turning-point, optimistic year after the slog of the past five pandemic-era years, the past decade with Trump. This cultural darkness has coincided a little too neatly with seasons of my life and reinforced everything I might have been feeling anyway: My carefree, hopeful 20s were the Obama years, the Obergefell decision, the indie renaissance. I turned the corner into 30 (i.e. gave up on my dreams and settled into Real Life) as Trump recast American culture and politics in 2016. I descended into the nihilism of my late 30s as COVID-19 redefined “normal” and sapped most of our remaining resolve. We’re not out of the woods as I turn 40, but we’re in another election year in the United States, one that gives me hope for a major correction from the sins of the past decade.

And that’s what 40 feels like for me personally. I spent my 20s starry-eyed and limitless, spent my 30s becoming cynical and stuck. As I cross this midlife milestone, I’m returning to hope. No longer the naive wishfulness of my youth, this time it’s a more haggard and scarred optimism that says, “Something’s going to happen; I should figure out how to be happy about it.”

This kind of optimism won’t fix everything the way it did in my 20s. I’ve learned and survived too much to bury my head in the sands of hope. But I’m tired of being cynical about it. I hope this new, wiser optimism can help me walk lighter and breathe easier, even as I continue to prepare for and survive the worst in the years to come.

I don’t have plans for my 40th year or my fourth decade. I’ve experienced enough surprises and opportunities to know plans aren’t worth the notebook pages I fill with them.

The only promise I can make to myself for the year to come — and the decades to follow — is that I’ll let them be what they will. I won’t expect too much of them, and I’ll be grateful for what I get out of them. I’ll be optimistic and kind, I’ll spend my time on things that matter to me, and I’ll continue to learn.

I’ll reflect on this post at the end of my year, and I hope to have spent at least a few days living up to this promise.

Your turn!

How have you felt as you cross life’s milestones — 18, 21, 30, 40, 50? How has your experience compared with your expectations and the cultural narrative about that milestone?

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Because, I suspect, that’s when I was the truest version of myself.

Just as I started laying the tracks for this experiment in self-discovery, I found this poignant post by Erica Barry at , where she shares the most perfectly astute insight for this moment in my life:

“Growing up is becoming who you were at 12, except this time you like her.”

I’ve spent my entire adult life simultaneously resisting and trying to return to the person I was before my sex drive, self-consciousness, social-awareness and need to make a living kicked in and scrambled my wires. When you’re living through that age, every innocent and natural thing about you seems awkward and wrong, and you can’t wait to grow up and become something better.

Then one day you find yourself grown and wonder how you ever let yourself stray so far.

As Barry explains, those pre-teen years perfectly represent the core of who you are:

“[At 12,] I wasn’t sure what I wanted, but I knew who I was…I was about to learn how many calories were in a Chocolate Chip Chewy Bar, what 32B meant and all the cruel arithmetic of womanhood.

But for that brief window, I didn’t know any of it. The world was still strange, shimmering, and enchanted…

Since then, I have probably committed a thousand tiny betrayals against myself in the name of being ‘grown.’”

Barry shares a list of questions in her post to guide a reconnection with your tween self, which I’ll use to remember my core self as I set out to discover who I’ve become in the meantime.

Let this also act an introduction, in case we haven’t met before :)

To set the scene, I was 12 years old in 1998. Friends was the top-rated sitcom, Titanic was smashing at the box office, Shania Twain’s “You’re Still the One” was everyone’s wedding song, and Savage Garden’s “Truly Madly Deeply” was breaking hearts at middle school dances. My family had one giant Compaq computer and no internet; no one I knew had a cell phone. I’d lived in my rural Wisconsin hometown my entire life and attended the same school district with the same 100-ish classmates since kindergarten.

What did you believe about the world before you learned to manage your expectations?

I believed success would always feel like you were flying. I cried at the moments in movies when the underdog would win unexpectedly, and an entire town would rush the field, hugging, crying, screaming and hoisting the protagonist on their shoulders. It was otherworldly; the camera would zoom out, the noise would give way to the movie’s theme song and everyone would start moving in slow motion, floating in a space of pure connection and joy.

(In real life, I don’t switch into slow motion when I experience success; it’s fleeting. I don’t savor the wins, because they’re so expected by the time they finally arrive, and I immediately raise the bar and look ahead to the next thing I haven’t yet accomplished.)

What did you love before you felt embarrassed?

I was a sucker for love! I was obsessed with the Ross-and-Rachel and Chandler-and-Monica storylines on Friends. I still loved the Disney movies of the 20th century, where an ethereal and clever princess always found her Prince Charming in spite of the barriers from her family or society or the fact that she was half fish. In addition to seeing Titanic in the theater three times and wearing out my family’s VHS, I was turning to rom coms, whose heyday was just getting started. I was constantly falling in love with a new crush and desperately documenting every sideways glance and brief hallway “hello” in my journal.

At 12, I also still loved soft things and make-believe. I held onto my favorite stuffed animals. Baby dolls and dress-up clothes came out when no one was around. I still had all of my Barbies and loved to imagine a life for them and set them up in poses like they were doing a promo shoot for the movie they starred in inside my head.

I wanted to be a ballerina. I had a book of beginner ballet poses I practiced at home and got slippers, tights, a leotard and a skirt for my birthday, but my family couldn’t afford dance lessons, and my mom thought 12 was too old to get started, anyway. I liked to wear jeans and a sweater over the leotard and tights — like Jessi Ramsey in The Baby-Sitters Club — and imagine I was just coming home from a class.

What did you dislike before you talked yourself into liking it?

I hated horror films and swore them off after seeing the first Scream movie and not sleeping for two weeks. I talked myself into watching them with friends in high school to avoid seeming babyish, but I mostly shielded my eyes if no one was looking.

I never liked spicy foods but trained myself to tolerate heat in my 20s. As I’ve gotten older, that tolerance has waned, and I’ve had to overcome a sense of weakness because of it. But it’s actually fine to not want to sweat while I eat noodles, right?

I was never a cynical person, but I came to value cynicism as I got older and saw cynics as people who knew something the rest of us didn’t. I’m actually quite optimistic and expect the best from people, but I’ve learned to dig deep for negativity to avoid appearing naive.

What could you lose entire afternoons to without anyone asking you to?

Reading! In seventh grade, I was still devouring The Baby-Sitters Club, even though my “reading level” and my mom both said they were too easy for me. But it was such a comfort to dive into that world, which I’d been in since I started reading the Baby-Sitters Little Sister spin-off chapter-book series in second grade.

That same year, I also went through a phase of Lois Duncan and other thrillers — which I loved as books but hated as movies. And I read The Diary of Anne Frank, went down a rabbit hole of novels set in the Holocaust, and learned that writing is vital not only for preserving the story of a profound time but also for surviving it.

I remember this era of reading more than any other in my life, because I probably read more than at any other time. Our middle school had just adopted the Accelerated Reader program, so I could get class credit for reading books of my choice, and at my pace. (As avid a reader as I was, I rarely made it through teacher-assigned novels in my entire K-12 career.)

Besides reading, my 12-year-old self could get lost in Prime Time TV every evening, and I was starting to stay up late watching reruns from the 60s and 70s on Nick at Night.

I also used to draw a lot. Through class. Idly in my room at home. I was never the best artist among my peers; that accolade went to this girl who I think was my fourth cousin or something, who drew cute cartoony characters with big, bashful eyes. My drawings were closer to realism, and I drew things like the Spice Girls with the addition of myself as “Mini Spice.”

What small comforts did you surround yourself with?

In 1998, I was listening to Hanson’s and Nsync’s debut albums on repeat. (I still listen to Hanson’s 1997 Christmas album, Snowed In, every holiday season.) There was a bit of Spice Girls in the mix. The next year, I’d replace it all with Britney Spears’s …Baby One More Time. For years, I also listened to a Madonna greatest-hits album called The Immaculate Collection that we got for a penny through a Columbia House promotion.

(I no longer love that old pop music or a lot of new pop music, but I still find comfort in listening to the same music over and over. For several years, my stim listens have been Butch Walker and the Hamilton soundtrack.)

My happy place was my room, because I had it to myself and was allowed to decorate it more or less the way I wanted. The walls were painted lavender, because I had to pick a favorite color for some reason and I’d picked purple. My bed was covered in the first quilt my mom ever made. (She’s become an avid quilter since and hates to spot the errors in this one, which I still have and love because of its imperfections.) I had a desk, where I’d sit and write in my journal while I told my parents I was doing homework. I had a CD tower with about 60 CDs, even though I only listened to those few. I had a lava lamp with purple “lava” that soothed me on (frequent) sleepless nights. And the piece de resistance: A translucent, purple, inflatable plastic chair filled with foam beads. It was too short, squeaky and incredibly uncomfortable — but so cool.

Who were you when you weren’t trying to be strategic?

I was an absolute dork! I played with Barbies. I twirled in pink skirts. I cried at rom coms. I crooned loved songs. I wrote stories in my head. I spilled my guts in my journal. I walked to school with my nose in a book.

I was a hopeless romantic with my head in the clouds. I read Ann M. Martin’s autobiography and wanted to be a writer. I watched You’ve Got Mail and wanted to own a bookstore. More than anything, I wanted to fall in love — and be fallen in love with!

And most importantly: What would change if you let her back in?

If I were more of my 12-year-old self today, I’d be lighter. She had plenty of baggage — unnamed anxiety and depression, insomnia, that feeling of not being fallen in love with — but she was so hopeful and silly.

When I attempt to construct my ideal environment now, it has a lot of the character of my 12-year-old bedroom. It’s more pink than purple, but there’s a lot of softness, a couple of dolls, fun art on the walls.

Letting her back in would mean being more playful and slightly less self-conscious. Less encumbered by expectations and obligations. Optimistic again. Less reflexively cynical. I’d see the best in people and believe I could achieve my dreams (I might even let myself dream again…).

I’d sing more and dance more and play my flute, and I’d believe I was pretty good.

I’d write for no one but myself.

I’d draw again.

I’d tell friends my wild-hare ideas because I’d think they’re brilliant and have to be shared.

I’d play make-believe and wear costumes.

I’d read books that didn’t make me look smart.

I’d add a lava lamp and an inflatable chair to my office.

I would do all of this again if I were to become my 12-year-old self — except this time, I’d love myself for it.

Thank you so much to Erica Barry for the inspiration for this post! This reflection was invaluable and a perfect way to kick off an exploration of where I’ve been and where I’m going next as I turn 40.

Your turn

Who were you at 12 years old? What would change if you let them back in — even some parts, even just a little?

Leave a comment

It’s easy to imagine entrepreneurship as the escape hatch from all the ways corporate employment stresses you out. In a lot of ways, it is. But working for yourself comes with its own host of stressors and challenges that impact your mental health, too. And — speaking from experience! — on top of the basic stressors of running a business, you also feel like a failure if you’re not basking in the freedom, autonomy and creativity of living the life you’ve chosen. There’s a lot of baggage to carry in self-employment.

Shulamit Ber Levtov, “The Entrepreneur’s Therapist,” recognized this lack of attention to entrepreneurs’ mental health as she struck out on her own and decided to turn her experience as a counselor and social worker into a practice dedicated to supporting women in entrepreneurship.

I invited Shula to talk about how she started her business and the challenges she’s faced — her journey to entrepreneurship out of necessity later in her career struck a nerve!

Name: Shulamit Ber Levtov

Business: The Entrepreneurs’ Therapist

About the business:

I provide mental health support for women business owners, because running a business is hard.

Business details

• Based in: Jasper, Ontario, Canada (near Ottawa)

• Year started: supporting women with their personal growth: 2000, as a therapist: 2012

• Profit structure: Traditional for-profit

• Legal structure: Sole proprietorship

• Who works in this business? Me, plus I have a few contractors: web designer, web maintenance, accountant, bookkeeper, VA

• Income contribution: My full-time job

• How much money does the business earn per year? $98,000 CAD gross. Profit on paper is about $50,000 CAD. I get paid around $40,000 CAD. It’s important to point out this is sustainable for me because I purposely have a very simple lifestyle with very low cost of living, and that my basic health care is paid for by my taxes.

• Hours worked per week: 24–32 hours

• Is your business profitable? Yes

Your experience doing this work

Have you run any other businesses in the past?

Yes. I’ve co-owned a Steadicam. I was a PR and media consultant and a freelance translator.

Why did you start this business?

I was injured at work and needed to do my own occupational rehab so I could change careers, because I could no longer do my job. I was an older woman starting at the bottom of a new career and wanted to be sure I had a job that enabled me to work until I died.

What surprised you most about starting a business?

How stressful it was.

What are some of the challenges you faced starting your business (and how did you overcome them)?

The entrepreneurial community’s total lack of understanding or even valuing a therapy practice and/or consulting as an actual business. The lack (at the time) of business coaching for therapists and therapy practices. The lack of bank financing for new businesses. Lack of affordable commercial space. The need to ensure a consistent and stable income without having personal wealth or investors to rely on. Fears of indebtedness and fears of being unable to pay back the debt. Total alone-ness in taking big risks like that.

I wasn’t able to surmount most of those barriers when I was running the first iteration of my therapy businesses, which was a group practice. That’s why I do the work I do now as The Entrepreneurs’ Therapist, so no one has to go through what I did as a woman business owner.

What’s the most rewarding thing about the work you do?

Being a witness to the transformations that take place both in businesses of my clients and in their peace of mind. The deeply intimate moments of change that occur with therapeutic processes can feel as intimate as physically intimate moments but on an entirely energetic level (and not sexual at all), but just as emotionally moving and connected.

These experiences connect me with a sense of meaning, and a sense that there are greater forces at work in the world that are helping us all meet our needs.

I’m so grateful to be able to do such meaningful work and have it support my financial sustainability. It challenges the notion that meaningful work and sustainability stand in opposition to one another.

In what ways do you take care of people in your business?

I carry my relationship and communication skills as well as my skills for having difficult conversations into all facets of my business and life. My presence is the most valuable thing I have to offer, so I bring it to all my interactions. In order to be sustainable in that, I have a fierce self-care practice.

One of my ongoing concerns is money conversations and empowering clients in our money relationship. I’ve recently moved to a fee range for everyone instead of a fixed fee or a sliding scale, and I invite clients to choose their own fee. In an extension of this, I also invited clients to choose the amount of their annual fee increase. I wrote a blog post about it here.

Learn more about this business

• Shula’s website

• Shula on LinkedIn

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