Money Date No. 15: Post-holiday gratitude
Surviving the winter malaise, a blasphemous Christmas decision and forging ahead as a freelancer
Who else is happy to move beyond the winter-break malaise? Sticking Christmas and New Year’s Day on Wednesdays was a particularly cruel trick of the calendar this year, delaying the recovery for those of us who suffocate outside of a routine.
I started self-employment wanting to design a life where I could take long breaks each winter and summer. It seemed like the epitome of work-life freedom to be able to walk away from earning money for any stretch of time. But five years into working for myself, I realize that’s not my ideal scenario. Through self-employment, I’ve designed a life where I can prioritize work as much or as little as I want day-to-day and week-to-week. I rest when I need it, knock off early to see a nephew’s play, start late to meet my mom for breakfast, shift a task to a weekend to prioritize errands — and I work hard when I’m eager to. I don’t need long breaks from this life, because it doesn’t exhaust me.
Holiday breaks are un-restful for me. The break in routine is more exhausting than any stretch of work I do the rest of the year.
December is not a joyful season for me. It’s a slow descent into chaos, where colleagues disappear, all the children carry viruses and grocery stores are never open when I need them. My calendar gets packed with extra obligations and travel that fit someone else’s schedule. The life I’ve carefully crafted for my sensibilities is impossible to maintain.
I don’t mind family time. I don’t mind small parties. I don’t mind quiet corporate days off. I don’t mind travel. I don’t mind children. But I drown during this period of the year when all of these things our culture neglects for 12 months get crammed into a single week that’s supposed to fill our annual joy quota all at once. I can’t think straight, I can’t make progress on anything and I certainly can’t get any rest.
I’ve been able to wade back into real life this week, and I’m grateful to be able to breathe again. Let’s get to it, 2025!
And, um… happy new year!
💡 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!
What’s the most joyful thing you did with money this week?
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