How to choose which work to do first

Make money or fill your creative cup?

A HUGE challenge when you work for yourself: deciding what to work on when.

The point of this whole lifestyle is freedom, but this amount of freedom can be incapacitating, too. Ironically, to be good at working for yourself, you have to have all those qualities from every corporate job ad: self starter, self-motivated, good time management… 

You have to wake up every day and decide what to do.

That’s terrifying, especially when what you decide could make a deep impact on how much money you make this month.

The toughest challenge I’ve always faced as a freelancer is the battle between doing (or seeking) client work and doing the work that builds my own brand.

Your heart might wage a similar battle between client work and an unfinished novel, or content marketing assignments versus personal essays.

One might mean an immediate paycheck, while the other might mean more freedom in the long term. One might be creatively satiating, while the other might be just another templated comparison of two bank accounts. I won’t say which is which.

Both are necessary — so how do you decide which work to do first?

I’ve heard opposing advice on this from two women I admire, and I see tremendous value in both approaches.

A. Focus on what pays

This advice is a throwback from Alexis Grant’s early days as an entrepreneur and a reminder that’s stuck with me since she published it in 2012.

“The smartest entrepreneurs and side-giggers and freelancers know they can’t possibly do everything, so they choose priorities. And when one of your goals is to make money, your priorities have to revolve around WHAT PAYS.”

That means, yes, building your following on YouTube could benefit your business down the line. Writing a free newsletter could fulfill the mission of serving your audience. But you don’t have a business if you don’t make money — therefore, prioritize what pays.

B. Do the important work first

This advice is from another entrepreneurial powerhouse, Marie Forleo, on an episode of MarieTV:

“I know you’ve got clients to attend to and work that pays the bills, and sometimes, yes, that’s urgent. However, you do have enough time to create your art and reach your goals as long you work on what’s important first and save what’s urgent for a little bit later.”

Marie’s advice is inspired by the famous Eisenhower Decision Matrix: Label your must-do tasks as either urgent or important, and do the important work first.

In this case, client work is urgent, because it comes with deadlines and expectations. Personal branding or business building work — but not, like, social media and email — is important, because it helps you achieve your goals and create a life you love.

What I love about this advice is Marie’s line, “You’ve gotta remember: The urgent stuff is always gonna get done because it has to.”

So, who’s right?

To be clear, I’m not pitting these women against each other. I’m certain they each support the other’s approach — and they’re not necessarily at odds.

I’ve learned the correct approach depends on what motivates you to get work done.

Early in my career, I had my head in the clouds. I loved to fill my day engaging people on social media, writing for my blog and crafting creative essays. I was terrible at convincing myself to pitch clients, submit proposals and get work in by deadline.

If you’re in that boat, you need to focus on what pays. You’ll always make time for creative work — you’ll lose friends and give up your weekends if you have to. Do what pays first, so you actually have a business to build.

Now, I’m great at doing what pays. I get ahead of deadlines, take calls, send pitches (occasionally) and hit weekly income goals. I’m not as good at convincing myself to try new things and take the kinds of creative risks that’ll push my business forward.

Now I need to prioritize the important work.

For me, that means taking on fewer assignments and giving myself more days off to create space for the big work. As I’m able to earn more money in less time, I’m using my extra time for business building work, instead of taking on more client stuff (i.e. more money).

If I stuck with the “focus on what pays” mindset at this juncture, I could earn a lot more, but never level up to the life I truly want to create. It’s time now to focus on the important work first.

Know a writer who needs these tips? Share Notes to get the word out. 

Image by @artxadanna via Nappy