Advice on jumping off the deep end

A new freelancer worries about challenging days ahead.

Welcome to the latest issue of Subtle Maneuvers. Previously: the joy of Fran Lebowitz. Today: my first advice column of 2021. (Weigh in with your own advice here.)

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Dear Subtle Maneuvers,

I’m writing because I’m at an unexpectedly pivotal moment (or feels pivotal) in my life. 

I put in my two weeks’ notice for my day job last week and I am inching through the final two weeks of this position. Instead of reporting to an office for 40 hours a week, I will be working part-time remotely online and, with that extra flexibility, working on freelance writing. 

In my bones I know it is the right thing for me to do right now and there has been momentum. In the past few weeks I have had multiple pitches accepted and executed, personal essays accepted for literary magazines and assignments from one publication when I didn’t even think I was at the level to receive an assignment. Still, even with these good signs and this feeling of momentum I can’t help but think of “Shallow” (the song): I’m off the deep end / watch as I dive in.

I’m simply a bit fearful that I’ll fail. I’m fearful that moonlighting creates more pressure to create an artistic life if you must spend 40 hours a week in a place you do not want to be in. I’m worried that once I have this time that I will squander it. I’m worried that I will get transfixed quickly on finances and not utilize this blessing of time to really work on my own personal writing too. 

Do you have any advice about the initial transition into a career rooted in independence? Specifically, do you have any techniques to help independent creators get through challenging days when they must work alone? Thank you for your time. I hope this is not too convoluted. —K in New Mexico

Dear K,

First of all, congratulations on taking this big step toward a writing career. I think anyone who writes for a living will tell you that it’s not an easy path—but it sounds like you’re already well aware of that, possibly too well aware. So I do have some advice for you.