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.)

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.

I anchored my last advice column of 2020 around a Susan Sontag quote, and it seems appropriate to kick off the New Year with another one. This is from a 1992 profile in the Los Angeles Times, in which Sontag described her youthful ambition to be a writer:

It never occurred to me that I couldn’t live the life I wanted to lead. It never occurred to me that I could be stopped. . . . I had this very simple view: that the reason people who start out with ideals or aspirations don’t do what they dream of doing when they’re young is because they quit. I thought, well, I won’t quit.

Few of us enjoy Sontag’s certainty and single-mindedness, not to mention her relentless curiosity and energy. (And maybe that’s not such a bad thing: By all accounts, she could be an infuriating person to be around.) But I like the simplicity of that attitude: All you have to do is not quit.

Well, that’s not all you have to do: You have to write and research pitches, send them out, secure assignments, deliver publication-worthy work on deadline, go through as many rounds of edits as your editor deems necessary (all gratis, of course!)—and after all that, harass publications for payment, sometimes for months. Even more daunting, if you’re writing personal essays or literary journalism, you have to give yourself a lot of time to read, to have experiences in the world, and to reflect on those experiences—i.e., to be an interesting person with interesting things to say. What a wonderful and also terrifying job description!

On a day-to-day level, negotiating this career is going to involve all kinds of ups and downs. There’s no avoiding it: Some days you’re going to feel like a brilliant writer carried along on a wave of enthusiasm—and other days, well, you’re not. You’re going to think: Why didn’t I become something practical like a veterinarian or a baker or a real-estate agent. You may even think, Hey, maybe it’s not too late to become a veterinarian or a baker or a real-estate agent . . .

But if you have a core idea, deep down, of what you’re after as a writer, of what kind of writing practice you want to build up and sustain, and you keep that in mind when you’re tempted to quit, and you don’t quit . . . I do think you’ll get there over time, I really do.

The other week I attended an online workshop that the writer Sheila Heti was offering, on strategies for completing long-term writing projects. It was really useful; Heti basically just shared a bunch of her own methods for getting writing done, in a very candid, open way, and gave the group some exercises they could use to deal with different kinds of blocks. She made writing seem, at once, like this truly exalted calling—you’re making work that could last for hundreds of years!—and also like being a kid in a room full of Legos: Maybe you should put them together like this, or maybe like this, who knows, give it a try, see what happens, get an outside opinion, keep playing around, keep trying different combinations . . .

One thing Heti said seems relevant to your dilemma. She mentioned that the therapist Esther Perel has this idea that relationships go through cycles of harmony, disharmony, and repair. And Heti said that she thinks the same thing is true of the writing process: You go through periods of feeling like a freakin’ genius (harmony), and also periods of feeling like your writing is utter garbage (disharmony). And after moving through these two extremes, you eventually end up with something that feels right (repair). And then you start the cycle all over again!

I think you could also apply this idea to a writing career. There will be the periods when you think you’ve got it reasonably figured out and things are coming together, and there will be periods when you 100% do not have it figured out. But it’s by going through both of those phases that you actually get better, actually get closer to that vision of your ideal writing practice.

As for fear—well, this can be a good thing! You need a certain amount of fear, or even if you don’t need it there’s no avoiding it, so you might as well accept it and make it work for you. I know personally that it takes a healthy dose of fear to finish a piece of writing or to commit to a new one—usually some mix of financial fear, fear of disappointing an editor or a collaborator, fear of losing relevance or momentum in my career, etc., etc.

You also asked for techniques. As you may know, I’m a big booster for the power of a daily routine. Following more or less the same schedule every day allows you to get into a rhythm, and this can be good for the writing itself—you might find yourself writing lines in your head while you go through the same familiar motions of, for instance, filling the coffeemaker with water, grinding the coffee beans, putting dirty glasses in the sink while you wait for the coffee to brew—but it can also be good for smoothing out the bumps in a writing career. On those days when your writing feels hopeless or an editor is driving you crazy, you can’t dwell on it for too long because at 11:00 a.m. on the dot you take a walk, take a shower, make a sandwich, water the plants—whatever. I find that a routine can be a kind of bulwark, something to lean on in times of distress.

You said, “I’m worried that once I have this time that I will squander it.” That’s where the magical combination of fear and a routine can work wonders! If you’re fearful of paying the rent and you’ve built up a regular working practice, I really don’t think you’ll squander your time. Also, keep in mind that some absolutely crucial parts of the writing process may look and even feel like squandering time—but they’re really not. Remember Iris Murdoch on the secret to writing a novel: “You have to spend a lot of time looking out the window.”

If you’re not sure where to start with a daily routine, I’d recommend that you pay attention to when you seem to do your best work—it might be first thing in the morning, after a mid-afternoon jolt of caffeine, late at night while the rest of the world is asleep—and then do whatever you can to carve out some uninterrupted writing hours at that time every day. That’s the foundation. The rest depends on your other commitments and priorities, your living situation, your temperament. A routine can and should be a work in progress. Personally, I enjoy tinkering with mine, finding the schedule that seems best suited to the project at hand, and then trying to streamline it, or trying to make it less grueling and more fun. (Don’t forget about fun!)

That’s a lot of advice—I hope some of it proves useful for you. If you’re not feeling me and Sontag and Sheila Heti, you can always turn to the co-writer of the song you mentioned in your letter. I’m speaking, of course, of Lady Gaga, who, in accepting an Academy Award for “Shallow” in 2019, gave some advice to the audience that’s actually a pretty good fit for your situation:

If you are at home and you are sitting on your couch and you are watching this right now, all I have to say is that this is hard work. I’ve worked hard for a long time and it’s not about winning. What it’s about is not giving up. If you have a dream, fight for it. There’s a discipline for passion, it’s not about how many times you are rejected or you fall down or you’re beaten up, it’s about how many times you stand up and are brave and you keep on going.

Thanks, Lady Gaga! I’m also hoping some of you reading this will have some additional advice for K. To that end, I’ve started an open discussion thread where you can leave your thoughts. Please weigh in with your own comments and advice, and I’ll be reading and replying this week.

Join the discussion


That concludes another installment of this advice column. To submit your own creative dilemma, email me at (or just reply to this email) and I’ll do my best to provide some concrete advice based on my research into writers’ and artists’ work habits.

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(Read my past advice here.)

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