Bullish Q&A: How Do I Stay Motivated on a Long, Self-Directed Writing Project?

Here’s a question I think a pretty large percentage of the Bullish population will be able to relate to.

I’m 27 and transitioning from non-career-track jobs to what I really want to do but haven’t been brave enough to try until now: journalism. Because I’m 27 and haven’t been to journalism school or done journalism in any way before, I’m just jumping in by writing my dream article, which is long and investigative.

My problem is this: for the first time in my life, I’m having serious trouble with motivation and focus. I think it’s partly that the task is so daunting (teach myself a host of new skills with next to no guidance! take on a huge project without having ever done smaller ones!). But it’s also that the work has no obvious structure and there’s no one to give me that structure. I’m good at going into the cave with progressive tasks that have deadlines, clear steps, and regular feedback. But this project isn’t something whose progress I can track on a spreadsheet.

Every day I wake up with this oppressive feeling of aimlessness. I try to make schedules and lists, but the items are a lot more nebulous than “take practice GMAT.” I find myself getting more distracted than usual by Facebook and crossword puzzles (at least I have a sense of accomplishment after the puzzle!). I don’t know if my lack of motivation means I’m depressed; if so, I think it’s over worry about this project, which I recognize is self-defeating. I was motivated enough to do this that I upended my life for it. How can I regain that motivation and move forward in the dogged, daily way I need to? How do I take this beast of a project and make it manageable? How can I stay focused without grades or scores or intermediate goals?

Hi there! You are absolutely on the right track. The most intrepid and successful writer I know is my best friend Molly Crabapple, who has been doing investigative journalism, mainly for Vice — while some of her success is due to her fame as an artist, a lot of it is due to the ballsiness of suggesting that she should be sent to Syria to talk to (and draw) snipers. She’s an art school dropout. If you want to do journalism, do journalism.

On the other hand, I once dated someone whose best guy friend constantly bragged about his masters in journalism, but literally could not write a paragraph. He had no idea what commas were for, much less did he have a working knowledge of Middle East politics. His degree is prominently mentioned on his About page, right next to links to articles that regularly misuse “there” and “they’re.” Embarrassing.

I know what you mean about big articles having no obvious goalposts or milestones. You usually don’t even write long articles in a linear way where you could celebrate being, say, half-done.

If you’re worried that you’re falling into depression (but you don’t think you have medical-grade depression that requires help) — well, I do think that’s normal with long, murky projects, but it’s also avoidable.

You need to talk to people about what you’re working on. Forcing yourself to explain (painfully!) to someone that you only wrote two paragraphs today but you figured out who else you need to talk to to get an outside perspective on such-and-such both makes you feel a bit better about your progress and tends to give you clarity in your own writing.

Keep in mind, I HATE talking about something I’m writing while I’m still writing it. I hate it, and usually avoid it. But that really is the trick for when you’re stuck.

Wait, but DON’T talk (only, or primarily) to other writers! Talk to some businesspeople and people with normal jobs who can bring things back into perspective in terms of health, sanity, getting things done, seeing sunlight, seeing the point of spending so much time on something.

Ask some friends and acquaintances and uncles and your mom out to lunch and say something like, “I want to catch up with what’s going on with you, and also get your perspective on this top-secret article I’m working on.” And your uncle will think, “That’s weird, since I’m an accountant. Is it about accounting? I guess I will find out.” Accountants are generally pretty good at asking the right questions and measuring things.

Have you considered a coworking space? Again, not a writers’ space — you’ll find people who have the same problems. Do your writing around a bunch of fast-moving, creative entrepreneurs, and talk to them over coffee breaks. (WeWork, for instance, has a pay-by-the-day option.)

When your work happens so much in your own head, it’s important to get back out of your head sometimes — and out of your own social circle. Talking to people who are like, “We optimized our keywords and increased clickthroughs 450%” will swing your perspective back around (even if you don’t really like those people, and even if optimizing clickthroughs makes you want to barf.)

Jen