August 03, 2016

Why I quit my full-time job

I was going to make a "Why I Quit My Job" YouTube video, but it was too hard to organize my thoughts on camera. I put on makeup with lipstick and everything and tried to film it four or five times, but it just wasn't coming together in the way I wanted.

Last week, I left my stable, director-level, twice-monthly paycheck digital editorial job at a century-old fashion media company... to go freelance. I resigned July 1st and my last day in the office was last Friday, the 29th. While there are a whole lot of personal reasons I have for leaving, far and away, the most important reason I left was so I could go back to doing the thing I love: being a full-time writer. What's funny is that sometimes, you don't even know you love doing the thing you love doing for work until you stop doing it. It took me six months to realize how much I missed it.

5 reasons I love writing:

1. Writing helps me think and organize my thoughts.
2. Writing helps me solve problems.
3. Writing is the best way I know to communicate clearly.
4. Writing is hard. If it were easy, I don't know if it would be as fun.
5. The kind of writing I do is very project-driven. I like projects that have a clear beginning and ending.

On a more abstract level, I've been thinking a lot over the past few years about what my "dream job" is. People ask you about dream jobs all the time, especially when you get to a certain level and you have meetings with senior execs. The more I thought about what my dream job looked like, the more I remembered a question I always ask job candidates when I interview them for entry and mid-level editorial positions: "What does your ideal workday look like?" I love asking this question because day-to-day stuff is something not a lot of people think about. But the reality of performing well at work— especially in a media office environment that's somehow both ridiculously over-structured and, at the same time, total chaos—is to know exactly what you want/need/should be doing at any given hour of the day. I heard somewhere once that Oprah's days are scheduled in 15-minute increments five months out (or was it five years out, I don't remember). So I've been asking myself that question over and over again—"What does my ideal day look like?—and after thinking about it a lot over months and months, I came up with the freelance daily workflow I wrote about a few days ago. And when I pictured myself in that workflow, I saw myself wearing my favorite sweatpants (I have many favorite sweatpants, actually, more on that later), working at home.

So, over the past few months, when people ask me what my dream job is, I've started to answer, sort of tongue-in-cheek (but mostly truthfully) that my dream job is to type at home wearing sweatpants. And now, here I am.

In the video that will never be made, I also wanted to offer advice to anyone thinking about quitting their full-time job and going freelance. I'm not sure I have any solid/true/real/empirically successful advice three days into this adventure (yet), but here are some things I thought a lot about before leaving my 9-5:

— It takes a long time. Quitting and riding off into the sunset doesn't just happen. I thought about making the move for months–and never mind just making the leap, there's a whole bunch of practical stuff that needs to happen, too. I saved money, I made sure my budget was in check, that I had a safety net just in case, and I also made sure to line up a few regular gigs ahead of time so I wasn't going out blind.

— You're not trying to launch Buzzfeed. I think sometimes, especially working in media, we have this notion that going out on your own means that you're going to have to make a bazillion dollars to stay afloat. Whether you're going freelance or starting a small custom content business, chances are the first few months, you won't need to be supporting a company of, like, 150 staffers. I had to keep reminding myself that I am a company of one. And I'm the only person I need to support. Of course, this changes if you are married, have dependents, or have children.

— Know who you are. Believe in yourself. Throughout your life and career, there are always going to be people you meet along the way—friends, family, coworkers, acquaintances, Twitter trolls—who will tell you that you can't do the thing. If you know yourself well, if you've made a plan, if you've thought things through and are realistic in your approach, don't listen to them. You should believe in yourself and don't let anyone ever tell you any differently.

One of my favorite lines from one of my favorite books (the first Patrick Melrose book by Edward St. Aubyn) is spoken by Melrose's father, who was a sociopath and pedophile. Still, it's a good line, and I sort of live by it:

"Observe everything. Always think for yourself. Never let other people make important decisions for you."