Jan 01

Two months without a job taught me what I really want from my career

Two months ago, I quit my job at Dropbox because something was very wrong. I didn’t know what it was, but I knew that I was broken and that I just needed to go. I already look back at that girl like she’s someone else–like I’m watching a movie of myself.

Linda sits awkwardly in a conference room waiting to have an exit interview with her boss, fully aware of the wide eyes and crazed look on her face. “Oh man … they think I’ve totally lost it, don’t they. I mean I kind of have. Maybe I should move back to New York. I think I forgot to take a shower this morning. Yep. Definitely did. Maybe Berlin?” She stares blankly with a weird smile on her face, imagining every possibility in the world all at once. She looks haggard and broken.

I was a mess–but I also felt free for the first time in way too long. I hoped that feeling would still be there when I woke up the next morning with nowhere to go and nothing to do. My life had turned into a daunting, tangled ball of iPhone headphones, and I knew I needed a month just to deal with it.

For starters, I wrote a blog post about quitting my job and it got some attention. I heard from so many people with the same story. From junior designers getting their feet wet for the first time, all the way up to senior executives and newly-established millionaires who seemed to have it all. Everyone said the same thing :  that they feel like they’re losing their souls by staying at their jobs, and yet they can’t find the courage to leave.

It was really fascinating to me — and almost a relief — to discover that no human being is immune to this phenomenon, no matter how large their paycheck or how ample their perks. The soul-sucking anxiety seems to get worse as you climb the ranks in Silicon Valley, if you aren’t climbing with the right people by your side and for the right reasons.

This is what my first month of being “unemployed” looked like:

It looks just like my Dropbox calendar would have looked. But instead of meetings and deadlines, it was now filled with “life stuff.” In two years, I hadn’t made the time for little things like the DMV. And I was having fun meeting strangers who wanted to share their stories. Being this busy was normal for me, so I kept it up for a while. It was my little calendar-shaped security blanket.

“If there’s lots of stuff on my calendar, that must mean I’m important and needed and busy making great things, right?” As it turns out, that wasn’t true. In between meetings and appointments, I would go on long hikes or drives by myself. It wasn’t long before the little orange dots on my calendar just felt like nuisances keeping me from freedom, so I stopped putting them there. I was my own project manager now, and I could just do that. And I needed to in order to deal with that ball of stress in my head that made me quit in the first place.

I couldn’t figure out the source of my stress while I was as busy as I was in my job. Stress is a really weird thing. When it’s happening to me, I know it’s happening, but I can’t see it with a birds-eye view. I can sometimes get perspective by going on vacation or drinking a few Negronis or running 10 miles at a time. But the only way to really figure things out was to give myself time. I couldn’t figure out the source of my stress while I was as busy as I was in my job. I had to go, if I was ever going to get my head straight.

I took a whole month to think about everything that I hadn’t had time for over the previous two years. I posted cool photos on Instagram to make it look like I was on some amazing adventure, but really I was just recalling every project I could have done better, every work relationship gone wrong, every weird email I misread and how inadequate I always felt in my job. I made time for all of those ugly and pointless thoughts. I cried a bunch. On some days I didn’t have the energy to move and I would just lay face-down on my couch. I felt all of those feelings right down to their core, and then I threw them all away. This process had great days and horrible days, and lasted about five weeks before I really started to feel like myself again.

I’m so glad I didn’t jump into another job. If I had, I would have been bringing all of that mess with me. I’m so glad I didn’t jump into another job. If I had, I would have been bringing all of that mess with me. I wouldn’t have the bird’s-eye view of my own life and I would have been tangling up the ball of headphones even further. I’m so glad that I gave myself time to breathe before making a huge decision about what I would commit to next. The scariest thing about not having a back-up plan turned out to be the best part–because my head feels 10 times lighter, and I feel far more focused than I have in a long time.
Where it all went wrong

I knew that my job was great in the beginning, and I knew that when it ended I was feeling like a complete mess. But I had no idea what happened in the middle. I think I figured out. This is a very simplified take on it.

I think that a tricky thing happens when a business grows incredibly fast. Any growth that isn’t slow and organic, but rather abrupt and hyperactive– it can make for a creeping separation between a company’s employees. There’s no time for casual small talk in the cafe anymore. There’s no banter, no down time, and no way to keep up with all the new faces coming in every day.

I have to care about the person on the other side of the conference table in order to do great work with them. Suddenly, it’s acceptable to just not have time for people. There’s no time to care about their life outside of the office, much less their life outside of the meeting you’re in with them. This was normal behavior in my environment. The people I was supposed to be building things with were too busy to care (and so was I).

But I have to care about the person on the other side of the conference table in order to do great work with them.

I know this about myself now — yay! For a while I thought that I just cared too much about the product or the work that I was doing, and it was just getting harder to get things done. But now I know that the work has nothing to do with it. It’s the way people treat each other when we don’t have time for each other. We’re short, we’re cold, we’re abrupt, we’re passive-aggressive. I didn’t like becoming one of those people, and I especially didn’t like working with them.

I said in my last post, “You will never figure out what’s right until you fix what you already know is inherently wrong.” So I’ve been doing that and simplifying the hell out of my life. That includes everything from breaking off relationships that weren’t good for me to ending bad habits like biting my nails. Recently I’ve even stopped consuming alcohol and sugar to help me keep this focus while I figure out what’s “right.”

The key has just been to slow everything down. It’s so hard at first, but it’s gotten easier every day. Now I’m freelancing with a few clients who are kind and wonderful and who care about what they’re doing. Turns out freelancing’s not so scary once you dive in. And while I don’t know what the new year will bring, I’m hopeful and happy, and I can’t wait to see what’s next.

An earlier version of this post originally appeared on Medium. We welcome your comments.

Leave a Reply

Your email address will not be published.