On Quitting: Part II

December 10, 2015

2 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 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? Whatever, fuck it, I’m going to the beach tomorrow.” She stares blankly with a weird smile on her face, imagining every possibility in the world all at once. She looks haggard and broken. She smiles creepily. Everyone around her feels awkward.

I was a mess but I felt free for the first time in a long time. 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 the most daunting tangled up ball of iPhone headphones and I knew I needed a month just to deal with it.

30 days of: How do I feed myself? Why have I been staring at this wall for two hours?

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 execs 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, 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, despite 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 my first month of being “unemployed”. It looks just like my Dropbox calendar would have looked, but instead of meetings and deadlines it was now filled with “life stuff.” In 2 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. 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?”

(No. It might actually mean the opposite.) In-between the meetings and appointments I would go on long hikes or drives by myself. It wasn’t long before the little orange dots just felt like nuisances keeping me from that freedom, so I stopped putting them there. I was my own PM now and I could just do that! Woah! Mainly I wanted to deal with that ball of stress in my head that made me quit in the first place.

Stress is really weird, you guys.

When it’s happening to me, I know it’s happening, but I can’t see it with a bird’s eye view. I can achieve that perspective sometimes by going on vacation (some prefer Burning Man) or drinking a few Negronis or running like 10 miles at a time. But the only way to really get — HAVE — that perspective is to slowly unravel that metaphorical tangled up ball of iPhone headphones. For me, I *couldn’t* get the job done 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 and I let myself think about everything that I didn’t have time for over the previous two years. I posted cool photos on Instagram to make it look like I was on some dope adventure, but really I was just recalling every project I could have done better on, every work relationship gone wrong, every weird email I mis-read and how insufficient 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, wondering why I wasn’t moving. I felt all of those feelings right down to their core, and then I threw them all away. That’s easier said than done, and it was a fucked up couple of years, so it took me a while. Lots of pit stained t-shirts to throw away, if you know what I mean. This process had great days and horrible days, and lasted me about 5 weeks before I really started to feel like Linda again.

I’m so fucking glad I didn’t jump into another job. If I did, I would have been bringing all of that mess with me. I wouldn’t have that bird’s eye view of my own life and I would have been tangling the mess even further. So, for those of you who have asked, yes. I’m so glad I did it. Even happier that I gave myself time to breathe before making a huge decision about what I would commit to next. The scary scary scary thing of 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.

That middle part where everything 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, and 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 room for a creeping separateness between the human beings who work there. 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.

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.)

I have to give a shit 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 we all 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.

What’s next!

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 relationships that weren’t good for me to bad habits like biting my nails. Recently I’ve even removed things like alcohol and sugar to help me keep this focus while I figure out what’s “right”.

The key has just been to S L O W it all down. It’s so hard at first, but it’s gotten easier every day. And 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 who knows what next year brings. I’m hopeful and happy and I can’t wait to see what’s next.