The events that led me to quit my job without a plan

There are a lot of reasons that people leave jobs. Fit, pay, bosses, fatigue, boredom, grass looking greener, frustration, opportunity. Some combination of these things eventually strengthen to a point where the time comes to leave.

Three things happened that pushed me over the edge. But first let’s talk about what it’s like to join a start up.

Rough Start

I joined the company in 2013, somewhere around employee number 20. I’ll never forget my first day. I show up at 7:45am like most eager beavers would. Drive into the apartment complex that inexplicably has an office building at it’s center. Walk past the questionable daycare on the first floor. Climb the stairs and feel my way down the dark hallway to eventually find the right door. It’s locked. Not wanting to look like a simp, I pace the hallway to make it look like I’m just walking up behind whoever will show up.

No one shows up.

Until 8:30. It felt like years. That’s when I met Josh at the door. He started a week earlier but at least he had a key. We go inside. Beer bottles on most desks. A mostly empty bottle of tequila sitting simultaneously next to the printer and the sink.

What the f**k did I get myself into?

I had left a “good job” at Chesapeake Energy (RIP), at the time one of the best places to work in the US. We abandoned the house we just bought in OKC and moved 7 hours from anyone we know to Houston. And this was my desk?

Obviously things improved from there. By the time we passed $10 million per year in software revenue, I had my own desk. (But I did have to pick it up from IKEA and build it myself.)

We worked our asses off and had a lot of fun doing it. I met the group of people that I want to work with forever during that time. Mud runs, late nights, doing the right thing, trying new stuff, huge contracts, customers that loved us, that trip to Cancun….

Unforgettable.

Things Change

Fast forward a few years. We were acquired and then did more acquiring, eventually having 7 companies in the fold. Through a combination of luck, timing, and skill I was moving up the ranks. I did good work, but it just as easily could’ve been someone else in my spot. I was fortunate.

I was a manager at 26, a VP at 28, and my responsibilities were only growing. I grew from leading an 8 person consulting team in Houston to leading ~20 people across 3 teams, from Calgary to Bogota, plus I was put in charge of building a new global department (Customer Success) from scratch. I was in the succession planning conversation, being mentored by the CEO.

On paper, everything looked great. I should’ve been happy.

I wasn’t.

There were the typical frustrations that come with working in a fast-growing tech company. The problems are similar to those in any company, but faster, more violent, and harder to solve because you’re running so fast. But those things aren’t that big a deal. The small stuff is tolerable if you have the real factors of job satisfaction right. I doubt things were too different there from other companies. The overall conditions were fine.

But…

I’ve always had the itch to start my own company. I always hated inflexible schedules, even back to high school. My attendance senior year was near the minimum amount to graduate. (Pretty sure I still got all A’s though, just saying…) I always had a low tolerance for “corporate” stuff, bad meetings, political posturing, the brand of company speak that never actually says anything, “messaging”.

I always had the, maybe naive, belief that I could run a successful company that avoided this stuff. So I had a feeling that, at some point, I would take off to try to start something. I just didn’t know what or when. All of this was an undercurrent as my time there was becoming more and more unbearable. My unhappiness was less about the work or company changing, and more about me changing.

No More Excuses

Here are the three things that decided the “when.” The “what” would come later.

I learned that entrepreneurs aren’t that special.

In my last year there, I met a founder/CEO that started his company straight out of college and had grown it to $5 million ARR over the last 5 years.

So he’s never had a boss. He’s having fun, calling the shots, doing his own thing at work. The niche is unbelievably small but he’s just getting after it and doing a great job.

This is going to sound bad, and I didn’t know him that well, but from our interactions I was remarkably unimpressed. During an hour long conversation, he asked me the same question 3 times. Not in the strategic way that one might do this to see if someone is being honest. But I think he simply forgot. He had us change rooms and complained to the building management because there was a dead bug in the corner of the room…

Not my kindest moment, but at the time I thought “If this guy can do it, surely I can.”

I proved that I was employable.

Since I wasn’t happy, I put some feelers out. Applied to a couple of jobs, went through a couple interviews, and thankfully got a couple of offers. The positions weren’t amazing, but I could see myself taking them if I needed a job.

I wasn’t excited enough to take them at the time because, as I would eventually learn, I didn’t want another job. But it showed me that if things didn’t work out, the likelihood of me being unemployed (while never zero) wasn’t too high.

I got some money

I have two kids. My wife didn’t work so I was our only source of income. When the company sold to a different set of investors, I had some options that vested. To steal a term from one of the best people I know, I didn’t have ‘fuck you money’ but I had ‘I’d really rather not money.’

That bought me time. It bought me at least a year to figure something out.

That was the last piece of the puzzle. It eliminated my last excuse. 

Looking back, that’s all these were. Excuses. We already had 6 months in savings. I had gotten other job offers. I knew a dozen successful founders and none of them were superhuman.

I thought that I needed more. More confidence. More safety. More money. But those were just lies that I told myself to avoid doing what I knew that I should. Because it was uncomfortable. It was just The Resistance talking.

But without question, at that point I had the belief, a reasonable safety net, and some cash (time) to figure it out.

At that point, I couldn’t not quit.

This is part 1 of “On My Own: how I went from working a job to leading my life.”

Next in the series is The Jump.