Knowing When To Quit

Note: I started this post in October 2012 after quitting my previous job at the end of February 2012. I never posted it, but feel it is appropriate now that the company exists in name only. I’ve made slight changes, but most of the post exists as I originally wrote it.

I haven’t been paid since August. The only co-worker I see on a daily basis is my cat, who always thinks it’s her turn with the keyboard. I would love to have a week of physical interaction with the rest of my team. And even with all of that, my new job is still awesome.


I’m not a quitter by nature, but in February I actually did it. I quit. I had been trying to make it work. I really was. Eventually though, I had to accept that sometimes a job just isn’t right for you. The tech may not be interesting. Maybe the pay is mediocre. Possibly your main project has no direction. And sometimes all of these converge into one… what? I mean, it’s not terrible. You can live with it. After all, they are giving you money to write code, right? And your co-workers are all really nice.

But what if you don’t need the money? Or you spend a good chunk of your time wondering why you came to work today? Or every time you look something up on StackOverflow you get distracted by the Careers 2.0 postings along the right side. That’s where I found myself this winter, so I quit.


I wrote an email on a Friday, slept on it over the weekend, and then sent it first thing on Monday morning. By mid-morning, I knew that I was going to be unemployed in two days. I had no plan, just the usual “exploring opportunities” and “researching startup ideas”. But I didn’t need the money and I felt amazing. The happiest I had been about my career in awhile.

Moving Forward

And then everything just fell into place. Former co-workers and classmates heard I was available and within days I had multiple options. I decided to work remotely for a former classmate’s startup. And when the money ran out I just kept working.

I get to work with an up to date stack on a greenfield project (the first true greenfield of my career). I get serious input into the architecture. I get the freedom to work whatever hours I want, from wherever I want. And, right now, I don’t get paid. Sometimes though, it pays to be a quitter.


It’s now May 2014. That startup never did get any more funding. I continued to work on it intermittently, but cut my hours back significantly. I got a lot of equity thrown at me, but even 100% of zero is still zero. Amusingly, I was so underpaid before, that even though I didn’t get paid for the last five months of work, I still made almost as much as I had the previous year.

I was already having doubts that funding was coming around the time I wrote this post, but I didn’t have anything else on the table at the time, so I stuck with it. I need to collect my thoughts, but for now I’ll just say that you should avoid a startup where there is an extreme risk imbalance among the founders.

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