The Circle of (Work) Life

By Adam Siegel

One of our developers left Cultivate recently to go work for a much larger company - an experience he has never had before. They are throwing more money at him than we ever could, and he will work on a team larger than our entire company. He wants to get in to data science but first he will be creating some API end-points on a relatively immature but unwieldy application that is probably 20x the codebase we have. He will have a boss, a boss's boss, a boss's boss's boss, and perhaps even a boss's boss's boss's boss. Despite our sadness he was leaving, we happily supported his move and even went to a relatively fancy bar to see him off.

The very next day I had coffee with the head of the Startup Institute here in Chicago. She told me their cohorts are filled with people who have been working at large companies similar to the one our developer left for, and want to make a change to work at places orders of magnitude smaller. Places that give them more freedom and flexibility and make them feel more passionate about their work, where they feel like they are making more of a difference. 

Places like our company.

I occasionally sit down with old colleagues I worked with at a huge consulting firm who are now senior executives. Sure would be nice to make all the money they do, I ponder afterwards. You’re so lucky to not have to deal with all the bullshit anymore, they tell me.

Around and around we go. Make a move, be content with that move, then start pining away for something else you think you should be doing. I've found a relatively simple exercise to get off this merry-go-round when it happens. I simply take stock of my life outside work which I’ve realized over the years has been a reliable barometer of how happy I am at work.

At that consulting firm I mentioned, I traveled regularly and worked on large teams on several multi-million dollar projects. Then I left all that to co-found my first company and worked with 1 or 2 other people for several years, often working at home by myself weeks at a time. I absolutely missed out on hundreds of thousands of dollars in salary and stock. I've also missed out on glamorous titles at a "name" company and working on projects at a scale we could never do in our company. But here’s what I do have: I have relative flexibility with my time. I can be around a group of people 8-10 hours a day whom I universally enjoy working with. I don’t ask anyone's permission to do anything. There are no office politics where I work. And I can do the things that life requires when need be. I won’t be seeing my kids off to college one day and thinking "damn, I wish I had spent more time with them." I don’t have a constant guilty feeling from being on the road that I'm an absentee husband.

So yeah, I know I’ll be back in this place in a few months - lamenting about my opportunity costs of having foregone a lucrative big corp career. And our former developer is probably loving the attention, resources, and infusion of cash he’s getting now. But in a year I wouldn’t be surprised if he's longing for his days in a small office where life was much simpler.

C'est la vie. :)


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Adam Siegel is the co-founder and CEO of Cultivate Labs.

change management