Business Relationships
Your employer is like your spouse; Your start-up is like your baby
Life has been a haze this last year. After selling my company, I find myself in the totally un-relatable position of never having to work again. Everything feels like a side quest, but not in an inspiring way. I don’t have the same base desires driving me to make money or gain status. I have infinite freedom, yet I don’t know what to do with it, and, honestly, I’m not the most optimistic about life.
We have three daughters. When the third one got her driver’s license, I cried. I was no longer going to be her chauffer.
Selling a start-up is like having your baby grow up. If the company that buys you keeps you on board, that keeps you busy. But it’s like changing from being the mommy to being the mother-in-law. You are not in charge any more, and you have to watch decisions get made that you think are wrong. Most of these arrangements break up within a few years, often acrimoniously.
If you make a clean break when you sell, then you have to figure out what to do with your life. After my business was sold, I went to the library and checked out biographies. I was trying to discover who I might like to emulate.
None of the biographies really spoke to me. Instead, I ended up thinking about my high school chemistry teacher, Frank Quiring. He had a real zest for teaching chemistry, and he seemed to enjoy his life. So I decided that he would be the person that I would emulate.
I decided to do volunteer teaching. I ended up doing it for fifteen years, usually teaching high school seniors AP statistics and AP economics. I got a lot out of it. I kept up with young people. I learned about the challenges and rewards of teaching.
Your employer as a spouse
It is common to have a very intense relationship with the company you work for. I think of it as like having a spouse. You tend to get very upset by all the little annoying things that your employer does.
People are afraid of breaking up their marriage, and rightly so. I am fortunate never to have gone through that.
But breaking off your relationship with an employer does not have to be so momentous. You ought to think of quitting a job as something you routinely experience every several years, not as a supreme trauma. I say that an organization is like college—after a few years you have learned most of what the organization can teach you. Then it becomes time to graduate.
But most people feel differently about breaking up with an employer. Maybe some people quit their jobs too soon. But I’d be surprised if you run into a lot of people who say “I really regret leaving that firm. I wish I’d stayed longer.” Instead, I think many more people stick with an employer too long.
You should not treat your job like a marriage. There are no kids that you would traumatize if you left. Go ahead and get the divorce.
That said, I would advise against leaving your job just because you don’t love it. If what you really enjoy is art or music, but your job is in accounting, that is fine. On nights and weekends, you can be an artist or a musician. Leave your job when you can grow by doing something else.
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That's a good comparison for people whose mental model set is at Kegan level* 5. Kegan 5, the fluid mode, is almost certainly a job requirement for startup founders, where you have to invent new roles and abstract systems of relationships rather than fit naturally into preexisting ones - that's Kegan 4 - or fit into them badly with behavioral hacks because you do not yet distinguish between your self and your relationships to other people, like many teenagers - that's Kegan 3. People at Kegan 4 are apt to be upset by your comparison, and people at Kegan 3 might be unable to process the comparison at all.
* I'm still in the middle of Kegan's book In Over Our Heads, but David Chapman of the Meaningness blog (IIRC he commented here once or twice) has multiple extended summaries and explanations of it, e.g. https://vividness.live/developing-ethical-social-and-cognitive-competence. Kegan theory is a hell of a job to summarize, as Chapman says many times, and at least at this point I can't do better than him.
ETA: I should add that what Paul Graham calls "playing [startup] house" does _not_ require Kegan 5, because people playing house are just LARPing with roles they have learned about in school or incubator. It is possible (but not a given) that people playing startup house will level up while doing it, because their lower-level model sets will be challenged from outside by the environment their startup puts them into.
I worked for the same location in basically the same position for my last 31 years. Salary grew beyond expectations and responsibilities grew somewhat too, though I never took a management position. Maybe the best part was I had an incredible amount of independence the last ten years or more. The projects I worked on were varied and changed year to year. Lots of new things, some better than others. I can't say I exactly enjoyed the job but I was always learning and growing.