Reasons:
- People assume that if you're a founder or shareholder, you're rich. This is false at least 98% of the time; shares mean nothing for a long while, especially in services, assuming they ever mean anything. Meanwhile, the founder generally pays herself less than almost anyone else for as long as feasible. (Money is a talent acquisition or retention tool. She needs no acquiring, and can't just leave.)
- People feel really good about speaking their truth to your power, even when they're absolutely wrong and have zero frame of reference. Yet there is so much you can't say back or explain, in great part for this reason: You understand why it's not in their interest to identify with an employer (was it ever in yours?), and recognise that asking them to is both shitty and futile.
- In relation to the above: When someone complains about the money they make, how hard it is, and how that's your problem, you can't say, "I've been struggling to pay rent for years, LOL; in fact, pulling from my laughable savings is the first thing I do in a month when I still have to pay you and you sabotaged all attempts to win that new client, thanks for that btw"
- No matter how long the company lasts and what good it's done, its end as we know it will always mark it in history as a failure. (Do we remember AOL fondly? Do we ever think about how much of America it got online? No and nope.)
- It is hard to find people who tell you the truth about how things are going without hedging for their interests. In fact, anytime most people find themselves alone in a room with you, they perceive it as an opportunity to hedge for their interests.
- There is always a better thing you could have done, and a better state the company could be in, and it is always your fault.
- You no longer identify with friends' problems—particularly the complaints about their shitty bosses. They identify with you less and less. As time progresses, you realise how few of them you actually ever want to see again.
- Your relationship to your partner or spouse changes. They talk a lot about your ego. You think a lot about your guilt.
- You fail at many things, every day.
- If you are a woman, people will consistently question your thinking, level of engagement and experience far more than they would a man. This is most flagrantly true if you have a male business partner.
- If you have a male business partner, people will assume you are sleeping together or have done.
- I still haven't figured out what to do when meeting with an employee who clearly believes I am hitting on them, or is clearly trying to pick me up. It is unnerving.
- The problems never stop. And they're never the problems you set out to solve in the first place.
- The problems you set out to solve in the first place exist for reasons you didn't see when you set out to solve them.
- I think a lot of people start companies because they think it's a good way to become free. You are not free. You are bound in ways you can't imagine. Your partnership is a marriage that everyone must reckon with, including romantic partners. Your company is a child whose needs will never escape the Terrible Twos, and who will frequently clamour for your attention, either because it is legitimately sick or because it just likes it when you look up (who's to know which, and when?).
- You can never just stop when you're too tired, don't want to anymore, or have become depressed.
- You need a whole new crew of people to help you solve your problems, or at the very least in whom you can confide. Most of these people you'll have to find. And most of them you'll have to pay for.
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