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0 pointsserjester4y ago0 comments

Sounds like you're open minded - the upside is you make a couple million in the next couple years. Your downside is you're unemployable and dealing with potential lawsuits. Anecdotally I've known people that have made "errors of judgement" and it took them years to find another job.

But let's say you pull this off. What then? You say you want to start a company but you're deluding yourself if you think it takes a couple million to do that. Constraints are a gift, you're more likely to burn through the couple million.

Maybe you could retire. But I don't get the impression you're the type of person to retire - you're already retired if your jobs take "5-10 hours a week".

So I have to ask what's the point of taking on the massive risk to your reputation? Is this something you're proud of? You're clearly already well off.

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froaway4job4y ago

This is probably a benefit of being in a major metro, working remotely, and general market conditions but I've never found it difficult to find another job. The past 10 years (essentially my working career) has been a great time to work and I've always hustled my way into making money or moving up somehow.

I'm pretty realistic about starting a company in the future. I'm not looking to invest and burn millions. I'd like to bootstrap with the benefit of having a very large backstop to my personal finances.

> Maybe you could retire. But I don't get the impression you're the type of person to retire - you're already retired if your jobs take "5-10 hours a week".

I think it's cool that you recognize that. Not a lot of people understand that I'm basically financially retired. I think that's the point for me. I don't actually think I'm financially retired yet, but soon. Once I'm done "needing" to make money I'll stop "working" altogether and keep on enjoying my life with my family. By no longer "working" I mean maybe working a single engineering job or getting a real job like a teacher or police officer. Something like that.

> So I have to ask what's the point of taking on the massive risk to your reputation? Is this something you're proud of? You're clearly already well off.

Not proud or ashamed. It's a neutral feeling of doing my work and getting paid for it. I come from a middle class background that was devastated by the financial crisis so I know from experience that "well off" is subjective and not fixed. Sure I'm worth a few million, but that could go away easily. I'll take my time off once I have 3-4 times what a normal person would consider "well off".