I've done some reflecting on this lately. I might actually get lucky with my startup (actually looks like there's a very decent chance) but the reality is that

I've done some reflecting on this lately. I might actually get lucky with my startup (actually looks like there's a very decent chance) but the reality is that I've not been earning a lot or saving a lot in the last ten years and this thing could go side ways just as easily. The getting lucky part is not the primary reason I'm doing this. If I wanted money and financial safety, I should have kept the nice corporate job I had, got myself a mortage, some pension savings, etc. And corporate jobs are not even that horribly soul crushing. At least they don't have to be. So, no shame in doing that and I'd be all set to retire in 20-30 years. If that's your life and you are happy, good for you. Don't change it. But for me it would be a compromise so that one day, I might retire to enjoy the few years I have left while I'm still healthy enough to enjoy that life. For most people that's 10-15 years on average. Some people stretch it a bit further. Except your life is not defined by how it ends but how you live it generally. And most of the memorable bits tend to be at the beginning way before you retire, not after. So, instead, I'm enjoying life now with a decent chance to level up the level of enjoyment at some point and a risk of losing some of what I have. I work hard but only on stuff I genuinely care about. What matters to me is doing things I like doing now exactly the way I want those things to be done so I can look back on those things with no regrets (other than having missed opportunities to do them even better). I'm not postponing enjoying life until I'm too old, broken, and miserable to enjoy any of that. I don't actually need a lot of expensive stuff in my life. I'm not even sure I'd actually want to change a whole lot if I suddenly got a lot of money. I might do a few decadent and frivolous things and I might even enjoy those things. I'd probably get a nicer place to live in (or several even) and a few other things. But I can't honestly say I really miss or crave these things right now. I'm more interested in securing the life I have than having a better life. Life is a journey, not a destination. You can't take any of the materialistic stuff with you in the end.