Sold company. Hate job. Stick it out or indulge myself?

· noise r/smallbusiness · ↑ 57 · 💬 61 · 2025-08-15 · kw: slow moving inventory · open on reddit ↗

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Issue

Entrepreneur dissatisfied with large corporation bureaucracy after successful exit; reports day-to-day ineffectiveness despite good compensation and team, creating internal conflict between financial security and operational autonomy.

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anthropic/claude-haiku-4.5 · 2026-05-08

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Long story short, been an entrepreneur since my second year university. Three businesses, first two fizzled out (first due to starting the third, 2nd due to Covid). Built up the third over about ten years to get acquired by a big multi national a year or two ago. Enough to not work again, but maybe not at the lifestyle I have been living the last 5 years (though probably close). Now work for them. They love me, treat me well, respect my input, the paycheques and zero stress is a nice change. They put me on a track to run their new amalgamated national company in a year or two. That would be a massive raise, a move across country, and really set me up for life (though I wouldn’t complain I’m not already). Except I don’t enjoy my day to day life. Not because it’s hard or the people are bad (they’re mostly great), but working for a large corporation sucks. Everything is so frustratingly slow and difficult and ineffective. Am I stupid to be considering starting a new venture, potentially investing some of my assets to the point I WOULD have to work to be able to retire very comfortably? I’m about 20-30 years from typical retirement age, and I have an idea for the next venture that I can’t stop thinking about and planning. I have a family but they’re supportive of both (honestly my wife keeps telling me to quit to be happier) and it’s not going to drastically affect them either way, at least in my estimation. Financial advisors tell me I can give it a couple years living off my assets without affecting current retirement plans (then I’d need additional income - either successful venture or find another job for a while). Should I let the idea go and just 9-5 it for 5-10 years and retire super comfortably? Or indulge myself?

Top comments (5)

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[score=117] dadusedtomakegames

Congratulations. I retired from IT as a CEO and run a small business with my adorable and very capable autistic son. I'll work until I can't any more because I get to see him succeed and overcome every day. There's so much more to life than the pursuit of money.

[score=28] Sunshine12e

Can you dabble in something on the side, first? It is typical to get bored, but also those of us in business, sometimes underestimate just how difficult it is to start all over with a new business. I have done it a few times, myself and now? I will never try starting all over again! One can get to the point where they feel invincible or as if they have "the magic touch", but then when you get out there, it is a struggle all over again. Of course, success will likely come, but may take a lot longer and cost a lot more than one thinks/plans.

[score=15] godzillabobber

I took the route of tbe Mexican Fisherman at 39. Quit working 60 hour weeks to work from home for myself. Haven't worked more than 20 hours a week since then (1998) Managed to put my daughter through college and pretty much live a simple satisfying life. My ex expected more and left. My current wife embraced simplicity and quit her Fortune 200 analyst job to work with me. When you only work part time, you can put your energies into other things and live really well in less. For example, we rarely go out for dinner and drinks. Thats easily $200. Instead we throw an extravagant dinner party and spend a day cooking. Our friends love it and a few have started to throw their own. I help with the cooking too. I really like doing something thst we both love. Work is play.

[score=11] 101Puppies

My dad had good advice for situations like this: when you're on your deathbed, which one are you going to regret giving up the most, wondering what might have been.