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Discussion on: What's the best career decision you've ever made?

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Ben Halpern

Personally, I'll say: Sticking in the entrepreneurial side of things. I almost jumped to a bigger company a couple years ago. Looking back on it, I am really glad I stuck to what we are doing.

The money, had I left, would have been better than anything I am currently earning, but I have learned that I really have to be navigating my own path. I am confident, with hindsight, that I would have been frustrated and ultimately burned out at a large organization like that. It's just not my thing. If I ever join a large organization, I want it to be for particular project where I'll definitely get to be creative and have agency. Being a cog in the wheel is not my thing.

I'd guess the opposite is true for many others. Stability and career ladders have never been my thing. I'm 28, though, and I might have a different perspective in a few years.

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Daisy Chubb

Thanks for your POV, Ben. I am also 28 and reeling against the corporate career ladder that so many people are preaching to me. I don't know if it's wrong or right, but I know I have worked my whole life up until now just to scrape by and pay the bills. If I can pay the bills AND enjoy the hustle - that is value on life investment (for me)!

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Zack Hall⚡

I find myself to be more entrepreneurial – I've started side projects and companies in high school, college, and now doing freelancing on the side. None of them home runs or ventures that generated fuck-you money, but non-trivial. But my day job and my primary income comes from working at a larger company.

I'm feeling that burnout and the frustration that I can't navigate my own path or trust my own judgement.

But despite having earned several thousand last year, I don't have the confidence to do it full-time yet. That it can provide a stable income for me to live on and save up for large goals, like a house, marriage, etc. How did you get started on your entrepreneurial tech journey?