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Ask Orbit · by Mehdi Benali · 2026-10-14

People who left a stable career for something riskier in their 30s/40s — was it worth it?

Seriously considering leaving a comfortable but stagnant corporate job to try something entrepreneurial. Not naive about the risk, just want to hear from people who actually did it, good or bad outcomes both welcome.

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Comments

Yasmine El Amrani · 0 likes

did this at 34, left a director role to start a small consultancy, first year income was half what i made before but i genuinely dont regret it even on the hard days

Silver Lantern · 0 likes

worth separating 'risky career change' from 'risky financial decision', make sure you have 12+ months runway before you jump regardless of the career question

Maya Williams · 0 likes

i went the opposite direction honestly, left startup life for stable corporate at 38 and it was the best decision for my mental health, worth considering that not every risk pays off in happiness even if it pays off financially

Valeria López · 0 likes

the thing nobody tells you is the social cost, a lot of my friend group was work friends and that network changes when you leave, factor that in emotionally

Rohan Mehta · 0 likes

do the math on healthcare and benefits if youre in the US specifically, that cost alone changes the calculation a lot for a lot of people

Ethan Brooks · 0 likes

best advice i got before doing this: start it as a side project first if you possibly can, de-risk before you fully jump

Rizky Pratama · 0 likes

40 here, left a stable engineering job to start a small saas, 2 years in and barely breaking even but the autonomy alone has been worth the financial hit for me personally

Minh Nguyen · 0 likes

regret is usually about the things you didnt try more than the things that didnt work out, for what thats worth

Oliver Smith · 0 likes

this is the line that convinced me honestly, thank you