Showerthought: I picked a boring stable job over a flashy startup and I regret nothing

Reese Jenkins · 2026-10-01T21:30:53.327841+00:00

Two years back I had two offers in the same week. One was a property manager spot at a 300 unit complex in Sacramento for $58k with normal hours. The other was a tech startup doing office ops for $72k but the whole place felt shaky and they wanted 60 hour weeks. I went with the boring one and honestly the pay gap stung for a while. But 14 months in the startup laid off half its staff while I was getting a raise. Has anyone else taken the safe pick and felt weirdly guilty about it at first?

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Showerthought: I picked a boring stable job over a flashy startup and I regret nothing | Career Advice - Chatter Central