Appreciation post: my old boss told me to take the boring temp job over the flashy startup offer, and 8 months later I get why

Jamie Webb · 2026-10-02T18:35:04.002149+00:00

Back in January I had two offers on the table: a small startup in Austin paying $68k with a fancy title, and a plain data entry gig at an insurance company for $52k. Everyone I knew pushed me toward the startup because it sounded cooler, but my old boss (who I trust more than anyone on stuff like this) said take the boring one because it had a real training program and a manager who'd actually been there 11 years. The startup folded in June and I found out from LinkedIn, while I got promoted to team lead and a $6k raise in the same month. The steady paycheck while I learned the basics beat the cool title every single time. Has anyone else picked the less exciting job and had it pay off like that?

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Appreciation post: my old boss told me to take the boring temp job over the flashy startup offer, and 8 months later I get why | Career Advice - Free To Speak