My parents took the news about as well as you’d expect from people who still call a pension “the plan.”
I left a bank job with a badge that worked on the first try and health insurance I understood. I joined a thirty-person startup where the snack fridge was full and the org chart was a rumor. I am not going to pretend it was pure courage. Part of it was boredom so thick I could taste it.
The conversation at dinner
I said the startup name. Dad googled it and found a blog post from 2023. Mom asked about “stability” four times. I didn’t sell them a dream. I showed them runway notes the company had shared, my emergency fund months, and the skills I wanted that the bank wouldn’t give me for another promotion cycle. They didn’t throw a party. They stopped arguing. That was enough.
What surprised me
Speed is real. So is ambiguity. At the bank, a wrong email went through three approvals. At the startup, I sent things that weren’t perfect and learned in public. Some days that felt like trust. Some days it felt like nobody was steering.
I also learned that “flat culture” still has power — it’s just informal. Who sits next to the founder in the all-hands? Who gets looped on the scary threads? Pay attention early.
Would I do it again?
Yes, with a clearer ask in the offer letter about title and review timing. No, I wouldn’t romanticize the chaos. If you’re leaving a stable seat, pack a financial cushion and one sentence you can say to relatives that isn’t a TED Talk. You’re allowed to want growth and still miss the cafeteria.
