Episode 137 64 min From the kitchen to code at 35
Former head chef Ravi Shah on teaching himself to program, landing his first engineering job and what restaurant kitchens taught him about software teams.
Season 4 · Episode 144 Career
Leaving a dream job at the top
Hannah Brooks on walking away from a VP role to start over at 41, and how she made the decision with incomplete information.
GuestHannah Brooks — Founder, Second Act Advisory
Episode 144 Leaving a dream job at the top
0:00 51:20
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Show notes
On paper, Hannah Brooks had arrived. After 15 years in retail operations she was a VP with a team of 300 and a seat at the leadership table. At 41, she walked away.
Maya and Hannah talk about how she made the decision — slowly, with a year-long experiment, a spreadsheet and a lot of difficult conversations — and what surprised her most on the other side.
What we cover
- Testing a career change before committing to it
- Building a realistic financial runway
- Leaving well: telling your boss and your team
- Rebuilding an identity that isn’t attached to a job title
Key takeaways
- Hannah ran a twelve-month 'quiet experiment' before resigning.
- She built a financial runway that covered two years, not six months.
- Telling her team early made the transition kinder for everyone.
- Identity, not money, was the hardest thing to let go of.
Timestamps
About the guest
Hannah Brooks
Founder, Second Act Advisory
Hannah Brooks spent 15 years in retail operations, finishing as VP of Operations at a national retailer. At 41 she left to start Second Act Advisory, which helps mid-career professionals plan deliberate career changes.
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