Jill on Money with Jill Schlesinger Burned Out in Tech, Can I Retire at 49?
Dec 24, 2025
In this engaging discussion, John, a senior tech professional who’s spent 29 years in the industry, shares his experiences with burnout and his dream to retire at just 49. He details his impressive financial setup, including multimillion-dollar stock grants and various asset breakdowns. They delve into John's living expenses and plans for part-time work post-retirement. Jill offers practical advice on managing mortgage payments and cash reserves while reflecting on the privilege of such financial freedom. Tune in for valuable insights!
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Long Tech Career And Burnout
- John describes 29 years in tech and feeling burned out after long tenure in the industry.
- He considers quitting immediately to escape the high-pressure role and reclaim his life.
Sector Timing Enabled Financial Freedom
- John reveals his windfall came from well-timed equity grants and headhunting moves in tech.
- That sector timing turned a career into a multi-million dollar balance sheet enabling early exit options.
Count Accessible Savings First
- Jill and John tally accessible savings: $4.1M brokerage, $1.1M retirement, $50K Roth.
- They use those figures to judge whether quitting now is feasible and how to plan expenses.