Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance) · Ari Taublieb, CFP®, MBA

Ex-Software Engineer Reveals Dark Truth Behind “Never Turning Off” | Retirement Reality

·49 min·3 clips

He avoided his phone for three months because the pager sound gave him “PTSD.”

1. Early Retirement - Financial Freedom’s episode “Ex-Software Engineer Reveals Dark Truth Behind “Never Turning Off” | Retirement Reality” centers on Darren’s retirement after years in IT production support. 2. Ari Taublieb hosts Darren, a retired computer geek and former IT production-support worker, because Darren spent years handling night calls, weekend interruptions, and implementation work. 3. The episode asks what retirement feels like when a job has made “your life was never felt like it was my own.” 4. Darren says his one-word description of retirement is “relief,” because the stress stopped once he quit. 5. He describes being paged at dinner, leaving Friday-night plans, and getting called in at 3 a.m. when something broke. 6. Darren says he retired at 54 and, in a few days, it will have been four years since he left work. 7. A financial-advisor meeting helped push the decision when he was told every dollar he made now would go to “someone else.” 8. Darren says that advice triggered a phase he calls “hate spending,” before he finally resigned when a coworker was about to quit. 9. He says retirement brought a new problem: days fill up with activities even when he thought he might get bored. 10. Darren’s ordinary day includes waking up around 4:30 or 5:00, drinking coffee, eating an egg, and watching videos. 11. He says he uses the rest of the day for finances, gym time, lawn mowing, DIY projects, and board games. 12. He says retirement made him more content because the stress level “went way down.” 13. Darren says the biggest IT problem was “responsibility without the authority,” where he had to deliver results while relying on other people. 14. He says the old company later asked him back for a long-delayed project, with the promise that he could set his own hours. 15. Even with that flexibility, he says being tied to a schedule again made him realize he was “unemployable.” 16. On spending, he says the household uses a $6,000 monthly allowance and that the real cost of things is often time, not just money. 17. He says healthcare runs about $16,000 a year through the ACA for his family because capital gains and other income affect subsidies. 18. The episode mixes practical finance detail with candid stories about retirement, family, travel, and the limits of spending on things like first class or an RV. 19. People who want a direct account of early retirement from an IT worker would likely like this episode. 20. People looking for a highly technical investing discussion with little lifestyle detail might skip it.

As heard by us

Early retirement becomes concrete when spending, healthcare, and tax uncertainty land on the same household budget.

The piece treats early retirement as a question of when work stops being necessary, how a household's spending sets the floor, and how healthcare and taxes complicate the math.

Read the full review in PlayNext →

Why you'd press play

You want a reality check on retiring before 65.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)