Retirement Regret? What I Wish I Knew 4 Months Ago

1 Jun 2025 · 12 min
12:25

Rob (AskRobAnything) reflects—four months into retirement after 17 years as an entrepreneur/coach—on unexpected emotional and practical challenges of leaving work. He worked down to roughly one hour a day while maintaining an online coaching program and passive-income plan, but found identity loss, temptation to keep working, and a recent market drop that cut his pension (about two years’ worth of expected income) made the transition harder than planned. He describes daily routines (7:00 start, gym, reading, brief work or YouTube), travel-heavy plans between Cape Town and the UK (plus Greece, Italy, Morocco) to occupy his first retirement year, and offers practical reflections: calculate ‘how much is enough’, save early, and accept gradual transition.

Questions this video answers

June 1, 2025

17 years

Four months

About one hour per day

Chapters

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