What Early Retirement Taught Me (That You Can Use Right Now)

Little regrets in early retirement can be used by anyone as great life lessons.

Everyone thinks Financial Independence and Early Retirement (FIRE) is the ultimate goal. And while I love my life and truly don't regret leaving the corporate world at 53, I was surprised by the little "dark" sides of having absolute freedom.

I retired as a corporate lawyer with a solid net worth, healthy, and living in Southern California. But freedom doesn't automatically create structure, and it often reveals the habits you never fixed. In this video, I share the 9 surprising things I regret—from the loss of structure and constant house cleaning, to the social gap with my friends who still work.

If you are on the path to FI/RE, you need to hear this before you step away.

Key Takeaways & Timestamps:
0:00 - The Paradox
0:40 - Regret #1: The Loss of Structure (My biggest struggle)
2:31 - Regret #2: The Endless Morning Routine
3:32 - Regret #3: Creative Goals Happen...Slowly
4:43 - Regret #4: House Becomes Your Messy Coworker
5:51 - Regret #5: I Miss Dressing Up
6:13 - Regret #6: Social Gap with Friends who Still Work
6:38 - Regret #7: Much Time on the Phone
7:50 - Regret #8: Random Spending Streaks
9:19 - Regret #9: The Pressure to Live the "Perfect" Life
11:02 - The Powerful Upsides

Note: I am not a financial advisor. I am a retired licensed attorney, and 200-hour YTT teacher, sharing my personal life lessons.

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