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First 100 Things I’ll Do in Retirement (Hint: It’s Not Just Naps and Golf)

101 Things I’ll Do in Retirement (Hint: It’s Not Just Naps and Golf)

Retirement isn’t an ending — it’s the start of the best chapter yet.

For someone like me who loves financial independence, tech, tennis, travel, wild adventures, and the finer things (yes, cognac and chocolate count), retirement isn’t about slowing down — it’s about finally doing life on my own terms.

Whether it's chasing sunsets, sipping espresso in Milan, or building a legacy project with my kids, here are 101 things I can't wait to do in retirement.

  1. Build an automated investing AI just for fun - and yes using Ai tools within 24hrs
  2. Teach financial literacy to underserved high or middle school kids
  3. Start a small fund to invest in wild ideas - I have so many
  4. Run a personal finance blog from a beach - which will it be?
  5. Help my kids launch their dream business or at least plan a fund
  6. Mentor someone just starting out in UX or a kid out of school
  7. Rebalance my portfolio while sipping cognac
  8. Review one new fintech tool every week or month
  9. Create a “no stress” estate plan
  10. Write a book about money and freedom. I love money talk
  11. Host FIRE retreats in scenic places - maybe I need to go to one first
  12. Grow a YouTube channel on AI + money - if the interest is there
  13. Build a mini AI startup with my family - will they like it as much as me?
  14. Give away surprise scholarships if I can
  15. Celebrate 1 year of no meetings ever 🎉 - YAH!
  16. Visit every Grand Slam tennis tournament - US Open every game
  17. Walk across a country (Italy? US from East coast to West?)
  18. Rent a villa in Portugal for a month, maybe Bulgharia
  19. See the Northern Lights with my kids
  20. Drink espresso in 50 cities
  21. Take a chocolate tour of Belgium
  22. Go white-water rafting in Chile
  23. Sleep under the stars in Morocco
  24. Explore Antarctica with scientists
  25. Go paragliding over Switzerland
  26. Watch the sunrise on every continent
  27. Take a spontaneous flight with no plan
  28. Ride the Trans-Siberian railway
  29. Visit vineyards in Georgia (the country!)
  30. Take my parents on a luxury train ride
  31. Camp out at a remote observatory
  32. Learn to fly a drone and film my travels
  33. Build a map of my favorite global cafés
  34. Create a “passport stamp” tattoo timeline
  35. Train with a pro tennis coach abroad
  36. Stay in a treehouse in Costa Rica
  37. Visit all U.S. national parks
  38. Watch a football match in Argentina
  39. Eat street food in Singapore
  40. Be silent for 24 hours on a mountaintop
  41. Try every origin of coffee I can find
  42. Create the perfect morning ritual
  43. Read 50 books in a year
  44. Write letters to my kids
  45. Perfect my dark chocolate tasting notes
  46. Collect sunset photos from 100 places
  47. Walk 10,000 steps every day
  48. Plant a meditation garden
  49. Own exactly 3 amazing outfits
  50. Spend 1 full week with no screens
  51. Bake bread with my kids
  52. Play tennis 3x/week
  53. Learn to roast coffee beans
  54. Master 5 card games
  55. Build the perfect playlist for every vibe
  56. Stargaze every clear night
  57. Keep a “3 things I loved today” journal
  58. Learn to draw just for fun
  59. Build my dream reading nook
  60. Watch the clouds for hours
  61. Host annual family reunions
  62. Build a photo archive of our life
  63. Take each kid on a solo trip
  64. Interview my elders on camera
  65. Make a documentary about our family
  66. Write a guidebook for my grandchildren
  67. Fund a memorial bench in my favorite park
  68. Make Sunday dinners a forever tradition
  69. Digitize every family video
  70. Do a 100-day gratitude challenge with my kids
  71. Make playlists for my loved ones
  72. Share life lessons on my blog
  73. Let my kids choose one place we all visit
  74. Teach my grandkids how to code
  75. Take my spouse on 50 unforgettable dates
  76. Create a “when I’m gone” time capsule
  77. Set up a family retreat cabin
  78. Have weekly “walk talks” with loved ones
  79. Collect horizon photos with my kids
  80. Just sit — quietly — beside someone I love
  81. Build an AI agent that understands me
  82. Take an MIT class online
  83. Learn to create VR worlds
  84. Teach AI to write poetry with me
  85. Build a Raspberry Pi espresso tracker
  86. Write a tech blog with my child
  87. Create a virtual memory palace
  88. Beta test a flying car (yes, seriously)
  89. Use AI to recreate my childhood home
  90. Learn to code in a language I don’t need
  91. Explore lucid dreaming
  92. Track my sleep with 3 different wearables
  93. Host “Ask Me Anything” sessions on tech & life
  94. Digitize my entire book collection
  95. Use AI to visualize my mood daily
  96. Design a custom keyboard layout
  97. Try neurofeedback
  98. Learn how to grow mushrooms (seriously)
  99. Train an AI to play chess like me
  100. Invent a ridiculous but joyful gadget, hey Apple!
  101. Build an app with AI and deploy it

Conclusion

Retirement doesn’t mean sitting still. It means finally having the time and freedom to explore the person you've always wanted to be — curious, joyful, generous, and endlessly creative.

These 101 dreams aren't about escaping life — they're about living it fully, on purpose, and with deep appreciation.

Here's to a retirement so rich with meaning, it might just be the most exciting phase of life yet.

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