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.

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