[Week 8/52]: Booking 5 Mini Adventures, 1 Giant Madventure... and how you can do the same!
Even if you're inanely busy, it's healthy to disconnect. And even if you aren't able to travel.. it's still important to take some time for yourself, even locally. I hope today's edition inspires you!
Feb 09, 2026
[Preview]
I thought I was just buying a giant calendar… then it snowballed into a year of mini adventures
Following last weeks theme of DJ’ing in Miami, I thought I’d share a bit more about some other adventures, and what motivated me to take them.
A little over a year ago, I listened to Jesse Itzler (self-made billionaire) on the My First Million podcast He said each year he picks a Masogi - which is a Japanese concept where you issue yourself an annual challenge that is personally defined and should be difficult enough that there is a significant chance of failure. He also mentioned he always attempts to have 6 mini adventures on his calendar per year, and one big one.
So I thought about the spirit of what he was saying, and decided I’d borrow one tangible idea, he suggested to purchase a “3 foot by 3 foot calendar,” and tape it up somewhere you can’t miss it. Here’s mine…
It has ‘Tampa, NYC, San Diego, Chicago, Michigan, Yellowstone” all marked accordingly to when I planned to travel there. Jesse advised to label your adventures on this giant calendar… this way you always have something to look forward to.
I liked the concept... so $10 later and 24 hours shipping, I had it hanging on the back of my closet door. Where I can’t miss it. I’ve already shared some of my adventures to Yellowstone,, but now I’m going to share a bit about how I planned my 2025 adventures. And, most importantly, how we can all set ourselves up for a fun 2026.
Scroll down to read about my adventure-strategy in today’s blog.
But first…
A word from our author in a Harry Potter style talking-painting
We are now on Week 8 of this!!! Time flies. I’m curious, would you provide your opinion in an anonymous manner? I’d love to hear everyones real feedback and ideas for how to improve, and what you’ve liked so far!
How I Arrived at my Travel Planning Strategy: Each adventure in 2025
So that as I said, I had a blank calendar on my door one day, and the next I had planned 5 trips I would take in 2025. I added my own twist, and knowing that it would be hard to plan this far ahead, I first would add an adventure to the calendar using a sticky note.... and then only once I had actually booked the plane/hotel did I write down the adventure in pen on the calendar directly. Picking adventuresI based where I was going around friends. I knew I would book two adventures with my two best friends (NYC, Texas), I knew I had a wedding for another best friend in California, and I knew my friends from London wanted a USA true American experience.
Booking our road trip adventure to Yellowstone National Park, Montana, Wyoming, and Utah
The London crew is extremely active and loves hiking, exploring, and driving (bc it’s on the opposite side of the road, how exciting). So we decided we’d go rogue for a week out West. It was an adventure for a lifetime; 1,800 driving miles in 10 days, 10+ cities, 4 States, multiple different campgrounds, and never staying in the same location more than 1 night.
Bonfires, smores, wild Grizzly bears, the whole thing was an adventure. I share the details of this full Yellowstone trip here
NYC: Best Friends and Babies
Another two incredible trips I had in 2025 was where I got to go see my best friend from high school and meet his new baby. I cried :). It’s pretty profound to hold the baby of someone who you knew since you were a baby! The circle of life.
While in NYC I even booked out a podcast studio for 3 hours and had some friends stop by for a fascinating convo about tech. Just for fun! There I am trying to get it set up:
San Diego: A timeless remote trip and wedding at the famous landmark, Hotel Del!
My buddy was getting married, and asked me to be in the wedding! And honor. So I booked a 10 day trip to San Diego. I’d work the first 8 days, and then spend the final weekend with him at the wedding. It ended up being even more fun that I dreamed!
First off, it was the first ever trip where I brought my dog! He did amazing on the plane, and more than that, he really loved the San Diego Farmer’s Market. We spent hours there… and here he is being dressed up by one of the shop owners who was selling… dog hats?
I asked ChatGPT, find me cafe’s within a 10 minute walk from my Airbnb that allow dogs, and are perfect for remote work. Wow, GPT did its thing! This was one of my fave coffee spots. They even let me bring my dog on the rooftop and work there all day.
The wedding took place at Hotel Del.. which found a home as a National Historic Landmark in 1977. Founded in 1800s, the venue has been proud host to celebrities, royalty, and U.S. Presidents. And little old me got to be a groomsman there, it was beautiful!
And like all true great adventures, this one had some unexpected love! I met an awesome lady there who ended up being my last minute wedding date! (p.s. if my girlfriend is reading this, she meant nothing to me, it was before we met, and you are more pretty!!!!!!!)
Tampa: Old school rap concert to re-live the high school glory!
Jfeld has been my bestie since 2nd grade, and we always bonded over our love of old school hip hop. One random day I found a ‘throwback concert’ where the organizer booked all of the one-hit-wonders from the 2000’s to perform their top song. None of the artist could sell out a stadium by themselves, but if you took their best song each, then they could. And that’s what we got!
A trip down memory lane, we were able to sing along and relive our high school days by enjoying some of the most catchy tunes. It was so cool. Here we have Trey Songz serenading the crowd:
Chicago: Proper July 4th Cookout and Nascar Race, ‘Merika!
Flying with my Dad to go visit my cousin, who treated us with two VIP tickets to the Nascar race they host in Downtown Chicago. Plus seeing the new house he’s building, and having this epic BBQ! Family and burgers, the best!
Plus having a sweet campfire on a private beach overlooking Lake Michigan.
Not to mention VIP pit tickets to see Zac Brown Band!
In 2026, what’s the Madventure going to be?
As of right now, we’re thinking about Europe. Specifically traveling through the Italian, Swiss, and Austrian Alps. But, meh, it’s a far trip! I’ll keep everyone updated as we decide.
If you have any travel tips let me know!
Today’s Actionable Insight is challenge yourself to think of a 2026 Adventure
Take 15 minutes to think about ordering a giant calendar, I promise it’s money well spent for me. When I bought it in early 2025.. it was blank. But as you can see, I left 2025 with an epic calendar of memories.
→ I highly suggest writing down who youd want to go visit in 2026, and one random adventure youd like to take. Even if local to your city, and even if only a couple of hours. Take it (ping me if you need ideas)
Here’s some suggestions for where you can find an adventure:
Want to suggest a cool topic we can learn on behalf of everyone and share with the group? AI Products? Investor intro’s? Pitch deck help? Startup idea? Co-Founder? Music? Want me to fund something? Something else?
