Travel 2026: Book Your Trips Before the Calendar Books You
There’s a quiet risk that sneaks up on successful people.
Not failure.
Not burnout.
Drift.
Calendars fill. Obligations stack. “Next year” becomes the default answer. And before you know it, the trip you meant to take gets replaced by another meeting you didn’t actually need.
That’s why 2026 travel is already on my calendar.
Not as escape.
As practice.
A Lesson That Didn’t Come From a Spreadsheet
One of our employees took a trip last quarter that scared her a bit. Not reckless. Not irresponsible. Just unfamiliar enough to require courage. When she came back, something had shifted. Perspective widened. Confidence expanded. The risk didn’t derail her work — it strengthened it.
I pushed her to take that trip.
Not because it helped the firm directly.
But because how we do anything is how we do everything.
You don’t bet the farm.
But you also don’t stop growing.
The same mindset applies to investing, leadership, and life:
Take measured risks
Learn quickly
Grow intentionally
Travel just happens to make those lessons unavoidable.
My 47th State (and a New Kind of Stretch)
This year, I’ll will book my 47th state — Idaho. A five-day trip with a close friend. On the surface, that sounds straightforward. But it’s actually the result of years of small stretch decisions.
I used to be a drive-to-the-trailhead guy.
Local woods. Familiar terrain. Predictable logistics. (And let's face it, low bower budget!)
Flying somewhere to then disappear into the backcountry was uncomfortable at first. Not the hiking — that part I trust. It was the combination:
Logistics
Gear constraints (you can’t bring fuel on a plane)
High-altitude passes
Desert exposure
10,000+ foot climbs instead of East Coast tree cover
Costs
Each step required more planning. More humility. More respect for the environment.
More balance between a familiar scarcity mindset and the unfamiliar abundance mindset.
That discomfort was the point.
The Bigger Target: Three Weeks, One Trail, No Mental Quitting
This year, the real stretch goal for me isn’t Idaho.
It’s the John Muir Trail — from Yosemite National Park to Mount Whitney.
About three weeks. Hard miles. High demand. A lottery system designed to protect a fragile ecosystem.
Is the permit process a hassle? Yes.
Do I respect why it exists? Absolutely.
As the father of an environmental studies major and someone who loves wild places, I’m willing to accept friction when it protects something worth preserving.
And if the permit doesn’t come through? I have a backup:
Vermont Long Trail
Different terrain. Same intent.
Why This Matters Beyond Travel
Here’s the real experiment:
Can I:
Travel by plane
Go mostly off-grid
Take on my hardest physical challenge yet
And still lead a growing wealth management firm well?
Not perfectly.
But intentionally.
I don’t want a deferred-life plan.
I don’t want “someday” to be the reward for decades of focus.
I want both:
Long-term success for clients
A business that endures and evolves
A life lived while it’s happening
That requires practice.
This year isn’t the final form.
It’s a rehearsal.
Wanderlust Isn’t Random. It’s a Discipline.
Layered into this year:
College track meets across New England
California travel tied to college visits for our younger child
Extended family time around those trips
A few much-needed couples retreats
My annual “short hikes” with different groups of friends
When I step back and look at the calendar, it’s not chaotic.
It’s aligned.
It reflects my values:
Growth
Relationships
Ownership
Wanderlust
(GROW — my personal compass.)
The Real Question
You don’t need to hike the John Muir Trail.
You don’t need to book Idaho.
You don’t need to chase discomfort for its own sake.
You don’t need to spend your money before you die. But you should!
But ask yourself this:
What trip would stretch you just enough to wake something up?
And have you booked it yet — or is your calendar already doing that for you?
Progress comes from practice.
Growth comes from repetition.
And travel, done intentionally, is one of the best teachers I know.
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This post is part of my Wandering Wealth Advisor journey — reflections on travel, wealth, leadership, and building a life that grows without waiting for permission.
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