The post we wish someone had put in front of us ten years ago.
I am an estate planner by profession. I spend my working life sitting across from individuals and families who have worked hard, saved carefully, and built lives they are genuinely proud of. They come to me to protect what they have built – to make sure it goes where they want it to go, to the people and causes they love. It is meaningful work.
But there is a pattern I have seen in that work, repeated more times than I can count, that I want to tell you about. Because it is part of why this blog exists.
Many of the people who sit across from me have spent their working years deferring the adventures. The travel, the experiences, the grand plans – all of it filed under “someday.” Someday when the children are grown. Someday when work settles down. Someday when we retire and finally have the time and the money and the freedom to do everything we’ve been dreaming about.
Someday, they tell themselves, we will see the world.
And then someday arrives. And the world, it turns out, has gotten harder to reach.
The People I Think About
I have sat with people who dreamed for decades of hiking in the Andes and can no longer manage the altitude. People who imagined themselves standing at the base of the pyramids but whose knees won’t carry them across the uneven ground. People who put off Antarctica because it was expensive and logistically complicated and there was always a reason to wait one more year – until the year came when the doctor said no more long flights, no more cold exposure, no more small boats in rough water.
Heart conditions that arrived without warning. Hips that needed replacing. Stamina that quietly declined. The window for kayaking among humpback whales off the Antarctic Peninsula, for watching a lion hunt a zebra from an open Land Cruiser in the Serengeti, for jumping out of a plane over New Zealand, for hiking the Inca Trail and dropping into Machu Picchu through the Sun Gate – that window is not permanently open. It closes. Sometimes slowly, sometimes suddenly. But it closes.
The someday dreams pass them by. And sitting across from them in my office, I can see it — the weight of the things undone, the trips untaken, the world unseen. It is not the heaviest grief a person can carry. But it is real. And it is often unnecessary.
“The people in my estate planning practice who deferred their someday had the money. Most of them had more than enough. What they didn’t have, by the time they were ready to spend it, was the physical capacity to spend it the way they had imagined.”
The Inca Trail doesn’t care about your net worth. Angkor Wat doesn’t wait for retirement. The window for doing the things that require a body in working order is open for a finite time, and none of us knows exactly how long that is.
This Is Not a Warning. It’s an Argument.
This blog is not, at its heart, a travel diary. It is an argument.
The argument is this: you do not have to wait. You can travel now. You can travel with your family. You can see the world while your body is capable of receiving it fully, while you can hike to the ruins and swim in the cold water and sit in a Zodiac boat with the wind in your face and the ice spreading out in every direction.
I know what the objections sound like. I have made them myself.
It’s too expensive. The kids are too young. Work won’t allow it. The logistics are overwhelming. Maybe next year.
Here is what we know, after six years and seven continents with six children:
- The expense is almost always more manageable than it feels. Carry-on only travel, vacation rentals instead of hotels, a family travel fund built over time, airline deals, and credit card points can take a trip that seems impossible and make it merely difficult.
- The kids are not too young. Our four-year-old hiked the Inca Trail. Our two-year-old climbed to the top of the dome of St. Peter’s Basilica. Our three-year-old parasailed over the Pacific. There is no age floor on adventure – only a planning adjustment.
- Work can often be managed with enough notice and the right framing. Our biggest trips happened in June and July, planned eight to twelve months in advance. Most employers can be worked with.
- “Next year” has a way of becoming the year after that, until the calendar has run out of next years that look the way you needed them to look.
Your Map Is Waiting
There is a map on the wall of our house. For a long time, it was mostly decorative. We started putting pins in it for places we had visited as a family. The first pins were modest — places we had driven to, the continental United States mostly, a pin across the border in Mexico and one in British Columbia.
After our first big family trip – three weeks in Europe in January 2020 – something shifted. We came home different. The kids were different. We were different. And suddenly the map looked less like a decoration and more like a challenge.
Seven continents. We had only experienced one outside of our own.
What followed was not a master plan. It was one trip leading to another. Costa Rica because it sounded fun and the kids had been cooped up from Covid. Peru because Machu Picchu had always been a dream, and if we were going to Peru we might as well do the Amazon, and if we were doing the Amazon we might as well keep going to Iguazu Falls, and if we were doing Iguazu Falls, then why not Rio de Janeiro. That’s how it works. One pin leads to another.
Don’t wait for someday. Someday is now. Your children are the right age right now. The world is available right now. You are, in all likelihood, more capable of this than you believe right now.
The map on our wall has a lot of pins in it now. Every one of them has a story. And not one of those stories begins with the words: “I wish we had waited.”
Where Do You Start?
If this post has done its job, you’re already thinking about it. Here’s what to do next:
- Read our guide to choosing your first international destination – practical advice on how to pick the right first trip for your family’s ages, budget, and comfort level
- Read how we fund our trips – the airline deals, the credit card points system, the family travel fund, and the choices that made seven continents possible on one income.
- Browse our destination guides – every trip we’ve taken, documented with the things that went right, the things that went sideways, and everything a family needs to know before they go.
- Put a pin in the map. It doesn’t matter where yet. Just pick something that excites your family and make it real.
The world is waiting. Your family is ready.
But only if you go.
— Matt
