The one trip she never took
- jajobraun
- Jun 24
- 6 min read
She leaned in toward me across the table, close enough that I knew whatever came next mattered to her.
“Make these memories now,” she said. “Because you don’t know when you won’t be able to anymore.”
I’d come for a history lesson. I left with something I haven’t been able to put down.
Let me back up.
I sat down for coffee with a woman connected to the organization I work for. My job that morning was simple. Learn our history from someone who had lived it.
What I got instead was a life.
She told me about raising her son, who has Down syndrome, in their home for years. About the season when her husband’s health declined and they made the hard, loving decision to move their adult son into a homeshare. About the trips the family took together, and how those trips became some of the richest memories her son still carries.
This was not a woman who sat on the sidelines of her own life.
When her husband passed, she didn’t fold inward. She went and did one of her big dream trips. Across Canada, by train and by car. The kind of trip most people talk about and never book.
She did it.
So when she leaned in and told me to make my memories now, this wasn’t a woman full of regret about a wasted life. She had lived well. She had loved well. She had gone and done.
That’s exactly what makes the next part land so hard.
Because there was one trip she never took.
England. Europe. The one she’d always meant to get to.
And then her body made the decision for her. Heart issues that required a pacemaker. A degenerative bone condition. The window for that trip closed, quietly, while she was busy living the rest of a good life.
She’ll never see England now.
That’s the part she leaned in to tell me about.
Here’s why I can’t shake it.
She had a good reason to wait. For decades.
Her husband’s health was real. Her son’s needs were real. The ordinary, sacred work of holding a family together was real. Every reason she had for postponing England was legitimate.
And not one of them was the actual reason England never happened.
The actual reason is simpler and harder. The window felt like it would always be open. Until it wasn’t.
If you’re building a business, you already feel where this is going.
You have your own England. The trip, the season, the unhurried weeks with people you love. And you have your own good reasons to wait. The team isn’t ready. The quarter is critical. Next year will be calmer.
All real. All legitimate.
And here is what her life makes impossible to ignore. There are four truths sitting underneath that “someday,” and every owner telling himself he’ll get to it later needs to hear them.
A full life and a missed window can sit side by side.
We tell ourselves that if we do most of it, we’ll have done enough.
And mostly, that’s true. She raised her son at home. She traveled with her family. She crossed a country alone after losing her husband. By any honest measure, she lived.
But “most of it” and “the one that mattered most” are not the same thing.
You can do almost everything right and still carry one window you let close. The fullness of the rest doesn’t fill that space. It just makes the one absence easier to notice when you finally slow down enough to feel it.
So the question isn’t whether your life is full. It’s whether the one thing you keep moving to next year is quietly becoming your England.
The reasons you give for waiting will always be legitimate.
This is the trap, and it’s a good one, because it doesn’t feel like a trap at all.
If your reasons for deferring were flimsy, you’d see through them. You’d act. The problem is that they’re sound. Your business genuinely does need you. The timing genuinely is hard.
Legitimacy is exactly what makes deferral so convincing.
Her caregiving wasn’t an excuse. It was love. And love is precisely the kind of good reason that can quietly cost you a window if you let it run unexamined for thirty years.
When the reason is real, you stop questioning the waiting. That’s how the years go.
The window closes on a schedule you don’t control.
You assume you pick the moment.
You’ll travel once the business runs without you. You’ll take the season off once you’ve earned it. You’re negotiating with a future you believe is holding the door.
She believed that too.
Then a pacemaker and a degenerating spine set the timeline for her, and her readiness had nothing to do with it.
You are not in a negotiation with a calendar that waits for you to be ready. The window has its own clock, and you don’t get to see it.
The business was never actually the thing standing in your way.
For her, the obstacle looked like circumstance. Health, caregiving, the season she was in.
For you, the obstacle looks like the company.
But the company is the excuse with the best alibi, not the real obstacle. The real obstacle is the quiet belief that someday is guaranteed.
This is the whole reason I talk about getting above the grind. Not so you can abandon your business. So you can build it into something that doesn’t make you choose between the work and the window.
A business built well is the thing that keeps England reachable. That’s the entire point. The freedom isn’t the reward you collect at the end. It’s the structure you build so you don’t end up leaning across a coffee table someday, telling a younger person about the one you never got to.
So let me ask you the question I’ve been sitting with since that morning.
If your body made the decision for you next year instead of in twenty years, what’s the one experience you’d be sick you kept postponing?
Not the whole list. The one.
You already know what it is. You knew before you finished reading the question.
Here’s the part I want you to actually hold onto.
She isn’t a warning. She’s a gift.
She handed me her hardest-won wisdom over a single cup of coffee, and now I’m handing it to you, decades before you’d otherwise learn it. You get to know the thing she had to lose England to find out.
The time you’ve been given is not yours to hoard. It’s yours to spend well, on the people and the moments that will still matter long after this quarter is forgotten.
You can build a business that protects your windows instead of closing them. That’s not a someday. That’s a decision available to you right now.
The Someday List
Before you close this, take five quiet minutes and answer three questions. Write the answers down somewhere you’ll see them again.
Name your England. The one experience you keep moving to next year. Not the whole list. The single one you’d most regret missing if the window closed sooner than you planned.
Name the real reason you haven’t. Be honest about whether it’s actually the business, or whether it’s the quiet belief that someday is guaranteed. One is a scheduling problem. The other is the trap.
Put a date on one small step in the next 90 days. Not the whole trip. The first move. The conversation, the deposit, the week you block off, the call you make. Something that turns someday into a date on a calendar.
That’s the whole exercise. Three answers. The point isn’t to plan the trip today. It’s to stop letting it live in “someday” with no edges.
So here’s what I’d love. Hit reply and tell me what your England is. The one trip, the one season, the one experience you keep moving to next year.
Just name it to me. Sometimes saying it out loud to one person is the thing that finally moves it from someday to scheduled.
I read every reply.
Make the memories now.
Jared
Jared Braun is the founder of Mountainview Consulting. He helps small city business owners increase profits and reclaim meaningful time — so they can live their ideal lifestyle now, not someday.
Comments