Mother’s Day was earlier this month.
Father’s Day is just around the corner. 
And as I sat down to write this week’s newsletter, I found myself thinking about one of the most important trips I’ve ever taken.
Twelve years ago, my kids were only 8 and 14. Leaving them at home for a week felt like a huge deal.
And there were a hundred reasons not to go.
We were raising kids, paying for private school, juggling bills, and
I was still building my travel business after leaving a successful career in financial risk management.
The timing wasn’t perfect.
The money wasn’t abundant.
Life was busy.
But my mom had lost the love of her life—my dad—four years earlier.
And around that same time, I had donated a gift card to a charity auction investment that had gone spectacularly wrong. I could have focused on the money I’d lost and written it off as an expensive lesson.
Instead, I used the gift card, paid the difference, and invested in something far more valuable:
A week with my mom.
Not Antarctica.
Not Africa.
Not Australia.
A cruise with my mom.
Just the two of us.
Twelve years later, I don’t remember what the trip cost.
I remember the laughter.
The conversations.
The quiet moments together.
The memories.
And it remains one of the best returns on life I’ve ever received. ❤️
What makes that trip even more meaningful is that it was the only trip the two of us ever took alone together.
We promised we’d do it again.
But life happened.
Responsibilities piled up.
Work got busy.
And somehow, “someday” never came.
Thursday marked four years since my mom passed away.
And if I’m honest, I don’t spend much time thinking about the trip we took.
I think about the trips we didn’t.
The memories we never made.
The stories we never got to share.
One of the reasons I love travel so much is that it gives us something increasingly rare in today’s world:
Time.
Uninterrupted time together.
Time for conversations that don’t happen over rushed dinners.
Time to laugh.
Time to reconnect.
Time to create stories that become family legends.
Because when we look back, it’s rarely the hotel room or the flight details we remember.
It’s who we shared the experience with.
So if you’ve been thinking about taking a trip with your mom, your dad, your spouse, your child, your sibling, or your best friend, consider this your sign.
Go now.
Not when work settles down.
Not when life gets less busy.
Not when the timing is perfect.
Because it never will be.
The perfect time is while they’re still here.
Or, as my dad used to say:
“While they’re still on the right side of the sod.” ❤️
As a former actuary, I spent years helping organizations manage financial risk.
Today, I help people maximize something even more valuable:
Their return on life.
And one thing I’ve learned is that the trips we regret are rarely the ones we took.
They’re the ones we kept postponing.
So this Father’s Day season, ask yourself:
Who is the person you’ve always wanted to travel with?
And what memory could you create together this year?
Because someday is not a date on the calendar.
And the best time to make the memory is before it becomes one you wish you’d made.