Why Waiting for the Perfect Time to Travel Is the Biggest Risk of All
Three years ago, my friend Teresa was newly divorced after 17 years of marriage and terrified.
She'd never traveled internationally by herself. She'd spent most of her adult life going to the same all-inclusive resorts in Mexico year after year.
So naturally, she signed up for a 10-day trip to Mexico City with a group of complete strangers for Day of the Dead.
"I remember thinking, 'What am I doing?'" she told me recently. "But I also remember thinking, 'If not now, when?'"
Teresa exploring Mexico City during Day of the dead. [2023]
Since then, Teresa has traveled to five countries, taken up painting and singing lessons, started her yoga certification, and is eight states away from visiting all 50 states before she turns 50.
When I asked her if she's ever been happier, she didn't hesitate: "Never. Not in my 20s, not during my marriage, not ever."
But here's the thing that makes Teresa's story so urgent: she almost didn't start. She almost became another person who waited too long.
The Story That Changed Everything
Teresa's parents bought an RV with plans to travel across all 50 states together. They'd see it all and finally have time away from work and raising kids.
They parked it in their yard, waiting. Waiting for the kids to be older. Waiting for a better time at work. Waiting to save more money. Waiting for the perfect moment.
Teresa's dad got sick and passed away. Ten weeks later, her mom passed away too.
The RV never left the driveway.
"That has stuck with me my entire life," Teresa told me. "When I got divorced, I knew I wasn't going to wait for the perfect moment that never comes."
The Excuses We Tell Ourselves
Let me address the big ones I hear constantly:
"I need to pay off my debt first."
In my late 20s, I had student loans and credit card debt. I knew I should be "responsible" and pay everything off before I traveled.
But I traveled anyway—responsibly. And I have zero regrets.
I did a whole podcast episode with financial expert Rachel Covert about this. The bottom line: you can balance paying off debt AND living your life. You don't have to choose.
"I'm waiting for my partner/friend/kids to be ready."
You wait. And wait. Your partner never gets enough PTO. Your friend can't commit. Your kids have soccer tournaments. Years pass.
Meanwhile, Teresa rode camels through the Sahara Desert, visited families in their homes in Morocco, and experienced something that changed her life.
Your people will understand. And if they don't? You can travel with them later. But don't put your dreams on hold waiting for someone else's calendar to clear.
Teresa meeting a new friend in Morocco. [2025]
"I'll travel when I retire and have more time."
We are not guaranteed tomorrow.
And even if you make it to retirement healthy and mobile, do you really want your first international trip to be at 65? When you're less physically capable of hiking to that viewpoint? When your back hurts after a long flight?
I see people in their 60s and 70s on my trips, and while some are rockstars, others are clearly struggling. They're seeing the world for the first time, often thinking, "I wish I'd done this sooner."
Don't let that be you.
What Travel Actually Costs (Versus What We Think)
My trips include nearly everything—hotels, transportation, most meals, activities, local guides. And that right there clears up a lot of barriers that keep most people from traveling. All the logistics are handled. Your new travel buddies are waiting for you. You just show up.
I'm not saying travel is free. I'm saying it's more accessible than you think—especially when you stop waiting for the perfect financial situation and start actually planning.
The Real Risk Isn't Financial—It's Time
Every time someone tells me "maybe next year," I think about that RV.
The real risk isn't spending money on a trip. The real risk is running out of time before you take it.
Teresa's parents' story has stuck with her for her entire life. It's why she says yes to everything now. It's why she took singing lessons even though she was terrified. It's why when I say "want to fill a last minute spot on my Morocco group trip?" a few weeks before leaving, she doesn't ask "when?" or "how much?"
She just says "yes."
Because she learned the most painful lesson possible: waiting for the perfect moment means the moment never comes.
What Saying Yes Actually Looks Like
I'm not telling you to be reckless. I'm not telling you to drain your savings and quit your job.
What I am saying is there's a middle ground between reckless and perpetually waiting.
Teresa found it. She:
Set a clear goal (50 states before 50)
Said yes to group trips that took the guesswork out of planning
Invested in experiences that aligned with her values
Showed up for her own life
She didn't wait for divorce to be over. She didn't wait to feel ready. She didn't wait for the stars to align.
She just started.
The Questions You Should Be Asking
Instead of "Can I afford this?" ask:
"Can I afford to miss this?"
"What am I giving up by waiting another year?"
"Will I regret not going?"
Instead of "Is this the right time?" ask:
"Will there ever be a perfect time?"
"What's actually stopping me—logistics or fear?"
Because here's what I've seen over and over: the people who say yes to that first trip come back transformed. They realize it wasn't as scary as they thought. They realize life is happening now, not in some distant future when everything is perfect. And they usually start planning the next one as soon as they get home.
Start Before You're Ready
The day Teresa and I met at a bar in downtown Eau Claire—on a BumbleBFF date, which is hilarious in retrospect (and you can hear it on this week’s Type 2 Travel episode)—she told me she wanted to start traveling more.
Not "someday." Not "when I'm ready."
Start. That was the word.
Within months, she was in Mexico City with me, getting blessed by a shaman and celebrating Día de los Muertos in a cemetery surrounded by marigolds and strangers who became family.
Three years later, she's been to four more countries with me, made lifelong friends, and completely rebuilt her life into something that makes her happier than she's ever been.
All because she started before she was ready.
Your Turn
What's your RV?
What's the trip you've been putting off? What's the dream that's been sitting in your driveway, going nowhere, while you wait for perfect timing?
Perfect timing doesn't exist.
But transformed lives? Those are real. And they start the moment you stop waiting and start booking.
Don't wait for perfect timing. It's not coming.
Start before you're ready. Say yes.
Want to hear more of Teresa's story? Listen to her full episode on the Type 2 Travel podcast where we talk about reinventing yourself in your 40s, the power of group travel, and why saying yes changed her life.
