Skip to Content

How to Pull the Trigger, Buy That One-Way Ticket, and Start a Life of Travel (Even If You’re “Not Ready”)

“Babe, you sure? Like 100% sure? Cuz there’s no turning back after I click Purchase…Say ‘yes’ and I’ll do it.”

My heart fluttered. I was terrified. I knew this was it. Buying this one-way ticket would be a defining moment in our lives. I was one click away from the point of no return. 

No more waiting. No more excuses. No more wimping out.

It was decision time

The “Perfect Time” to Start a Travel Life Doesn’t Exist

See, Dayan and I have dreamed of exploring the world together and living a life of travel ever since we met. After a month of dating, we set a goal to leave for Asia within six months.

It has now been three years

Three years of finding reasons to continually push back our travel plans…

First we just wanted to get to know each other better.
Travel plans delayed.

Then we realized we loved each other and had to wait for the wedding.
Travel plans delayed.

Then we figured the first year of marriage is hard enough as is—mixing in a nomadic lifestyle with no stable income was just asking for trouble.
Travel plans delayed.

Then we started investing in real estate.
Travel plans delayed.

Then we needed an online business.
Travel plans delayed.

You know what?

I’m fed up with excuses.
I hate that I’ve fallen back into my comfort zone.
And I’m ashamed every time I look at the travel goals I wrote THREE YEARS AGO and see this:

This is what happens when you make goals without a specific plan to achieve them...😣

It’s Now or Never

Dayan and I want kids someday. And we’re not getting any younger.

One day at lunch she said what we’d both been thinking…

“If we want to explore the world before having kids, our window is closing.”

It was true.

The problem was, we weren’t ready.

My online work still isn’t where I’d like it to be. She has an important job in her family’s business. We have properties we need to sell. We have a mortgage. We have a car. We don’t have enough money saved to start a travel life…

But despite all that, we decided to have a “travel planning night” – just to explore our options.

Things escalated quickly.

I stumbled on a killer deal for one-way tickets to the Philippines—a flight leaving less than 4 months out.

What was meant to be a fun “where do we want to go someday” research night instantly turned into one of the biggest decisions of our lives. 

I typed in our credit card info without really thinking, then just stared at the screen.

All our excuses started flooding through my head. 

No. We weren’t ready. Not even close.

Day saw I was worried and said…

“Babe, if not now…when?”

She was right. It was now or never.

I said, “Ok, let’s do this! I love you!”

And clicked “Confirm Purchase”.


My wife and I buying our one-way ticket to start our life of travel
No turning back now!

UH.OH. What Have We Done??

Taking the leap and buying your ticket makes everything REAL.

It doesn’t change the fact that it isn’t the “perfect time”. It doesn’t make your excuses instantly disappear. It doesn’t fix all your problems.

But it does fix your BIGGEST problem…your “I’ll Do It Someday” Problem.

After buying a ticket, there is no more “someday”. Now you have a date. Time to get your shiz together. The clocks ticking.

Time to figure out how to save more money.
Time to figure out what to do with all your stuff.
Time to figure out how to become a digital nomad that actually works and travels simultaneously.
And, perhaps hardest of all, time to figure out how to break the news to your family…

Life’s About to Get Complicated…

107 ways to make money traveling ebook

Grab the most GARGANTUAN list of travel jobs known to mankind (FREE)

By signing up, you will be added to my legendary travel lifestyle email newsletter.

  • 65-page eBook jam-packed with every imaginable way to earn money on the road (107+ ideas)
  • Learn ways you've never thought of before (it only takes ONE to kickstart your travel lifestyle)
  • Everything you need to know in one handy document (income potential, how to start, resources)

Speaking of family—prepare yourself for pushback.

See, when you sit your family down to drop the bomb—the “I’m abandoning my career, college degree, earthly possessions, security, loved ones, life progress, etc. so I can live a life of travel and take an open-ended adventure around the world” bomb—how do you think they’ll respond?

Probably not well.

And in their defense, it’s understandable.

They want what’s best for you.
They’ve helped you build the life you have.
They can’t just sit back and watch you throw it away.

They mean well. But they’re completely missing the point…

You are not meant for a comfortable, ordinary life.
You want more.
You want EXTRAordinary.

Some People Just Won’t Understand (And That’s OK)

I dealt with this type of pushback when I left the U.S. four years ago to start my travel life…

Everyone told me I’d regret it. That I was wasting my potential. Being irresponsible. Running away. 

I didn’t care.

There was nothing anyone could do or say to stop me. I knew what I wanted. I was all in. And I haven’t regretted it for a second.

This time around, things are a bit different.

Breaking the news to my family was easy. (They’re used to me being gone.)

But Day’s family…now that’s a different story.

See, Colombian families are what you’d call “tightly knit”.

Colombian family
The Gringo and (half of) his Colombian family

When someone leaves, it’s complicated.

To give you an idea…

Day is the definition of a “daddy’s girl”. She’s the right-hand woman in her dad’s real estate business and the only person he trusts to handle sensitive information. For the past several years, he’s taken her under his wing and taught her everything he knows about real estate.

Now that she’s leaving, he feels like it was all a waste.
He’s losing the only person he trusts.
He’s devastated.

Then there’s her mom. Her mom lives alone, depends on Day financially, and suffered from depression the last time Day left the country. 

We still haven’t told her yet.

(See what I mean by complicated?)

It’s Not Easy, but It’s Worth It

Here’s the thing.

The truth is, you’re never going to feel completely ready to leap outside your comfort zone and start your life of travel and adventure.

It’s terrifying!

And unless you live in a vacuum, that “leap” is going to make some waves.
Things might get complicated.
People might get upset. 

But you can’t let that stop you.

Remember—it’s YOUR life we’re talking about here.

YOU are in control.

And if YOU don’t act on your travel dreams, nobody’s going to do it for you.

So…you want an extraordinary life, do you?

Then go buy that ticket. Fix your “Someday” Problem once and for all.

No more waiting. No more excuses. 

Because the “perfect time”?

It actually does exist.

It’s right NOW.

If you liked this post and want to see what it REALLY looks like transitioning into digital nomad life (including the highs AND the lows), sign up for my private email list below. I’ll be sending out live updates of our journey (as well as other free travel hacks and inspiration).

Like it? Pin it! 😎

Mitch's Travel Recommendations:
Travel Planning Resources - Everything you need to plan your trip on one convenient page.
Going Cheap Flights Newsletter - Get flight deals from your airport up to 90% off sent straight to your inbox.
Safetywing Insurance - This cheap travel insurance has saved me over $15,000 in medical bills. - Book accommodation without adding your credit card (in case you need to cancel).
Trusted House Sitters - Take care of pets in exchange for free (sometimes luxury) accommodation.
Flexjobs - Find remote jobs without having to sift through crappy ones.
Skillshare - Free trial to take unlimited classes that teach digital nomad skills.
Wise - Send and receive money abroad cheaply (great for freelancers).


Saturday 22nd of February 2020

I sooo feel you! I'm from a very small family. And when I told them I was leaving Chicago and moving to Penang, Malaysia, my family freaked out. I was the sunshine keeping my family glued together! My gramma actually said to me, "You should wait to move until I'm dead!" She's 103 now, what if I had waited? There is no good time. But you need to do you! I'm looking forward to following your journey!


Sunday 23rd of February 2020

Oh my word you're grandma is a champ! Yeah, it's definitely hard feeling like your letting your family and friends down...but at some point you just have to live your life! I can't speak for everyone, but in my experience, it's hard for them at the beginning, but after a while you being gone becomes the new "normal" and everyone survives :-) So glad you had the guts to pull the trigger, Kirsten!


Monday 5th of August 2019

My heart started pounding just reading this. Oh my gosh! So exciting!!! It’s real.

I’m so excited about following your story.

Plus, I kind of want a peek inside your travel journal...


Monday 5th of August 2019

Thanks, Cathy! And don't worry - I'll be sure to give you plenty of journal peeks!


Sunday 4th of August 2019

Mitch, you nailed it - just terrific. Made me laugh and I recognised a lot of it from way back. When we (family of 4) left to live in Dubai and travel the Middle and Far East.

You'll have a ball! You'll have so many memories, you'll never regret it. Enjoy every second of the preparations, family troubles and all - it's all part of the big experience.

Have the best time ever. Looking forward to hear how you both overcome the problems, do your packing, pack up your house and make it to the departure gate. Rosemary


Sunday 4th of August 2019

Thanks, Rosemary! It definitely should be an interesting adventure we'll never forget!

P.S. - I'd love to read all about YOUR experience leaving for Dubai someday!


By signing up, you'll also be added to my legendary email list and receive exclusive travel lifesyle tips I don't share anywhere else.

Discover how to travel FOREVER

Grab this "Cheat Sheet" to discover the tricks full-time travelers use to slash their costs to practically nothing.

Money-Saving Travel Hacks eBook Cover




Plus get access to my travel lifestyle newsletter.

You're Seconds Away...

What to expect:

  • Bonus guides, ebooks, and other freebies

By signing up, you'll be added to my legendary email list.

  • Realistic advice on setting up life on the road (no hype)

  • Cool travel hacks that'll save you money

  • Direct access to me for questions

From learning exactly how to travel the world full-time, earn money from anywhere, and live a completely "untethered" life.

Where should I send your itinerary PDF?

By signing up, you'll also be added to my legendary email list and receive handy travel lifestyle tips and inspiration I don't share anywhere else.

Where should I send your packing checklist?

By signing up, you'll also be added to my legendary travel lifestyle email list.