If I Could Start Over on Our Adventure
What I'd change and do differently if we started our road life journey today.
Today, as I hastily accept the move into wintry Oklahoma weather and begin my transition into a cold, grumpy old man with sandpaper skin, I have decided to start my sacred yearly pilgrimage toward a two-week hibernation.
While the Christmas holiday season is not traditionally my favorite time of the year for various reasons, I do look forward to this time of self-reflection and rest, something I’ve not been able to do for most of my working life!
During these moments when things slow down, I’m finally able to think about all the crazy adventures Donetta and I’ve experienced the past year, as well as remember all the valuable lessons we’ve learned along the way. It’s something I’m truly grateful for and never take for granted.
As much as I love to write about the extraordinary places we’ve been and the amazing people we’ve met in our travels, my purpose today is to focus on what we’ve learned over the past four years because it’s where I believe I can provide the most value to you, especially if you’re planning on living your own epic road life adventure.
While your journey will be very different from ours, there are pieces of advice that apply to almost any situation and will benefit you greatly.
Lessons I’ve learned and things I’d change.
Obviously, when you’re first starting out as a full-time traveler, you don’t know what you don’t know. Even with travel writers like us sharing our experiences and recommendations, the only way to really figure it out is to do it.
In 2020, our goal was simple — get out on the open road.
We knew what we didn’t want: planning every detail in advance and not buying an RV or pulling a damn trailer behind us. Other than that, we were just happy to go and learn as we went. So we bought a new silver Chevy Silverado 1500 pickup, which we lovingly called Belle, and headed out west.
Even though there are still no regrets, there are many things I’d do differently.
🚐 I’d buy a travel van from the beginning.
Living in hotels is mostly a great and easy experience, but a house on wheels would’ve been the best way to travel for us.
A converted camper van could take us everywhere we wanted to go, offer more comfort than a rooftop tent, provide much better climate control, and keep us from blowing our budget on shitty hotel rooms.
While some people upgrade or downgrade their vehicle as they figure things out, this isn’t always possible, especially if they don’t have the funds or credit to do so.
My advice is to choose your “home” wisely from the very beginning.
🔍 I’d research travel point systems better.
I knew people like Nomadic Matt and The Points Guy existed, but it just seemed too overwhelming to figure out how to get started.
We’ve slowly learned how to use our Capital One card and Choice Privileges to earn free flights, excursions, and hotels, but we could’ve done a LOT better (and still can) by racking up a ton of points from the very beginning.
One of the best decisions we made was buying a timeshare package with DRI, now known as Hilton Grand Vacations. Even though it cost us $9,500 back in 2021, we’ve been able to take advantage of deep discounts at amazing resorts while earning thousands of dollars in free stays.
My advice is to find a couple of travel point programs and work them like crazy!
💰 I’d save more money.
Aside from the things we must have like food, water, gasoline, and shelter, I would’ve done better at keeping money in the bank or investing it instead of wasting it.
Truth be told, I’m a whore for tasty beers and shiny decals, and I’ve probably spent at least a few grand on frivolous items I really never needed. While small in price, they really add up over time.
Additionally, I would’ve worked harder from day one to launch my t-shirt products and custom artwork business, rather than living off our savings for a year. It was fantastic to take a sabbatical, but today I’d rather have the money.
My recommendation is to only buy what you really need and stretch your dollars.
🏨 I’d stay in amazing places longer.
When we first hit the road, our objective was to check off as many places on our list as possible, rather than taking our time to really explore the areas we stopped at.
Overall, this wasn’t a bad strategy, and we did get to see a lot. Yet we also feel we missed out on some beautiful, fun places because we kept moving. If I could do it over, I’d focus on a region and experience everything I could before leaving.
My advice is to take time to explore rather than rush to check off a bucket list.
✈️ I’d visit other countries sooner.
This wasn’t really a viable option in 2020-2021, thanks to the pandemic bullshit, but I wish we could’ve traveled abroad before conquering the United States.
Visiting other countries back then (or even earlier, before the virus) would’ve been a great way to see the world while saving lots of money, and there were fewer people traveling, creating fewer problems for locals and tourists alike. Today, overtourism and revenge pricing make travel in 2025 and beyond harder.
My advice is to get overseas before everything is ruined.
🏄♂️ I’d be bolder with my adventures.
When I was younger, I took more risks and lived without much fear, but now that I’m older, I’ve kinda become lame and complacent.
There are people I meet who do kick-ass things like overlanding, surfing, mountaineering, skydiving, or trail riding, and it really makes me want to be part of these communities.
Then there are brave adventurers who simply buy an old van, throw in what they need, and go way off the beaten path to discover a world those of us on the asphalt may never know or experience.
I truly admire all these people!
But in some cases, it’s a young person’s game, and I don’t know if those of us in our 50s or older have the capabilities to live that lifestyle. Yes, age is just a number, but there are limitations to certain activities. Not doing some of the things I hoped to do earlier in life is the regret I live with now.
My advice is to get going and be bold before it’s too late.
It’s all been worth it.
Life from the road changed me, and it literally saved my life. I’m extremely fortunate to be here, and every single day, there’s a deep feeling of gratitude within my soul.
No, our digital nomad lifestyle has not been perfect. Yes, we’ve experienced some hardships and crushing blows over the last four years. That’s just how it is. But one thing is for certain, I’m glad we took a leap of faith into the unknown.
So my last piece of advice is this.
Get out there and try it for yourself.
I’ve said this numerous times since we started this publication, and I’ll keep on repeating it until you take your own leap of faith into the unknown.
Don’t let fear keep you from living the dream.
While there are things I would’ve changed or done differently, nothing would’ve ever happened without jumping in. Even if we never get to travel and explore as we did in the beginning, I will always be grateful for what we DID do. It’s been worth it.
Donetta and I used to say, “This could be our year,” as we walked and talked about our dream of traveling every day.
2025 could be your year!!!