My Travel Dreams

My plans to ditch 9–5, complete a quest, and do something remarkable

When I turned 20 years old back in 2007, I had never been out of the country before.

Just three months later, that would change.

I wish I could say that I took the initiative to decide that I was going to seize the day and live life to the fullest, but the opportunity just kind of fell into my lap.

There was a girl from my church who was already the brave adventurer that I wanted to be and she decided she was going to go backpacking in Europe for two weeks in the summer with three of her friends.

Her dad told her that she needed to also invite some boys for safety reasons. I probably wasn’t the best choice along those lines since I probably couldn’t have taken anyone over 150 pounds or so, but hey, I was good friends with the other guy she invited — so I got invited too.

We went to England, France, and Italy that summer and then all got back together the next year to go to Germany, Austria, and the Czech Republic.

We stayed in hostels and had got most of our meals by going to market, buying a loaf of bread, along with some meat and cheese from the deli and making sandwiches.

We did eat at least one sit-down meal in every city we visited.

And it was amazing.

Here I am just straight chilling in Venice circa May of 2007:

Or check me out here, calmly surveying some majestic mountains in Berchtesgaden, Germany (before this trip I didn’t even know there was a place called Berchtesgaden):

When traveling I learned that the world is a fun and exciting place with lots to offer.

The main downsides to my trips were that they were only two weeks long. I’ve known for a while that I want some extended time adventuring, exploring, and experiencing life outside my hometown.

Of course, sometimes life gets in the way…


Life has become very different in the decade since my international adventures. In the most important ways, it’s gotten better.

Just a few months after my first trip to Europe I met a girl that I fell in love with and married four years later.

In the summer of 2013 we welcomed our son into the world and in 2015 our daughter was born.

I love my family.

Of course, in some ways, life isn’t quite as great as it was 10 years ago. I went from school (which was bad enough) to a career (which — for me — is worse).

My problem with school is that it isn’t built for people like me — people who want to learn. I’m not really sure who school is built for to tell you the truth. I guess it is for people who like to obey rules and get good grades.

If school wasn’t built for people like me, it seems like the working world was actively built to annoy people like me. Or at least my job was.

I’m grateful to have a job and there are certainly parts of my job that I like, but mostly it just feels like a prison.

I’m (metaphorically) chained to a desk in a dingy old building and from where I sit, there isn’t a window in sight.

I’m constantly interrupted and forced to work on the “urgent” (which is almost never urgent) rather than the important.

There were a few times I decided to go on a walk to clear my head. I was told in no uncertain terms that I shouldn’t be doing that. The smokers can have as many breaks as they want to destroy their lungs, the office gossips can have as many breaks as they want to chatter at each other and destroy morale, but if you want to do something healthy that could recharge your batteries and make youmore productive, you’re stealing company time.

But having a boring job is just part of being an adult, right? You have kids to support and so you become responsible and get a real job and settle for your two weeks of vacation a year and forget about anything else that you may want to do until you’re 62 and a half. I mean, you definitely can’t pull off extended travel while you’re raising kids, right?

Designing My Future

If I were to just let other people tell me what is practical, I probably wouldn’t be thinking about taking my family, kids and all, on a lengthy trip.

Its not that I’m tuning out all practical wisdom. My wife suggested that we wait until the kids were a little older and I think that’s a smart idea.

I’m also going to get some ducks in a row financially before we embark on anything too crazy.

But man, I want to actively design my future, not settle for the one that gets handed to me by default.

Don’t get me wrong here, no one can fully control the future. It is a fickle, unpredictable thing that will in large part do what it wants to do.

But you can control where you are aiming your life. You might not hit a bulls-eye every time, but you can steer things in the direction you want to go.

I think it’s a critical step to have the courage to define what you actually want. So few people decisively commit to a course of action that will improve their life.

For me one of the most critical steps I’ve taken over the past year plus is to create a 10 Year Plan For a Remarkable Life. This simple yet powerful exercise gets your creative juices flowing and helps you visualize a compelling destination to pursue:

My personal 10 Year Plan includes the ambitious goals of escaping the rat race and becoming financially independent.

While these goals are aggressive, I also think they are achievable. If you work on controlling your spending, increasing your income, and investing wisely, the path to financial independence is incredibly simple, even if it’s not easy.

One of the major reasons why I want money and freedom is to gain the ability to travel.

I think a lot of people want to be able to stop working. I don’t. I’d love to stop working a soul-crushing job that I took out of financial necessity, but I would never in a million years want to stop working.

If I can get to the point where I can make a living off of either investment income, passive income streams that I’ve set up online, or some combination of both, then I’ll have the freedom to work from wherever I want.

This will allow me to stay home with the kids more often, but it can also allow us to get away as a family together.


In his book The Happiness of Pursuit , Chris Guillebeau describes a practice that he calls “Questing.”

The idea behind Questing is to lose yourself in pursuit of a challenging goal that is personally meaningful.

His first quest was to visit every country in the world — a quest in which he has been successful.

Quests don’t have to be about travel, but they often are.

Quests involve smashing your own self-imposed limitations as well as those that society has dumped on you. They involve the courage to imagine the unimaginable and the desire to pursue a goal for its own sake.

Your quest might not be something that everyone understands. In fact, many people will think you are crazy. But as Chris wisely says in the book:

“Not everyone needs to believe in your dream, but you do.”

My Quest

For my first Quest I want to take an extended two year trip with my family and visit all 50 states .

The time frame of two years gives us a full two weeks to spend in every state, plus some extra days built in for travel.

I would love to live super minimally during this time. One carry-on bag with a well-crafted capsule wardrobe and a few other essentials such as a laptop and our Kindles.

The idea is to stay mostly in Air BnB’s, sometimes crashing at the place of someone we know, and occasionally using credit card miles to get a hotel.

Sure, I still want to do plenty of international travel, but it’s always been in the back of my mind that I haven’t even explored my own country yet.

I’ve lived in the U.S. my whole life and I’ve never been to New York, L.A., or San Francisco.

I have been to several famous destinations like Boston, New Orleans, and Miami, as well as some underrated gems like Estes Park, Colorado. But how many amazing opportunities for adventure are lying undetected all around me?

You could even argue that I haven’t come close to mining my home state of Florida, or even my home city of Gainesville for all that they are worth. You would certainly have a point there, but it’s exciting to pack up and just leave for an extended period of time.

You don’t feel like a “traveler” when you are going on in-town micro-adventures.

There’s nothing wrong with those kinds of trips. They’re just not part of my quest.

The Journey to the Quest

While I truly believe that it’s possible to travel with kids (and an amazing book that I’m reading called At Home in the World by Tsh Oxenreider confirms that it is), the planning needs to be a little more deliberate than if you’re flying solo.

One thing that my wife and I have talked about is that we’d like our kids to be a little older. Our youngest is 2 and a half and that seems a little young to carry a backpack everywhere.

This desire to have our kids be a little older is further complicated by the fact that we are having discussions that our family might not be done growing yet.

There’s also a series of complex financial considerations. As I’ve mentioned, I’m currently pursuing the twin goals of freeing myself from the rat race and achieving financial independence.

I’m doing this through a combination of paying down my debt (my mortgage is the only debt I’ve ever had, right now I’m on pace to pay it off ~13 years early), investing, and building passive income online.

I really want my house paid off before I go. The idea would be to rent it out so that the taxes, insurance, and maintenance costs are covered and it’s actually making money for my family while we are away.

The real key though, is building enough income online that I can afford to step away from my job. The biggest thing keeping me chained to to my home city is the need to bring home the bacon.

One way to approach things would be to try to save enough money up front to be able to fund my travels.

The reason I don’t like this approach is because money stashed in a savings account and earmarked for a trip is money that could have been invested. I’m already settling for a below market rate of return by paying extra on my mortgage (when you pay off your mortgage early, the extra money you pay is essentially earning a rate of return equal to the interest rate on your loan).

If, on the other hand, I can build my influence and income online, I will have passive income rolling in that can fund my trip as I’m on it, while giving me the potential to actively earn more money through my laptop wherever I am.

Obviously when I’m traveling I want to spend most of my time enjoying my family and the destination and to try to not need to do too much work, but writing is work that I enjoy. Plus, I already wake up at 5:30 am to get my writing done while my family is still sleeping. I could just keep that practice up while on the road.

It’s an ambitious thing to want to take a Tim Ferriss style “mini-retirement” while shooting for a real early retirement, but just because something is hard doesn’t mean it isn’t worth doing. As my friend Tom Kuegler says:

“Struggling Is Freaking Good For You”


“Problem Solving Is A Good Skill To Have”

(both of those quotes were taken from this awesome article ).

Your dream isn’t just going to happen. You have to plan it and work towards it.

Your Quest

Speaking of your dream, what stage are you at?

Is your dream floating in the back of your head, half-formed?

Has it started to nag at you like a rock caught in your shoe?

Has it been formalized into a plan?

Have you started working towards it?

This is the one area where procrastination is most deadly. Procrastination is most commonly associated with putting off doing doing an assignment until the last minute.

This is not a helpful way to look at procrastination. The procrastinators may incur some stress every time they are up against a deadline, but they always come through in the 11th hour.

When it comes to your dreams, there is no 11th hour. There is no deadline unless you create it. And if you don’t, you can casually push your dreams down the road indefinitely without even realizing what you are doing.

In my opinion, the best thing you can do with a spare 30 minutes this year is to create a 10 Year Plan for a Remarkable Life. If you’ve read my writing before, chances are you’ve already heard me talk about this (in fact, if you’ve read this far in this article you’ve already heard me talk about it),but there’s a reason I bring it up so often .

If you want to actively design your future, the first step is to create a blueprint. This exercise helps guide you in creating one:


I know what my dream is and I’m working to make it a reality.

It’s a tough road, but what’s a worthwhile dream without a worthwhile challenge?

(Shoutout to Kristin van Tilburg for helping me refine that last quote)

There’s no guarantee that I’ll achieve everything I want, but I sure as heck have a better shot than if I weren’t trying.

If you have the courage to define your dream and the discipline to pursue it, you can live a live a life that most people think is impossible.

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