That's actually like a hundred bucks or something.

Do You Have a Trust Fund? Thoughts on Financing Long Term Travel

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One of the questions I most frequently receive is “How are you able to afford taking a year off to travel, mess around, and not work?” One of the (basically) homeless, alcoholic retirees living on the shores of Lake Mead put it as such: “Oh, his daddy’s got money, that’s how he’s out here traveling…”

Do You Have a Trust Fund? Thoughts on Financing Long Term Travel

So, do you need to have a rich daddy or dead oil tycoon uncle in order to take time off from work to travel? The short answer is no, definitely not. And if I was a Trustafarian, I would’ve moved to Boulder and become a ski bum…

Living like a glorified bum out of your vehicle is actually not that expensive (nor is international travel to developing countries, similar ideas). Arguably the biggest expense is in foregoing income during your travels.

Here are a few thoughts on enabling the financial side of long term travel, written entirely from my perspective and experience, and probably most applicable to 20-something recent college graduates and young professionals. If you have a mortgage, kids, or are living hand to mouth with minimum wage jobs, I can’t speak to that perspective.


The biggest and most difficult obstacle I have heard among people in my age cohort who have the dream or desire to travel is debt, bar none. Debt is nefarious and debilitating if you are hoping to take a sabbatical from the rat race.

Do You Have a Trust Fund? Thoughts on Financing Long Term Travel

School loans and college debt is something that can be worked with (interest rates are low and payback times are generous–not counting private loans–so you might be best off paying the minimum with savings while traveling), but credit card debt is a whole other beast that will limit your perceived options and keep you in a job or other circumstances that you might not otherwise want to be in.

It hampers what you think is possible and what you can do.

This isn’t a personal finance blog, but if you have dreams of long term travel you must tackle your high-interest debt. It is possible to finance a portion of your dream trip with debt before you return to the working world and pay it off, but I would say it is not advisable to start such a trip with this burden.

So, first and foremost, if you don’t have any debt, keep it that way! And if you do, aggressively pay it off. Forego whatever luxuries you can to get it done. Check out blogs like I Will Teach You To Be Rich, Get Rich Slowly, the Simple Dollar, etc, or books like Your Money or Your Life to get some sound advice on tactics to tackle debt and cut expenses.

Credit cards should always be paid off in full each and every month. They can actually work to your advantage with cashback, airline miles, hotel points, and more with some of the best travel credit cards. If you’re paying interest on your spending then, well, you’re doing it wrong.

I highly recommend signing up for–you can track your spending and income across all accounts and get a long term picture of where your money is going.

Read More: Conquering Debt Mountain

Lifestyle Inflation

The other big obstacle for twenty-somethings with a longing for long term travel is lifestyle inflation. Many of us go through college like a glorified dirtbag… Living in lousy housing situations, eating top ramen and PB&J, drinking cheap beer, barely working, and lacking the pocket cash to go out and do the things we want.

But then we graduate. We get an okay job that pays the bills. We go out more, we eat out more, we buy nice things to fill our room in a shared group house.

Do You Have a Trust Fund? Thoughts on Financing Long Term Travel

Then we get a raise at work and some increased responsibilities. We’re really adults now, right? We can up our standard of living a little by moving into a one-bedroom apartment, going out more frequently, buying a nicer car, nicer clothes, and buying slightly more expensive things to fill our apartments… Our lifestyle and spending inflate with our increasing earnings.

In some cases, we’re accustomed to the nice things our parents had, that we recall growing up. The furniture, cars, big house, toys, etc. In most cases, we fail to recognize that that was the culmination of 20 something years of their work, not a starter package right out the gate. But we still want to have similarly nice things for ourselves.

Hopefully, at the least, the lifestyle inflation is on par with your increased earnings and has not been leveraged with credit cards and other debt…

Other Hang-Ups

Obviously a mortgage, kids, marriage, dogs, and similar things can hamper or derail the possibilities of long term travel. There are plenty of exceptions to this, but if you’re serious about it, I’d try to avoid the aforementioned items.

Mortgage–there’s a reason mort, Latin for death, is part of this word. Seriously. People like to think of a home as an asset, but it’s a liability and is really only an asset if it is actually generating cash flow (which could work to your advantage if you buy a house, and leave it to travel and collect rent above and beyond the monthly mortgage amount).

Kids and Marriage–first and foremost, obviously as a couple you would both need to be 100% on the same page about going and living in your vehicle or sleeping in cheap hostels in Southeast Asia.

Kids add another complexity, but there are quite a few families with kids who are out there on the road and doing exceptional things. They are far and above the exception to the rule though. If you are serious about long term travel, I would recommend steering clear for the time being.

Dogs–I love dogs. Well, other people’s dogs. Dogs are a HUGE time and money sink. Not only do they severely hamper your lifestyle as a normal 9-5 working stiff (got to head straight home to walk/feed/whatever my dog) but they also inhibit any long term travel plans you might hope to undertake.

Do You Have a Trust Fund? Thoughts on Financing Long Term Travel

Backcountry climbing or backpacking suddenly becomes more challenging, National Parks are now mostly off-limits, traveling overseas is much more complicated with exposure to new parasites and diseases. Dean Potter and Steph Davis are both noteworthy climbing exceptions to this rule, but they’ve also been at the dirtbagging thing for so long that they’re in a different realm of thought and lifestyle…

Enabling Long Term Travel

There are countless blogs and “lifestyle design” gurus out there that can show you how to “live the dream”. There’s the old school way where you save up a bunch of money and then take time off to go spend it, or there’s the new school, internet 2.0 way where you build an online business or create some sort of passive income stream that finances your travels each month.

I’ve met fellow dirtbags on the road who manage it by all different means. Some do the seasonal employment gig where they work 6-months out of the year and climb the other half, some do part-time work via the internet a couple of days per week. And some just save up a chunk of change and go for it.

Whether you have the desire to go the 2.0 way, I still highly recommend you check out books like Tim Ferriss’ the Four Hour Work Week or Chris Guillebeau’s the Art of Non-Conformity. These books will get you thinking outside the box, and thinking about what your options might be.

Ultimately, I ended up going the old school way, just going off of savings.

Read More: Save Money for a Trip

How I Did It

The gist of my story is that I did nothing special financially-speaking for this trip… I wasn’t planning it for years on end, it was basically just something floating around in my head. If my job hadn’t come to an end, I’d likely be sitting right there at my old desk.

I socked away a little money every month for some reason. That’s just what you’re supposed to do, I guess.

I was fortunate that I had middle to lower-middle-class parents (divorced), neither of whom are big spenders that saddled themselves with huge credit card debt, so I at least learned from their example.

I was fortunate to have landed a pretty good job out of college. I graduated with below-average school loans (thanks to two years of community college) and got those paid off over the years. I’ve never really racked up much credit card debt–the one exception being when I spent all my savings while studying abroad and upon returning started racking up debt I couldn’t pay off each month.

I also managed to avoid major lifestyle inflation. In my working years, I lived in a… how shall we put this? Less than the ideal living situation for many years. It was cheap. I didn’t buy any furniture whatsoever. I used public transportation.

I’m currently living in and driving the same truck I had in high school–an old school 1991 Toyota Pickup. Fortunately, it has low mileage since it was mostly sitting idle while I was living in DC.

That’s not to say I’m someone who has it all figured out and only spends his money wisely. God knows I have spent (and continue to spend) too much of my money on the eating out and drinking side of things. I’m just not a cook, I don’t like it–so take out was always a big expense.

I had gym memberships (both climbing and regular) that I used infrequently. Also, I’ve spent a lot of money on gear and guided instruction over the years… Which is definitely not cheap. But it’s important to identify what areas of spending are important to you and what isn’t, and then ruthlessly cut your spending in those areas that aren’t important.

So, yes, I am absolutely fortunate that things worked out the way they did for me. But ultimately, I think the key to financing long term travel and living like a dirtbag, whether it is a domestic trip like the one I’m on or the more popular overseas adventure, is to live like a dirtbag even when the money and circumstances don’t dictate that you have to.

Long term travel requires sacrifices–both to save and prepare for it and while you’re actually out there traveling.

The question is: is it worth it to you?

Read Next: How I Get Paid to Travel the World

Further Resources

Rolf Potts’ Vagabonding: An Uncommon Guide to the Art of Long-Term Travel
Tim Ferriss’ the Four Hour Work Week
Chris Guillebeau’s the Art of Non Conformity

P.S. That shot of all that money up top is actually the equivalent of something like $100 US Dollars. It only looks like a lot of money.

You might also like…

Downsizing and Minimalism for Long Term Travel
Stop Buying Things and Start Doing Things

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Do You Have a Trust Fund? Thoughts on Financing Long Term Travel


Author, Writer, and Head Honcho at Desk to Dirtbag
Ryan is an author, adventurer, perpetual wanderer, and self-proclaimed dirtbag (but that might not mean what you think). Originally from Seattle, he headed to Washington D.C. where he spent five years working for Congress before heeding the call of the wild. He set out truck camping to road trip across the American West. Since then he set out traveling to Colombia, drove across all of Central America, and also wrote a best selling book: Big Travel, Small Budget. He just finished driving his old truck across all of South America. Follow the adventures on social media or read more about me.

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    Love it. I have been out of a job since Dec 2011 and sometimes I get similar comments. Having no kids helps.

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