5 Truths About Traveling the World in Your 20s

Now that I'm forty, I look back at traveling the world in my 20s through a different lens. Here are 5 truths about travel from an old washed-up backpacker. Shwedagon Pagoda.Traveling the world in my 20s was my top priority after college. I ended up visiting more than 40 countries before turning 30, carrying with me a small Eagle Creek Backpack and no more than six pairs of underwear at any time. 

Now that I’m over forty, I look back on my days of full-time travel through a different lens. I’ve realized some truths about traveling the world that wasn’t so obvious at the time.

I’m 15 years older and wiser now. Four other people rely on me for food, shelter, healthcare and piggy-back rides. I’m more cautious. I’m wealthier.

Travel remains my number one motivation for financial independence. But when our three kids were aged five and under, we mostly avoided travel.

Now that kids are out of diapers, we’ve started to set off on new adventures, starting with a Disney cruise and family-friendly road trips. 

At some point, we’ll head off to explore the world again, both as a young family and as retirees. Until then, I’ll have to make do reminiscing about the good old days.

As a washed-up old backpacker, I’ve put together a list of 5 truths about traveling the world in your 20s to share a few things I’ve learned, and to encourage you to hit the road too… at any age!

1. You’ll Need More Time and Less Money Than You Think

The type of traveler you are is a function of time and money. More time increases the quality of a travel experience. More money increases the comfort level.

Now that I'm forty, I look back at traveling the world in my 20s through a different lens. Here are 5 truths about travel from an old washed-up backpacker.

I wrote about this a while back in a post I called The Holy Grail of Travel.

Too often, aspiring backpackers overestimate the amount of money they need to travel. Waiting until you have more than enough money delays the trip.

Traveling on a strong currency like the US dollar will take you very far for a surprisingly small amount. You don’t need a costly round-the-world flight to see the world. Buy a one-way ticket somewhere.

You’ll need more time in your 20’s, not money. Double, triple, or 10x the amount of time you originally wanted to spend traveling.

No backpacker returns home wishing the trip was shorter.

An advantage of traveling in your 20’s is that your tolerance for shitty accommodations and uncomfortable conditions are high. Local transportation is sometimes uncomfortable, but the price is right. Rooms are really affordable, and new services like AirBnB give you lots of choices. Travel to inexpensive countries and stay in small towns for extended periods to keep costs low. Eat cheap.

During a 3-day stay in Otavolo, Ecuador, I only ate bananas to help lower my average daily spending. At the time, my priority was extending the length of my trip, not the diversity of the food I consumed.

You’ll quickly learn to live on a tight budget without sacrificing fun. Don’t let money hold you back. Leave your return date open-ended.

2. Your 20s Are the Best Decade to Travel (but others are close)

College is a great time to explore the world on an exchange or study abroad program. But long-term travel will delay finishing a degree. And unless you have a trust fund or spend-happy parents willing to foot the bill, you can’t stay on the road for long.

Travel in your 30’s and 40’s starts to interfere with real-life responsibilities like retirement savings, family and careers. Traditional retirement-aged travel is certainly rewarding, but the youthful spirit of adventure is long gone.

Setting off to travel the world in your 20s is the perfect time. After experience in the professional workforce, you’ll have some perspective on life as an adult and the pitfalls of the nine-to-five. Working before travel also allows you to pay off debts and save money to fund a long trip. On top of that, traveling the world in your 20s has a few other distinct advantages over every other age bracket.


Aside from the occasional overindulgence of alcohol and unhealthy food, your twenties are the healthiest years of your life. Most people can climb, hike, swim, bike, ski, jump out of planes and spelunk without the limitations of excess weight, bad knees or back pain. Travel presents those kinds of opportunities and many more.


Your 20s are a time to be fearless.

During my trip, I was faced with all sorts of decisions and activities I would never choose to do now that I’m a Dad. Back then, it was no big deal.

Like riding motorbikes helmet-less through insane traffic in extremely congested Asian cities. Bad idea, but incredible experience.

Or hiking into a known dangerous territory and nearly losing my neck.

Or detonating explosives 100 meters underground in a Bolivian zinc mine.

Fearless is accepting invitations to uncertain adventures and escapades. Fearless is approaching the most attractive person you’ve ever seen without hesitation. Fearless is plunging into unknown murky waters with strangers and alligators, at night, naked (for the record, I did not do that. But I know people that did!)

Youth and travel will take you to extraordinary places. The fearless mindset begins to fade in your 30s.

Untethered from Responsibility

Your 20s are an easy time to avoid real-life responsibilities… no kids, no house, shitty car, and often, no significant other. As you get older, responsibilities tend to pile on.

The best method for maintaining freedom in your 20s is to avoid owning things altogether. Rent a small apartment in the early stages of your career. Don’t accumulate crap.

Before you start traveling, clean up all your outstanding responsibilities. I made the mistake of not selling my car before traveling. Consequentially, it sat in my parent’s driveway rotting away for 14 months.

Another mistake is putting your stuff into storage. I have a friend who left to teach English in Africa eight years ago. Last month, he was back visiting and spent two days clearing out a storage locker full of junk. He didn’t even remember what was in there, and he paid for it for eight years!

Don’t accumulate stuff if you want to travel. You’ll never know how long your travels will last and possessions will be unimportant when you return.

3. It’s Selfish

Taking off to travel the world is a selfish venture. The people who care about you will worry a lot. You’ll miss out on weddings, funerals, birthdays, babies, graduations, retirement parties and anniversaries for people you care about. People who you love will need your help. You won’t be there for them. These are sacrifices you’ll have to be willing to make.

Many of the places you’ll go won’t have WIFI (gasp!). You’ll start avoiding it.

Now that I'm forty, I look back at traveling the world in my 20s through a different lens. Here are 5 truths about travel from an old washed-up backpacker. Li River.
The Li River, China

Years after I returned from my long trip, my parents told me how much they worried while I was gone. My aunts worried. Family friends worried. But I was in my own selfish bubble.

Now that I have kids, I understand.

When Lower Manhattan and the Pentagon saw their worst days, I was kayaking down the Li river in China, unconcerned with the magnitude of what transpired.

After thirty-five years of teaching, my Dad retired while I was away. To this day, I don’t even know if he had a retirement party. Not that I thought to call or buy a gift. I was off doing my own thing.

Of course, the sacrifices you’ll make are worth it. But stop and think how your adventures will affect others.

4. Traveling the World Will Not Help Your Career

After returning from extensive travel, most people you encounter won’t give a shit about your trip. This includes friends and family. They’ll ask what your favorite place was, then what you’re doing next with your life.

Bet your ass this applies to someone who is interviewing you for a job back home.

Unless you’re aiming for a career in public health, animal watching, guiding tours, or international development (and that last one’s a stretch), travel will not help your career aspirations. Some travelers have no goals other than to travel. But anyone trying to build a “real” career will fall behind their professional peers.

While I was traveling, my friends were busting ass earning advanced degrees. Yeah, they were jealous of me and all the fun I was having. But when I got back, that envy was gone quickly. I didn’t have much to come back to except a rusted red Mazda and an out-of-date resume.

With some planning and hard work, traveling can be parlayed into a career a la Blake Mycoskie, Chris Guillebeau, or Nomadic Matt. But entrepreneurial success is just as likely/unlikely and difficult at home as it is on the road.

If you’re traveling to find a career, you’ll probably find what you’re looking for. But if you’re taking time off before going back to school or a career, then longer travel will delay your ability to grow wealth. The traveling is worth it, but returning home broke and living with your parents can be a difficult reality.

5. Travel Changes Your Perspective of Humanity (for the good and bad)

Personal encounters with people from around the world will forever change your perspective of humanity. Most everyone I met traveling was genuine and kind. But some encounters were weird, and there were some real assholes and sickos too (nationalities redacted).

Here’s a short list of the some of the most memorable people I encountered:

  • The two rouge Red Bull salesmen that scammed me out of $2.50.
  • Two little girls that secretly placed a big lotus flower on my motorbike while I was away, and hid in the bushes to see my reaction. Then ran away.
  • A drunk, walrus-looking {redacted} who single-handedly ruined a two-day boat journey for 40 people in Laos.
  • An Irish tire shop owner and his apprentice who advised me to be a penny smart, a pound foolish.
  • A young kid who took a shit off a dock while our boat was passing by, then canon-balled into the same water without a care.
  • A fellow western backpacker from {redacted} who bragged about spending two weeks with a 14-year-old prostitute and her family in Battambang, Cambodia.
  • A Burmese bicycle vendor who swapped me the world’s ugliest dollar bill.
  • An agent orange victim who tried to sell me a book about agent orange victims.
  • The man who offered his daughter to me after a five-minute conversation (unclear if he meant marriage or prostitution!)
  • The old friend I ran into walking down a street in Bangkok (years before Facebook existed).
  • Grown women peeing on the side of the road.
  • A biker and traveling tattoo artist named Pluto.

Good or bad, there are interesting people at every turn traveling the world. The digital world has made our earth seem smaller, but there’s no substitute for leaving your home and comfort zone to explore this crazy place and its people.

The best time to do it is in your 20s. The second best time is now.

Photo Credit: RBD

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  1. My Dad emailed me today. Said his coworkers had a small party for him. Nothing big, he didn’t even invite my Mom (who is forever regretful she listened and didn’t go)!

    1. UPDATE: I think I fixed the problem. Give it a try and we’ll see.

      Sorry everyone. It appears something is wrong with my commenting functionality today. I’ll hopefully have it fixed this evening. You can try, but people are saying there’s an error.

  2. Sounds like some adventure you had RBD! I agree traveling in your 20s with no responsibilities is much different than in your 30s or 40s with a job, family, etc. What advice will you give your children? I want my kids to enjoy themselves, but still save and invest as early as possible.

    1. Brian,
      Great question. My kids are still young. When they are older, I definitely want them to travel, but it makes me nervous thinking about them doing what I did. I’ll want to go with them! My hope is that while they’re young, I’ll travel with them and teach them the street smarts that I developed on the road. That will give them to knowledge to travel independently if they choose to. By the time they’re in their twenties, Mrs. RBD and I should be on the road quite a bit too. So I like the idea of meeting up in different parts of the world. Long way off, but fun to think about.

      Thanks for helping with that comment problem. It was a tricky fix!

      1. Glad to help. Pretty cool to think about the kids traveling and you and the Mrs. and meeting up out in the worl some where. Great stuff.

  3. We both did a mini version of your trip, but only in Europe, and I was straight out of high school, Mr. ONL was mid-20s. That was enough to give us the lifelong travel bug, though we’ve been unable to indulge it the way we want to — and that’s a HUGE part of our motivation to retire early. Though we’ll be 38 and 41 when we quit next year, we have been trying hard to keep that spirit of adventure and possibility alive so that we can still be open to the unexpected in our future travels. Here’s hoping it’s not too late. 🙂

    1. ONL,
      Of course it’s not too late! You already know what it’s like out there. I started in Europe too. Some of the big cities are just as intimidating as third world countries. Now that you’ve worked hard and waited until early retirement, you should be able to travel in more comfort. As long as you give yourselves plenty of time, your experience should be amazing. But I think you’ll be wise enough to stay out of the murky waters 🙂 I am really looking forward to the day your blog switches to a travel blog.

  4. Dollar Flipper says:

    What better time to travel and be selfish than when you’re young?

    We went to Thailand for our honeymoon and it was amazing. We really want to go back but also have kids under 4. I think we’re going to do a Disney trip this fall, but that’s because we’re planning on having another kid and want my wife to enjoy it prior to being pregnant (miserable) again.

    1. DF,
      Nice. Thailand is awesome. I hear the cruise is a good way to start with Disney. The parks are so big and overwhelming. They really wipe you out. The cruise on the other hand, you can put in the kids in activities and go relax. You and I haven’t relaxed in about four years, so I like the thought of that! There’s no being selfish with young kids.

  5. Having traveled extensively in my 20’s I can’t agree with you more. Traveling in your 20’s is once-in-your-lifetime experience. I was fearless, sleeping in airports, train stations, bus stations, and even ran after the pocket picker in Barcelona to get my wallet back. Certainly not something I’d do now with a family.

    1. Tawcan,
      Love it. Pick pockets never got me, but they certainly tried enough times. Not sure I’d run after them either. Not worth it! The key is to secure anything worth taking, and the passport of course. Thanks for chiming in.

  6. James (@RetirementSavvy) says:

    Some great insights. The only point I would quibble with is the 20s being the best decade for travel. Two thoughts. First, I’ve traveled extensively throughout adulthood – I’m sliding into 50 – both on business and pleasure and my experience has been that travel continues to get better, primarily because I continue to build and learn off previous experiences. Second, it’s impossible to know how travel in your 50s and 60s will compare to earlier decades. It’s entirely possible that once the kids are gone, you have decades of prior experience to work from and greater wealth – even though more money isn’t necessarily a must, it doesn’t hurt – your travel experiences will surpass your expectations.

    1. James,
      Good counterpoints. True, I’m not in my fifties or sixties yet. Experience helps to make future experiences even better. I have high expectations for excellent travel experiences in my retirement years. Time will tell. But I am sure I won’t be doing some of the riskier things I did in my 20’s. Doesn’t mean I won’t enjoy!
      Thanks for your insight!