Updated: 08/04/2019 (Originally posted 8/17/11)

When I started traveling the world on my first RTW trip, I planned out everything. Where I was going to stay, what I was going to do. “First I’d visit X, then I’d take the train to Y, and then I’d bus to Z.”

Not only was it fun to plan, but I genuinely thought all of my well-laid plans would guide me along as I traveled the world solo.

It was only a few days into my trip when I realized that, while planning is important, those plans will quickly fly out the window.


Because you’ll meet people who will tell you not to miss a certain city or country.

Because you’ll arrive somewhere and love it and want to stay longer.

Or, you’ll hate it and want to leave sooner than you planned.

While the planning is fun, at the end of the day, this is why I love solo travel: it gives you unlimited freedom.

Admittedly, I can be a very indecisive person. (I’m a Gemini after all). That usually means that I end up doing things last minute. And then I usually change those last-minute plans again because I get a sudden, better, brighter idea in my head.

And when you’re a long-term traveler, that’s perfectly ok.

In fact, it’s preferable.

While there is no wrong with enjoying a well-laid plan, when you’re traveling for weeks and months at a time, you need to make room for change. You need to allow serendipity space to come and lure you into an adventure.

That’s what happened on Ko Lipe, which do this day, is one of the best months in all my travels.

By giving myself room to change my plans, to test the waters, I allow myself a chance to experience new things that I would have never dreamed of. Sure, planning is great, but even the best plans can’t account for everything.

I remember growing up and always desiring to be “the captain of my ship.” You know, working because you like what you do, not because you need a paycheck; being able to jet off to some place you want when you want; and having ultimate flexibility, time, and freedom for anything.

But then you graduate college with debt, you start working, the responsibilities pile on, you start planning out life, there are societal expectations put on you, and before you know it, you’re stuck. You’re part of that vicious rat race, and it seems like time is never your own.

Then one day you just think to yourself, “How did things get this way? I want out of this box.”

That’s why I quit my job and went traveling.

Though the leap was the hardest part, you realize everything else is easy, and it’s not traveling that draws you in, it’s the freedom and flexibility. It’s about waking up today and saying, “I’m going to Ukraine tomorrow.”

Or you’re going to play golf.

Or maybe take guitar lessons.

Or start that bakery you always wanted to.

Or move to Thailand to teach yoga or English or anything else that your heart desires!

I think this topic recently struck me because I’ve been thinking about the last ten years of travel and reflecting a lot.

It’s so easy to get caught up in the rat race. Doing what you’re “supposed” to do because that’s how you’re told life is supposed to be lived. You get a job, a wife, a house, kids, and then retire. But one day you wake up, and you’re 30, or 40, or 50, and you realize you never did a lot of the things you really wanted to do.

Maybe that’s why so many people have a mid-life crisis. Maybe that’s why my dad decided he was going to take up motorcycles again. Or why he bought that car he always wanted. Or why my friend’s mom changed careers.

I think that feeling is what causes so many people to turn to travel.

Yes, it’s great to see the world, but most travelers I talk to are really drawn to the sense of freedom and adventure — the endless possibilities.

While you’re traveling, the days seem to hold limitless potential and opportunity. It’s also why I think long-term travelers have a hard time adjusting back into “the real world.”

After you’ve been out of the box, it’s hard to go back in.

As much as I travel to explore new places and learn about people, I live my life because every day I wake up, I know I can open the door and do anything I want.

For now, that’s travel. Exploring my world. Maybe a few years from now it’ll be different.

But no matter what I do or where I go, I’ll never really change how I live because I’m not giving up my freedom to do whatever it is that makes me happy anytime I want.

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Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:

  • World Nomads (for everyone below 70)
  • Insure My Trip (for those over 70)
  • Medjet (for additional repatriation coverage)

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.


Random Musings
17.08.2011 / backpacking / SHGI / travel inspiration
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