I often laugh when people call me a free spirit or say “I wish I could just drop everything and travel like you do.”

I say, “Are you kidding? It took me two and a half years to quit my job so I could travel around the world. It wasn’t exactly a spur-of-the-moment decision.”

Of course, I understand the courage one has to muster to take the leap, whether you spend years planning for it or decide to leave tomorrow. And one of my goals with Nomadtopia is to help people figure out what they need to have in place to make the leap a little less scary (for me, it was having at least $10,000 in the bank, hence the two-and-a-half-year delay).

On that first trip, as I traveled solo for almost nine months, I built in some structure so I wouldn’t feel quite so lost at sea. For example, I booked the long-haul flights for my itinerary in advance, so I wouldn’t have to scramble to figure out how to get from South America to India, for example.

But I also allowed plenty of room for flexibility and spontaneity. I knew, for example, that I was flying into Peru and out of Argentina, but how I would get from one to the other, and what I’d see along the way, was a rough sketch at best.

Yes, I can be a bit of a planner if the circumstances call for it, but on that trip and ever since (and, now that I think about it, earlier in my life as well), as I’ve wandered, improvised, dreamed, schemed, and refined my ideal lifestyle, I find myself winging it more and more, and I’m constantly reminded of why it’s a good idea to not plan things out all the time.

Here are five reasons you should wing it—in life, in travel, and in everything else.

It creates space for synchronicity and magic that’s almost impossible to plan for.

See Exhibit A, La Casa de la Literatura Peruana, in the photo above. Wandering in Lima, Peru, earlier this year, I ambled down a side street and found myself in front of this beauty. I love literature and learning about the literary scene in different countries, and I probably would have sought this place out if I had known it existed. But what an awesome feeling to randomly end up finding it, all on my own, and feel like I was exactly where I needed to be.

It allows you to try things you might hesitate to do if you had too much information.

It’s kind of laughable how little research we did before we arrived to spend three months in Malaysia. Pretty much all we knew was that we could easily get a three-month tourist visa on arrival, that it was in Southeast Asia so it must be affordable, and that the food was probably pretty good (I had a rough sense of the mix of peoples who’ve influenced the culture here).

I had no idea, however, that this was a predominantly Muslim country until I was reading a guidebook on the plane! Having never been to a Muslim country, but having heard a bit from other travelers (never mind the fear-mongering on the news), it did give me pause. But I was already on my way, so there was no changing my mind now! And honestly, it’s turned out to be an eye-opening and enjoyable experience, so I’m really glad there wasn’t an opportunity for this knowledge to shape my decision in any way.

You’ll spend less time planning and trying to anticipate every eventuality (which you can’t really do anyway).

At times, I’ve spent embarrassingly long hours reading hotel reviews, researching, and deciding where to stay, as if there is a perfect solution and I must find it. And in the end, even after all that time spent, the places we stay are rarely perfect (and we do just fine).

It helps you focus on what really matters and forget about the rest.

I wrote the other day about how few things you really need to be a nomad. When you can break it down to the bare essentials, it makes you realize how little everything else matters. As I always tell myself in the cab on the way to the airport, I’ve got my passport and a credit card; it doesn’t really matter if I forgot my toothbrush or the charger for my cell phone.

It teaches you to trust yourself.

There have been plenty of times over the years where I literally didn’t know where I was going to be sleeping the next night. Sure, sometimes that makes me a little nervous, and for the most part I’d probably rather not cut it that close! But every time it happens, things work out just fine in the end, giving me even more confidence that I can handle the unexpected—and proving that things often turn out even better than I could have planned.

How about you? Are you more of a planner or do you like to wing it? In what ways has planning held you back? What amazing experiences have you had because you went with the flow?

Now that you’ve learned why you should wing it, read the companion post, 5 Reasons You Should Plan Ahead.