How to Start Traveling: An Expert’s Guide to Overcoming Fear & Taking the Leap
Every year, it’s the same resolution: “This year, I’m finally going to travel more.” You dream of distant beaches, vibrant cities, and incredible adventures. But then, life happens. The dream fades into a “we’ll see,” and the excuses pile up. To break this cycle, we sat down with a seasoned Travel Expert to understand the mindset that turns wanderlust into reality. If you’ve ever wondered how to start traveling, this conversation is your first step.
Interviewer: So many of us dream of traveling, but we keep putting it off, waiting for the “perfect moment.” Is that something you see often? What is this trap we fall into?
Travel Expert: It’s incredibly common, and you’ve hit on the core problem right there. We fool ourselves into thinking an ideal time will just magically appear—a time when we have more savings, more vacation days, or when life just calms down. We tell ourselves, “Then, yes, then I can travel,” as if the stars have to align perfectly.
But I’m going to let you in on a big secret:
That “perfect moment” to travel simply doesn’t exist.
It’s a beautiful illusion, this idea that you’ll wake up one day and everything will fit together like a puzzle. Today isn’t perfect, and guess what? Tomorrow won’t be either. Tomorrow, you’ll just find another reason to postpone it. There will always be a bill to pay, the money will never feel like “enough,” a friend’s wedding will pop up, or you’ll convince yourself you need to plan just a little bit more. Perfection doesn’t exist. So much of adult life is just saying, “Next week will be better,” knowing deep down it will be just as chaotic as this one.
Interviewer: That’s a sobering thought. If there’s no perfect moment, how does anyone ever actually leave? It feels like you just have to take this terrifying leap of faith.
Travel Expert: That’s exactly it. You have to take the leap. The most difficult part of any trip is simply crossing the threshold of your own front door. To make that first step less intimidating, you have to accept that the stars will never perfectly align. You just have to dare to go. You have to trust in yourself, trust that everything will fall into place along the way. Because it will.
I can tell you from my own experience, if I had waited for my friend to join me (he never did), or to have “a little more money,” I would probably still be stuck at my office desk. I remember worrying so much about not having saved enough or whether I could manage on my own. There was always a perfect excuse not to go.
But sometimes, you just have to jump. Think of it this way: ships aren’t built to stay anchored in the harbor. And you weren’t born to stay at home wondering, “What if?” Believe me, one day you will run out of “tomorrows.” And all that will be left is a sharp pang of regret.
Interviewer: I’m feeling inspired, but those practical fears about money and security are very real. How do you advise people to overcome those very concrete limits and fears?
Travel Expert: You face them head-on by starting small. Stop waiting. Stop making excuses. This is YOUR year! It doesn’t matter if you can only save one dollar a day at first. The important thing is to start. You’ll see how one small action leads to another. Don’t get overwhelmed thinking about tomorrow. It will all work out, truly.
And if you’re worried about what might happen, think about this:
- Your bills will actually decrease when you start canceling unnecessary services before you leave.
- You’ll make friends on the road you can’t even imagine right now.
- You can work while you travel—there are thousands of options!
- And if, for whatever reason, it doesn’t work out, you can always come home. There is absolutely nothing wrong with that.
The world is a canvas full of possibilities, and you have everything you need to paint something incredible. But only if you dare to start today!
Interviewer: Okay, let’s talk about that start. The planning phase can be overwhelming. Could you share some of your favorite, battle-tested resources to make that first step less intimidating?
Travel Expert: Absolutely. I’m happy to share the tools that I personally use and trust to make planning easier.
First, if I’m being honest, the book I wish I had when I started is my own, How to Travel the World on $75 a Day. It’s a New York Times best-seller that teaches you all my secrets for traveling smart: how to save a ton of money, find the best deals, and have deep, authentic experiences. The BBC even called it the “bible for budget travelers.”
When it comes to the logistics:
- For Finding Cheap Flights: My favorite tool is Skyscanner. It searches all the websites and airlines, so you always find the best available offer. It’s a genius tool.
- For Booking Accommodation: For the classic hostel experience, Hostelworld is your place. But if you prefer a small hotel or a guesthouse, Booking.com always has the most competitive prices.
- For Rental Cars: If you need a car to explore at your own pace, Discover Cars is an incredibly affordable global search engine. No matter where you’re going, they’ll find you the best option.
- For Finding Activities: To squeeze the most out of every destination, Get Your Guide is amazing. It’s like a giant online showcase where you can find everything from walking tours and fun excursions to skip-the-line tickets.
Interviewer: You haven’t mentioned travel insurance. Is it really necessary? It often feels like an extra expense people are tempted to cut.
Travel Expert: I’m glad you asked, because this is critical. Travel insurance is not an expense; it’s an investment in your peace of mind. It covers you if you get sick, injured, robbed, or if something gets canceled. I never travel without it, and I can tell you I’ve had to use it more times than I’d like to admit. My personal favorites, for their service and value, are SafetyWing for budget travel, World Nomads for a great middle-ground option, InsureMyTrip for travelers over 70, and Medjet for extra evacuation coverage.
Interviewer: This has been incredibly helpful. For that person reading this who is finally ready to stop dreaming and start doing, what’s your final piece of advice, and is there anything you can offer to help them take that very first step?
Travel Expert: My final advice is simple: just start. That’s it. And to give you that extra push, I’ve put together a completely FREE Travel Starter Kit. Just leave me your email, and I’ll send you step-by-step planning checklists, free guides, and a ton of money-saving tricks to help you plan your trip like a real expert.
The kit includes:
- A 17-step checklist so you don’t forget anything.
- 61 life-changing travel tips.
- A super practical packing list.
- Your personal guide to getting free flights (yes, free!).
The waiting is over. Your adventure starts NOW.
A quick note on transparency: Some of the links above are affiliates. This means that at no extra cost to you, I might earn a small commission if you decide to buy something. I want you to know that I only recommend companies and products that I personally use and fully trust. My opinions are my own and are not influenced by anyone else.
