5 Things I Wish I Knew About Travel

by / ⠀Entrepreneurship Travel / April 12, 2022


1. Someone once told me, travel brings about transformation.

It only rang true because I was just recently on a ferry from Croatia to Italy and borderline at the most uneasy place in my life. Sounds odd, and if I paint you a picture you might think I’m crazy. Sun was setting. Only one sailboat on the horizon. Water bluer than a Corona commercial. But what was really going on inside me was anxiety, overwhelm, and uncertainty over-kill. Then the other half of me completely filled with shame, guilt, and judgement for not “whole-heartedly” enjoying myself on that view.

Those words changed my perspective on travel. Up until that point I always placed attachments on travel. I assumed it would bring me: happiness, joy, freedom, abundance, and spontaneity.

When it came short of those expectations, I was left let down, angry, upset, and disappointed. And then in judgement with myself for holding those emotions.

When I learned to let go of the attachments. And welcome the transformation, growth, and opportunities that it brought. Everything began to shift.

Travel does bring about transformation. And so does life itself. Welcome it. And you would be amazed at what’s to come.

2. Free travel is not a gimmick.

When I met Travis Sherry at an Entrepreneur’s Book Launch in NYC in 2013, we hit it off like old time friends. Travis is an amazing dude and has made a life and career out of traveling with his loving partner. It doesn’t get much cooler than that. Travis shared with me some simple tips on utilizing credit card sign up bonuses for travel and scoring free trips (in the form of 30,000, 40,000, and 50,000 free air miles) from multiple airlines. I used these tips, and worked these credit cards and ended up covering a full roundtrip ticket to Anguilla, $450 off my Nicaragua ticket with Under30Experiences, and a one-way back from California (which I still regret and judge myself on completely, every day).

Travis is a great friend and a solid resource to making travel easy and accessible, and finding ways to live and work from anywhere in the world. If you are thinking about traveling to national parks, check out my friends national park guide.

3. Travel isn’t always better than home.

I was in Italy riding a bike next to the flor da mince. (Okay, I’m not entirely sure that was the name, but the last part definitely sounded similar). It was beautiful and I was with a friend who I had met through Marcella, author and entrepreneur from Nicaragua. We were talking about our homes and the beauty in it. For him. Italy. This bike path. This river. Was ordinary. The castle not five minutes past his backyard was nothing more than a part of his town. For me it was exotic. I was living an adventure. And I felt like I was exploring places that I’d never dreamed of seeing.

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When my friend saw the excitement in me, it changed his perspective on his home town. He had never seen it through an expat’s eye before. It changed his entire view on his surroundings, thereon after.

Sometimes when we get so used to seeing something, we often overlook the beauty right around us.

I promised myself that after that bike ride, when I returned home, I would make my everyday feel like an adventure. Despite if I was somewhere “new” or not. My dog has helped me keep my word on it.

4. Everyday I look around and wonder about the people I pass, if their thoughts, ideas, opinions ever change, or how long they have been around for.

I wonder if people’s thoughts sometimes stop evolving, if and when their lifestyles stay stagnant.

When we get caught up in the grind, and the days turn into weeks, and weeks into months, it’s easy to get bogged down in the gloom and the monotony of our sometimes “less than ecstatic” world we have created for ourselves.

When you step out of a plane, or a boat, or somewhere in a new territory for the first time, your body and mind does something that it does no where else. It opens up more than it ever has in your entire life.

This happens all the time for me, and I wonder if it will ever stop. I am starting to think ‘no’ and realize it is just part of the game, of what we get to enjoy as life, and travel.

When you walk out of that plane and take those first few breaths of air in an entirely new place and your eyes, ears, and all your emotions and senses soak in your surroundings. You are forever changed. Your mind can no longer move back into the box it used to call home and reside in. You are expanded. Forever. When you first taste an ounce of this expansion you will realize the power of how new surroundings open your eyes, mind, and heart; and create a new world for you, simply by expanding yourself: physically, mentally, and spiritually.

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5. The internet, the phones, the social networks are constantly over run with news and flooding information on whatever it is we want to dive into.

This can be good. And also bad. it can be very overwhelming to see what is out there and find out who to trust or whose resources are accurate.

While trying to navigate the realm for myself I’ve seemed to find true, that when the “student is ready, the teacher appears”. The key is to be open as to who/where/what this teacher might look like.

Sometimes it comes in books. Other times in people. A few times it may be the sign next door that you’ve walked by a dozen times and never noticed.

Whatever it may be, be open to receiving. At any given point we are walking around with a question. The answer’s always waiting for us. It’s just a matter of if we are open enough to perceiving it.

I’ve been grateful for the community of friends and people who float into my life and bring me just what I need to get me to the next stage of where I am going.

Travis was one of those people that jump started my ability to travel as was Marcella and Matt. One trip soon turned into three, and three soon turned into a lifestyle. It’s no longer a question of whether or not I will “travel” this year or this month, but that is where it began. Making it a conscious effort to want to grow, expand, and explore. Everyone has their own reasons for travel. Back then, those were mine. Right now, to teach, contribute, and learn seem to be my calling and the forces pushing me towards to new places in the world. Whatever your reason or cause may be. If you have a yearning. Follow it. That is your body and soul’s, calling to you. Listen to it.

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As you embark on adventures, be sure to seek out the resources that can help you get there. The 80/20 rule still applies, as: if you put in the 20% of the hard work now, (learning about travel hacks, talking to people, and hustling to get clear on what it is you are seeking) you make the 80% ‘life on easy street’. Travel will never be what you expect it to be. And that’s the beauty of it. You can’t be sure what kind of transformation or growth it’ll bring, but you can be sure it’ll be something special, and definitely life-changing.

It’s worth checking out these resources Travis has put together for you.

I look forward to crossing paths at some point and if you’re ever unsure or overwhelmed or even just plain confused when it comes to travel. Feel free to reach out. There’s a community of like-minded ambitious people behind you, that want to see you explore and expand yourself and take on the opportunities and travel that will help you do that.

Kevin Diamond is an entrepreneur, website designer and educator. He speaks at and runs workshops for youth and young entrepreneurs, empowering them to step into their power and design the lifestyle and business of their dreams. He runs a digital marketing agency and designs websites at diamondesignstudio.com, and is the founder of Squirr3l, An Entrepreneur’s Platform. He can be found at kevinjdiamond.com living a #LaptopLifestyle and continues to work remotely and globally from off-the-beaten path parts of the world. He has a passion for the beach, and an unhealthy obsession for New Girl, reading, and candles. He currently leads seminars on entrepreneurial mindset growth and development, and teaches a variety of design courses both online and offline, internationally. He loves co-creating with digital entrepreneurs and internet marketer’s growing businesses and lifestyles that blend their work and play.

Related Post: 8 Surprising Advantages of Work Travel 

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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