An Explorer’s Dilemma

Sitting on top of Wayna Picchu waiting for the clouds to clear to view Machu Picchu
I find great pleasure in knowing that I have no idea what's ahead of me.

On February 1st, I moved into a one-bedroom apartment in my hometown of Rochester to work on the launch of two new projects, plan the next adventure, catch up on video footage and see about a girl.

This past Sunday marked my 29th birthday, and I found myself in the familiar birthday mindset of being confused and frustrated with my life and where it’s heading.

I decided to sit down and share this state of mind with you in hopes that I would find some comfort within my rambling writing…

I sit alone in my newly rented apartment as 29 slowly sinks in. It’s late on a Sunday night and another birthday has come and gone.

This is the first time that I’ve been home for this occasion in many years, and it makes me realize that things are changing.

Signs of a domesticated traveler are evident as you scan the apartment. A desk sits in one room and a bed occupies another. Nothing more. This is all I own.

Now, I just need to fill the place with things, right? Things that weren’t relevant to me over the past three and a half years – things that I can live without.

I think about the plane tickets I could buy with the couch money. I think about the adventures I could have with the TV money.

But, this is what I want, right? This pause from the road will rejuvenate my passion for travel, give me time to create new videos with massive amounts of archived footage and allow me to focus on generating new revenue streams for more expensive locations like Brazil, Spain and Japan [breathe]… Right?

Let’s be honest, I’m lost.

I have no idea what’s next, and it’s tough to keep moving forward sometimes when you don’t know in which direction you’re heading.

Even as well thought-out as this plan seems, birthdays tend to make me question my choices and discount the accomplishments.

When I returned from Guatemala, I knew I was ready for a change. I was tired of living and traveling alone, and I felt like I had lost some love for the journey. I questioned the point of all this, and I wondered where it was taking me. I was drained from it and felt bad because of it.

On the other side, as any long-term traveler knows, it’s difficult to adjust to life back home. Stimulation and growth inevitably slows and motivation becomes more internal. Your friends and family are the same, but you see things differently. I can’t talk about my travels without feeling like a worldly douche (“This one time, in Greece…”).

So, where do I go from here?

I want to continue doing the things I love, like volunteering in Bolivia with BiblioWorks and working with Kiva in Guatemala, but I also want to start building wealth and maintaining relationships with people at home.

I don’t want to be a lonely vagabond at 50, nor do I want to wonder what if I did more…

Is it possible to have it all? Financial success, world travel, social impact, healthy relationships, personal growth… Is it possible to balance these two worlds?

When I feel lost like this, I try to relate to the great “explorers” and the psychological battles they must have faced when pursuing their dreams…

How many times did Columbus think about turning around? How often did Richard Branson get frustrated with an idea or business? What if Felix Baumgartner let doubt and fear control him?

I wouldn’t put myself in their wheelhouse by any means, but mentally and emotionally, you have to assume that they felt lost and unsure of their direction at some points along the way.

This is an explorer’s dilemma.

What’s the answer?

This lifestyle has been a rollercoaster of emotions and excitement. One day, you feel like you’re on top of the world as advertisers deposit money while you explore ancient ruins. The next day, you’re sleeping in a dirty hostel with $30 to your name and nobody around to confide in.

The only way to overcome the psychological droughts and insecure moments is through absolute perseverance and belief in one’s self. Step by step, the small successes lead to a growing self-confidence.

This was the same when starting a business as it is for travel.

When you decide to step out of your comfort zone and chase your dreams, you’re going to run into obstacles, you’re going to get lost, and it’s up to you to decide if it’s worth it or not.

Being lost is a feeling I’ve experienced many times before and one that I hope to have many more times in my life.

I understand that you rarely get lost on a well-traveled trail.

So, as I sit here while the relaxing silence of an empty apartment is plagued by the perpetual commotion in my mind, I find comfort in the idea that it’s up to me to write the next chapter.

I embrace the fact that I don’t know what’s next, exactly, because it tells me that I’m doing something right. I’m creating my own path and writing my own story, even if I don’t know where it will lead this year.

Who’s ready for chapter 29?


My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


  1. I’ve been in this exact place for the past two years. I’ve accomplished a lot being home. Worked a stable 9-5 job (which I had never done before), explored relationships, strengthened family bonds and friendships, but the call of adventure and the sea still feeds my soul and I’m planning my return. Make some short roots, get some stability, and plan your next big trip. You’re not done traveling yet, my friend. 🙂

  2. I’m sure you have many more adventures ahead of you, Gareth!

    As you said, it is completely up to you to write the next chapter of your life. As long as you feel fulfillment from your actions – whether that means traveling more or settling down – you are acting on your highest good.

    Best of luck! I look forward to hearing what your next chapter holds.
    Adventurous Andrea recently posted..The Game Changer for My Travel!My Profile

  3. I can relate to everything you said, except I’m 7 years older (yikes)! I feel like a pendulum that keeps swinging from one extreme to the other.

    I’ve felt a lot more balanced since wrapping up my travels in 2012 and bringing some stability back to my life.

  4. I’ve only recently found your blog, website and videos. You are very talented. I enjoy them tremendously. Whatever you do, you will be successful. You are living my dream life. I look forward to the “next chapter”. Best wishes.

  5. I read T2T not b/c of what you do, per say, but b/c of how you do it. You have a vision, a dream, that most respond to by saying–that shit cray or pfft, like it’s possible for “someone” (Columbus??), just not you–and you make it happen. Over and over and over again. To read the experiences in this post inspires me more than all of the dream seeking & goal accomplishing you do. For me, I read this, & I see my own stuggles & questions & doubts. I realize: the great have to struggle. This post reassures me to go & to do especially when it seems unsure. I wish I found more pleasure in knowing that I have no idea what’s ahead of me. Thanks for posting!! You got this. #ROC.

  6. I am that vagabond at 50 you spoke of. Ok, so I’m 49, same difference.

    Here’s what I can tell you.

    When I was 30 I settled down got married had the 9-5 for 5 years. I was miserable. It didn’t cause my divorce because I would not do that to someone, that’s just not cool. It was something else.

    I was back on the road until 3 years ago when I met my wife that I’m with now. I did it again, I settled down I work 12 hour+ days (the economy stinks) and I took 2 days off last year. Yep, 2 days off in one year.

    What do I do when I have any free free time at all? Torture myself looking at places I would really like to go.

    After all that what can I tell you? Not much except this:
    True happiness is life’s highest attainment!

    Whatever that is for you, just do it. As far as we know you’re only going to be on this rock once. So, ROCK ON!!!

  7. Hey Gareth,
    I can relate to your situation as I’ve been there before. After having been settled for a while, I uprooted (again) a few years ago and am loving the teaching/traveling/backpacking, and now, volunteering life. I’m happy to say that I’m currently helping to promote what you started in Sucre last year: BiblioWorks is getting ready for their Literacy Festival and you have set the bar high. Thank you for your work. You can be sure that your style of travel is worthwhile and you’ve put good things in motion. Enjoy your rest for now. You’ll know when it’s time to go out into the world again.
    (Seeing about a girl is an important journey too.)
    Robyn recently posted..BiblioWorks’ Annual Literacy FestivalMy Profile

    1. I’m sooooo happy you are working with BiblioWorks Robyn, they are an amazing team. Give them all a big hug from me and best of luck with all your adventures! Thank you so much for the comment.

  8. Just stumbled across your blog while I thought I was searching for Bayonne on Lonely planet. So glad I came across ya.
    I can relate to you on many levels. I turned 29 in October and this is my second year living abroad in Spain. It’s been a great year and I’m learning a lot about what I want, and more importantly what I don’t want. LIke you, I’m realizing how important relationships and growing and maintaining a sense of community are. Travel is great but my idea of travel has shifted, what I want from it has shifted in ways I couldn’t imagine when I was 24 and taking off to Africa solo with a backpack and no return ticket. It’s ok for things to change, for us to question our direction and what we want and then take new steps to create new things in our life!

    Congrats on your kiva fellowship! Hope it’s going well.

  9. Here’s something that will make you feel better…i’m in the exact same mindset only i’ve just hit the big 30! Awesome article.

  10. I loved your reference to the segment from Good Will Hunting… there is a popular children’s book “from the day” called the The Little Prince. It parallels your thought process. The story line profoundly proclaims “that one only sees rightly from the heart.”

  11. Great post. I know exactly how you feel. I traveled for over a year and then was a bit lost when I came back and filled my room with ‘things’ but slowly you get into it and its hard now to quit everything again to go travelling. Best of luck in the new venture
    Ross recently posted..Gorilla Trekking in RwandaMy Profile

  12. such a heartfelt post…..I felt your dilemma, I ended up composing A traveler’s prayer for you. Hope in keeps you safe…

    Dear God,

    You are my true Guide and Light. Shower me with Your goodness that I may travel the safe path. Calm the hearts of my love ones so that they may not worry so much about me. Fill my heart with contentment in every journey that I embark on so that I may have the satisfied and blissful soul as I return home. Please protect me from harm and danger. Purify my heart’s intentions that I may have a faithful heart. All of this I ask, in Your Most Holy Name……Amen.

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