7 Tips To Get The Most From Your Travels (and 2 Reasons I Failed)

by Benjamin Jenks on September 14th, 2011
1 CommentComments

“If you are not failing every now and again, then you are not being very innovate.” -Woody Allen

This post is for those that want to learn from my travel failures or those who are curious about what I learned after a lot of thinking about my year of hitchhiking around the USA.

Woody Allen has made 41 films in the last 45 years. Some of them have been great (Annie Hall won four Academy Awards, including Best Picture) and some of them have been horrible. I bet, if we were to sit that funny little man down, he would say something like, “Without those failures, I never would have had my successes.” Today, I want to bring attention to my own failures, so that maybe you can learn from them to succeed in getting the most from your travels.

Embrace Failure

Since I stopped my hitchhiking project back in May of 2010, I have had a lot of time to think about my successes and failures. In fact, although my year of hitchhiking over 14,000 miles around the USA was one of the most fun and enlightening in my life, it was also a failure.

I know… I know…in most social circles that I hang out in, the word, “failure” is avoided at all costs. I do it myself with others as well, so that I don’t hurt their feelings or devastate them. I try to put things in a positive light and frame a failure as a “setback” or a temporary challenge. In doing so, it seems that some wisdom is lost. That there isn’t trust that an individual can have failures… real failures… real screw ups… real mistakes… yet will still be okay. In fact, will actually be able to handle what life gives out even better than before.

My project of hitchhiking the USA for a year, not paying any money for accommodation, and sharing the “Goodness” of people was a failure. Here’s why:

1. I quit early.

With 3 weeks left to go in my year of hitchhiking, I decided to stop writing on my blog. I deactivated my Facebook account. I stopped checking the Internet. I didn’t return emails.

I was exhausted.

I felt like I had been giving, so much for an entire year that I couldn’t give anymore. I was operating under the philosophy of leaving everyone better than I found them and in doing so, I was frustrated that it didn’t seem like I had much to show for it. Some people just plain sucked the life out of me.

Plus, being “alone” for a year, without anyone whom I was sharing my experiences with for more than a few days… left me feeling more desperate than I had ever felt. My emotional needs were not met. I had tried to talk to others and tried to connect with something very deep within myself, yet I was not feeling full and happy. At times, I was astounded at what I was learning (like the brief moment of ecstasy I felt, after 5 days of forced meditation on a rock where I didn’t talk, speak, write, read, or really do anything for that time) or really happy about sharing a journey with another traveler (Zohar, who would become my friend,  shared a few days with me exploring the Grand Canyon, hiking dangerous snowy trails in Zion National Park, and just talking about our lives). However at night, when I was alone in my tent in some forest outside a subdivision or in a field outside of a town, there was such a powerful feeling of loneliness that was tough to stomach.

So after I had finished making my movie… I gave up.

At first, it was so pleasant not to have to check the Internet for comments or remember conversations with people I hitched a ride with, so that later I could write about it. When I had returned to Michigan I stayed with my Aunt to rest and recuperate. Yet, as weeks turned into months, my energy (that sometimes feels boundless) didn’t return. I had a hard time socializing, concentrating, or really doing much of anything. Eventually my energy returned, but it wasn’t because I was rested. It returned because I shared what I was going through with others.

In hindsight, I missed a prime opportunity to learn about myself had I continued to write for those last 3 weeks. Looking back on it now, I feel like I was very close to a realization about myself or maybe about the world, yet I backed off. I didn’t push on. This was really when it got the most interesting and the most rewarding.

In fact, when I had said that I was not posting anymore… that I was done. The emails that my readers and friends had sent me were very fulfilling and rejuvenating. Some shared stories from when they were just “done,” others gave me words of encouragement, or shared moments in their lives where they felt the same. Sharing with others and getting support really felt great.

Looking back now, I realize that I can’t go back and in fact, I am very happy with my current situation (traveling again and using what I learned to follow another of my dreams). But the next time I feel the way that I did…

I’m going to push through and keep on sharing.

2. I wasn’t honest with you.

There was a lot more to the trip than what was posted and a lot of it was meaningful insights or at least interesting. My blog posts were a collection of facts, photographs, and details from the people I met. But in only “sharing stories of the goodness of people” I didn’t tell the stories that of the hardships I had to overcome or about the wisdom of the “badness” of people.

To get all philosophical on you, a mentor of mine helped me realize that you can’t have goodness without badness. Goodness is just a word to describe a characteristic. Without it’s opposite, it does not exist. It would just be nothing.

The movie, Vanilla sky, has a quote, “And I know sour, which allows me to appreciate the sweet.”

Or if you were to think that if it never got dark… would we say that it is light in the daytime?

I never got to tell you about the time that I stole 6 orange from a farmers tree in California and how I didn’t feel bad about it. I didn’t mention how I felt the presence of evil from 2 men in a tiny, Japanese pickup truck who were offering me a ride in a parking lot outside of Amarillo, Texas.

I never told you that in some cars I rode in, I felt that if I just were to say or do the wrong thing that things could get very ugly.

I felt how evil feels on this trip. I felt “badness” in some people.

In my coming journeys I plan to capture all sides. To record what really happens, even if it is scary or even horrifying.

7 Tips to Succeed At Getting The Most From Your Travels

Despite these failures, I realize that it really was an amazing journey. Here are 7 things that helped me get the most from my travels:

1. I created my world.

I was so confident and positive about my trip (most of the time) that it effected the people around me. Have you ever been around someone that was in such a good mood that they made you in a good mood as well? This is how my trip went a lot. I was so sure that I was following my dream, that I would be safe, that I could handle myself, and that others should too that many people went right along with me.

I am sure that anyone that might have had the inkling to take advantage of me would be put off by my confidence and belief in what I was doing. I also made sure that I was in charge of my energy. If I was in a good mood or inspired, I would try my best to not let the attitudes and beliefs of others effect what I was doing.

Do you let others control your energy? Or do you steer your own course?

2. I was genuinely interested in people.

The gift I brought to others was my curiosity and love of people. It was amazing to watch people relax, unfold, and open up when I was really interested in them, their dreams, and their failures.

In a car in Alabama a man and I had a talk that got really deep. The man spoke about a time that he almost committed suicide. He described how the knife felt on his neck, how ashamed he felt when his wife walked in, and how he coped afterwards.

Now I am not suggesting that you get everyone to talk this deeply, however if you forget about your own dramas and excitements for a minute and inquire about others, you will be very happy with the result.

Can you get over your own drama for a minute? Try to be curious about someone nearby and see what happens.

3. Home can be anywhere.

Some people tell me that they couldn’t travel for more than a week or two weeks. I remember what that feeling was like… wanting to be home. Wanting to be comfortable. The challenge on this trip was to bring that comfortable feeling of home everywhere that I went. I had to. To have that moment when you walk into your home or your bedroom and you can get to a deeper level of relaxation is such a pleasure. I had to do that wherever I was.

Try it right now. Kick off your shoes. Take an “Ahhh….” breath. Enjoy wherever you are or move to a place that you can enjoy.

4. Say Yes.

In the movie, Yes Man with Jim Carrey, the main character challenges himself to say, “Yes” to everything for an entire year. This ends up turning a negative and bitter guy into a happy and loving man, who goes on some crazy adventures (and of course falls in love).

When I watched that movie, it reminded me of how I traveled. I said, No, a lot at the beginning of my travels. I was trained to by my parents and our culture. I didn’t want to rely on anyone else. I could fend for myself. However, every time I said, No, I could feel how let down people would be when they offered me a meal or a pair of old gloves or a night’s sleep on their air mattress.

People enjoy giving and when I started saying, yes, it was awe-inspiring to see how it not only made me happier, but it also helped the people who were helping me.

Have you ever wanted to say yes, but didn’t and thought about it later feeling regretful about what had happened? What could you say Yes to today?

5. F*** what other people think

Some people didn’t get my journey, in fact it would really piss some people off (the gas station, carpet salesman in Junction, Texas kept yelling at me that he was watching me to make sure I wasn’t pan handling, as I waited with my thumb out by the side of the highway). The hardest part was that some of my close friends and family didn’t get my journey. I even lost friends because of it.

But it feels like this is how it must be.

I can’t please everyone and when I try to, it just ends up worse.

The best seem things to happen when I follow my own wisdom, which is what this trip was all about.

Don Miguel Ruiz writes in the book, The Four Agreements that you should never take anything personally. His book details the “four agreements” you can make to stop your suffering. He goes on to explain that everyone looks at themselves as the star of their own movie and when it seems they hate you or you are bad, really you have just went against the “script” that they have going. It isn’t about you, it is about them.

Are you holding back from doing something that you feel called to do because of what others would think? What is the worst that would happen if you said, “F*** it” and did it anyways?

6. Use my gifts

A mentor of mine asked me an insightful question. “How do you think your journey would be different, if you were African-American?” He was challenging me to see that I was on a special journey that few could take.

At the time I was lost for words. I had felt ashamed of myself for not having more forethought that I might be offending someone else. Was I encouraging people to do something that only I was really able to do? Or maybe someone else would try it and get seriously injured?

Since then I have realized that I am gifted to be able to hitchhike the USA and not encounter dangerous situations. Well… gifted and also trained. I am gifted because I am a white male. I am rich compared to most people in the world. I have a “nice face.” I am relatively intelligent and self-aware.

However, I had also spent my life training for this (although if you had asked me I never would have been able to predict it at the time) because I spent years training to be able to “read” the troubled young men that I worked with at a therapeutic school. They were less than honest about their motives so it took keen senses to stay on top of them. Plus, I had endured feedback from the kids and my peers in an attempt to grow, so I was used to people giving me “criticism” or even being furious at me. Not to mention, I had taken a number of hiking and wilderness trips, even leading many of them. Finally, I was trained to de-escalate and resolve conflict about many issues.

At one point I realized, why not embrace these gifts and my training to follow my dreams? To stop feeling bad, because others don’t have these gifts and use them for “good.” Why not use what I know to travel in a way that very few have an opportunity to do?

Are you using your gifts in your travels (or your life)? Are you playing to your strengths? Or are you trying to be something you are not?


Now it is your turn…

Have you had a failure that lead you to see things in a new light or to achieve other successes in your life?

I would love to hear your thoughts in the comments to help me learn more and the other readers of my blog.

Rock the world,


“Often the difference between a successful person and a failure is not that one has better abilities or ideas, but the courage one has to bet on one’s ideas, to take a calculated risk — and to act.” – Andre Malraux


Categories: Travel Advice


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  • Wow, quite a statement after a long silence – bravo, Benjamin! Humble and real.

    Here I am in an airport in Katowice, Poland, about to fly to Ecuador to meet one of my brothers and travel three months in Ecuador, Peru and Bolivia.

    I am a man on the move. I have been for nearly eight years and countring. In that time, the longest I’ve stayed in one place was six months in Cartagena, Colombia.

    And that was this year. Know why?

    Because I was tired, too! Tired of constantly hauling my stuff around, and losing a lot of things along the way because I couldn’t take them. Tired of saying goodbye to new (and old) friends. Tired of not being grounded. Tired of moving. Like you, I was also tired of being alone.

    Benjamin, you know what? After Cartagena, I’ve been through Poland, Spain, Romania, Bulgaria, Turkey and Germany… and I’m still am tired!

    At certain points I thought I’d just freak out.

    Humanity was kind. Humanity was mean.

    I was fulfilled. I was empty.

    I was confident and radiant. I was self-conscious and expired.

    But… that’s what it seems to about.

    Even if you’re in one place, these same feelings come and go. Sometimes you’re drifting, sometimes you’ve got a paddle, but always you’re flowing.

    And I wouldn’t give up being free to move right now because there’s so much more to see.

    Around the next corner is another challenge that will make me grow, whether I like it or not. The next bend will yield something unexpected, something unplanned-for. Perhaps something wonderful, perhaps something difficult. But something new.

    I think Laozi (Lao Tsu) said it best: “A true traveler has no fixed plans and is not intent upon arriving.”

    In the same breath, he also said: “A true artist lets his intuition lead him wherever it wants.”

    We are travelers and we are artists. We Create our World! : )

    Whether moving through physical, mental or spiritual space, we’re always going to have strong moments and weak moments.

    Curiosity is our fuel! And sometimes we run on fumes.

    “We are never going to look back and regret the things we did, only those we didn’t.” (Not sure who said that, but some wise person.)

    Keep up the good, brother. You’re an inspiration.

    I look forward to regular helpings of world creation topped with adventure sauce. Yum!

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