The Coldest (Loneliest) Day Of Your Adventure






Cold and alone…

I’d come for freedom, but I’d never felt more stuck.


It was Christmas Eve on the onramp of a town that didn’t want me. SUVs drove past full of Smiley Moms, Dads, Kids, and presents. Sparkley-Eyed Lovers didn’t notice me on the way to visit the in-laws. Big Texas Trucks roared past full of Dudes Wearing Hats, who made sure to rev their engine in response to my lonely thumb.

They all looked so… (insert whatever word means the opposite of lonely to you here). And they didn’t have any room for a homeless hitchhiker.


I’d been waiting for over 8 hours, but this wasn’t uncommon.

I’m taking you right into the middle of my year of hitchhiking around the USA. I’d already logged over 1,600 miles around the USA. And this was my adventure, my rite of passage, and my quest to find myself. I’d committed to not paying anything for transportation or lodging for a year. This would force me into hitchhiking and having to accept the gifts of strangers. It would also test my intuition, confidence, social skills, and give me some badass stories.

This would the adventure of my lifetime… one I dreamed about, planned, worked for, and drooled over for the past 7 years.




But on that lonely, cold onramp, all I’d learned was being tested.

And if you strike out on your own adventure, you will come to this place too (OR maybe you’ve already been there? Please share below).


There is a fine line between a brave adventurer and a foolish escapist.

Just ask people about Chris McCandless’ trip to Alaska or ask writers what they think about Jack Kerouac. And on this day, I wasn’t quite sure what I was. Every doubt I’d had about my trip and about my heart was hitting me in the face.

And when fear grips your brain tight, it is easy to mistake it for the Truth.


Maybe it was cold front that brought out every demon in my head.

I was in one of the most barren parts of the USA… West Texas. The icy wind could build up speed over hundreds of miles of bare, brown land and blow right through my fleece jacket, 2 t-shirts, a button-up, and a layer of long underwear. I was kicking myself for not bringing a winter coat.

The scarier thought was that I’d chosen a light sleeping bag and anytime the temperature got close to the 30′s, I spent the night having to shimmy and shake to stay warm.

Tonight it was supposed to be in the 20′s.


Maybe it was the dude who had heckled me the day before at the same spot.

“Hey… You know it’s illegal to panhandle in Texas.” I never panhandle. “I’m watching you.” Asshole. “What would Jesus do?” Probably not heckle some dude and wasn’t he traveling around sort of like myself? I restrain myself from yelling back, but he’d rattled me.


And there was no Adventure Sauce, no Posse sending me nice emails, and no mini-viral video to help convince me I was doing something legit.

I had a small website and a couple hundred of my friends were my facebook fans, but it all seemed so amateur. I was just fucking winging it and I knew it. I’d put everything I had on the line for this trip, because of the compelling feeling in my guts…

And I was wondering, whether my guts, or my Intuition, or my soul, or my passion, or my dreams, or whatever you want to call, it was full of crap.




Every doubt and fear I’d been able to get past, when I warm, laughing, or riding in cars, was echoing in my head.

  • “You will freeze and be a less ballsy Chris McCandless.”
  • “You will foreclose on your house… soooo irresponsible.”
  • “You will spend all your savings, your 401k, and be a broke bum living in ‘van down by the river.’”
  • “You are just not over your ex-girlfriends… crazy fuck.”
  • “You will never find true love… just like your dad.”
  • “Couldn’t you have thought up a more creative trip? This one’s been done.”
  • “Wanting a job you really love is silly, childish, and stupid.”
  • “You can’t believe your gut instincts… be smart.”


I’d bet it all to follow my own heart and as I questioned, doubted, and struggled in my head, my world transformed into a dark, cold, forbidding nightmare.

And the Texas people kept driving past.


The best I could do… was to act like I was still confident.

I hoped.

I prayed.

I tried to smile.

I bought a hot cocoa.

I graciously accepted an oil-smeared raincoat that helped keep out the wind.

I tried not to hate all the Lovey-Warm-Happy People, who didn’t have room in their lives for me.


And I just kept putting my thumb up.

Have you had a lonely cold day on your adventures? What kept you going?

Thanks for taking a minute to share in the comments.

Your friend,


20 Responses to The Coldest (Loneliest) Day Of Your Adventure
  1. Jamie
    February 6, 2013 |

    I know this feeling so well. From my own hitchhiking trip I learnt many things. One such thing that kept me going through the hard times is the notion that, “Tomorrow is another day.” No matter how high or how low you go, tomorrow will be different. Enjoy the highs. Hold tight through the lows. Without one, you couldn’t possibly hope to have the other.

  2. Ulli
    February 6, 2013 |

    Germany, somewhere on a big highway, it was my first day… I never hitchhiked before and I never met someone who could give me a good advice on how to do it. I just wanted to try it out but nobody gave me a ride and I simply thought “This will never work! NEVER”…
    Finally – after half a day of waiting – an old guy showed up and drove me all the way through the country. At the end of the day I was camping at a riverside with five polish hobos (I couldn’t speak polish, they couldn’t speak german/english), sharing some eggs and wine, laughing, enjoying life.
    It worked!

    What kept me going ever since?

    Experience, I guess…

    To know that it (Hitchhiking) works provides you with confidence. It worked in the past, it will work in the future.

    So…don’t be afraid!

    Thumbs up!

  3. Marcus
    February 6, 2013 |

    When things get really dark, the only thing that keeps me going is knowing that I’d add to the problem by giving up. All the sneers of doubters, criticisms of old lovers, self doubt, anger, insecurity, dissapointment, and embarrassing memories can surface. All of our weaknesses and “if only”s can enjoy free reign in our heads. They can demonstrate proof of their veracity by any means they can muster. For me I know I can be all the things they say I am, because in due time they will call me something different. But shame of throwing away my gifts and my word to myself is the darkest of all. When we have our dignity and our mission we brave the cold night warmed not by our positivity or good attitude, but by our resolve and faith in something greater than our own troubles. Without those elements, we freeze to death.

    • Benjamin Oliver Jenks
      February 6, 2013 |

      Yes… our faith in something greater than our own troubles.

      To look back on our life of always giving up just when it got tough for us… would be the true horror.

  4. Susan @ Travel Junkette
    February 6, 2013 |

    Hey Benjamin! Very honest post. I think we’ve all had that feeling before while traveling — what the hell am I doing? Why am I not at home in my PJs watching “The Bachelor”? Well, that’s what I’m thinking, at least. I love the quote “Travel is only glamorous in retrospect.” I try to think of that on my awful days, and I remember that these are the moments that I’ll grow the most. And nothing ever seems as bad the next day!

    • Benjamin Oliver Jenks
      February 6, 2013 |

      Haha… I’ve never actually wanted to be at home watching the Bachelor, Susan ;) . Maybe Jersey Shore though. heh.

      It always gets better doesn’t it.

  5. Karen
    February 6, 2013 |

    Ha! You are truly amazing. I just had my day yesterday. I am not hitchhiking but I am trying to navigate uncertain waters where the ones you think would be the ones to give you that much needed ride are never who you’d expect. Or someone says they’ll be back to get you and they don’t stick to their word. It just reminds you, no one will ever care about your quest as much as you do so just be brave and figure out how to do it yourself! Also, thanks for being your brave sharing self Benjamin! You rule! :)

    • Benjamin Oliver Jenks
      February 6, 2013 |

      Oh yeah, hitchhiking seems a minor adventure compared to some of our adventures in life. Mucho love come in your cold day from here, Karen. :)

  6. Justin Gray
    February 6, 2013 |

    It was the Friday before Fat Tuesday. I’d just arrived in New Orleans after catching a ride with a couple headed there to see the parades. I had planned on spending a quiet week exploring the French Quarter and watching the buskers on Jackson Square, but it appeared as though Serendipity had other ideas, for I had not known that it this was the weekend of the grand celebration. I had been on the road for a month, working my way south from Ohio and gradually letting go of the impulse to know the time and date. I had not connections in the city, and didn’t know its layout very well so I simply began walking around. As night gradually descended, I looked for a remote park or discrete bushes in which I might inconspicuously sleep. Twice I thought I had found my place, and twice someone attempted to steal my backpack as I dosed off. Thoroughly rattled, I couldn’t sleep the rest of the night so I walked around and enjoyed the drunken spectacles offered by the tourists. It began to rain around 4am, and gradually built up to a downpour which lasted all day and night during which time I slid from place to place hiding from the cold wet weariness which was beginning to set in as my new reality. I failed to find a dry place to sleep which had not already been claimed by another displaced soul, and thus endured a second night without sleep.

    I hoped I might find rest in a church somewhere on Sunday, but found that the single meal I had ingested the day before (a sandwich with some hot sauces and a coffee) would not agree with me and thus was forced to relegate myself to the confines of a port-o-potty until my body had cleaned itself. I felt far from clean, and hunger began to gnaw at my core while the weights of sleeplessness slowed my motions and thoughts to a vague mush of nonsense. My weary body trudged along the wet streets, gaining moments of panicked clarity whenever a stranger brushed by me as I checked to make sure I was still carrying my backpack and my pockets were still inhabited by my personal effects. Leering police officers, jumpy from being understaffed and overworked on this long weekend, stared me down as I wandered the streets trying to find food and shelter. But my delirium was too great, and before I knew it another night had passed.

    Walking was the only thing that kept me awake. I dared not sit down for fear of falling asleep. And after witnessing the arrests of several individuals for loitering, I did not want to provoke their ire when my hazy mind was not capable of explaining that ‘no, I’m not on drugs, just tired’ to any inquiring individual. Hallucinations began, and I heard my name being spoken by anyone that I passed. I recklessly spent money on small portions of crappy food, not wanting to eat too much for fear of having it disagree with me. I found a port-o-potty to handle another disagreement, but I fell asleep instead. A bang on the door 15 minutes later from the cleaning men nearly had me walk out the door with my pants down. I composed myself as best I could, and wandered on.

    Whenever I tried to get a ride out of the city, a cop would show up and tell me to get off the street because hitchhiking was illegal. The only hope I had was a transit that ran from NOLA to Lafayette for $5. But it wouldn’t resume its schedule until Wednesday; today was Monday. Hope stirred inside me. I hadn’t felt it since childhood as keenly as I felt it now. It filled me with strength, awareness, and relief – there was an end, and it was coming. I just had to endure another day. But Hope would not let me go. As I prepared to face my 4th night without sleep I was discovered by two friends I had made in Florida two weeks before. Barely being able to communicate, they took me to the apartment they were staying at where they let me shower, fed me, and let me sleep. I slept 20 hours, and awoke early Wednesday morning to my friends watching me sleep and listening to the dreams I had been verbalizing. We shared a laugh, and I thanked them for their kindness before I left to catch my bus.

    Never before have I faced so intense a trial, or been tested in so many ways so severely. Looking back after I had recovered, I see many ways I could have rescued myself. But I am glad I didn’t. The perspective I gained by enduring that process gave me a glimpse of the determination I am capable of, and allows me to appreciate many things to a greater degree than I did before.

    • Benjamin Oliver Jenks
      February 6, 2013 |

      Wow that was a doozy, Justin!

      I’m not surprised this set of trials when down in NOLA. That place. Dark. Sexy. And Ruthless, she is.

      Thanks for sharing your story in detail

  7. Kira
    February 15, 2013 |

    Ah, West Texas…..that’s where I’m starting out from here in a few weeks, and this will be my first hitchhiking experience. Already I’m feeling doubt as some of my close friends and family members are (to say the least) not very supportive of my mission. I hope I can keep your lessons in mind and realize that there are better things in store for us!

  8. janet
    February 19, 2013 |

    The story seems short! But I guess you just have to keep your thumbs up.

    I think it’s illegal to hitchhike in some states?

    I totally feel like an escapist sometimes, living abroad. Sure, it’s pretty much my home country since i’m originally *from* here, but I grew up and do still have allegiance to the USA. At this point, I wouldn’t seriously consider renouncing my citizenship. And took the steps to be a dual citizen.

    Yet it’s hard to be ‘away’ from the US. There’s a lot of logistics that make it harder to live as an expat and I feel really clueless about being a wordly citizen especially with finances/taxes. Doesn’t help that I don’t have an expat community I hang out with..

    There are a lot of things about American culture I don’t like, that I feel like a bit of an escapist. But I know there are people like me living in the US who ‘get it’, and who are living simpler, less material lives.. That’s what I ultimately want, I just have chosen the international route to get there.

    You know by now my big adventure was walking about 800km in a tropical island. No hitchhiking. Just walking. It was very humbling though, and people were very kind and receiving so I never had to experience waiting as long you did for anything. Things seemed to manifest pretty fast, actually, in the most accelerated way, that I have never quite experienced before or since then.

    But there were still moments where it felt hard and I questioned my life choices, as I still often do, and I felt like a bum. And completely inferior and unconfident and unsure of myself sometimes. Yes, Jesus did something similar. I’m not really into the bible but I learned a verse that resonated with me while I did the walk: And Jesus said to him, “Foxes have holes, and birds of the air have nests, but the Son of Man has nowhere to lay his head.” Matthew 8:20.

  9. TLock
    March 11, 2013 |

    Here are a couple journal excerpts from my attempted thru-hike of the Mountains to Sea Trail across North Carolina, which I did completely alone, despite being a total extrovert (I say attempted because I completely ran out of money and had to call it quits… for now):

    Day 20, Monday 9/17

    16.5 miles today. Rain is Relentless. Had to night hike through rain to find suitable water source & set up camp in rain. Eating, pissing, sleeping… all under a diamond shaped tarp that barely covers my outstretched body. More on this tomorrow. Hope I stay dry and warm tonight…

    Day 21, Tuesday 9/18

    Rain continued hard all through night and morning. Trees falling all around me in hard winds. One was too close for comfort (though it sounded much closer at night than it actually was in the morning). Packed up in the rain & hiked through some of the hardest rain yet. Sections of trail completely flooded. An entire mile and most of the next was ankle to shin deep ford. Reached Linville river around noon. It is UNFORDABLE. My fears have become my reality. If I attempted to cross, it would be impossible. I don’t think I could even swim to the other side, let alone carry my pack over. If I even made it to the other side, I would no longer be in a camping situation, but rather a survival situation because my down bag would be soaked. With no way to stay warm & dry I could become hypothermic. So now I’m stuck 31 miles into a 73 mile section. I feel f***ed. If the river is not fordable tomorrow morning I will probably decide to turn back and hike till I get cell phone service (probably all the way to NC-80 where I started this section), and ask to be picked up. If that happens I don’t know if I will try again or not. I don’t think I have enough money to finish the journey anyway. Considering quitting at this point is really pissing me off. Not being able to ford the river is pissing me off. Wishing I had more time and money. Wishing I could have predicted this & just stayed in Asheville until the rain passed. Cannot express my frustration in words. Woke up in a watery Hell-on-Earth and just hoped I could ford this river when I got here and that the rain would stop. Well I can’t. The rain did stop just now while writing this, so now I’m just hoping it won’t pick back up again so I can get out of here soon (tomorrow morning at the latest). Probably will not get to post office in Linville in time for mail. Hope I don’t run out of food, may have to ration myself. Will probably stay in/near Linville until post office opens, if I even make it there. Things have consistently gotten worse & worse since I started this section. Am I finally at it’s worst? Will it finally start turning around and looking up? I don’t know. Wait and see.
    Well it turned out I made it out of there, just had to wait a while and calm the mind. it was about 20 hrs after writing that that the water came down enough for me to ford naked with my pack over my head (water was still chest deep). The weather was beautiful and I climbed Shortoff Mountain and marvelled in the beauty all around me, atop Linville Gorge, surrounded by Peregrine Falcons!

  10. [...] could just be a couple teenager girls offering you a hamburger, on a day you have never felt lonelier. Or a place to crash, when the temperature might drop below. Or even just a smile from a stranger, [...]

  11. Russ
    September 1, 2013 |

    dude, solid post! enjoyed reading it.

  12. Childers
    September 25, 2013 |

    The decision to transfer to a more challenging college where I knew no one after the death of my older brother brought many cold days. Many of them were filled with hopeless feelings and thoughts of giving up. I constantly questioned my decision despite knowing it was for the right reasons. Marshall’s framed photo sits on my desk and reminds me why I made this decision; to make him and my family proud, to challenge myself, and to become the best person that I can be. Life has a funny way of working out, but you have to persevere to experience the true beauty of it.

  13. Changbai
    October 24, 2013 |

    I enjoyed reading this one!

  14. Becky
    December 26, 2013 |

    This is very off topic of the post but-
    What happened to Lily? Has she contacted you?

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