On July 19, 2020, Keen started a hitchhiking and cycling pilgrimage bound for the southern tip of Argentina.

Pilgrimage Route

Starting in a city outside of Chicago, Keen has already traveled over 5,000 miles and has made it as Neiva, Colombia

He has even been featured in the Derby Informer:

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“I know people are important. If I met no people along the way, wasn’t able to share smiles, laughter, or stories, then I doubt that I could continue. “- Keen

He’s met a lot of people in the USA, Mexico, and Central America.

The Backbone helped him carry his 44L hiking backpack!

USA (Q3 2020)

Mexico (Q4 2020)

Central America (Q1, Q2, & Q3 2021)

So far, he has biked over 3,500 miles, hitchhiked 1,000 miles, and bussed 500 more on his way to the southern tip of Argentina.


Where are you coming from?

Valparaiso, Indiana. A city outside the Chicago

Where are you going?

The goal is to make it to southern Argentina.

How long will it take?

I originally planned 18-months for this pilgrimage. There are cyclists who’ve cycled the whole length of the Pan-American Highway in less than 3-months. But the point of my trip is not to break a record but to learn more about myself, people, and what people do. That is why I call it a pilgrimage.

You are hitchhiking and biking?

Yeah, mostly biking but I’ve hitched rides from amazing people. I’ll need to sail or fly to cross the Darien Gap.

What kind of bike do you have?

I have a custom made Roark 3×9-speed titanium road bike with 7700 Shimano Dura Ace components on 28mm tires that I’ll be riding down to Argentina (if it makes it haha)

When did you decide to do this?

I was stretching one morning doing my normal thing when the idea of going on another bikepacking journey (I had been on 2 already. A 100mile, 1-day trip. And a 790mile, 14-day trip) spawned in my mind. “Cycle where?”, I thought. An internal dialog started playing and I’d answer myself but the dialog just continued “No. Where?”, as if the answer I gave didn’t suffice. It kept on going until someone or something in my mind said “the southern tip of South America”. The dialog stopped. Everything stopped. Moments later, I continued my workout as if nothing crazy happened but I never forgot what happened. Days passed and I still remembered. So, I started googling and found it’s been done before. And not only that but there was a whole world devoted to traveling ultra-long distances by bicycle. I found cyclists completing a trip from northern Alaska to southern Argentina in 100 days. I thought “why not me too”. Not in a 100 days but in 18 months, I thought to myself.

How did you prepare?

The purpose of my workouts were no longer just to get big and strong. Now I was on a mission to train for this insane pilgrimage. My workouts intensified. I did more cardio and stretching. I started learning how to punch and kick. It was great. I was focused and I felt great. I was in the best shape of my life physically and mentally. But all of this preparation was an act. I honestly wasn’t certain I’d have the cojones to start. Preparation is one thing but starting what you prepared for is a pivotal moment. It’s a pivotal moment that doesn’t come to fruition for most people. Often, people eternally wait and wait for the perfect moment or find endless excuses to post-pone the “start”. Hey, I understand, it’s honestly a life-changing decision.

Did you tell people?

So with all the terror that comes with preparing for a life-changing moment, I was simply just acting as if I would go, all my actions proved I had made a firm decision. I told people. But, mentally I felt less firm in what I was doing. No, not just “less firm” but I was shaking inside. I was putting on an act for myself and others. But the act was not a lie. I was aware of the mental backdoor I gave myself if I needed to escape this idea of biking south. And the mental backdoor was just that, an idea. I had yet to decide to bike south. It was just an idea that I pretended to take seriously. It was an idea that changed my actions as if I had decided on it. The distinction might sound like I’m splitting hairs or that there’s a meaningless distinction between acting on an idea or delivering on a decision but I didn’t feel that way.

Why is the distinction between “idea” and “decide” important?

Being honest with myself is important and by understanding words and their nuances then I have a higher proclivity to believe in myself and what I say in the future. For example, to mentally say, not to someone else but to yourself, “I will ______”, is a deceleration. It might as well be printed out, framed, and put above the fireplace mantel. “I will” statements are serious. On the other hand, by saying, “I am acting as if I will _____” then I’ve created a backdoor. Whatever comes to fruition is the truth. Not to say the latter is not serious but it’s just honest about the possibility I don’t fulfill it.

Cultivating my mind to take small or big declarations seriously and to create similar grammatical and nuance backdoors, I think, has contributed to the self-belief I needed to prepare for my pilgrimage and then start it. To what extent, I still don’t know. Maybe it was negligible.

What a contributing factor to you actually starting your pilgrimage?

I acted as if I would start.

Who inspired you?

Honestly, Ragnar Lodbrok in the show Vikings partly inspired me.

What keeps you going?

People. If I met no people along the way, wasn’t able to share smiles, laughter, or stories, then I doubt that I could continue. So, I know they play an important role in my drive.

What have you learned about yourself during your pilgrimage?

That I have patience. A trait that contributes to my willingness to bike far

What is something you thought before this trip that you now know is wrong?

I thought adults had things figured out and that they knew more than me but, not necessarily. Age and knowledge/maturity/wisdom do not correlate. This is hard biase for me to correct and I still struggle with it because I want it to correlate for me as I grow older.

Do you ever feel lonely or afraid? And do you ever want to give up?

I’m quite content with being alone for a while

I’ve felt afraid during my initial interaction with an angry coach on his baseball field. But later he was more intrigued with my travels

I think about giving up nearly every ride but the thought doesn’t stay around long enough. I know I just cycle throughs and emotions and that is okay.

If you had to tell one piece of advice to someone based on your experience what would you tell them?

Don’t take things so seriously. We are a speck on this planet and our planet is dust in the universe.

Do you have a job? Or how do you pay for your expenses?

I’m good with my money. I started saving since I was a kid. Then, started investing in the stock market at 17 where my investments have more than doubled as of 01/01/2021. I also was homeless to save on expenses (you can read more about that here lol). But since I’ve started my pilgrimage I’ve only been spending what I’ve saved; I haven’t earned any money. So, I started this website in hopes that my content will eventually make me money. If you like my free content and want to see more please support me by donating here. I appreciate your financial investment in my website and future

An interview about my method of transportation