Quit Your Job and Take the Train

Every once in a while in life you get to meet someone who challenges how you think about your life and your money. What if I could act as if I had no fear? I had the opportunity to meet one of those special people on my trip to Portland, he was a 19 year old named Max.

Just looking at him you might assume Max is 16 or 17, he’s quite thin with a baby face. He looks a bit disheveled, his shirt is smudged with dirt stains and his face is glossy with oils. He’s not homeless like some of the other young people I meet traveling the country by rail. Max is clearly taken care of by someone as evidenced by his new smart phone. He carries with him a green canvas grocery bag, a blue skateboard, and a backpack so heavy it might be filled with rocks. As we’re getting on the train to return back to California he offers to carry my suitcase up the stairs for me. He’s gotten strong through his travels.


Gundo: I saw you on my train up here to Portland, what’s a young guy like you doing traveling around for so long?

Max: I’ve been on the train since July 1st, I just bought a train-hopper pass it should get me through the month.

For the next thirty hours or so I spent some time talking to Max and learning about his life. I was especially curious to know how someone like this would feel about money.

Gundo: Where are you from and how did you end up in Portland?

Max: I’m from Portland, Maine. I broke up with my girlfriend and just sort of decided to start traveling. At first I drove my Jeep across a few states but by the time I got to Ohio the transmission blew up on me. So I got on the train and rode to Truckee, CA. I stay in a place for a couple days at a time and then get back on the train. I usually meet people along the way who let me stay with them, or sometimes I use the couch surfing app.

It isn’t surprising to me that Max is able to find places to stay. Despite his homeless appearance, grimy clothes and sun roasted skin, Max is very thoughtful and attentive. He manages to seem humble while holding onto a tough guy demeanor. He’d talk to you for hours if you let him, and I’m sure some people do.

Gundo: Do you have a job? Where’s your money coming from?

Max: I don’t have a job right now. I quit my job at the fish market to come on this trip. I’m good with my hands so I’ve always done handyman work. A lady used to pay me $800 to fix up her house while she went on vacation. I’d live there and the house would be clean and fixed when she got home. A guy offered me a place to stay last week if I’d help him with a little mechanic work. I decided to stay with another guy who just wanted to flirt with me. Rather deal with that than hard labor. Anyway, I started this trip with a little less than $2,000. I’ve got $300 left.

Mind you, I spent almost $800 on my trip to Portland so obviously I have some things to learn about traveling on the cheap. Max won’t stay in a $50 per night hostel it’s way too expensive. He won’t even stay at an airbnb for $30. He meets nice people who take him in while he’s in town. When he doesn’t meet anyone, he sleeps outside.

I have to say, Max has a way of asking for things without asking for them. You don’t feel like he wants anything from you or like he can’t take care of himself. Really, he just wants someone to talk about the journey with. But still, you feel like you want to help somehow. People along the way make their small contributions. Every few days a nice adult will buy Max an $8 beer. My contribution was the instant rice and extra top ramen I didn’t eat.

Gundo: What have you been eating on your trip?

Max: I found out pretty quickly that you shouldn’t eat the train food. I spent like $30 just on cheeseburgers and random food the first couple days. I bought about 7 cans of beef-a-roni last week. It hasn’t done me too well my face is starting to brake out. I bought a bag of green apples for $5 in Santa Barbara. Also I have some cheez-its.

Gundo: What will you do after the trip is over?

Max: I joined the Navy I have to be there August 10th. I’ll get to travel the world for free and they’ll pay for my education. I want to get a Liberal Arts degree. Also they’ll pay my medical expenses. I think I want to get a gold cap on my tooth. The Navy has been a real bummer for the trip because it means I have to stay away from weed. I quit smoking cigarettes for the trip. It’s really hard to keep up the habit when they never let you out.

Gundo: What’s been the worst night you’ve had since you started the trip?

Max: Probably the two nights I spent in LA sleeping on the street. When I got off the train I met a homeless guy who showed me around the city. We walked around for hours before ending up in Venice beach. I hadn’t realized how hard it would be to carry my stuff around. My knees were shaking and I was drenched in sweat. I figured out later that guy was completely insane, so I waited until he fell asleep and got away. I would move around every couple hours when things got sketchy around me. I ended up skating down Sunset Blvd as the sun was rising. That was an aweful few days.

I wear these steel toe boots that protect my feet but I don’t take them off. Inside my feet get so hot and scratchy. At first they would bleed and be open blisters all the time. Now they’re just permanently scarred over. I brought a pair of converse with me to skateboard in but they got too heavy so I cut them off my pack and threw them over a power line. Whenever someone lets me stay with them I set my boots outside and run right to the shower to wash my feet.

Gundo: What’s been your best night so far?

Max: There were two. One was when I spent the night with a family of Jehovah’s Witnesses. Nicest people ever, the church congregation were dressed up really fancy and still hugged me and talked to me looking like this.

The second was when I met Annabelle. She was traveling on the train as well and we just clicked. We talked about our whole lives and what we want to do together. I think she might be the love of my life. We can’t be together, you know, because I’m going into the Navy but she wanted me to meet her in Boston. That’s the most money I’ve spent so far. $100 for two nights at airbnb in Boston. Do you think they will have a kitchen?

Gundo: What about beyond the Navy? What aspirations do you have for a career?

Max: I don’t know what I want to do. I want to save up all the money I have from the Navy and just spend years after that traveling. I can make the money last. Anabelle and I want to get a sailboat and sail down the coast.

Gundo: Have you saved for retirement?

Max: No, I’d really like to I know it’s important. I think in a few years I’d like to invest my savings in the stock market. Not in a retirement account but just an investment account. I’ve done some research on stocks and I think I could make some money at it.

Gundo: What’s something you blow money on?

Max: I tend to spend a lot of money on cars with the intention to fix them up. Sometimes I do but other times they just sit there. My friends and I got this car then just spray painted it and drove it into the ground. That was fun.

Gundo: What’s something you worry about?

Max: I worry about relationships. I’m selfish. I tend to meet people who want to stay in touch with me, then I just disappear like dust in the wind. I’d really like to do some of the things I promised when I get back from the military.

Max and I spent some time talking about personal finance and what I do to save money. With how frugal he had become on the trip, he didn’t seem terribly interested or concerned about money. I talked about some of my career plans and about how far I had come since I was around his age. It’s amazing how many things change in 5 short years.

Although we were seemingly close in age, I felt sort of like a big sister figure. I remember being that age and sort of feeling lost in life. I certainly wouldn’t have embarked on such an adventure.

One of the reasons I’m so fascinated with Max is he’s not worried about the uncertain future. He’s excited.

That got me thinking about the motives behind why I save my money. I always talk about how money equals security. If you have money you have options. Money is used as a tool to provide maximum freedom.

Here is a 19 year old who’s living his life as if he has no worry in the world. Where I would be nervous and anxious, he’s quite at ease. He thinks my writing is somewhat hypocritical in fact. I shouldn’t tell people to be happy with what they have because that’ll make them lazy. They won’t work hard or have any dreams.

That’s the difference between personal finance nerds and the general population; we tend to be overly planning and finicky and we need to be reminded to relax and go with the flow, don’t force everything. For Max, he pretty much lives in that state of being. He doesn’t want to hear that he should sit back and be patient, he wants to charge at life head first.

I’m not saying we should all quit our jobs and take the train across the country forever, but we should live life with that attitude. You don’t have to be naive or have ignorant confidence to live your life like Max does. After all, being fearless doesn’t mean you lack fear. It means you greet fear and spend quality time with it. I say take some chances, do things that scare you or make you feel uncomfortable. If you don’t enjoy the journey and constantly wait to feel the joy of achieving a goal you will be unhappy most of the time.

Life is all about the journey, whether it be crossing the country by train or achieving your financial dreams.

Special thanks to Max for talking my ear off for two days. Wish him luck, he is in Boston as this is being written.


  1. Jenn says:

    Love this story! I wish I could have met him, he sounds like a badass!

    • Elsie says:

      He is a super badass. Either he’s brave or too reckless to care, both of which are pretty badass in my book.

  2. Mrs Groovy says:

    I love the story but I have mixed feelings about Max. On the one hand, I admire him for living his life so boldly. But on the other hand, he seems to be carrying around a bit of emptiness.

    I had a discussion once with a very intelligent homeless person. He told me he was offered a good job he was skilled for, but was not taking it because he knew he could no longer live with rules and expectations. He had been on his own too long to deal with authority figures. Max reminds me of that. And with what he said about keeping up with relationships, I just hope he’s able to abide by the rules when he’s in the military.
    Mrs Groovy recently posted…Why Aren’t You Turning Japanese?My Profile

    • Elsie says:

      I agree with you on that I think Max does carry some sadness around. Putting oneself in an uncomfortable new situation is definitely a good avoidance tactic but I think it can also be a way to shake things up and create a different life. I think you can only use avoidance so long, my hope for Max is the trip taught him about himself, and he uses that knowledge to be successful in the Navy. Thanks for the thoughts Mrs. Groovy!

  3. Luann Brown says:

    There’s nothing like really listening to strangers, while on our own journeys, that teach us the most. This, to me, is all about BALANCE.

    • Elsie says:

      That’s true. I’ve tried to listen to people more. I’m an especially good listener when I’m traveling, I’m not sure why.

  4. Great story. It seems he knows how to manage finances and will be a more disciplined person after the military. I think everyone can learn from him. Can’t wait to see how he will turn out in the future!
    Finance Solver recently posted…How I Got to a 5 Figure Net Worth in CollegeMy Profile

    • Elsie says:

      He’s definitely had a good lesson in saving on the trip. I felt that way about myself too. Theres nothing to help you spend less on food like being in an environment where all the available for is marked up 200%. In regular life I tend to go “oh, it’s ok it wouldn’t be that much cheaper to buy this at the grocery store and make it myself.” I need to stop that.

  5. ZJ Thorne says:

    While Matt has some things to teach, he also has a lot to learn. Most people can’t make it through long term on the kindness of strangers. He is not paying his own way, he is charming others to do a lot of his heavy lifting. It’s nice he’s not doing worse things with his charm.

    Most women I know would not be willing to spend a night on the street, because the risks to them are far greater. His experience is not really reproducible and he is literally hurting himself, see the feet and nutrition.

    What he has to teach is listening to others and being open to new experiences, but the costs he is inflicting on others and himself is pretty darn steep. There has to be a better balance available.

  6. Elsie says:

    Thanks for the insights ZJ. Matt is clearly young and has lots to learn, including that long term transience isn’t really a way to live. What I loved is his willingness to try something seemingly crazy, difficult, and frightening. I think there are areas we can apply that within our lives. I definitely don’t plan on quitting and taking the train, but I would hope I’d have the courage to do it.

  7. Brent Truitt says:

    What an interesting person Max is. Don’t you just love people like that. So original. Those are the people we learn from, and you were observant enough to pick up on his specialness.

    Great post!

    • Elsie says:

      Yeah he was such a cool guy. His demeanor was very calm and relaxed, the kind of person you want to spend some time with to suck in that positive energy. It’s been a year since this writing and I’ve kept in touch with him on Facebook. He did in fact join the navy and I see pictures of him with his family now and then. Most of us would be terrified to embark on a journey like that. He seems no worse for the wear, in fact he seems super excited about life. I really admire that gusto.

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