The Biggest Lesson I Learned from Working 50 Jobs in 50 States

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Something my best friend James and I invented in college was called “Coffee Pops”. It was this brilliant idea of freezing coffee with just the right amount of creamer into recycled plastic popsicle containers. Living in the scorching summers of Austin, Texas we thought it would surely be a refreshing hit. I could already see University of Texas students walking around campus, sipping their coffee pops and cooling down.

We tried out several versions of coffee and flavors until we found just the right combination. I came home from work one day and James stood proudly in the kitchen. “Try this,” he said. It was delicious.

After creating our first coffee pop, our next step was to check out out to make sure all domain names were available, as well as twitter handles, Instagram, Pinterest and every other social media. We talked about the possibilities of starting Coffee Pops LLC. It was exhilarating to dream up all the possibilities for Coffee Pops. It was going to be a million dollar business.

But then something happened… well more accurately, nothing happened. We never started the business. It fell off into the abyss somewhere and we never talked about it again. It was like the girl I was “best friends” with in high school for a few years who I finally confessed my deep love for via text message. One day we were best friends- talking, hanging out, and the next day it was like we’d never met. I had fallen so hard for this girl and let her slip away, and my only attempt at making her like me back was sending a few text messages confessing my love. I didn’t even give myself a real chance to be rejected.

Now that I think about it, I’ve treated all of my ideas in the same way. I’ve confessed my passion for them to myself and a few close friends, but never given them a chance to succeed or fail. Every time I have an idea, I bundle it up inside until it festers, and then just let it go. Most of my ideas have died somewhere between conception and action, very few of them ever released into the world to succeed or fail.

In fact, looking back over the past 24 years of my life I can see a clear trend for every time I’ve had a new idea.

  1. It starts with the brilliant idea. I’m extremely excited, my adrenaline is high and my mind running at a million miles per second.
  2. The next phase is calling up my three closest friends to share my world-changing, awesome idea. Whoever answers the phone first will be the winner of getting to hear my idea first. For some reason my cousin Jake ended up being the one who answered the phone most often. After awhile I’m sure he must have realized he was my go-to-idea-sharing-guy, but he seemed to share my enthusiasm most of the time so I welcomed his voice on the end of the line.
  3. After the phone call, I will do a bit of note taking about the idea and stash them away.
  4. Check the url to see if it is available.
  5. Go make a sandwich and never think about the idea ever again.


My past has been a massive litter of abandoned ideas. Some that possibly could have made an impact in the world, but who knows? Nobody. Because I never acted on them.

I didn’t struggle to dream big. I struggled to take any kind of action on my dreams and ideas.

It wasn’t until right before I left for Hourly America that I was hit with this reality. Standing in an apartment kitchen and talking to two of my best friends, this is what one said.

“Heath, I love you man. But for the past two years I’ve seen you come up with idea after idea, get excited about them, only to let them fall by the wayside. You’re about to get married and it’s not just your life anymore. You have responsibilities to Alyssa. I think this 50 state trip is a cool idea, but more than anything I just want to see you finish something.”

When I heard these words, my immediate instinct was to be insulted and defensive. But I couldn’t be mad, he was right. I was an idea guy. I wasn’t an action guy.

The prodding of “following through on my ideas for once” came at a great time. I was about to fly up to Richmond, VA to meet the company that would end up sponsoring part of our cross-country journey. A couple days later after meeting their team, the in-house videographer who was mentoring me for our documentary asked me a question.

“Heath, this is going to be a long journey. Why do you want to do it? What’s your real motivation? When it’s three months in and you’re in the middle of nowhere Kansas, it’s raining, and your RV breaks down– what is going to keep you from quitting?”

I thought about it for a few moments. On a surface level I wanted to give a more “selfless and holistic” answer like, I’m doing this for hourly workers or for the greater good of humanity. But I knew those weren’t the reasons that would keep me going through difficult times. I already knew the answer.

“My whole life I’ve been an idea guy, but I’ve struggled with following through on them. I don’t want to just be an idea guy. I want to finish something.”

I didn’t mean to, but I felt a bit of tears welling up when I told him this and he could see my sincerity. “Okay,” he said. “Good luck.”

I flew back to Texas a few hours later and began getting ready for what would be the biggest adventure of my life. Four days after our wedding we left Austin on a quest to travel to all 50 states in the coming year. Along the way, we were going to make a documentary (with no previous experience) about hourly jobs throughout America, while I attempted to find a job in every state. Not only was this my biggest idea I’ve ever had, it scared the hell out of me. It wasn’t the job searching or breaking down in the RV that scared me most, but what if I quit halfway and came home?

If I quit, I’d prove to myself and to everyone else that I wasn’t capable of finishing anything. I’d grow into an old man, talking about all of my ideas I had for frozen coffee pops instead of showing my grand kids all the cool things I’d done with my life.

So I put all my focus into not quitting. Every hurdle we faced on the road, I remembered why I was doing this.

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I remembered my reason why when three hours into our trip, our Honda CR-V was falling off our tow dolly and we had to leave our car in west Texas.

And ten days in, when our RV completely broke down in Williams, AZ and we had to replace an expensive piece.

Or a month in along the Pacific Coast Highway when our engine started overheating.

And in South Dakota, while watching Gladiator, we had to seek shelter during a thunderstorm and in the process our RV was struck by lighting and fried our house battery.

And while parking at a friend’s house in St. Louis when our refrigerator coils blew up and we went for a month without a working fridge. Without enough money to replace it, we kept our food cold by stuffing bags of ice into what used to be our freezer.

Through all of these moments, I thought back to one singular focus: finishing.

I had to finish. I had to keep going through all of the mess if I wanted to be the guy I hoped to be. I couldn’t live my life as an idea guy. I had to be someone who did stuff, who finished what he started. So we kept driving, I found us a new fridge, and as a team Alyssa and I held each other accountable to our goal of moving forward; one state and job at a time.

Last week Alyssa and I climbed into a helicopter and departed for my fiftieth job at Denali National Park in Alaska. We landed on a glacier at 7,200 feet, the base camp for Mt. McKinley. My job was shadowing a park ranger for the next 24 hours. After stepping off the helicopter I looked around, surrounded by peaks that were thousands of feet up in the air, jagged rocks on every side of me, and every few minutes there would be a mini avalanche that would come firing off one of the mountains. If I had just come to Alaska as a tourist, this moment would be one I’d remember forever. But because it was my 50th job and the end to Hourly America, it meant so much more.

It meant I had finished. Hourly America was no longer an idea. It was finished.

A week later, I’m sitting back in Texas and I wanted to share with you the biggest lesson I’ve learned from working 50 jobs in 50 states. And it didn’t come after my last job, it actually came three days before we ever started our trip. It was the night after our wedding and I wrote this in my journal.

Sunday, May 25th   12:39PM
Mt. Gainor Inn     Dripping Springs, TX

It hasn’t hit me yet- the fact that we’re about to be on the road for seven months and not see our friends and family. I don’t know how to mentally prepare for that. I know how to financially prepare (some what), I know how to physically prepare (packing, taking care of previous apts, etc), but I’m not quite sure how to mentally prepare. I mean, do I get excited about certain parts of the country? How am I going to balance working and being with Alyssa? If I have to choose, I should always choose her. It’s in my vows, after all.

Everything is different now. Everything. It’s just not the same. I don’t think there’s any way I could have really prepared for getting married. I mean we did pre-marital counseling, we read books, studied the bible, prayed for each other, but at the end of the day there’s no place you can be mentally that says– I’m ready to be married. It’s always going to be a huge leap of faith.

What I’m beginning to see is that maybe it’s like that with all big decisions in life. Any time we decide to take a risk and live a good story. We say we are going to do this big, audacious goal and then when it finally comes time to go and move– we pray like hell we can do it. The funny part is, most of the time we can do more than we ever imagined. The only thing we really need is the courage to commit to going on the adventure in the first place.

I asked Alyssa to marry me because I was in love with her and I knew I wanted to spend the rest of my life getting to know who she was and how I could love her more. I wanted to share my life, my faith, and everything with her. I probably could have used a few more months of being groomed to become a husband, but what the heck, sometimes it’s better to just jump in and learn the ropes as you go.

I won’t be the same after last night, not ever. In a good way. Just like after we get home from Hourly America, we won’t be the same. We’ll be changed. We’ll have met people that challenge our thinking and what we believe, and we’ll encounter circumstances that test our weaknesses and our relationship with each other.”

As I was trying to find the words to describe how I felt after finishing Hourly America, I realized I had already found them in this journal I wrote from before we ever left. And I was right. There was no way to prepare for this moment, or getting married, or traveling to all 50 states. I think what holds us back the most in life is that we put off our dreams with the excuse that one day we’ll be ready. We convince ourselves that one day the timing will be right and then we can leave our jobs and go travel the world. When there is the perfect amount of money in the bank, then we can start the business. But if there’s anything this trip has taught me, it’s that there are certain things in life you can’t truly prepare for. After a certain point of planning and preparation, you just begin procrastinating out of fear.

As I look forward at the next part of my life, I’ll remember that with any big dream or goal I will never be fully prepared for that moment. When I sit down to write my book, I won’t be prepared. When Alyssa and I are getting ready to have our first kid together, I definitely won’t be prepared. But I’ll also remember that is what makes life interesting and beautiful, to experience moments we weren’t entirely sure we could handle in the first place. After all, if we were 100% sure everything was going to be fine, what’s the point?

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3 Responses

  • Heath, THIS needs to go in your book.

    I’ve told you before that I’m an ideas person – that I can totally relate to how you feel. Maybe I wasn’t in the thick of the last seven months with you, but I can massively appreciate what you’ve been through to get here. Congratulations on accomplishing your goal and dream, and definitely keep those ideas coming!

    • Thanks Janelle 🙂 I really appreciate it. And I hope to craft my book around this similar topic of idea execution, working on that right now :).

  • […] bought an RV, we found a sponsor, and in the past 14 months we’ve traveled to all 50 states (including an epic RV road trip to Alaska). After all, we had the energy and the time to adapt to the traveling […]

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