How Developing a Tolerance for Risk Changed My Life

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Before Alyssa and I packed our lives into a twenty-year-old RV back in 2014, my friend Jonathan said something that caught me off guard.

“Heath, you might be wildly more successful than me in life because of your high tolerance for risks.”

I remember this conversation vividly for a couple reasons.

One reason is because the last thing I felt when I quit my only job out of college was “successful”. The other reason I remember it was because my friend Jonathan is a rising star in a tech company and the youngest person to ever graduate from Harvard Business School.

By most measures, he was doing well in life and I was temporarily living in a trailer park inside of an RV that all too closely resembled Walter White’s Winnebago from Breaking Bad.

However, over the past few years I’ve thought back to this conversation and the relationship I’ve developed with risk.

In some ways, I’ve continuously made decisions that seem incredibly risky (i.e quitting my job to go live in an RV and travel). But in other areas of my life I’ve become much more risk adverse (i.e finances, health, relationships).

I wanted to write this post to share a few things I’ve learned about risk over the past few years. Specifically, how taking disproportionate risks can change your life.

1. More risk = more potential for total disaster or crazy success.

When we decided to uproot our jobs, buy an old RV and go travel the country for seven months — this was a substantial risk.

We risked putting our careers on hold for an extended honeymoon road trip. We risked our safety while traveling the country in an old motorhome and staying in random parking lots and campgrounds across the country (for some people this might feel like more of a fear before you start RVing, but in reality, we rarely felt unsafe).

We risked our financial well-being and our savings account because we didn’t know how we were going to generate income. We risked putting a strain on our relationships with family because of a crazy life decision.

tolerance for risk
4 days before we hit the road 

However, because we jumped into this big risk, there ended up being disproportionate room to succeed.

Here’s what happened:

We didn’t go broke. However, we did end up building our video, writing and business skills which helped us grow a client business on the road. This past fall we even finished paying off $27K of student debt.

Kyle Kesterson

Our relationships weren’t strained with family. As it turns out, they came to love our lifestyle and frequently meet up with us on the road. Because of RVing, we’ve created some amazing memories with our parents and siblings while going on adventures in beautiful places.

Our RV never left us in an unsafe situation, but often created amazing memories. The only time it ever did break down, it created a spontaneous adventure that we cherish to this day (it involved free beer, breaking our first martial arts boards, meeting a semi-famous person at a gas station and the Grand Canyon).

You Can't Force Magic

Ultimately, this seemingly huge risk to leave it all behind and go travel the country in an RV created an amazing lifestyle and business for us.

Could there have also been a chance that our RV quit running and we went broke? Absolutely. These scenarios were baked into the risk we accepted before leaving.

More risk = more potential for total disaster or disproportionate success.

2. If you’re able to foresee and accept the worst-case scenarios, it boosts your risk-tolerance.

During the fall of 2016, my friend Eric suggested something crazy — we should host a conference for RVers.

While my ego loved the idea of bringing together a bunch of travelers like us, the rational part of my brain freaked out at the prospect of hosting a conference where nobody showed up.

“I will look like an idiot,” my brain said.

While I sat down to think through this idea a little more, I started thinking through what a worst-case scenario might look like.

I realized that we had quite a few of RV friends who would be in Texas for the coming months. In a worst-case scenario, I calculated that we could persuade 10–15 of our closest friends to come and join the event. I decided to accept that potential fate and then move forward with the planning (okay maybe Alyssa did more of the planning).

As it turned out, more than 15 people show up. We sold out and had over 120 people come!

We booked out the entire Jellystone Campground and it led to a crazy number of relationships and opportunities for us in 2017. This year we’re hosting the RVE Summit again and the event has doubled in size, selling out again.

While this risk wasn’t as intimidating as the one we faced in 2014 (telling our parents we were leaving our well-paying jobs to live in an RV was definitely scarier), there was still risk involved. We would have to learn how to put together a conference, we’d have to put ourselves on the line and say we were hosting an event (even if nobody showed up). We’d have to create a ticket price to justify a conference and then find people who would come and speak at it. And in the end if we failed, we would be failing in public.

The risk in this scenario was more of a potential ego bruise, but I think these risks are important because they are the risks we have a chance to face on an often basis. Should we write a blog that shares something personal, or tell someone how we really feel? Each of these moments we risk putting ourselves on the line.

However, by acknowledging (and accepting) a potential worst case scenario, it becomes much easier to accept the risk.

3. If you can view each dumb mistake as a learning experience, you can create a habit of risk-taking.

I thought about sharing another risk-example where I took a risk and did something cool, but it’s probably more useful to share a couple of the dumbest risks I’ve ever taken.

Case in point #1: Heath risks dropping out of college and quitting his job for “living the dream in California”.

Risk: Heath accepts first paid internship in college. His parents buy him some fancy clothes and are proud that he’s growing into a responsible human adult. Two weeks later after receiving his first large paycheck, he promptly quits job without notice, tells his parents he’s dropping out of college (but it doesn’t matter because he’s going to be a successful entrepreneur) and then moves to California and lives on his friend’s couch.

Result: I came home a month later with my tail between my legs after running out of money and decided to finish my last year of college. My mom eventually forgave me, although she likes to bring it up every now and then just to remind me that I’ve occasionally made terrible life decisions.

Yes, I was a huge idiot. I took a disproportionate risk and hurt several people in this process. I was entitled, immature, and I thought this risk could be a positive, life-changing one for me (not sure what logic I was measuring that by). As it turns out, it only hurt my mom, dad and caused a lot of stress to those closest to me.

Case in point #2: Heath spends $5,000 buying t-shirts that are never sold.

Risk: Heath starts a fledgling clothing line in college, sells out of first couple orders, and his father invests $5K to help him grow inventory. Thinking he would sell out immediately, Heath spends almost all the money on buying inventory.

Result: The shirts sit on my shelves for 12 months and the business runs out of money.

Once again, substantial risk in starting a business. This time, it didn’t pan out. I spent money that wasn’t mine and created my biggest life failure to date (something I’m still embarrassed to share today).

When I look back on these risks, they both taught me a substantial amount:

By all means, take risks but take calculated ones.

I didn’t calculate the potential downside of quitting my internship to move to California and drop out of college. It was selfish and the downside of screwing over my parents and employer wasn’t worth the risk. I took this knowledge with me for the next time I quit a job. Instead of just quitting, I gave 3 months notice so they’d have plenty of time to fill my role.

Be conservative with your projections.

AKA, never blow all your money on physical inventory because you think you’re going to sell it all in a week.

Even if you do sell out of a physical inventory (or insert “x” product here) in a week, you can spend a fraction of your money on inventory and then just buy more when you need it. The long-term success of any business largely depends on a healthy financial runway. Don’t blow it all because you’re being a cocky idiot (advice to future Heath).

Even if you screw up, you can bounce back.

I think this realization was the one that allowed me to take the next big risk when it came to full-time travel. I knew that even without preparation and in haste, I was able to bounce back after the California fiasco (and learn in the process). I would take what I’ve learned from that experience and try to ensure success for the next adventure.

Ultimately, both these experiences taught me that even when risks don’t pan out for the best, they often yield themselves to the best learning experiences.

Side note: I 100% admit that I couldn’t have gotten through either of these without the help/support of my parents. I also realize that my “bouncing back” isn’t realistic for many people who don’t have that same kind of support system. Hopefully, you can make better life decisions when it comes to not embarrassing your parents.

I wrote this post because developing a tolerance for risk has changed my life for the better.

If I hadn’t bounced back after the California incident, I probably wouldn’t have had the confidence to buy an RV and go travel the country. Last year I decided to start, even after taking a risk and failing at my clothing company. Why? Because closing up shop and feeling like a complete failure turned out to be a somewhat tolerable process. I knew that even if this next business didn’t succeed, I could survive the consequences, which made it worth the risk.

Each risk I’ve taken (whether it worked out or not) has helped me develop a habit of taking risks.

Risk is an essential part of bringing in opportunities and going after the things we want most in life.

Challenge question for anyone reading this: What has been the biggest risk you’ve ever taken and what came from it (good or bad)?

13 Responses

  • Heath, great post and its too bad the Tampa RV show is not in February. We don’t return to the warm of Florida until 2/1. Would have loved to have met you all in person. Since we start our life as full time RVers in February maybe we will see each other on the road at some point.

    I very much agree with you points 2 & 3. #2 is all about risk mitigation. I’ve spent my career in the IT field so this is one thing we are all about. #3 as you’ve stated is about learning. The more you know the less risk there is next time.

    But I’m not completely in your camp on point #1. And maybe it has to do more with the definition of success then it does with risk tolerance. As someone in middle age I am in a position to opine on my life success. And I feel I have been very successful. I’m content, happy, comfortable and to me that is MY definition of success. And maybe I’ve gotten here because I’ve done a lot of #2 (I research the $h#t out of everything) and a good bit of #3 (though could do more).

    I have not taken many “risks” in my first 1/2 decade on this planet but I think I am about to. As mentioned, we go full time in February and I do see this as a big risk. But I’ve done a lot of #2 (squirreled away a lot of runway) just in case we have to come off the road, and I’ve done so much #3 that at times I feel overwhelmed. Thank god for folks like you and Alyssa, YouTube, Facebook. Tiffin RV Network and all the people behind all these. How else would I have figured out my batteries were frozen and NOT to try and jump start them (BOOM).

    Keep up the fantastic work and enjoy sunny Florida.

  • Wow! so inspirational !
    2 years and a half ago decided to quit my job and leave my country. If I had stayed in my hometown, I surealy knew that the future would bring, I had stability but not much room for developing myself. So I left everything behind to start from 0 in a country whose language did not speak at all ! (France). I started working as an au pair, living in someone’s one house and working lots of hours taking care of two girls. So many times I felt frustrated, wondering If I had made a mistake, If I was throwing away 7 years of education plus all my work experience just to be in a place where it was cold, I could not even engage in a conversation and doing a job that was way worse of what I could had back in my country.
    I can say that today I can speak the language, I have found love and I have found a new profession that I love and that I would had never been able to do if I had stayed home (I work in the features movies industry, and we dont have any studios where I am from). And I am earning twice as much as I could have ever earned if I had stayed in my old job. To me money was not the priority, but it is allowing to pay off old debts and to help my family a bit.
    So it has been incredibly hard and challenging, but as you said learning from mistakes of the past (when I gave up on things maybe too quickly) has helped me to carry on in despite of the frustration, loneliness or cold weather (I am from Tenerife, the European Hawaii, so moving to the Alpes area was indeed a big challenge!)
    Thanks again for your post ! Hopefully I will see you here when you come for your rv adventure in Europe !

  • So enjoyed meeting you and Alyssa @ RV show TAMPA yesterday. Keep up your wonderful work to keep the rest of us so inspired. Jacque

  • […] cup of tea and while we may not do this forever we would have never known unless we tried. Here’s another 20 something couple creating a tolerance for […]

  • Another great post. Thank you for sharing it, Heath. The reflection you two do and open communication about goals,successful choices and failures is wonderful to see. Encouraging to repeat. Biggest risk? Following my husband to Europe with his job, learning another language (still not fluent though) and living there for six years was up there. It was worth it even if didn’t fallout 100% like I planned. Still an AMAZING thing to do from 26-32. Also taking guardianship of my three younger siblings. Two graduated now and last one in her senior year. Some bad fallout from it on myself and us as a couple at times but very much a good turnout for them and THAT is a true success for me. Even if I have ripped half my hair out and rock in a corner ( 🤔😂) THEY are becoming the best version of themselves and have been happy and safe. Look forward to the next posts.

  • Since “stuff” always seems to happen to me. I recently realized that people that “stuff” never happens to are people that don’t go out an “Do”. I’d rather do…

  • At 33 with a wife and two kids, I quit my job of ten years, cashed out my life savings, borrowed $70,000 more, and bought a small hamburger and ice cream parlor in a rural small town mall. I knew within 90 days that I had made a massive mistake. But contracts had been signed.

    Four years later we finally sold the restaurant for the balance of the note to a buyer who paid cash. We still owed $28,000 on personal credit cards, and I was working a job earning only $12 an hour.

    The lessons learned are many. My successful entrepreneur friend says I earned the equivalent of an MBA. I know I learned America is a great country. I didn’t end up in debtors prison and I eventually paid off my credit cards.

    My wife didn’t leave me, and you know in this age of no fault divorce she could have and no one would have blamed her. But we got through it together as a family. My kids saw their parents keep their word even when it was very difficult.

    I learned I can learn anything and do just about anything I put my mind to. So it is important to apply myself to projects that are meaningful and rewarding and not just financial.

    Now, I am hyper aware of the risks to rewards ratio. I have completed a few projects since the restaurant. But I lost a part of me because of the stress, and I am not sure that is a bad thing.

    • Hey Michael,

      So appreciate you sharing this story. I can’t imagine what that journey was like. I’m glad to hear you came out the other side with your family and optimism still intact.

      Best of luck for whatever entrepreneurial ventures come your way next,


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