Heath and Alyssa

RVE 89: How 11 RV Entrepreneurs Define Success

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For the past 70 something interviews I’ve done on this show, I always end by asking them how they define success in this lifestyle. Whether that is spending more time with their family, travel, or just having the freedom to choose how they spend their day.

In today’s episode I’m going to share some of my favorite answers since the beginning of this podcast.

But first, I want to talk about why I ask this question in the first place.

1. It helps to challenge me

It challenges me because this is a question I feel I’ve been wrestling with — well, for as long as I can remember. Before we started RVing, I remember I had just sent this cold email to Snagajob — the company who ended up helping sponsor and back our documentary and our initial roadtrip, and I was sitting down to try and figure out how I defined success in this trip.

I started writing about how it would be successful if Snagajob could get x or y publicity out of our journey and how if so many people found out about what we were doing — that would be successful. I promptly realized how dumb this was as I started looking at all of these success metrics that were ultimately out of my control.

Instead, I said that if I grew in my faith, grew closer to Alyssa and grew in my craft — as a writer or storyteller from going on this trip — that would be successful. When I realized this, it felt like a huge weight was lifted off my back.

No longer was success this arbitrary thing, out of my reach, but something I could attain (and attain relatively easily through my own actions). If our story was picked up on CNN or we premiered our documentary to a full theater — those would be a bonus (both of which did happen).

Setting Goals

My friend John told me that what I did in this moment was redefine my goals from lagging goals to leading goals.

A leading goal is that I want to become a better writer. When I think about that goal, it leads me in the direction I want to go. There are a thousand different results or opportunities that could arise as part of that journey.

A lagging goal is that one day I’d like to become a New York Times best-selling author. This is ultimately a result of my actions and not something that I have direct control over, hence the term lagging.

I realize that my tendency in business and everything else is to set lagging goals. Example: I want this podcast to reach a million downloads by the end of this year. My gut starts to tell me that this is my goal. I become fixated on how to grow the show and reach as many people as possible.

But then I realize I’m being dumb again because that isn’t my goal. My goal is to provide value for people who want to transition their lives and business to traveling full-time. My goal is to extract stories, provide value, document our journey and be helpful for you guys.

2. It helps me stay in this moment

The second reason I ask this question in each episode is because I’ve realized my tendency to place my current happiness on future successes.

Before we started traveling in an RV, I remember sitting at my desk at Youearnedit (the software company I used to work at) and looking at people traveling in truck campers and getting to explore all these awesome places. It felt miserable. I was cooped up in an office and these people were able to go explore the country. I knew once I had this, I would feel successful.

Once we made the transition to traveling full-time, I felt the pressure to continue growing our income. I knew once our income was at a sustainable amount, then I could feel successful in our travels.

I could keep going on and on, but I think you get the point. It’s easy to say that once you get to this point — then you’ll feel success. But in my experience, that mark always moves to the next one. I rarely feel any kind of success in between.

I fight back against this to try and put success in the here and now. As much as I want to accomplish big goals in our business, I don’t want to do these things at the expense of living in this moment.

How 11 RV Entrepreneurs Define Success

1. Episode 44: Dapper Drive 

Jordan Griggs

How Jordan and Brittany define success: Following your passion and creating a full-time income.

“My purpose is to learn as much as I can and experience as much as the world as I possibly can. Success is being in alignment with that. Filtering everything through that mission.”

2. Episode 47: Less Junk, More Journey

Nathan Moss Less Junk More Journey

How Nathan and Marissa define success: Having family time, freedom, and flexibility.

“Success is where you can clearly get to what you want without a lot of things in the way. If we say yes to too many things, that takes away from it. The reason we’re doing this is because we want more family time, more freedom and flexibility.”

3. Episode 52: Wayfarer Vans 

Ian Horgan

How Ian defines success: Being able to design your own lifestyle.

“I don’t want to just sell camper van kits. I want to sell you the ability to go out and do the things you want to do.”

4. Episode 58: The Freedom Theory 

Kali Spiers

How Kali defines success: Following your passion and creating a full-time income.

“Success would be for Josh to be able to quit his job and for us to find a way to make vlogging and blogging our full-time income.”

5. Episode 68: Tim Paige

Time Paige

How Tim defines success: Spending time at his family’s favorite places and teaching his kids something in the real world

“Success is being able to spend a whole lot of time at our favorite places in the world — DisneyWorld and DisneyLand.”

6. Episode 70: Inn town Campground 

Inn Town Campground

How Erin and Dan define success: Being happy with the success we have and continually working on work/life balance.

“Build a legacy for our community. I feel like success is already here.”

7. Episode 75: RV Love 

RV Love

How Marc and Julie define success: Freedom and being able to live a life that we love.


“So often people look at one measure of success, like financial success. When you really dig down into why a person wants financial success, it’s to provide freedom (and often travel is a part of that!). Success is being able to live a life that we love now because there are no guarantees in the future.”

8. Episode 35: Paul Singh and Dana Duncan

RVing Across the Country

How Paul and Dana define success: Be happy and have professional freedom.

“I want professional freedom. I think the RV helps us go do that. Plus, you really can’t be an asshole in an RV. I just want to be a good person helping other people.”

9. Episode 17: Jill Sessa

How Jill defines success: Having contentment.

“Contentment. Each day I’ve made a choice to be where I am. Sometimes that means I’m working like crazy, other days I’m reading a book next to a creek. Success is supporting my staff.”

10. Episode 12: Peter and Cathy Holcombe 

How Kathy and Peter define success: Spending time doing the things we want to do and setting our own terms.

“I want it to look like an awesome travel adventure movie. When I look back at it, that’s the life I want to live and that’s it. It’s not about money, it’s not about sexy cars. It’s about spending time with whoever you want to be with. Spending that time doing the things we want to do and not feeling like there is anything pulling us away from that.”

“I think for me, I want Abby to see that we very carefully thought through what was important to us and what we wanted this life to look like. We didn’t let anyone dictate what we wanted it to be. Sometimes it is really hard and we have to work like crazy for it to happen. I want her to see that we set our own terms, and that anything is possible. And if we can give her that it will be a big success.”

11. Episode 38: JD Roth

JD Roth

How JD defines success: Living in accordance with your purpose.

“My purpose is to learn as much as I can and experience as much as the world as I possibly can. Success is being in alignment with that. Filtering everything through that mission.”

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6 Responses

  • Great podcast! Hearing each persons vision of success for themselves back to back made it easy to see the common threads. Also enjoyed your own transparent reflections on the subject. 40 years ago we stepped off the cliff after reading Getting Rich Your Own Way and started living from our passions. We didn’t get rich but we have lived a rich life. Delighted so many are embracing a new way of visioning their life.

  • I’m 61, and I’m so glad success is being talked about for younger people. In my time people did conveyor belt careers. I followed that path, and I spent 30 yrs. doing something I really didn’t love enough. My health failed at 56, and I had to retire early. Cancer forced me to rethink my entire life. Success to me is: being paid for doing something you love which uses all your skills and talents in a positive and constructive way to benefit others and yourself as well. It should be sustainable and not limited by age, location, or a cultural belief system. Success should be the architecture of yourself on a daily basis.

    • Love that definition Michael! Too many people aren’t doing what they love, but it makes such a big difference to chase after the things you care about.

  • Thanks Heath, this is exactly what I need to hear today. Working hard on my business and some days I start to feel a bit discouraged so thanks for the encouraging podcast.

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