Stephen and Shae Pepper have been married for 13.5 years. They’ve lived in the UK, Thailand and the US on both the East and West Coast. They added a fur-baby to their lives 4.5 years ago, Truffles, and she is a silky-poo (silky terrier-poodle mix) and is 10lbs of pure joy. Stephen worked in the insurance industry and Shae was a youth worker and teacher before leaving on their road trip. Stephen now writes for No Home Just Roam and Frequent Miler while Shae is working on her photography, transcribing Truffles’ blog and has an educational website in the works. Additionally, Stephen (the introvert) is in charge of the spreadsheets and budgeting and Shae (the extrovert) is in charge of public relations and Truffles’ baths. Truffles is in charge of being cute.
We are both dreamers, but very different in our execution. As Jon Acuff says, I’m ‘WOW!’ and Stephen is ‘HOW?’ and while that works well for us as a couple, it can make following our dreams challenging. I’m ready to go to the next big, new, WOW idea right now- I’m all in from the moment the idea pops into my head. Stephen needs details, support systems and the HOW ready to be answered before he’s ready to commit fully to the dream. So, when he approached me with his WOW idea of making our dream of a fifty-state road trip a reality, I was shocked and said ‘but, wait- HOW?’
Everything seemed to come together over the course of a few weeks. The youth nonprofit I’d started (my dream) wasn’t gaining the support we’d hoped for and it was quickly becoming clear that it was time to think of next steps. This was in March of 2016. We went to discuss what to do with the organization with my mom, and she turned to Stephen and asked him ‘What’s your dream?’ I said, ‘good luck getting blood out of that stone, I’ve been trying to find that out for 11 years!’ and Stephen turned to her and said ‘well… actually…’
I was shocked. What!? He shared that he’d really like to do the fifty-state road trip we’d discussed in passing over the last six years living in the US. And that he thought it should be five years, so we could really take our time to experience each state at an average of 4-5 weeks per state (10 states a year). As I thought about it over the next week, I looked back over our time together and knew that he’d always supported my dreams. Even when the ‘how’ was a little sketchy. It was his turn. So, I said one night, let’s do it, and we closed the nonprofit and began to look at the logistics of how to make this five-year, fifty-state road trip work.
First, when should we go? We’d already scheduled a trip to Australia and New Zealand for a month in December 2017. So, it seemed that January 1, 2018, was a great date to start a new life and a new adventure. This gave us a timeline for all the other things that would need to happen.
Second, what would we do with our home and all our stuff? We listed our property with my mom’s brokerage and sold it to the first person who looked at it. We rented for a year near the school I was going to work at for the year and started our extreme minimalism challenge.
Third, who should know about this? We started with our parents, then our friends, jobs and finally the world! We started the blog May 1, 2017, which included our planning stages as well as our travels leading up to the trip.
Fourth, where should we go? We laid out the plan for the five years in a basic format and then created a spreadsheet with all fifty-states that includes accommodation, dates, cities, and ideas of things to do. We aren’t doing a very efficient road trip. We are following the good weather (for the most part) and the fun and quirky things that make American awesome like Goat Derby’s.
Finally, how would we pay for it? After years of building sites to generate a modest passive income, Stephen had figured out that we could just about make the trip happen on $100 per day. We finished paying off our debt (which we had been working towards for a few years) on December 31, 2016. We saved, gathered hotel points and airline miles, and worked two and three jobs respectively to leave with the savings goal we had in mind.
For me, the hardest part was all the goodbyes and endings. Closing down the nonprofit was hard, that was the dream I’d been working toward for eight years. While I’m not a hoarder by any stretch, I definitely have more of an emotional attachment to things that Stephen. We had to compromise and agree to keep some things in storage plus figure out what could fit in our car. We are doing this trip in a 2004 Toyota Carolla so space is limited. Saying goodbye to family, community youth, colleagues and the students I taught was especially hard.
For Stephen, it was giving up the financial security. We were finally in a position to be debt-free and build up savings only to then earmark it for this trip was really hard for him. He used a lot of great ideas to get discounts for gift cards, getting AAA and AARP (it’s not just for old people!) memberships and becoming a Groupon guru helped him get ready for our new budget lifestyle.
We’ve only just started on the actual doing of the dream itself so we haven’t achieved all we hope to yet but the first four weeks have definitely been a learning process. We are much more tired than we anticipated (but let’s be honest when you spend a year and a half being excited, nervous, scared and enthusiastic it’s bound to catch up with you), and we’re having a harder time getting on a schedule than we thought.
But we’ve had some real ‘wins’ as well. We’ve already met amazing people and puppers. We did fit what we wanted into our car. Truffles is slowly adjusting to her new vagabond existence. We’ve seen the World’s Largest Fire Hydrant, ran a 5k, eaten bison, seen a 400-year-old tree, made our own Kazoos at a Kazoo Museum and Factory and much more and this is only ¾ of the way through state one, South Carolina.
For anyone thinking about their dream. Do it. But don’t just follow the WOW of your heart, listen to the HOW of your head. Do your research. It sucks sometimes, but I know that if we’d just left in the summer of 2016 like I wanted to we wouldn’t have been ready for this and it could have really been a mess, financially, emotionally and in our marriage. You have to find the balance between preparation and procrastination. I’d recommend checking out Quitter by Jon Acuff and 4-Hour Work Week by Tim Ferris for inspiration. Don’t let your dream go unfulfilled because it’s hard or seems overwhelming. Break it down into chunks and eat that elephant one bite at a time. Then do it. Step out. Try the thing.
Ultimately, you will probably regret trying and not quite meeting the mark much less than never trying it at all and having a life of ‘what ifs.’