On a cold winter morning in New York City’s West Village, I sat across from my wife (then girlfriend) Brittany, enjoying conversation over a typical Saturday brunch. We chatted about the prior night’s festivities, the freezing weather, the blueberry stuffed french toast – typical light-hearted banter to ring in the long-awaited weekend.
As it often did, the topic of work arose. It had been “one of those weeks.” 6:00 a.m. wakeup calls followed by intense 15-hour days. Lots of stress, little sleep and even less quality-time together. As I vented about the grind, Brittany listened intently and then asked me the question that changed our lives forever:
“Jordan, what to do you really want in this life?”
Follow My Lead
As a 26-year old capital markets analyst for a large bank, I found myself at the office early, late, and anytime in between. And while I enjoyed the challenge and found the work interesting, banking was not my true passion. It provided a nice lifestyle, but as Brittany had recently found out, there was far more to life than working for the weekends.
Brittany too had spent a few years in the finance, but quickly realized that the cubicles and regimented schedules of Corporate America were stifling her creative mojo. She knew it wasn’t the best fit for her and made the decision to pursue her passion of photography.
Brittany freezing time for a client during a lifestyle photography session
The new photography business venture wasn’t without its early struggles, but one year in and she was finding her groove – booking clients regularly and watching her studio grow. She now understood the exhilarating feeling of waking up each day to chase a profession she loved. And, she wanted nothing more than for me to share that same feeling.
Face Your Fear
So we talked and planned and dreamt about me leaving to pursue a lifelong dream of creating a business around golf. It’s a game I’ve loved from the moment I picked up a club, some 20 years ago. From late nights on the putting green as a teenager, to several mile bike rides to the course (clubs on my back) in college, I’ve always had a true passion for the game.
Rolling putts circa 2002!
We made the move from New York City to Charlotte, North Carolina, where I continued to work, but had more opportunity to move toward making golf a full-time job. However, taking the leap from a steady, well-paying job to an entrepreneurial endeavor turned out to be harder than I imagined.
Letting doubt and fear overshadow the potential for turning my passion into a career, months went by until finally, it was time to face the fear. Time to pursue my passion.
Marrying Our Passions
With a plan in place, I said goodbye to the banking world and ran full-steam ahead toward an exciting new venture in golf. My focus would be two fold: 1) playing professional golf events (think minor leagues for professional golf) and 2) working to grow The Dapper Drive (www.thedapperdrive.com), a golf and travel website we had hatched a few months prior.
Taking a swing at the uniquely beautiful Streamsong Resort’s Blue Course (Bowling Green, Florida)
The Dapper Drive was our way of marrying our passions for golf and photography. Through the website, we share our experiences at the many golf courses and resorts we travel to, offering readers a glimpse at the experience they too can expect. Visual content is a large part of how we share these stories.
Enjoying a stroll down the 17th fairway at the breathtaking Cabot Cliffs (Inverness, Nova Scotia)
Between golf events and traveling for The Dapper Drive projects, we were looking at a ton of time on the road. We tossed around various ideas from temporary housing in frequented regions to buying a Prius (a scary concept for a 6’5’’ guy!), but the prospect of long car rides, expensive airplanes and living from a suitcase didn’t strike us as all that appealing.
Suitcase living? No thanks
And then, as fate would have it, on a long-drive from North Carolina to Pennsylvania, we passed an Airstream. Brittany’s eyes lit as she excitedly proclaimed, “Wouldn’t it be awesome to travel by RV?!” Her free-spirit adventurous side bubbled with joy as I (reluctantly) entertained the idea.
My practical side was searching for reasons to shoot it down, but the more we discussed, researched and explored the idea of traveling full-time by RV, the more attractive it appeared. Cheaper, much better than suitcase living, and most importantly, a means to travel together as a family with our dog Ella and cat Mr. Penelope.
So after months of research, we made the move, purchasing and renovating a 30-foot travel trailer.
Working in our renovated camper under the watchful eye of our dog, Ella, and cat, Mr. Penelope
Mom, Dad … We’re Moving into a Camper
Can you imagine how that initial conversation went!? Six-months prior I had announced I would be leaving my 7-year banking career, and now a decision to travel full-time in a camper? They must have thought I’d gone off the deep end!
As a couple who had never even been camping, to say Brittany and I were “green” is an understatement. Our first months on the road were quite the learning experience, but we found our groove and quickly fell in love with the freedom and sense of discovery felt while traveling full-time.
A last minute detour off-route led us to Teton National Park to meet some fellow photography friends. Some of our best memories on the road are those unplanned!
As the first year flew by, I began shifting focus away from the grind of competing in golf events toward really growing The Dapper Drive brand. We loved traveling to new golf courses and sharing our experience with other travel-loving golfers. What could we do to really elevate our content and continue with this nomadic lifestyle, we asked ourselves? And then bam! It hit us.
Capturing the moment on the 18th green at Bay Hill Club (the late Arnold Palmer’s home club) in Orlando, Florida
The Ultimate RV for the Ultimate Golf Road Trip
To up the ante, we decided to embark on the Ultimate Golf Road Trip (www.thedapperdrive.com/ultimate-golf-road-trip) – an epic golf journey where we’re traveling the U.S. to play each of the top 100 ranked public golf courses. Oh, and we’re planning to do it all in 2017! Beyond golf, we wanted to pursue this year-long project to inspire others and to share an inside look at the people, stories, and tales we experience while discovering America through the greatest courses accessible to all.
A map of Golf Digest’s ranked America’s 100 Greatest Public Courses that we’re aiming to travel to and play in 2017
Logistically, this trip requires lots of travel – 20,000+ miles and 35+ states in just one-year. Because we’ll continuously be on the move, we decided to trade in the camper for the class-C Winnebago View. The compact and mobile View is perfect for life on-the-move, allowing us to park in individual parking spaces (think golf course parking lots), easily dry camp for days, and quickly move from place-to-place.
A few weeks into the Ultimate Golf Road Trip and we’re loving life in our View.
Enjoying a sunset with the whole crew at a winery. We spent the night here, too! (thanks Harvest Hosts www.harvesthosts.com)
The Pursuit of Passion
I often think back to that one moment 4-years ago, in that little cafe in downtown Manhattan, and the question that sparked it all: “What do you really want in this life?”
If you haven’t found you passion, keep searching. If you know what it is, keep chasing. Because the old saying really is true: If you love what you do, you’ll never work a day in your life.
Pursue your passion – I promise, it’s well worth the journey!