Climbing The Ladder: A Simple Technique That Could Change Your Life Forever

Photo: Peyton Hollis

In March 2017, Mike Ragsdale of The 30A Company served as Guest Editor of Good Grit magazine. This article by Ragsdale and photos by Peyton Hollis are reprinted with permission.

“Go confidently in the direction of your dreams! Live the life you’ve imagined. As you simplify your life, the laws of the universe will be simpler.”

Everyone stared up at me, shielding their eyes from the sweltering noonday sun. From my gusty perch, they all looked like ants baking on white hot concrete.

“DO IT, YOU WUSSY,” someone taunted from below.

Teenage girls snickered. I couldn’t actually hear them snicker from way up here, of course, but I knew they were regardless. It’s what teenage girls do.

I inched as near to the edge of the platform as I dared and nervously peered over. From this vantage, the Olympic swimming pool below looked like a bucket that some deranged carny might plummet into.

Point Mallard’s “Emasculator” in Decatur, Alabama.

Growing up in Cullman, Alabama, our family made frequent summer pilgrimages to Point Mallard Water Park in Decatur. With a video game arcade, a riverbank beach that was only frequented by the kids smoking Vantage Ultra Lights, and a huge “wave pool” that tossed around exhausted children like an angry old washing machine, Point Mallard was a teenage right of passage.

The towering chain-link fence that surrounded the compound wasn’t as much to keep freeloaders out, as it was to keep hormone stricken teenagers corralled while their exhausted parents ducked out to the shopping mall or the closest package store. It was the perfect cage in which to pit awkward token-rich boys against one another in gladiatorial feats of pre-masculinity before a blood-hungry audience of giggly girls in bikinis. It was a terrible spectacle that sent scores limping home with savage strawberries from being dragged along wave pool walls, and even deeper psychological scars from the “Beyond Thunderdome” manner in which we all plowed our way headfirst into puberty. Point Mallard was also home to a 10-meter high dive platform where Olympic gold medalist Greg Louganis once trained.

“C’mon kid,” sighed the lifeguard. “Either jump or climb back down.” It was a motivational speech he gave a hundred times a day.

My choice was simple: Jump and risk dying upon impact… or suffer a long, humiliating climb back down the 3-story ladder while throngs of teenagers laughed and jeered. Death wasn’t so bad. I jumped.

Mike behind the wheel of “Truman,” his daily drive. Truman is a 1986 British Ministry of Defense Land Rover. Photo: Peyton Hollis.

About ten years ago, I read a book called The 4-Hour Workweek by Tim Ferriss. The book’s “work smarter, not harder” mantra really spoke to me, as I was deeply fatigued following a couple of failed business ventures. Ferriss’ best-seller spun larger-than-life tales of solo-preneurship and unlimited global travel, fueled by powerful new internet marketing strategies. I soon set out to create such a business, and by 2011, my startup had become self-sufficient enough to actually entertain the notion of unbridled travel through exotic lands.

But could we really do it? Could we really bounce around the world for a year? I wasn’t too worried about our income stream, as I was already running the business entirely from my laptop at home. Couldn’t I run it just as easily from Kuala Lumpur or Bosnia? I didn’t have any employees or office to worry about — just a global network of freelancers who helped me keep all the wheels turning, precisely as Ferriss had prescribed.

Turkey, Indonesia, India.

But what about the kids and their school work? Who would watch our house? Who would take care of our dog? What if something happened to our parents or grandparents while we were trekking through some Cambodian rainforest? “What if’s” are anchors that can prevent our lives from ever setting sail. Truth be told, we had absolutely no clue how to pull off something so gargantuan. We just had my zealot-like belief in a book that promised me we could.

So, late one night on a wine-fueled spousal dare, we charged four non-refundable around-the-world plane tickets to our credit card for about $2,000 each ( We bought them six months in advance, giving us time to figure things out… we hoped. Then, we blurted out what we’d done on Facebook.

We had climbed the ladder.

Terrified, we now stood on a social media stage for some to speculate. Would we do it? Would we actually jump? Like the Olympic platform of my youth, it was either jump, or suffer public humiliation if we chickened out (not to mention a brutal financial loss).

“I almost went around the world,” I would one day tell my grandkids.

Spain, Morocco, Croatia.

Six months later, we boarded our first flight on an epic journey that would span over 20 countries, experiencing adventures ranging from cooking lessons in Budapest to exploring snow-covered caves near the Syrian border to being guests of honor at a wedding in Rajasthan to being evacuated from our home during a prison riot in Bali.

How did we do it? I honestly don’t know. Five years later, it seems inconceivable — “too big” to have achieved or to ever repeat. But we did do it, all because our irrational fear of ridicule outweighed our rational fear of failure.

Tips for “Climbing the Ladder” to promote life change:

Is there something you’ve always wanted to do, but are simply afraid to pull the trigger? Use these simple tips to help you finally take that leap of faith.

COMMIT in a tangible way.

Buy a plane ticket. Submit your two-week notice. Make a big downpayment. Put some skin in the game. This is climbing the ladder. Your decision is still reversible at this stage (well, except losing your job perhaps), but you can’t back out without feeling some serious sting.

BRAG about your plan to anyone who will listen.

Now that you’ve scaled the ladder, gather an audience as quickly as possible before you start having second thoughts (trust me, you will). Be shameless. Tell as many people as possible. The goal is to back yourself into a reputational corner. Always wanted to take surfing lessons in Nicaragua? Buy the ticket and then boast about it to your cubicle-locked buddies. Quitting your desk job so you can fulfill your dream of starting an eco-tourism business? Put in your notice and share a Facebook page promoting your new endeavor. Serious consequences? Big time. Terrifying? Absolutely. But you will figure out a way to make it work. When landing on the shores of Mexico in 1519, invader Hernán Cortés famously ordered his soldiers to “Burn the boats!” When returning the way you came is no longer an option, it’s amazing what you can accomplish.

BRACE yourself for the jeers.

“You couldn’t pay me to go to China,” they’ll brag. “Four of five startups fail,” they’ll warn. “Aren’t you worried about terrorism,” they’ll exclaim. You will start to question whether you’re being responsible. You will start to wonder if you’re crazy. Perhaps we are. But rest assured, the biggest rewards in this life go to those who take the biggest risks. Albert Einstein once said, “Great spirits have always encountered violent opposition from mediocre minds.” Don’t let mediocre minds taunt you back down the ladder.


When the moment of truth finally arrives, you will have the courage to jump. And when you finally step off that ledge and begin your irreversible free fall, that’s when you’ll know: This is what it feels like to be alive.

Photo: Peyton Hollis

Mike Ragsdale is Founder and CEO of The 30A Company (, a brand inspired by the small-town beach life his family enjoys along Florida’s gulf coast.

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