From 100-Hour Workweeks to a Laidback Life of Luxury

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Posted by The Savvy Retiree on October 23, 2020 in Make Money

“Are you out of your freaking mind? When you’re retired, you’re supposed to be enjoying life—not working!”

That was the loud, emphatic reply I heard after sharing that my definition of retirement included at least one part-time job. And my subsequent explanation of doing “fun” jobs where the money wasn’t the primary goal rang hollow in my then-wife’s ears.

That conversation occurred over 25 years ago, when retirement was still a distant goal for me. And while I had a vision, at the time I had absolutely no idea how to make it happen. I just knew I wanted to work in retirement…but when I wanted, where I wanted, and for whom I wanted.

Fast-forward a decade. I’d started a successful technical training development company where my engineering experience—combined with my business partner’s instructional design expertise—gave us a competitive advantage.

Work was good and my bills got paid. But we often had to submit proposals with very short turnaround times. That meant proposal time consisted of 100-hour workweeks juggling kids and current clients’ work while writing technical proposals that would hopefully bring us more clients.

After a few years and a couple of dozen proposals, that pace began taking a toll. My engineering brain kicked in and I found myself asking, “How can I streamline our proposal writing process so it doesn’t kill me?”

The “Eureka!” that transformed my life

In early spring of 2012, I was in the middle of an intense gym workout when it hit me. I returned home and scoured my archives for a 10-year-old Early to Rise email from Michael Masterson, aka Mark Ford, the co-founder of AWAI.

In it, he described this direct response copywriting thing, which he’d personally used to create hundreds of millions of dollars in wealth for himself, his partners, and his protégés.

Over the next eight months of study, I learned and practiced the basics of sales letter structure…which were eerily similar to our proposal format. Because of our proposals’ success, I knew firsthand this sales letter structure worked.

So to make sure these lessons “stuck,” I spent six weeks writing a sales page—for free—for an online marketer whose email list I was on. It was a mental challenge filled with dozens of rewrites. And one curled-up-on-the-living-room-floor existential crisis triggered by the, “Why’d you think you could write?” question.

But the resulting copy worked. And then the client told me the going rate for my project…

After collecting my jaw—and the phone—from the floor, I calculated that I could have made as much money in six weeks of “spare time” as with my training company.

And I was a rank amateur. So the potential was even higher.

A copywriting life

Over the next few years, I kept working the copywriting “side gig” until it was generating as much income as my training company. And both sources were portable.

Caving to my restless spirit, I tossed the laptop in my backpack and hit the road. With my hang glider on the truck, I headed south for the winter…eventually settling on a sailboat in the Sea of Cortez.

One day while sipping a homemade margarita in a Mexican bar, it dawned on me—I was living the retirement definition I’d expressed more than a quarter century ago.

But thanks to copywriting, that simple realization was just the beginning.

Soon after, I met and became friends with top copywriters like Bob Bly, Nick Usborne, Gordon Graham, and Clayton Makepeace. I’ve shared conversations—and laughs—with them about childhood hijinks, our kids, and our respective goals for the future.

I’ve been blessed to work with amazing copywriting clients on five different continents…while sailing on the Sea of Cortez and hang gliding over the Rocky Mountains.

And I’ve met amazing clients and friends who are living mind-blowing lives totally under the radar.

People like Jimmy Tuma Tandu, who stowed away on a freighter from Africa—only to wind up in Mexico after two years and four continents to embark on an entirely new life… Leticia Latino, who leads a multinational wireless communication company while writing books, hosting a podcast, and raising two young children… And Jerry Cirino, who sells the world’s most unique—and best tasting—Bloody Mary mix from the California Sierra foothills at an age when many other folks have retired to their rocking chairs.

So if your ideal life includes thrilling adventures, amazing people, freedom to enjoy both, and a little cash to help pay the bills, copywriting could be the key to realizing your dreams.

By Keith Trimels