How I Managed to Spend a Month on the White Sand Beaches of Florida

About seven or eight years ago I bought AWAI’s Accelerated Program for Six-Figure Copywriting.

I still have the magalog that sold me on buying the program. When I got it in the mail, I literally blocked out the next evening to read it. So when I got home from work the following day, I sat down on the couch and read the 60-odd-page magalog start to finish — including every sidebar and testimonial.

I bought the course and dove into it immediately. But it took me more than a year to complete it because I was dividing my attention between multiple programs and projects. Nonetheless, the knowledge I learned from the program gave me a much-needed advantage when I finally quit my job in 2005.

Now, some of the promises in AWAI’s marketing quickly came true for me. Others took some time. Here’s a snippet from their current sales letter:

In this world [of copywriting], it’s not unusual to have a shiny new car (or two) in the driveway every year…

To take exotic trips to faraway places several times a year (often for free…)

To be strolling on some ocean shore or tossing a ball with the kids while most people are slaving away in some ever-shrinking cubicle or driving to their next sales call.

Have I tossed a ball with my kids during the work day? Absolutely. We’ve gone on hikes, played at parks, and done all sorts of activities while most people are working.

But I didn’t truly experience the “strolling on some ocean shore” part until just last month — nearly six and a half years after launching my freelance copywriting career.

I want to tell you more about that story. But first I need to back up to the beginning of this year when my wife and I were faced with…

An Unexpected Challenge

The year 2011 did not start well for us.

In January we discovered that the fourth child we were expecting had died. My wife had to go through a long and drawn out late first-trimester miscarriage that was more challenging than we ever expected — both emotionally and financially.

With my vision for the year totally blown to pieces (I thought I was going to be raising a newborn and experiencing sleepless nights in August), I spent a couple months envisioning what I wanted the rest of the year to look like.

During that time, I re-read The 4-Hour Workweek.

I started the Product Creation Work Group to motivate me (and a select group of entrepreneurs) to develop more low-maintenance sources of income based on the sale of products.

And I came up with a rough plan for the year, which I shared here on this blog.

Thankfully, my plans slowly fell into place. Before I tell you about all the things we did, let me explain a little bit of my thinking…

Examining the Facts of Your Life

Most of us have a tendency to restrict what we’re capable of doing and accomplishing to what we observe other people doing and accomplishing.

If all the people in your life are working 9-5 jobs and sending their kids to public school, then it’s easy to decide — unconsciously, of course — that you should be doing the same thing.

And if everybody in your life thinks it’s crazy to go spend a month on a beach, then you’ll probably think it’s crazy, too.

But by unemotionally examining the facts of your life, you may discover you have more opportunity, flexibility, and untapped potential than you realize.

With that in mind, here are two facts about my life:

Fact #1: I’m a freelance copywriter. I don’t have to be in Denver to do my work.

Fact #2: My wife homeschools our children. We don’t have to be in Denver for our kids to receive an education.

Based on these facts, I thought: Why not leverage our location independence to realize a seemingly unattainable dream? And why not do it this year?

“The guard is changing. Being bound to one place will be the new defining feature of middle class. The New Rich are defined by a more elusive power than simple cash — unrestricted mobility. This jet-setting is not limited to start-up owners or freelancers. Employees can pull it off, too.” -Timothy Ferriss, The 4-Hour Workweek, p. 209

I was especially motivated to travel and do more recreational activities because I knew we might still try for a fourth child after summer.

And So the Adventures Began…

For a brief period this past spring, I went on a Groupon-buying binge. As I wrote at that time, “By buying Groupons, I’m not only saving money on fun activities… I’m forcing myself to make time for activities I enjoy doing.”

Plus, every Groupon has a deadline, so I was forced to plan out the entire summer just to squeeze in all the activities I had signed up for.

Here’s a quick summary of the things I did with my family and friends:

  • We spent a weekend in Steamboat Springs to participate in my wife’s cousin’s wedding. Great time with friends and family.

Deep Snow on Trail Ridge Road

  • I went on a 2-day biking trip with two of my brothers, my friend, and his dad. We started in Granby, bicycled over Trail Ridge Road (at 12,183 feet above sea level, it’s the highest continuous highway in the U.S.), then dropped down into Estes Park where we stayed the night. We rode back the next day. More than 140 miles and 9,000+ vertical feet in two days.
  • Spent almost a week working on-site with a client in Illinois. I really enjoyed this. While I was there, I boated on the Mississippi River and took a long leisurely bike ride on the trails that run along the Mississippi.
  • Took the family up to Granby and stayed overnight. Spent a day in Winter Park doing the alpine slides, miniature golf, a maze, the climbing wall, and the trampoline jump where you’re hooked into a harness attached to bungee cords. The kids LOVED the alpine slides. We’re going to go again next summer.
  • Watched a UFC fight on an iMax screen with a few of my neighbors.

Ryan about to Drive a Dodge Viper

  • My dad turned 60 this year, so I bought tickets for us to drive exotic sports cars at Pikes Peak International Speedway. I drove a Dodge Viper at 100+ mph three times around the track. My dad did the same, except he drove a Corvette Z06 and Shelby GT500.
  • My wife and I went white water rafting down Clear Creek, which runs alongside I-70 as it winds up the eastern side of the Rocky Mountains.
  • That same night, my wife and I stayed in downtown Frisco, then biked from Frisco to Breckenridge and back the next morning. Gorgeous scenery. (We drove back into Breckenridge for a little shopping on Main Street later that day.)
  • Enjoyed a night of improv at the Impulse Theater in downtown Denver. (Impulse Theater is the longest running show in Denver. It’s hilarious.)
  • Went downhill mountain biking at Sol Vista with my brother and friend. Another perfect day in the mountains.

Of course, all of these activities were leading up to

Our 1-Month “Mini-Retirement” in Florida

In the spring, I negotiated a deal with my uncle to stay at his condo on Siesta Key for a whole month. I made the reservation and paid a deposit months in advance, so we were committed to go no matter what.

Pool and Beach at Sarasota Surf & Racquet ClubSo in early September we packed up the Odyssey and left the rarefied air of Denver for the sun-baked beaches of Siesta Key.

It was a three-day drive across eight different states: Colorado, Kansas, Missouri, Illinois, Kentucky, Tennessee, Georgia, and Florida.

Once we arrived, we unpacked and settled in for a full month on the beach. We practically lived in our bathing suits and went down to the beach and pool twice every day.

Of course, during this time, I still did some work. I bought an iLugger bag for my iMac and hauled my computer down to Florida. I worked 3-4 days a week for about 4-6 hours a day. Just enough to keep my business running.

This made me realize: I have more time flexibility than I think I have. I don’t need to be in front of my computer eight hours a day, five days a week. It’s just not necessary. One of my goals now is to better utilize work time so that I can pursue more recreational activities.

Anyway, while we were in Florida, we decided against visiting the big amusement parks. Not only were they a two-hour drive from where we were staying, they were also exorbitantly expensive. One day at Disney World was going to run us $407 for the tickets alone. Tack on parking, food, and souvenirs, and it would have topped $500 easily.

If we had hit three big amusement parks, that would have cost around $1500 to $2000 — a price I was not prepared to pay, especially given the age of my children.

View of Sarasota from the BayUltimately, we decided to do some less expensive “non-touristy” things.

  • So we went to Lowry Park Zoo in Tampa, Florida — the same zoo I had visited as a 4-year-old child.
  • We went to the Mote Aquarium in Sarasota and took a boat tour of Sarasota Bay. We saw dolphins playing, dozens of blue herons and cormorants, as well as fish, crabs, and sponges that are native to the bay. (Catching the sea life and holding it up close was Owen’s favorite activity.)

The Dali Museum - Helical Staircase

  • To cap it off, Steph and I dropped off the kids at my aunt’s house in Tampa and visited The Dali Museum in St. Petersburg. The Dali houses “the most comprehensive collection of original Dali artwork in the world.” And, as you can see, the building itself is a work of art.

A month is an ideal length of time for a mini-retirement. It was a great experience, and I do miss the white sand beaches and brilliant sunsets. But I’m also glad to be home. I’m a social person and being away made me realize how much I value my family and friendships. (My wife, on the other hand, fell in love with the beach and would have been thrilled to stay another week or two.)

The St. Louis ArchOh, we did one more thing before we got back to Denver.

  • We stopped off in St. Louis for a day and went to the top of the St. Louis Arch — the Gateway to the West. The arch is 630 feet wide and 630 feet tall. And did you know there’s a free museum under the ground underneath the arch?

As I’ve reflected on our summer of adventure — and our month-long “mini-retirement” in Florida — I’ve realized we’re all capable of doing much more than we think we can.

The key is to live intentionally.

Certainly, you will face obstacles just as we have.

But you don’t have to let obstacles dictate how you will live. Instead of letting life happen to you, you can make life happen.

What’s stopping you?

-Ryan M. Healy

P.S. A parting thought for you:

“Sabbaticals are often viewed much like retirement: as a one-time event. Savor it now while you can. The mini-retirement is defined as recurring — it is a lifestyle.” -Timothy Ferriss, The 4-Hour Workweek, p. 235

I’m already thinking about what we’ll do next year. :-)

Playing on the Beach

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Ryan Healy

Ryan Healy is a freelance copywriter, list manager, and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like,, and

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