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7 Things I Learned Living Alone on an Island for a Year

things i learned living on an island
Longboat Key, FL

In 2013, I was inspired by a TED talk to spend a year “away.” I moved from Louisville to Longboat Key, Florida.  I rented a house on the beach for an entire year.  I didn’t know anyone there.  These are the biggest things I learned:

1. Embrace the Seasons of Life

I realized that life is not supposed to be the same thing, day after day, year after year.  The seasons of nature should also apply to our own lives.  I listened to Tommy Nelson’s ‘A Life Well Lived’ sermon series and read Necessary Endings by Henry Cloud while I was on the key and it helped me understand the idea of embracing and implementing seasons in my life.

  • There are seasons for education and seasons for doing
  • There are seasons for traveling and seasons for staying home
  • There are seasons in community and seasons of solitude
  • There are seasons to make money and seasons to spend money
  • There are seasons to speak and seasons to be quiet
  • There are seasons for endings and seasons for beginnings
  • There are seasons to work hard and seasons to relax

Suggested Books: A Life Well Lived, Necessary Endings

2. Walking Has Hidden Benefits

I discovered the hidden benefits of walking.  I made it a habit to go on long walks every morning and every evening. Walking helped me get away from distractions, be alone with my thoughts, process emotions, brainstorm business ideas, think creatively, and many more things.

The book Digital Minimalism by Cal Newport explains why walking is so important. Here’s an excerpt from a review of the book:

“But the best way to find solitude is, quite simply, by walking alone. Newport pays tribute to Abraham Lincoln’s time at the Soldiers’ Home cottage in North DC as a reprieve from the busyness of the White House, as well as Friedrich Nietzsche’s long sojourns in the Italian Alps. These times of withdrawal provided both men the space and time necessary to make hard decisions and produce great works. As Newport puts it, we need solitude to flourish, for “humans are not wired to be constantly wired.” Likewise, Henry David Thoreau, one of Newport’s constant companions, would walk to town rather than using a horse and wagon, thus exemplifying technological minimalism. In fact, Thoreau calculated how the hours it took him to walk from Walden pond to Concord offset the amount of labor hours it would have taken him to afford the wagon. Tragically, we have surrendered this calculus, Newport argues, to the purveyors of the attention economy. We’ve traded our souls for a few small conveniences, and we need long periods of solitude to recenter the self that is now scattered across the digital landscape.”

excerpt from Taylor Fayle’s book review of Digital Minimalism by Cal Newport

Suggested Reading: Taylor Fayle’s Article, Digital Minimalism

3. Always Have Something On Your Calendar to Look Forward To

The idea of being alone for a year on an island was a little depressing. The beach is fun for a few days of vacation…but a year?  I had made plans to go on a cruise with my friends John and Clint about two months after moving to the island.  I thought about that cruise everyday.  Looking forward to the cruise was better than the cruise itself!  After that,  I made it a point to always have something on my calendar to look forward to every few months.

You should always have something fun or adventurous to look forward to every 2-3 months on your calendar.

4. Moving Makes You Richer

Sounds crazy, but hear me out.

Every time I moved to a new place, I made more money. I made better friends. I broke bad habits. Weird, right?

Here’s why I think it happened:

When I moved, it forced my brain out of autopilot.  I figured out new ways to optimize my life, had fresh ideas for how to improve my business, had a new sense of clarity, and met new and interesting people.  Every time I moved I purged all the junk in my life and refined what I thought was really important.

My theory is that when you live in the same place, your brain gets lazy.  Moving is painful, but it forces your brain to create new neural pathways.  This article by Tara Swart explains it much better than I can.

5. Don’t Work At Disney World.

While I was living on the island, my cousin Thad and his wife Andrea came to visit me.  We took a road trip to Disney World.  I hadn’t been there in 25 years, since I was a kid.  We had a blast!  It was one of the greatest days of my life!  I had coffee with one of the Disney princesses who told me she had to stay skinny to keep her job.  And, then it dawned on me…Disney is a giant machine and hires and fires people constantly.  I realized that if you really love something, you should keep your distance.  

I had spent six years working at a mega church in Louisville.  Bob Russell and Dave Stone had helped grow the church from a few dozen people to more than 25,000+.  I got to hear their preaching when I was a kid and really loved both of them.  After finishing grad school, I got a job at the church.  Six year later, I dreaded going to church.  I still loved Jesus, but I saw too many behind -the-scenes “things” that going to church gave me severe anxiety.  Going to Disney World helped me realize the mistake I had made.

Lessons learned:

  • If you really love Disney World, don’t work there.
  • If you really love your church, don’t work there. 
  • If you really love a person, don’t work for them.
  • If you love the beach, don’t live on an island.

6. Weird People Are OK

I met a really crazy old guy in Sarasota named Chuck.  I’ve never met anyone like him.  At first I thought he was homeless because when I first met him he was hanging out with homeless people. Then I thought he was crazy, because…he seemed crazy. He wore swim trunks and a fanny pack wherever he went in Sarasota…he didn’t own a car. I didn’t have anyone else to talk to so I thought, “I’m gonna take Chuck to lunch.”

I ended up spending a lot of time hanging out with him while I was in Florida.  He was crazy, loony, and weird, but he actually knew what he was talking about.  I grew to love him and he taught me a lot of wisdom about life.

Chuck had lived a wild life.  He was a successful salesman.  He was rich at one point. He had been married several times.  He told me about wild parties with sex and drugs and crazy times living in an RV.  Things changed…his health declined and he got old. He had no family that I knew of, and his wives and friends had all scattered.  He stumbled into church in his old age, accepted Jesus, got baptized, attended Bible studies, and volunteered faithfully.  Chuck died the year after I moved away and I paid for his funeral.  I still think of him often…I’ll never forget Chuck and all the life wisdom he taught me.

Don’t Be Afraid to Hang Out With People Who Are Weird

I learned that there are weird people in our lives that we should take time to befriend and our lives will be richer for it. Kill your pride and be a friend to the friendless. Make time for the special people you meet.

7. Into The Wild Is An Amazing Movie (and book)

I watched the movie Into The Wild for the first time while I was living on the island. The true story about Chris McCandless hit me in my archetypal center like nothing had ever before. Risk taking is something we are compelled to do, and it is a rite of passage, and in some ways is mandatory for survival. Sean Penn, the director, explains in this interview why Chris’ story feels so familiar and is such a shared experience we all yearn to have.

Some movies you watch and you will think about for the rest of your life. This is one of those films. Sean Penn explains it really well in this interview.

I only lived on Longboat Key for one year. My life was radically changed by taking that small leap of faith. The journey I started then, continues on today.

Special Thanks

I’m grateful for all the wonderful people I met in Florida and especially the people I met at Sarasota Christian Church: James & Nicky, Damon & Lienna, Ray & Jody, Marty, John & Deb, Chad & Sara, Scott, Jonathan, Scott, Rachel & Jamaal, Lee, Wayne, Wayne, Michael, Ray, Kris & Meg, Blair, Rob, Paul and Susie, and can’t forget Chuck.

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