Reid & Robie

Long you live and high you fly, and smiles you’ll give and tears you’ll cry.

And all you touch and all you see, is all your life will ever be. 

-Pink Floyd

I kept trying to remember how we got here.

Not so long ago we were sailing the blue waters of the Caribbean, snorkeling with sea turtles and sharks, dining on lobster and lomo fino, walking along ramparts of long abandoned fortresses, dodging pirates and watching dolphins play in the bow of our boat. The wind blew in our hair and the sun tanned our faces as we explored footprint-free beaches, anchored in secluded harbors, slept under the stars, swam in beautiful turquoise waters and moved to the rhythm of swaying palm trees. After decades in the workforce rushing to meetings, scheduling appointments and making deadlines, our lives had slowed to the pace of the tropics where things were put off until tomorrow because today life was just as it should be. Tranquil, good, easy.

Then we came back to the real world, a new home and demanding jobs that trapped us inside windowless offices surrounded by fake plants and ugly beige filing cabinets, and those memories of serenity started to recede. Before we knew it, two years turned into five and five into thirteen. Life crept up on us gradually, deliberately, painstakingly slow. Yet looking back, the changes felt like they happened in a flash. One minute we were sitting on the stern of The Last Resort, healthy, tan and relaxed watching gorgeous orange and silver sunsets. The next we were old, pale and overweight.

The difference in our lives was staggering. Despite getting rid of nearly everything we owned that wouldn’t fit on a forty-one foot sailboat, we came back and bought a house that we filled with furniture, tools, toys and backyard paraphernalia even when we rarely had time to enjoy it since work consumed our every waking hour. On the boat, we had time to read and listen to music, swim in the ocean and walk everywhere. On land we had to schedule time to work out and paid for the privilege through expensive gym memberships. Every month I watched the bank balance balloon up only to get sucked dry with payments for a mortgage, internet, TV, cars, cellphones, lawncare and house cleaning services, insurance and home security. Because the price of having things came with the added bonus of paying to keep them safe.

Life was easier on a sailboat. We went to bed when it got dark, arose soon after daybreak, caught rainwater and ate simple meals. On land we slept too little, ate too much and worked long hours only to collapse in exhaustion on the weekends. In the Caribbean we didn’t know whether it was Tuesday or Saturday, couldn’t hold a conversation on the latest movies or TV shows and had little idea what was happening in the world. With a near two-year cultural hiatus, we hadn’t been around for the meteoric rise of Justin Bieber, Kim Kardashian, the Twilight saga, Taylor Swift or Jon and Kate plus eight. And we didn’t miss it.

But when our sailing adventure was over, we sold The Last Resort. So now we needed a new plan in retirement, and to get the conversation started, we listed every possible option then sat back to wait for the dust to settle. Robie and I discussed moving to a central place and traveling around like the old airline hub and spoke model. We scrolled through home swapping websites and subscribed to International Living to read about well-known expat communities in Mexico, remote villages in Malaysia and towns in Ecuador. I researched how to build a top-rated home and pet sitting business abroad, teach English in Taiwan and become senior Peace Corps volunteers. We postulated buying an RV and roaming the Pan American Highway from Alaska to Argentina. We investigated living off the grid in a cabin in Montana, thought about running a bed and breakfast in North Carolina, and envisioned being homeless in Hawaii. No idea was too farfetched because when Robie finally announced he was thinking about retiring “sometime in the future, in the next few years, eventually but not soon,” we had time to figure things out.

And the interval gave me time to work out the best arguments for why we didn’t want to run a bed and breakfast in North Carolina (or anywhere else for that matter), go off the grid in a snowbound cabin in Montana during winter (but I might consider New Mexico), or drive the Pan American Highway in anything less than a brawny, military-grade Humvee. But when it came to being homeless in Hawaii, I was ready to give it a shot. Despite my best efforts describing what it would be like to pitch a tent near lava flows, learning to surf and foraging for pineapples, Robie wanted nothing to do with it. And as we continued working, we left the retirement ideas to germinate imagining those first tentative steps toward freedom.

Things would be different, we knew, but starting over wasn’t unknown to us. The difference this time was that we had no fallback position. When Robie and I left on the boat, we took everything with us including our two cats, Tigre and Noche. But to pay for our retirement dream we knew we’d have to sell our home and everything in it to augment Robie’s social security payments.

And that meant that whatever we decided to do, wherever we eventually ended up, this endeavor was going to be nothing if not a giant leap of faith.