Most of us have imagined what it would be like to completely change our lives.
Maybe we dream about leaving a career, selling the house, traveling the world, or finally doing the thing we’ve talked about for years. But there’s usually something that keeps that dream safely in the “someday” category.
Allison Gieschen didn’t leave hers there.
At 62, after a 25-year teaching career and raising three children, Allison and her husband sold their home, farm, cars, equipment, and nearly everything they owned. What remained fit into a few boxes and, eventually, one suitcase each.
Then they moved onto a sailboat.
Eight years later, they’re still sailing around the world.
When Allison joined me on Living Ageless & Bold, she was speaking to me from their boat in Nuku Hiva in the Marquesas Islands of French Polynesia, about a five-hour sail from Tahiti and Bora Bora.
But if you’re picturing eight years of turquoise water, tropical drinks, and beautiful sunsets, keep reading.
Allison’s story is about adventure, but it’s also about fear, resilience, family, letting go, and what can happen when you finally decide to live life on your own terms.
The Dream Started Decades Earlier
Interestingly, this wasn’t a spontaneous retirement decision.
Allison met her husband at a sailboat race shortly after college. That very first weekend, he told her he dreamed of sailing around the world someday.
Her response?
So did she.
They married less than a year later. Allison had studied English and originally wanted to become a journalist, but life took her in another direction. The couple moved to New Jersey, built a horse farm, and had three children in four years.
Allison began teaching riding lessons and eventually became a teacher because she wanted summers with her children while earning more money. After discovering high school English wasn’t for her, she moved to third grade and found what she calls her “happy place.”
Meanwhile, horses remained a huge part of the family’s life. Allison taught equestrian vaulting, essentially gymnastics on horseback, and built one of the largest teams on the East Coast. Her daughter eventually qualified for the 2018 World Equestrian Games and placed eighth in the world.
It was a full life.
But then it changed.
When Life Pushes You in a Different Direction
After earning her master’s degree in administration and leadership, Allison was offered what seemed like an ideal opportunity running a new $25 million horse park being built just six miles from her home.
She left teaching.
The job turned into something very different from what she expected. Allison describes the environment as corrupt and abusive. She and three other women eventually filed a lawsuit and won.
But when she tried to return to teaching, she struggled to find a position at her previous salary level.
She fell into a depression.
Her daughter had moved to California. Her youngest son got married. Allison was substitute teaching and unhappy, and her husband could see that she was struggling.
Then one day he looked at her and said, “It’s time.”
Time for what?
The dream they’d talked about decades earlier.
They would make a five-year plan, sell everything, and sail around the world.
And almost immediately, Allison felt something shift.
She had something to move toward again.
Preparing to Do Something That Scared Her
They didn’t simply buy a boat and head out to sea.
They spent years preparing.
Allison’s husband had experience as a merchant marine and had sailed across oceans. Allison hadn’t.
So before committing to the lifestyle, she signed up for a 1,000-mile, 10-day heavy-weather training passage in the Caribbean with an experienced captain who specifically trained sailors to handle difficult conditions.
At one point, in darkness, they intentionally sailed directly into a squall.
The winds picked up. Waves reached 11 or 12 feet. The boat pounded through the water.
And Allison was alone at the helm while the men onboard were below deck.
Instead of being terrified, she felt exhilarated.
She remembers thinking how incredible it was that she was the one up there sailing through the storm.
It was an “I can do this” moment.
Unfortunately, her first real ocean crossing would test that confidence in a way she never expected.
At 62, They Sold Everything
It took four years to find the specific type of boat they wanted. Only about 50 had ever been made, and several sold before Allison and her husband could even get on a plane to see them.
Eventually, they found one.
Then came the part most of us probably can’t imagine.
They sold everything.
They owned a farm with barns, riding equipment, tractors, and years’ worth of possessions. They held a massive estate sale and essentially told people to make an offer on anything they saw.
Eventually, everything was reduced to a few boxes and a pickup truck.
The day they signed over their house, they drove to the boat.
When the truck was finally gone too, Allison realized there was no safety net left.
They were boat-bound.
She was 62 years old.
Then Came Their Own “Perfect Storm”
In 2018, they left the East Coast of the United States.
Their very first ocean crossing nearly ended the adventure.
After crossing the Gulf Stream, Allison and her husband found themselves between two storms. Waves that began around 10 feet continued building until they reached approximately 20 feet.
The boat was crashing through them.
Then things started breaking.
A wave ripped their dinghy loose, tearing rails and screws from the deck. Because the dinghy was still attached near the mast, it threatened to pull the mast down.
Their anchor had also come loose and was banging against the bow, threatening to puncture it.
Allison’s husband had to harness himself to the boat, go outside into the storm, secure the anchor, and cut the dinghy free.
Allison watched it disappear into the ocean almost instantly.
And she had one thought:
If her husband went overboard, she was going in after him.
She couldn’t imagine remaining alone on that boat in that storm.
Eventually, they reached someone by satellite phone who told them another storm was approaching and they needed to turn around immediately.
They did.
And almost unbelievably, as they headed back toward the United States, the sun came out, the waves began settling, and dolphins appeared around the bow.
They made it back the day before Thanksgiving.
The boat had sustained about $14,000 in damage.
But the damage to Allison’s confidence was harder to repair.
When Fear Almost Ended the Dream
They eventually tried again and made it to the Caribbean, but Allison wasn’t the same sailor.
Whenever the weather changed, anxiety took over.
She began thinking she couldn’t do it anymore. She would fly to meet her husband and let him find another crew member to sail with him.
She kept telling herself she needed to have that conversation.
Then they pulled into a harbor in St. Martin.
Among roughly 100 boats, just three boats away was John Kretschmer, the same experienced sailor who had led Allison’s heavy-weather training passage three years earlier.
She told him everything.
He laughed.
Then he told her how lucky she was.
Her boat had survived. Her husband had handled the emergency. She was still out there.
Many people, he explained, would have immediately sold the boat and quit.
And the chances of experiencing another storm exactly like that were incredibly small.
“You are going to be fine,” he told her.
Allison believed him.
Eight years later, they’ve encountered other storms, but nothing remotely like that first one.
Sometimes courage isn’t being unafraid.
Sometimes it’s finding a reason to continue after something makes you afraid.
Eight Years of Adventure Hasn’t Meant Eight Easy Years
Allison and her husband eventually sailed to Bermuda, the Azores, and Ireland.
Then COVID hit.
They were essentially stuck in Ireland for two years because boats weren’t permitted to enter many countries.
Even that chapter became an adventure.
They sailed around Scotland when restrictions briefly allowed it, drove around Ireland without the usual crowds of tourists, and even ended up house-sitting an enormous historic home Allison compared to Downton Abbey.
When travel reopened, they continued to Spain and Portugal.
Then their mast needed repairs.
Five months in Lagos.
At the time of our interview, they’d been in the Marquesas for months because of an engine problem.
That’s the side of this lifestyle we don’t see in beautiful travel photographs.
Parts break.
Weather changes.
Plans disappear.
Sometimes you’re not exploring the world. You’re waiting months for an engine part.
And yet Allison says she has zero regrets.
What Happens When You Get Rid of Almost Everything?
This may have been my favorite part of our conversation.
After eight years, I asked Allison what she would do differently.
She said she would have gained more cruising experience before attempting that first ocean crossing.
Other than that?
Nothing.
She talked about what it feels like to get rid of the property, animals, cars, and possessions you’ve spent a lifetime accumulating until virtually everything you own can fit into one suitcase.
Then you go live on your own terms.
For Allison, there’s no feeling like it.
Even when the engine breaks, she and her husband can look around and say, “Wow. Look where we are. Today this is our home.”
In the Marquesas, they can go for a walk and return to the boat with backpacks filled with mangoes, papayas, avocados, limes, and coconuts they’ve gathered along the way.
It’s an extraordinary reminder of how differently life can look when we stop measuring it by what we own.
Adventure Doesn’t Mean Leaving Family Behind
Of course, there are sacrifices.
Allison has three grown children and five grandchildren. Her daughter lives in California, her sons on the East Coast, and she and her husband still travel home to see their families.
Her children miss having their parents nearby.
But technology has allowed Allison to create a different kind of relationship with her grandchildren.
She talks to them regularly through Starlink. She can turn the camera toward the water and show them a manta ray swimming beside the boat.
She gave each grandchild a world map, and every time she enters a new country, they add a pin.
She also creates postcards with photographs and stories from their travels.
One day, after Allison showed her three-year-old grandson manta rays from French Polynesia, he walked over to his map and pointed to where his grandparents were.
That’s where manta rays live, he told them.
They’re far away.
But they’re also giving their grandchildren a front-row seat to the world.
There Is No Expiration Date on Adventure
At the end of our conversation, I asked Allison how much longer they plan to do this.
Her answer perfectly summed up the life they’ve created.
They don’t know.
They don’t even plan much for tomorrow.
For now, New Zealand and Australia are next. After that, they’ll see.
And maybe that’s the bigger lesson in Allison’s story.
You don’t have to sell everything.
You certainly don’t have to live on a sailboat.
But you can ask yourself whether you’re holding onto a version of life simply because it’s familiar.
Allison was 62 when she gave up almost everything she’d accumulated and began again.
She has faced 20-foot waves, fear, broken equipment, months-long delays, and two years stuck during a global pandemic.
She’s also sailed oceans, lived in places most of us will never see, gathered tropical fruit on remote islands, shared the world with her grandchildren, and woken up for eight years knowing that she chose this life.
Maybe living boldly isn’t about eliminating fear or uncertainty.
Maybe it’s deciding that the possibility of an extraordinary life is worth navigating some rough water along the way.
And Allison Gieschen is certainly living proof of that.
Listen to my full conversation with Allison on Living Ageless & Bold wherever you get your podcasts.
Watch her full episode here:
https://www.youtube.com/watch?v=0j1tn_EWToQ
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