A few weeks ago, I left paradise on the Italian Costiera and boarded a flight to alter my life, again. I went back to Tennessee to do something I never expected. I went back to sell the home that saved me.

~

Just married in our 20s, my husband and I searched the historic downtown area where we lived for a home we might afford. Sunday afternoons were always our day to explore. We would drive the small city blocks and imagine living there. Each old house unique and charming and surely with stories to tell. I wanted desperately to call one home. A tiny house on a corner came up for sale. We discussed it and could probably buy it. But with only one bathroom, no yard to speak of, and zero money for repairs that surely awaited us with such an old home, we chose safety in a new neighborhood three miles away.

After children arrived and a bigger custom home even further out of town, our life was full and joyful. Until it wasn’t. Stained by the ultimate betrayal. A perfect home no longer, and one I could not afford alone, the kids and I needed to embrace something smaller. Sunday drives through downtown resumed and we found a place I could potentially afford. It was in the heart of the historic district and even had a bit of yard, though deeply sloped. The quirkiness and age of the home also worried me as much as the cracker box sized rooms. Flying solo on big decisions wasn’t easy. I chose safety again with a new loft.

Years later, with teen years finished and kids nearly launched, my own dreams began to snake their way back. My Microsoft job had provided well for us, but the intensity had taken a toll. I needed a real vacation, just for me, something I hadn’t done in years. I made plans, then went. I rented an apartment just outside Positano for a month. I woke each morning and wrote as I gazed at the colorful stacked city and the bluest sea. I rode my rented Vespa by day, taking every curve as it came and exploring every town on the coast. Nights were for mouth-watering dinners and late-night jazz over the sea. Cocktail in hand. I could easily live this way.

Back home in Tennessee, my mind kept floating back to the sea, but life was still plowing on. There were things to be done. In just a few months my daughter was to graduate from college with honors in construction management. Her plan, among a sea of typical non-female construction students, was to build eco-friendly homes with upcycled and recycled materials. Her strategy was sound and her professors loved it. She was excited about her future. A night celebrating with friends, however, didn’t go as planned. One wrong move and her heart stopped beating. Police at my door. Unable to breathe. My world went dark.

~

A few months later, as I continued to navigate life with a gaping hole in my chest, Thanksgiving finally arrived. Time with my son and extended family would be greatly welcomed, as well as the traditions that would provide anchor in the storm. The annual family portrait of everyone in attendance was beautiful, but nearly impossible. Uncle Walter’s favorite shrimp cocktail always came next. Then the feast of family favorites spanned the buffet. Naps and football followed for the guys. For the women it was time to catch up and shop online. For me it included real estate.

My virtual drive yielded only a few homes, but one caught my eye. A small cottage only five blocks from downtown. A fenced back yard. A two-car garage with adjoining apartment. This was promising. The outside was okay, but the inside had been recently renovated with modern and special touches. Buying a home was the last thing on my mind. The year prior I completely renovated my loft, with updates to everything. I fully intended to stay and enjoy it for years. But for some reason this house pulled at me. I had dreamed of one exactly like this. Intrigued, I decided there was no harm in seeing it. I wrote the realtor and scheduled a house tour that very weekend. I wouldn’t buy it, but I had to see it.

Two days later I rapped on the bright blue door, eager to see inside. I entered the house and introduced myself, then paused and glanced around. Empty of furniture, it still felt welcoming. As I moved from room to room, I had to hide what I was feeling. The reclaimed brick in the kitchen looked like my recent remodel. The dark navy walls in the main bedroom were my color. The mercury glass wall in the bath, the special salvaged doors and the barnwood statement wall, each choice as if I handpicked it myself. I was in trouble.

My loft sold quickly. The renovations prepared it well. It was difficult to say goodbye to the Italian marble bathrooms, as well as the custom French linen blackout drapes that cost a mint. But this felt right. And just after Christmas, a moving truck with everything I owned pulled into the driveway of my new home. A home just for me in historic downtown.

A few months into getting settled, the world had started to lock down. A pandemic was brewing and I was grateful for a peaceful spacious place to call home. My daughter’s birthday was approaching, my first one without her. How I would cope I had no idea. I ached to hear her debate about what she wanted for dinner and if we could bake her cake together.

The next morning the dogs and I took a long walk around town. This ritual and those loving animals became a therapy that saved me.

On this particular day as I returned from our walk, I happened to glance at my house number on the mailbox, 328. What a great number I thought. I actually grinned to myself. It made me happy. Then I looked at my neighbor’s house number, 330. I reflected that it was a nice number too, but that 328 was definitely better. As the dogs and I turned to go up the steps toward the front door I froze. Confused, I spun around and stared at the mailbox again. How could this be? How did this happen? I longed for this historic cottage for decades. I talked about it with others. I knew it was out there waiting for me. Was it destined all along? Because the house number of this home is my daughter’s birthday – March 28.

~

As the pandemic got worse and the world stood still, the gift of this new home became clear. My son moved back for several months and lived in the apartment out back. We built raised garden beds and grew things to eat. The dogs played freely in the backyard and kept the rabbits and squirrels at bay. I even bought a Vespa. I couldn’t get to Italy, so I found my own version close to home.

This house nurtured us. Saved us. Kept us together when life was hard.

~

Nearly seven years have passed. Life has evolved. My son lives in Alaska, and I on the Amalfi Coast. My sweet dogs, aged 16 and 17, passed away nearly two years ago. Life is truly different. Last week I sat in my cottage in Tennessee with workers all around me. The smell of paint permeated the air. Every inch of the house was being tended. It loved us well, and I wanted it to feel my love in return.

Knowing when to sell a house is just as important as knowing when to buy one. This is the house I have come home to sell.

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When I was a teenager, I was asked on a date by a guy who had a Camaro and a motorcycle. To say that my dad was worried about my safety was an understatement. That’s when he declared with authority that if he ever, and he meant EVER, saw me within a three-foot radius of a motorcycle I would be grounded for a month. I was a pretty good kid when it came to following house rules and my parents trusted me. Dad rarely gave hard and fast rules, but when he did, they were legit. He then added the loaded statement, “I was once a teenage boy, and I know how they think.” I didn’t want to die at the hands of a reckless boy either.

This rule and everything it stood for kept me from ever climbing onto a motorcycle as either a passenger or a driver, despite my yearning to drive one. I played sports growing up. Loads of them. And I participated in so many after school activities it would take time to remember and list them all. I just loved trying new things.

Two things never seemed doable as a kid, but I yearned to do them, thanks to movies and tv shows. I wanted that feeling of freedom I knew I would have if I did them. I dreamed of flying a seaplane to tropical islands only accessible by water, and I dreamed of riding a motorcycle on faraway roads with adventure in my heart. When I learned a private pilot license was necessary before the seaplane license, it felt too involved. In my future dream life, I would hire a pilot if needed. But a motorcycle license seemed more doable. Well, except for the three-foot rule and my healthy fear of death.

Decades later, my 19-year-old son told me he planned to buy a motorcycle. Putting gas in his 20-year-old SUV was expensive and a motorcycle would help his budget, he claimed. I was a single parent now, and Dad’s words came to mind. With no real means to prevent his purchase, and a genuine desire to stay connected with my son, I made a decision.

Early on a clear Saturday morning, we showed up together at the Harley Davidson dealership. Newly purchased helmets and gloves in hand, we were ready for our multi-day motorcycle safety program. I could see the delight and anticipation in my son’s eyes. But I could feel the apprehension in mine. I had various mantras running through my mind on repeat. People ride motorcycles every day. If they can do this, so can you. It’s just a machine. The instructors will tell me what to do. People do this every day. If they can do it, so can I.

Walking up to the classroom, a perfect row of Buell motorcycles stood ominously out front. They looked big and I tried imagining myself on one. My heart rate increased. I flipped back to my mantras and breathed deeply.

It was a small class, seven in total, all men my age who wanted to ride again, plus my son and me. The first part of the course was classroom instruction. Rules of the road. Riding courtesies. Common mistakes that cause accidents. I had to remind myself every few minutes why I was there. My son was soaking it up. I was too. Life depended on it.

The Buells were waiting and after lunch we would have our turn at them.

Fear doesn’t work on a motorcycle.

I was told I must ride with confidence or not ride at all. So, I bundled up my fear and put it away. Channeled it as confidence and had to fully believe I could do this.

When I swung my booted leg over the cycle, I balanced it underneath me. Felt its weight. I learned the purpose of each part. Practiced the mechanics while rooted in place. A lifetime of fear became less heavy. A cloud no longer dense and ominous, it began to dissipate. Action, it seemed, transformed my state of mind completely.

I spent eighteen months after that deciding which Harley Davidson to buy. My son and I had purchased a used Honda Rebel immediately after passing our class. It was the perfect starter bike, and we shared driving it to improve our riding skills. He during the week, me on weekends.

I test-drove many Harleys before I made a purchase. They’re massive machines and each model rides differently. The salesman, with little faith I would actually purchase one, finally showed me a new Dyna Lowrider that was perfect. Everything about it felt right and balanced, despite its weight of over 600 pounds. I was having a milestone birthday that year, so I bought it. I drove far out of town on winding treelined roads, wind in my hair, I remembered why I’d done it.

I never could have imagined where my decision to finally ride a motorcycle would lead. But four years later I took a much-needed vacation that changed my life. I rented an apartment for a month in Arienzo, just outside Positano on the Amalfi Coast. No rental car, just living. But when I saw all the scooters and motorcycles on that coastal road, I knew what I had to do. Walking into town I found a rental service. I wanted a Vespa! The older Italian man looked at me with skepticism and asked me if I knew anything about riding a scooter. A quick scan of my motorcycle license and the photo of me next to my Harley was all it took.

Driving that Vespa out of town, I kept going. Dramatic mountains with rocky outcroppings, terraced gardens of lemon and olive trees, windswept foliage and wild herbs, all crashed down into the sapphire sea sprinkled with yachts. Houses and hotels clung to the mountains. Always with stairs to the sea. And the brightest fuchsia bougainvillea tossed everywhere, nature’s most elegant summer jewelry. Wind in my hair, curve after curve, life had truly turned magical.

~

Trust yourself.

Give it a go! 🛵 -Cindy

My dream was this house. The arch at the end of the hall with a view of the sea. I am yours, it said. Stay. It wanted me as much as I wanted it.

I returned in February for a furniture delivery. My new sofa was expected in a few days, and I was looking forward to sitting on something cozy and comfortable. The entire previous summer I used outdoor terrace furniture in my living room. It wasn’t all that pretty, but functionality and availability made it perfect. I was also set to receive the platform for a large double bed in my bedroom. I’d been sleeping on one of the twin beds I asked to remain with the house and was eager to have more sleeping space. It would never be the king-sized bed I had back home, but here it would be grand.

It was my first experience of winter at my marvelous new home on the Amalfi Coast, and I was curious how it would feel. Cold and damp was the answer. Wind and rain transformed my stunning blue coastline into a desolate gray landscape and inside the house, little was better. Excited to have finally arrived, I unlocked the door. I had to push to make it move.

Swollen with moisture, the old wood door scraped hard across the terracotta floor as it opened. I felt the humidity immediately. I felt it on my face and my clothes. I reached out to slide my hand across the plaster wall. A ritual I started without realizing it from the first time I came into the house. The plaster here feels so different than sheetrock. The slightly irregular texture is surprisingly soft and alive. When I moved my hand across the wall I swore I felt the energy of the person who made it. But that terribly dreary winter day, the wall was crying. When I touched it, my hand came away wet. I almost cried myself as my heart sank and knots formed in my stomach.

Resigned that I couldn’t solve the problem immediately; my brain turned to heat. Heat would definitely help. I felt sure I was given instructions the previous summer when everything was handed over to me. But with temps over 100 degrees, I likely wasn’t focused on the heating. A quick search of my notes and my memory turned up nothing useful. Rolling my eyes, I promised myself I would get better at notetaking.

A hot shower called my name. The ache from twenty-four hours of travel was deep in my bones. Exhaustion had set in hard.

Modern and tall, my shower was enviable here. I looked forward to soaking myself in all the hot water. Sliding back the glass door I turned on the water. Success! Then waited. I gave it ample time to do its thing, but I saw no steam. A tentative touch of the water and I gasped. The water was arctic.

If anyone had been within a three-block area, they would have heard my screaming and yelling. I know how to cuss, and at that moment, I was an Olympic champion. The worst part though, I was still cold and if possible, even more tired. And it was then I noticed plaster buckling under the window in the bathroom. Water was leaking into the wall. Even a kid could see it.

The feeling of overwhelm knocked hard at the door. I couldn’t let it in. So, I sat. I sat on my makeshift furniture and just breathed. No problem solving. Just air. In through my nose, and out through my mouth, slowly on repeat until I felt my body and mind calm down. I mean, people live here, and they solve problems, so I can too.

Wrapping myself in warmer clothes, I needed to inspect everything, inside and out. The sun had fallen behind the mountain, so I grabbed my phone for light. The breaker box looked foreign like everything else, but all the switches were up, so I called that one a win. Next, I entered the mechanical/storage room, which housed my gas tanks, hot water heater, and various gardening supplies left behind by the previous owner.

Dodging spider webs and wet fallen ceiling plaster, more water leaks apparently, I inspected the water heater. It was blinking. I switched it off and on again and it seemed happier. Back inside I looked back at my notes and found something scribbled sideways on a page – Turn on water, then gas, then water heater off and on again. Mio Dio, I would get a hot shower after all. The relief washed over me like the hot water soon would.

And you know what? The next day I solved the heating problem too. I went to the local housewares store and bought a portable heater. We quickly became inseparable. My new best friend followed me everywhere, from room to room, loyal as my precious dogs had been back home.

The rest of the problems I added to my growing list, certain there would be more. A gentle new confidence quietly rose. Maybe I could do this foreign house thing after all.

~

Whatever hard thing is waiting for you — take a deep breath. Then go inspect the mechanical room.

Give it a go! -Cindy

I was so frustrated and stressed I almost burst into tears. Crying while driving would be bad. I was anxious to get to my destination early, and this car had absolutely no place for my phone. Bluetooth wasn’t working either. I was heading to a neighborhood I’d been to only once before and, elegant as it may be, it was riddled with one-way, crowded, narrow streets and all I could think was, I needed gum.

No easy way to navigate, I held the phone precariously in my gear-shifting hand and angled it so Google Maps faced me with the sound at full volume. It may not have been my best idea, but it seemed to work. If only the start and stop traffic would end. I couldn’t wait to get where I was going.

I was in a newer model Fiat Panda, which until that moment had worked well. I love these cars. They are the perfect car for where I live. They navigate narrow roads and tight turns and win on functionality with 4 doors and just enough room. My favorite long-term rental is a slightly older red Panda that’s been mine for the last two years and I know every nuance of that car. This trip they gave me a newer model that seemed better at first. But when I realized there was no way to mount a phone, I became concerned. I knew it would be an issue at some point. That day had arrived.

I enjoy driving in Italy, but Naples always feels like a test. They really should have assessments as you enter the toll road heading into the city.

· Agility? Check.

· Peripheral awareness? On point.

· Reflexes? Quick.

· Mental toughness? Relentless.

· Thoughts on aggressive driving? Do it. He who hesitates loses.

From my first terrifying experience driving in this city and even now, I can say with certainty, it’s not for the faint of heart and it’s never easy.

Life on the road in Naples was chaotic. Nearly 100,000 scooters a day claimed the streets. Like wild bees they swarmed in and around every car, bike and person on the road. Nonnas walked in the streets wearing black, which may as well have been an invisibility cloak, laden with market bags headed home to make lunch. Moms with baby carriages and kids on bikes were braver than I thought they should be. A way of living I’d never seen firsthand. Main roads felt like alleys with laundry wafting overhead and cars double parked. And roundabouts – pandemonium. No one appeared to care about street signs, parking zones, or blinkers, until they did. Horns honked constantly. The cacophony, a symphony woven into the fabric of this passionate ancient city. Navigating Naples was an expedition. Progress belonged to the brave.

The mother of one of my closest Italian friends passed away in her sleep (amen) on Mother’s Day. A family prepared to celebrate, was now in mourning. And while I never had the chance to meet her, I knew her grown sons, their wives and partners, their children. I wish I’d met her.

Today I was on a mission. The funeral was to begin at 10:45am at a church I didn’t know, and I was determined to arrive at least thirty minutes early. If things went smoothly, the journey from my house to that church in Naples would take ninety minutes but rarely was a driving day perfect. I spent the prior night mapping the route to the closest parking garage – curvy roads, tunnels, bottlenecks, unexpected road closures, city traffic, and parking. Madonna mia. I would need at least two hours, probably more. The last and only other time I was in that area I missed the side street for a tucked away parking garage. The one-way streets, and likely more driving misses, added twenty minutes around the hillside to get back to that turn. I promised myself to be in the car by 8.

It was 10am and I had been driving for 2 hours. Tuesday morning work traffic had definitely been a factor. But I was close now. The phone in my hand said 18 minutes out. I wanted to be optimistic but couldn’t afford even a basic mistake. I was on my third piece of gum, with every traffic light a test. Beasts on the road, buses blocked any chance of seeing what was ahead. Drivers claimed micro gaps between cars as an opportunity to edge in and out of nonexistent lanes and scooters never stopped. The short tunnel a reprieve with slightly more civilized driving but lagging cell coverage nearly caused me to miss the turn at the end. As I curved through more elegant streets, I made a mental note to return with more time.

The big P parking sign was hidden by a delivery truck. I pulled over, knowing I was close. Dio mio, I missed the turn by ten feet. Backing up was the only option. I climbed out of the car into full morning sun in my black funeral attire looking for help. A gentleman standing nearby saw me and jumped into action. Traffic now stopped by my new best friend, I backed up the car and turned right up the alley. I swear I heard angels singing as I drove into that garage and parked.

Chaos dampened, I took a beat and simply sat. I had made it. And I nearly cried for the second time that day.

I swapped my flip flops for heels, tossed my gum in the bin, and took off on foot. Down a flight of stairs and around the corner. And there they were — the friends who welcomed me into their life three years ago when I took a chance on a life in Italy – standing in front of a 14th century chiesa that once saved the life of a Portuguese nobleman more than four hundred years ago. They turned as I approached, as if they somehow sensed my arrival. We locked eyes and smiled. Funerals are for the living. Abbracci e baci profondi. And this time, I let the tears fall.

The year I bought my home on the Amalfi Coast is the year my olive trees were butchered.

It was 2023 and I was finally looking at a place that had potential. I had come to Italy to buy a home, and with one missed opportunity after another, three weeks’ worth, I was excited to see one in person.

I climbed exactly 76 steps before turning left onto a terrace of terracotta tiles that needed scrubbing as well as sweeping. It was littered with fallen olives and skinny dried olive leaves. The crunch underfoot forced me to look up.

Swooshing above me were several good-sized olive trees. Tall and broad, they cast shadows on the tile while the sun struggled to make its presence known with little diamonds of light. It was cool up here, more than I would have guessed. And the views were already visible through the trees. Climbing up seven steps more and a second terrace said hello. How many trees is that now? I should count them. I wonder how much olive oil they will make? I had seen images of the most amazing green oil, sluggishly pouring out of the first cold press. I heard it was peppery perfection and I wanted it. I wanted my version of it.

I was already starting to see myself here.

April winds blowing, I glanced at the trees again, surprised they were so quiet despite their near constant motion. There was a softness to their rustling, happy and alive with a confidence and certainty I wish I had.

And wow, there were sea views everywhere, outside and in. As if I needed another sign, this sealed the deal. I would do whatever it took to buy this house. It was mine. It just had to be mine. I had found my place in the sun. I prayed it would all work out.

Fast forward two months, and with an entire story in between (I promise I’ll share), I unlocked the front door of my house on the coast with keys that were mine.

These sea views were mine. The olive trees, too. It was time to settle in, regardless of my shortcomings. I had to learn the language, put utilities in my name, buy furniture, locate a plumber, and a gardener too.

It was the gardener I found first. In classic Italian form, a local friend knew someone who would take great care of the garden. No need to worry at all, I was told, and his price is right. That should have been my first clue.

Pasquale turned out to be more like a jack-of-all-trades, than a gardener. He also appeared sooner than expected, which caught me off guard. I had entertained the idea of getting estimates from several gardeners, but Pasquale was here and honestly, he was the only gardener I knew. So, with a lot of arm waving and pointing and pantomiming pulling weeds, I hoped from his nodding, he was clear on what was needed. I mean, most anyone could see the weeds were nearly waist high.

Va bene, he said nodding some more, but his nod slowed and began to turn into a shake. Something was wrong. He looked up and said, ma prima, gli alberi. I checked the translator on my phone to understand he wanted to do the trees first. What trees? I never mentioned the trees. The olive trees were perfect. Beautiful, and everything I had dreamed of, after a view of the sea of course. Questi ulivi, he said pointing directly at the olive trees, must be pruned immediately. It’s the only way I would ever have new olives and that oil I wanted so badly.

I called Italian friends, I had two, and they confirmed what he said. Olives need new branches in order to grow and flourish. The trees must be trimmed to get olives and oil.

I messaged Pasquale and said okay. Let’s trim the trees, but just enough to ensure there are olives. I was already imagining tasting the oil.

He arrived on a Friday when I was leaving town, and by my return on Sunday the trees were barren. No flowing boughs billowing in the wind. No rustling whispers to welcome me home. They were gone. The devastation was absolute. My beautiful olive trees, the ones I just paid a life’s savings for, were scalped beyond recognition.

I was too shocked to cry. I stood on my terrace for minutes that seemed like hours. My mouth agape and my eyes trying to comprehend what happened. There were piles and piles of branches, three and four feet high. The terrace was covered with them. I couldn’t see Pasquale. Probably for the best. I couldn’t speak. I slowly turned and went into the house and slumped into an ancient aluminum director’s chair left behind by the previous owner and put my face in my hands. The tears finally came. Buckets of them. What on earth was I doing here? I had changed my world, and any semblance of control was gone. I was in a foreign country, living foreign dreams, with the language skills of a 4-year-old. What have I done?! Dear God, please tell me I brought Kleenex.

Mom always said a good night’s sleep brings new perspective and as usual she was right. I felt calmer, but saved myself from looking out the window at the terrace and decided to focus on the sea. The beautiful cerulean sea that makes everything better reminded me why I was here.

I was going to have to trust Pasquale and my friends. After all, they had olive trees of their own and they didn’t seem worried at all, regardless of my slight ranting and raving. È normale, they reminded me. The trees need nuovi rami, new branches, in order to grow olives. And the truth is, what’s done is done. I couldn’t change it. All I could do was go forward.

And now, this very week, I walked out to my terraces to thoughtfully inspect my trees. It’s been two and a half years since the butchering, and I’m delighted by what I see. Tiny flower petals are sprinkled like snow on the terracotta tiles and there are a million more on the beautiful new branches of my olive trees. I nod to myself. This is good. But some of the slender leaves on the trees are yellow. I stare at the soil, and it looks a bit dry. We haven’t had much rain of late and my research, and more importantly the locals, all say the trees need more water when they’re in full bloom. I open my weather app and see rain in the forecast for several days in a row. I smile and think, those flowers will become olives very soon. And by fall, the golden green oil will flow.

I spent decades climbing the corporate ladder at places like Microsoft before I decided to climb a different kind of mountain entirely.

When I was a child, I secretly dreamed of a life in Italy. I wanted houses in the mountains and by the sea. I wanted to travel and explore. Life was bigger than the small but beautiful place where I grew up, and I wanted to see it. I didn’t yet know how I’d get there. Then technology showed me a path.

Personal computers (PCs) came on the scene when I was in high school and my kid sister got one for Christmas. Any chance I could get, I used it. I saw the possibilities it created – for computing, for humanity, and for a life I wanted to create. I fell in love with technology and built a successful career on it. All the while, Italy rested quietly in the background.

It was 2015 when I first set foot on Italian soil. A lifetime of waiting finally arrived. I was meeting friends for a weeklong cooking school, one of whom was fighting for her life. A reminder that life was meant to be lived.

We happily moved fully into our roles of Italian cooks. Cappuccini to launch the day, and wine before noon while we made sauces for pasta, rolled involtini, and fried soft and aromatic zucchini flowers filled with fresh ricotta. We cooked and we laughed and we dined on terraces of ancient villas overlooking a valley where Etruscans walked millennia ago. It was in those moments that my Italian dream, the one I had so carefully tucked away, was no longer hiding.

When I left my corporate career for good, I could see colleagues’ mouths drop open as I told them I was leaving to buy a house in Italy. The immediate response, complete shock of course. Then comments like, wow, okay, and good luck. And while some genuinely meant it, many of the comments came with raised eyebrows and an attempt at optimism. But they couldn’t hide their slightly skeptical tone and sideways glances. After all, who leaves a firm where people would kill to work to pursue a crazy dream instead of the next big job?

That’s a story in a book, not real life, right?

A decade ago, when I was thriving in my work, a coworker once shared a story about a successful woman who left a leadership role to become a painter on the coast of Spain only to return about eighteen months later to a less impactful role. I was told this in passing as a cautionary tale – you can chase your dreams, but you’ll come back anyway while losing two years of seniority, income, and stability. There were other stories about failed exits. Bantered about as part of the culture to keep you invested. The ones who succeeded in creative endeavors maintained their 50+ hour a week jobs and did creative and charitable pursuits on the side, often relegated to nights and weekends, at the cost of losing even more time with family and friends. But I didn't see cautionary tales. I saw this as a problem that needed solving. I had given decades to these firms and this work. There had to be another way. These stories raised more questions than answers.

Why did they fail?

What do I need to consider in order to succeed?

Would I really have the courage to leave it all behind?

Do I trust myself enough to do this?

A few years later, in my home office after yet another conference call, I remember thinking, my life is no longer my own. All my waking moments are consumed with work for someone else. Life is not being lived. And for what? Security? Money? Health insurance? Because isn’t that what scares us most? But I had had enough. I stood at my desk, cluttered with everything I needed to do. Tears welled in my eyes. My life was calling. My mind knew it and my heart knew it. It was time to live it on my terms.

I cancelled my next meeting and went for a walk. I needed to make a plan. My plan. If I was going to leave this rat race and chase my dream of a life in Italy, I would have to be all in. Fear be damned.

Losing one of the two people on earth who matter most changed everything. Worst fears had been faced. One future gone. One to protect. And now mine, still unwritten. The clarity it brought surprised me. My future was no longer negotiable. What once had been a quiet dream now called to me with urgency. Did I know exactly how it would turn out, nope. But I knew there was a house in Italy waiting for me and I was going to find it.

adventure (noun): an exciting or remarkable experience. The exploration of unknown territory.

I have always seen life as a grand adventure. Big and small, near or far, adventures come in all shapes and sizes. Many think of adventure as dangerous or risky. I prefer to see it through the eyes of an explorer — curious, excited, and full of opportunity to learn. Not only about what you decide to try, but most importantly about yourself, no matter the outcome.

We ask children to try new things without hesitation — the unfamiliar food, the new playground, the friend they haven’t met yet. They are the world’s greatest adventurers. And then somewhere along the way we grow up and start hesitating. We don’t want to feel silly. We don’t want to fail. We don’t want to feel like we wasted our time. But if we stop trying new things and getting out of our comfort zones, ruts form and our spark fades. And let’s face it — life becomes monotonous.

I firmly believe whatever is around the next corner is a chance to see something beautiful or for something remarkable to occur. Sure, going around that corner can be scary or even a bit risky. But to not go around that corner is an even bigger risk I am unwilling to take.

One of the things I learned along the way is that adventuring — really adventuring — first requires genuine desire. Next, permission. Permission from yourself to let go of expectations and just see what happens. Then, action. One small step in the right direction. You have to take it. No one can take it for you. It could be signing up for a class or simply buying a book about a dream you’ve had. That’s what I did.

In 1996, Frances Mayes published her memoir, Under the Tuscan Sun. As I turned each page, I could smell and taste the life she was living, and something in me cracked open. I’d dreamed of Italy since childhood, flipping through Mom’s travel magazines, but I had never been. And yet here was this lovely woman who actually bought a home in Italy. I didn’t know it was even possible. The most beautiful, culture-rich, history-soaked, endlessly delicious country in the world — with miles and miles of coastline. It was a dream. And now here I am, 30 years later, writing from my home on the westernmost point of the Amalfi Coast with views of the bluest sea imaginable.

Adventures in small things lead to adventures in big things. If you have a thought, something you’d like to try, try it. Who cares what happens afterward. Just take the time to appreciate that you did it! And be proud of yourself. Every time you push past ruts and comfort zones, something interesting happens and you see things you never would otherwise.

Whatever your version of adventure looks like, the only thing standing between you and that dream is the decision to give it a go and see what happens. One small step at a time.

I didn’t fall in love with the winter Olympics in a single moment. It was a culmination of little things that began with my parents.

They were happy, adventurous people who met water skiing at the local lake — Dad a handsome and athletic showoff, Mom beautiful and gregarious. A year later they were married, and in an effort to find couple friends, Mom suggested they join a new ski club forming nearby. The plot twist came at the kickoff event when they discovered the ski club was not water, but snow skiing! Never daunted, curiosity won out. I still hear Dad’s voice: “We thought, why not? We’ll give it a go and see what happens.”

Their love for snow skiing was nearly instantaneous. It didn’t matter that getting to good powder meant driving 24 hours nonstop through the night, rotating drivers with friends, just to ski Colorado for a weekend. They bought gear — leather lace-up boots, the longest skis you’ve ever seen, poles with metal rings at the bottom also lashed with leather. They were hooked.

By the time I was 4, that dive-right-in energy had passed to me. Dad was teaching me to ski at a small resort 30 minutes from home, and I loved it immediately. The thrill, the challenge, the feeling of freedom. My parents’ ski crowd exposed me to a world beyond small-town Tennessee. There was a tall German couple I adored. The man’s name was Dieter Baer, which sounded like Deeter Bear to me. He offered tips as I learned, but more importantly he shared stories about skiing the Alps that opened my young mind to exciting possibilities.

The 1980 Olympics at Lake Placid sealed my passion for these historic games. It was probably my age and my love of sport, but I was captivated by it all. The stories of athletes overcoming hardship and challenges were especially incredible. But it was the U.S. hockey team that blew me away. Rag tag college kids against professionals who had played together for years. Game after game I watched Team USA advance. Then, the Miracle on Ice, a 4-3 victory over the Soviets in Game 6 that no one saw coming. I’d been sitting on the floor glued to the TV and when we won, I screamed and fell back on the floor and let the joy wash over me. The miracle team. I was a fan for life.

February is my birthday month, which means the winter Olympics arrive like a gift every four years. In 2014 I leaned into this fully and bought myself an official Team USA knitted earflap hat, designed by Ralph Lauren for that year’s opening ceremony. It was pricey. I ordered it anyway. I wore it everywhere, even inside while watching events on TV. That hat made me happy.

The 2026 winter Olympics were approaching, this year hosted by Italy — my Italy. I bought a home on the southern coast a few years ago, and now the Games would be here. Friends called wanting to stay at my house, and I had to explain I lived nine hours from the venues. I was determined to go. I simply had to.

By fall 2025, accommodations in both host cities, Milan and Cortina d’Ampezzo, were nearly gone. Studio apartments started at €700 a night and hotels €1100. I’d waited too long and knew it. But I also believed, relentless optimism intact, that something would show up. It was out there somewhere. I just had to find it.

After Christmas and on a road trip with my kid sister, I scoured apps while she drove. The Olympics were six weeks away and Milan was a bust. I tried Cortina one last time and wow! An entire four-bedroom apartment, two blocks from the main piazza, €500 a night. Someone had cancelled. And just like that, I was going to the Olympics.

We arrived opening night. Five friends, one glorious apartment, and a four-minute walk to the cauldron. I put on my storied 2014 hat, a giant new golden puffer coat looking very on point, and we walked into Cortina as it twinkled hello, the snow-covered Dolomites its backdrop, formidable and magnificent.

What followed was a comedy of gates, security checkpoints, bomb-sniffing dogs, and baffling badge requirements for an event we’d been told was free and open. After being turned away repeatedly, I overheard a couple say they had dinner reservations, and the guards waved them through. We called the pizzeria just inside the gates. They had a table. And in we went.

Fortified by negronis and genuinely divine pizza, we made our quiet escape through the restaurant door, climbed a flight of concrete steps, and slid into a crowd of winter coats as light snow began to fall.

I looked to the right and had to muffle my scream of delight.

Fifty feet away stood the largest Hoberman sphere I’d ever seen. A massive glowing geometric structure, the Olympic cauldron, waiting for its moment. Just like me.

The parade of athletes filled the piazza with sound as each country was called. Italy was announced last and the crowd erupted in synchronized chants of joy only Italians can do. Then the music swelled, ethereal and grand, and Italian alpine skier Sofia Goggia walked onto the stage carrying the flame. A flame that traveled from ancient Olympia to arrive here, for this.

She raised the torch. The music peaked. The sphere glowed orange. The cauldron ablaze.

I cheered and cheered until I could cheer no more, then quietly stood in awe. Happy. Full. Grateful. Tears on my cheeks as snow landed on my fated Olympic hat. History had been made, and now it was part of mine.

Dreams are worth the effort. Why not give it a go and see what happens? Life will surprise you in the best possible way.

I didn’t expect to be here. Not on the Amalfi Coast, not writing to you, not living the life I’m living. But I never stopped dreaming of it either. For a long time I was living a different one entirely — working hard on a career that landed me in my dream job at Microsoft, raising two children mostly alone in ways I never expected, then losses changed the shape of everything.

What I know about hard things is that they don’t disqualify you from an incredible life. Sometimes they’re exactly the thing that wakes you, that finally sends you toward one.

I spent decades dreaming about living and traveling abroad. Decades. And then one day I stopped dreaming about it and did it. I live on the Amalfi Coast now. I have incredible views of the Tyrrhenian Sea, a garden alive with olive trees and mandarins, flowers and herbs, and a newborn avocado tree. I drive roads that would make most people grip the door handle and pray. I cook, I travel, I ski, and I try new things. I show up when I’m not sure I’m ready. I give it a go.

That phrase and philosophy came from my dad. One of many from my parents. But this one ran deep. Not just for the big leaps but for the ordinary weekday when you’re not sure you have it in you.

This is where I write about it all. Adventure and travel to places that delight and open your mind. Glorious food and life around the table. The plants and garden I tend with a light green thumb. The life I built from scratch after the one I had came apart. My family and friends, my anchor and home port as I explore the world. And the quiet but absolute belief that no matter what happens, you can do your version of this too, whatever it looks like for you.

I’m here to encourage, because I went first. To tell you it’s possible.

I’m glad you found your way here. Pull up a chair and stay for a while. There’s more to share.

-Cindy