Paradise Schmaradise or The End of Walking About

I decided to end Walkabout 2017 in Maui. It seemed a fitting way to decompress from my month-long decompression from my seven years as CEO of 826 National. I had spent the majority of my walkabout exploring some of the major cities of the world, in continual motion and perpetual thought. It you wanted to go by steps and miles, my Fitbit tells me I clocked more than 500,000 steps, about 195 miles of walking and seeing. Thankfully you can’t measure the amount of thinking I did but it was quite a bit, maybe two thoughts to match each step. I earned that lounge chair on the Maui beach.

The view from my hotel balcony

I booked myself into the Sheraton Maui Resort and Spa. Quite a lovely hotel looking out on the Pacific Ocean, the weather hot but not too hot. I was excited to kick up my feet and do nothing for three days before I headed home and back to 'real' life. I admit that I was dreading going back to the US. I had been watching what was going on in the country through my friends on Facebook and through foreign news outlets. Our country’s Orange Apocalypse, as I lovingly and frighteningly call it, seemed to escalate on an almost hourly basis, an 'apocalypse in slow motion' to steal a quote. A friend in Melbourne said America looks weak and sad to all of us overseas. I didn’t disagree, it felt sad to many of us in America. However, being in Maui felt like I was still far enough away to not feel the flames of America as it burned.

“Will you be joining us alone sir?” The woman at the front desk of the hotel asked, breaking me out of my thoughts as I wheeled up to check in.

I had never been asked this question during the Walkabout. Not once. No one in any other country seemed to care if I was alone or traveling with a companion. Suddenly I felt like I was being judged by Kiki, whose name tag said she was from Detroit and loved warm hugs and sunsets.

“Yes,” I replied. My head held high as I slid my passport (I couldn’t bring myself to use my CA driver’s license yet) and credit card to her for incidentals. I had hoped I didn’t sound annoyed in my response to the question. Meanwhile a couple and their 2.5 children strolled by. The woman was holding on to the man’s arm as he pushed a baby stroller, their two incredibly blond children walking in front of them. 

“That’s okay,” Kiki said to me as she slid my identification and card back to me. “There’s loads for you to do here at the resort.” Her smile broadened as she spoke and I knew at that moment she was lying.“Would you like help with your luggage?” 

I said no and headed to my fourth floor room which had a lovely balcony overlooking the resort and a hint of an ocean view. On my walk to my room, I passed several couples and families enjoying the resort activities Kiki talked about. No one was enjoying them alone. I was beginning to feel ostentatiously single.

I had only felt alone once or twice on the walkabout before I had reached Maui. One of those times was in Sydney on a ferry heading to the suburb of Paramatta. There was nothing about the ferry ride or the people that brought it on. It was that desire to turn to someone you know really well and acknowledge the absurdity of existence, the journey that life is. The friend you can turn to and with one look convey, “Do you believe this shit?” 

In the span of 20 minutes in Maui I was acutely aware that I was alone and not just alone but alone in paradise. I began to feel like I had erred in coming here and should have extended my stay in Melbourne or Tokyo where being single didn’t feel like a crime.

One of many Mai Tais consumed in paradise

I pushed those thoughts aside and made my attempts to enjoy the resort. It was not easy. Trying to find a single lounge chair by the pool or at the beach was  impossible. Luckily the bars overlooked the ocean and were full of empty seats. I tried several variations of Mai Tais during my first few hours in paradise. I am not usually a rum drinker but when in paradise, a Mai Tai is my drink of choice. 

For my first dinner, I decided to make a reservation at the resort’s version of Benihana called Teppanyaki Joe’s. I love Benihana, dinner and a show without the bad singing and dancing. The young woman at the restaurant reservation desk asked instinctively, “Two for dinner?”

“No.” I responded and took a sip of my Mai Tai. This one had more rum than pineapple juice.

“It’s difficult to find seating for one,” she said to me as she looked at her computer. 

I took another sip of my MaiTai and thought 'Fuck You.'

Despite her comment, she was able to find me a seat at one of the table grills. If you have ever been to a Benihana, you know how the tables are shaped. The guests sit around the rectangular table surrounding the grill, two people at short ends of the rectangle and six people at the long end facing the chef who will perform and prepare the meal for the evening. I arrived at the table first and was seated at one of the corners of the long end of the table. I sipped my Mai Tai and waited for the other guests and the chef to arrive. 

Sunset at the Sheraton Maui resort

The next people to arrive at the table were an African American couple, older than me but I thought not by much. We exchanged casual hellos and waited for our other table companions. Next to arrive was a Caucasian couple and their two sons. The last couple to join us was a husband and wife from Italy. Both greeted us with a 'buonasera' as they sat down and I instantly fell in love with them.

We all began to engage in small talk while ordering drinks, appetizers, and our meals before the chef arrived to prepare our food. I despise small talk but I was elated to engage in it with the people at the table. I had spent a month in self-imposed solitude, a silent retreat with walking and thinking but not very much talking. Don't get me wrong, I met people, engaged with friends while on the walkabout but being able to talk without explanation didn't happen often. And the last week in Tokyo was intensely isolating. This table of people gave me the first sustained conversations where I didn't have to explain slang and the peculiarities of American phrases. 

The black couple had been at the resort for a week already and this was their last dinner before they went home to Denver. She was a teacher and he was a firefighter. They had two adult daughters both in their late twenties. One of their daughters had followed in her mother's footsteps and become a teacher herself. The family next to me was from Illinois, their two boys were twelve and nine. They had a third son, age fifteen traveling with them but he had made friends with some other young people at the resort and had determined Teppanyaki Joe's was too uncool for him. He was enjoying a teen outing the hotel put together at the beach. The husband worked in tech and the wife was also a teacher. The two teachers at the table bonded instantly and talked shop for a bit. The family was also coming to the end of their vacation and preparing to head home for the start of school. The Italian couple, who by the way were dressed impeccably, way beyond what you would wear to a Benihana-inspired resort restaurant, had come over from another hotel for a romantic dinner together. I don’t think Teppanyaki Joe’s was what they thought it was but they went with it. They were on week three of their holiday and had left their four year old son at the hotel's kids club. The two mothers at table smiled nicely but I could see the slight disapproval in their eyes over this news. Or maybe it was jealously.


I learned all of this in the first twenty minutes of the meal. I switched from Mai Tais to sake and slowly sipped it from the small cup they provided me, listening intensely as the three couples shared information, but not names, with each other. Finally, after they had all decided they had learned enough about each other, everyone's attention turned to me.

"How long have you been at the Sheraton?" The wife from Illinois asked, looking down the table at me.

"I just arrived today," I answered between sips of sake. The chef arrived right as I started speaking and introduced himself.

"My name is Tako and I will be cooking for you tonight." the chef, a young Asian man, pulled out a slip of paper to confirm all of our dinner orders. After making sure he had everything correct, he began to cook. I was excited to not have to speak again during the meal making performance. My excitement was short lived.

"Traveling by yourself? " The wife from Denver inquired. I thought to make up a story about a companion that hated Japanese food and was eating at the American restaurant next door. I decided against it.

"Yes. On vacation," I smiled as I answered and looked back at Tako who had begun to furiously chop vegetables.

Sunset in Lahaina

The husband from Illinois jumped into the conversation. " Is this the beginning or the end of your vacation?"

Now many of you know, I am not hugely forthcoming with information about myself, especially to complete strangers at a dinner grill in Maui who I will never see again. I consider throwing out another one word answer but thought better of it since Tako is at the beginning of the dinner preparations and with a table this large, it would take awhile.

"This is the end of the trip," I replied. "I've been traveling for about a month or so."

"How lovely!" The Italian husband exclaimed and his wife nodded vigorously. "Where else have you been to?" His accent wrapping around every word as he spoke. Italians can make the simplest things send sexy. Words like pancakes, breeze, or asshole sound wonderful.


I gave the itinerary for my trip as well as the number of days I was in each place. My adult table companions were completely fascinated with what I had been doing with my time for the past month and a half. The two young boys had tuned out to the conversation long ago, opting to instead discuss the differences between Marvel and DC superhero movies. A conversation I would usually interject myself into. After giving my itinerary, the husband from Denver looked at me and pointed, not rudely but pointed nonetheless.

"You did all of that by yourself? And they gave you that much time off from work?" His baritone voice made me feel like I was being interrogated by the father I never had. "What do you do for a living?" he questioned.

I considered what to say carefully and then went all in.

"I was CEO of a national education nonprofit organization until July. I left my job and decided to take a break from working before I find my next job,"

Tako and the onion volcano

I realized this is the first time I have needed to respond to this line of questions since I left the US in late July. As Americans, we ask the profession question, "What do you do for a living?" in every new conversation in an effort to determine how to relate to a person, what category to put them in. Telling people I was a CEO was always alienating, as if I had reached an exclusive club full of high brow people. Saying I was CEO usually elicited a 'well look at you' look or an audible wow. Now I had delivered two pieces of news that made the husband from Denver and the other American adults at the table give me looks of astonishment and tell me how envious they were. Even Tako stopped cooking for a moment and went off script to tell me how much he would like to do that much traveling. Then he went back to the script and made a volcano out of onion rings and oil, flicking the lights on and off as the fire blazed out of the top of the mountain of onions.

The Italian couple was complimentary and the wife asked where I was off to next. My kind of people. The rest of the dinner was a lovely discussion of the best places to go in Maui and where else to eat. Tako flipped shrimp tails into his pocket to the delight of the two young people at our table and finished cooking. Once the dinner was complete, we all said our goodbyes and went back to our respective resort lives.

Sadly, Teppanyaki Joe's was the highlight of my time in paradise. I could blame this on the resort (which wanted to charge me for the use of lounge chairs) but really it was my disdain for paradise, or at least being alone in paradise. I had been to Hawaii before with my friend Margaret and had a blast. Enjoy an all inclusive Mexican resort with my friend Avery and relished in all the comfort paradise can bring. But being honest, even with friends, I still find paradise vacations a bit too tranquil.

Another sunset

I have no problem being alone in a city. You have so much to do and see, or not do any of it but at least you have so many options. In paradise, life is a bottomless glass of Mai Tais, inappropriate swimsuits, and a string of gorgeous sunsets, each one as gorgeous as the one the night before. Every restaurant in paradise has a view of the ocean with breezes that caress your skin and ease your mind. I thought after being on the move for several weeks, sitting by the pool or by the ocean was exactly what I needed. Three days of stillness where my major decisions were how much sun to get and how many Mai Tais to drink before the start of job searches and interviews leading to my next career move.  Instead, paradise was the quiet I didn't need. 

Sunsets are made for sharing. The orange and gold beauty of a setting sun over the ocean should never be experienced alone or, in my opinion, cocktail-less. There is only so much sitting in quiet contemplation a Black Unicorn, even one decompressing from a demanding seven year job, can do. This Black Unicorn thrives on rush hour.

P.S. None of this means you shouldn't invite me on a vacation in paradise or ask me to spend the weekend at your beach house. Just don't expect me to go alone. 

Every sunset is beautiful!