The Chapter Between Chapters

Three weeks between the life I left and the life we're building

It’s been a while since I’ve written a blog post, but I hope to be able to write them more often. I just freed up about 50 hours a week which should help 😊 

The Life I Left

On July 29th, I walked away from a career that I spent over 15 years building. I quit my Senior Director position at Aetna and left pharmacy, a field I always assumed would define my entire career. The surprising thing to most people is that I genuinely enjoyed my job. I had a great team, a solid incentive structure, upward mobility, and good stable benefits.

But it was also a job that quietly boxed in the rest of my life. Real estate had to be squeezed into nights and weekends, which meant sacrificing time with family and friends, hobbies, and even sleep. And even with all that effort, it still slowed the growth of our business, costing us money in prolonged carrying costs and vacancies when we didn’t have the time or bandwidth to focus on it. It limited time off and travel to three weeks a year. The IMs and emails never stopped, keeping me on a treadmill with no end in sight.

I knew that it was a move that had to be made. I know deep down that we will do just fine, eventually even better in entrepreneurship than we ever could in pharmacy. But knowing something intellectually isn’t the same as taking the leap and stepping into the unknown. Fear doesn’t disappear just because you can apply logic. Still, I leaped.

The Bridge Between Lives

I started writing this while sitting on a balcony in Mallorca looking at sunshine and palm trees. I continued in Rovinj, Croatia, staring across the 500-year-old rooftops of historic Old Town. I wrote another section at 38,000 feet between Croatia and Amsterdam. And I am finishing it in Amsterdam while watching the endless parade of bicycles and trams outside our hotel room window.

In short, I’m on a three-week trip across Europe with Holly and Lily. While we’ve traveled plenty before, this trip felt different. It was more than a vacation; it was a bridge between two lives.

With each day that passed, I realized that this change in direction wasn’t just the right decision, it was the only path that made sense for the life and future that we’re building.

We decided that the best way to transition from W-2 work to entrepreneurship was to take a full stop break. It’s easy to move from one thing to the next without ever pausing to reflect, think, and plan. We wanted to truly decompress, relax, enjoy family time, and come back feeling refreshed and ready for the next chapter.

Anyone who talks business with me knows that I’m a true believer in working in sprints. Set a goal, attack it full speed, accomplish it, and then take a break to relax, reset, and plan for the next sprint. We plan to organize our entire business around quarterly sprints with breaks (and ideally traveling) in between. My corporate job was a marathon. It slowly grinds you down over years, not weeks. It seems fewer breaks would boost productivity. It doesn’t. Hyper-focus is the biggest driver of productivity, but it can’t be sustained forever. After being a pharmacist for 14+ years, I knew that I needed a significant reset before diving into something new.

Mallorca: The Soft Landing

On August 4^th, we flew overnight from Chicago to Mallorca with a layover in Paris. If geography isn’t your thing, Mallorca is a Spanish island in the middle of the Mediterranean. We spent eight nights on the island, and the first four were at Zoëtry Mallorca on the quiet desert side. As many of you know, we often stay at Hyatt properties when traveling. Zoëtry, a health and lifestyle-focused luxury all-inclusive, was the perfect soft landing to begin our trip.

We spent those first four days almost entirely at the resort, and it was amazing. The days fell into a predictable rhythm: sleeping in, breakfast buffet, lounging and playing at the pool with flowing drinks and appetizers, resting in the room before showering, heading out to dinner, and going to bed late (it is Spain after all, everyone eats late!) It was easy, relaxing, and exactly what we needed to adjust to the six-hour time difference. More importantly, it was a much-needed break from phones, computers, meetings, and schedules.

After four nights, we moved to an apartment-style hotel in Palmanova. Palmanova is much more active: beautiful beaches, restaurants, shopping, beach clubs, and endless things to do. After four days of lounging, we were ready to explore. While we still spent time at the hotel and pool, we spent far more time out and about. We spent a day in Palma visiting the cathedral, the market, the shopping district, and getting family photos taken. We spent another day at Palmanova Beach, renting sun loungers and an umbrella. And we saw an incredible total solar eclipse from Punta de El Toro just before sunset. Palmanova was the perfect ramp-up from lazy vacation to exploring the sights of the area.

Croatia: The Gentle Transition from Vacation to Travel

After four nights in Palmanova, we flew to Pula, Croatia, with a layover in Zurich, Switzerland. That was an adventure in itself! We had a 55-minute layover, and our first flight was delayed 40 minutes. When we landed on a back runway in Zurich, a bus took us to the terminal. Our second flight was scheduled for departure at 12:40 with boarding closing at 12:30. The bus reached the terminal at 12:27, which gave us three minutes to get to our gate before boarding closed. I’ll also mention that the next flight from Zurich to Pula was in two days. We ran through the airport carrying Lily and our carry-on bags and got to the gate at 12:32. The gate agent laughed at me sweating and wheezing carrying a four-year-old and carry-ons. Thankfully they were holding the plane for us, but they said that in three more minutes they would have had to close the door. As soon as we stepped onto the plane, the flight attendant announced “boarding complete”. Phew.

We started out in Rovinj, Croatia, and stayed in Old Town which was very cool. It is a small peninsula in the Adriatic Sea. It sits directly across from Venice, and as a former part of the Venetian Empire, has a lot of Italian influence. Like many cities in Europe, it has narrow, winding, cobblestone, car-free streets with shops, restaurants, and cafes below, and residential units above.

We rented an apartment in the middle of the city center. While we kept the pace slower than many past trips, this is where we transitioned from vacation to traveling. We explored the town every morning, stopping into cafes for espresso drinks, enjoyed leisurely happy hours with appetizers and cocktails in the afternoons, and let Lily squeeze in gelato as often as we would allow.

We walked to the beach one day, which was interesting because the beaches there are all small, smooth rocks instead of sand. The water was crystal clear and very refreshing. We also took a sunset boat cruise and saw dolphins. Holly and I sat on the boat watching Lily squeal at the dolphins and talked about how life is really about experiences.

We rented a car from Rovinj and drove an hour inland to the hilltop town of Motovun. The Croatian countryside is beautiful and pretty remote. Along the way we stopped in a very small village with a population of 77 and ate at their only restaurant for lunch. The traditional Croatian food was excellent and the views were amazing. They originally didn’t have a table available outside, but the server (who by the way spent most of the meal sitting at a table drinking with his friends) grabbed a table and chairs from inside the restaurant and brought them out for us.

In Motovun, we stayed in a boutique hotel and winery that gave us plenty of ideas to replicate for a future real estate project! We took a shuttle to the top of the 277-meter summit and had dinner at a restaurant with panoramic views of the countryside below. '

Holly and I also had a “date night” with a winery tour, wine tasting, and dinner at the hotel’s restaurant. Lily tagged along of course, but the iPad was a more

than sufficient babysitter and gave us time for some grown-up conversation.

Motovun is in Istria, Croatia. Istria is known for truffles, and Holly is known for loving truffles. One of the days, we did a three-hour truffle experience. We met and played with the truffle hunting dogs (Lily’s favorite part), went hunting in the forest and found two truffles (my favorite part), and then went back

to the restaurant and ate a variety of truffle dishes for lunch (Holly’s favorite part). It was a very fun day. Our guide told us in 2023 he found a white truffle worth over €28,000!

Amsterdam: The Re‑Entry

Upon leaving Croatia, we took a short flight to Amsterdam for the last couple of days of the trip. I’ve written this post as we’ve traveled around, and I’m completing it here in Amsterdam on the final night of our journey. We explored all over the city by tram, by boat, and on foot. We took a canal cruise through the Jordaan and Nine Streets neighborhoods. We walked through Vondelpark, had lunch at Foodhallen, and saw key historic sites like the Anne Frank House.

After spending the last couple of weeks in smaller cities, Amsterdam felt like our reintroduction to a big city and some of the conveniences we are used to. It was the first place in weeks where I could order an iced vanilla latte! We also found a real grocery store, and restaurants with good food from every cuisine (we ate at American, Asian, and Dutch restaurants).

It was great to explore a city that we hadn’t visited before, but we could feel the trip coming to a close. The best part was realizing I wasn’t dreading going home. I wasn’t bracing for an inbox with 7,000 unread emails. I wasn’t hopping right back on the treadmill.

Work, But Different

Speaking of work, family and friends have asked whether we worked at all during the trip. Yes, we definitely did some work along the way. We still have a hotel to operate, and we were managing it from abroad. Every morning I reviewed the day’s check-ins and check-outs, loaded door codes, sent any needed messages, and coordinated turns with the cleaner. We responded to a few inquiries, paid a few bills, and kept up with emails. Most days it was 15-30 minutes.

I don’t mind doing a little work because it’s something I’m passionate about. It’s also satisfying to run our business from anywhere with a low level of effort. That has been one of our goals for a while. The most challenging part was the time difference, like needing to wait until 2 PM to text the cleaner, or getting a message when a guest checked in at 1 AM. Besides that, it was really smooth.

The Reset I Needed

This trip was the exact disconnect I needed to slow my pace, lower my stress, and remind me what actually matters. While things will ramp up again with our businesses when we return home, I plan to revisit this post from time to time to remind myself that spending time with family, traveling, and enjoying experiences are the reasons why we are doing all of this.

Entrepreneurs often focus on things like revenue, profits, asset value, and net worth. Along our

journey, we saw many small towns where people live much simpler lives. They don’t have much, but they have enough. They reminded us that life isn’t about net worth. Adding a zero to your bank account won’t make you happier (really it won’t). Experiences with loved ones will. We had some big ones like the eclipse, the sunset dolphin cruise, and the truffle hunt.

We also had some very memorable small ones like a cappuccino in a quiet square, a cocktail at a small table by the sea, and a gelato on the walk home before bed.

The Chapter Between Chapters

The pharmacist chapter of my life has come to an end. The full-time real estate and entrepreneurship chapter is about to begin. But these 18 days in Europe were the exact mini-chapter I needed. The perfect chapter between the chapters.