A CEO's Guide to "Workations": Balancing Global Business, Family, and Trail Running in Italy

Hello everyone, I am Henry.

Today, I want to briefly share my itinerary for the next week or so. Tonight, my family and I are flying to Italy to celebrate my daughter's high school graduation.

The Graduation Trip Tradition

We made a promise to our children: upon their graduation, they can pick anywhere in the world for a family trip, and they can even invite their friends. Last year, my son chose the South of France and Spain. This year, my daughter selected two destinations in Southern Italy, including a beautiful island. So, our entire family is heading there to accompany her.

Aligning Global Time Zones: My "Workation" Mindset

My travel schedule is essentially built around work. When I am in Europe, I dedicate my mornings entirely to business.

I wake up early and work straight until noon. By 12:00 PM in Europe, it is 6:00 PM at our Asian headquarters. Working through the European morning perfectly covers the core business hours in Asia. After noon, I step away from my laptop. Since my family usually sleeps in anyway, this schedule allows me to stay fully engaged with the company without missing out on the vacation.

Beyond my daily work hours, I have three main priorities for this trip:

● Quality Time with Family: My family has planned several activities, including dining at local restaurants and visiting the Blue Grotto. My afternoons and evenings will be dedicated to exploring these incredible spots with them.

● Intense Trail Running Training: We are staying at cliffside hotels, which is perfect because I am bringing all my trail running gear. Shortly after returning from Italy, I am competing in a 100-mile (roughly 170-kilometer) trail running race. To be honest, I am feeling the pressure. The longest I have ever run is 120 kilometers. This will be my final major prep race before a massive competition in August, and I am slightly anxious about whether I can finish it. Therefore, I plan to run up and down these coastal mountains every day to build my endurance and confidence.

● Sharing Insights on Southern European Global Mobility: Since I will be in Southern Europe, I plan to leverage this trip to produce a content series covering the region. I am highly familiar with the lifestyles and immigration policies of Portugal, Spain, Italy, and Greece. I hope to share some valuable insights on global mobility and residency programs in these four countries. If I capture any beautiful scenery or interesting moments, I will be sure to share them.

My Unconventional Vacation Philosophy

My approach to vacations is somewhat unconventional: I always work.

There is a running joke in my family. Whenever we stay at luxury resorts, I wake up early and head down to the lobby or business center to work, simply to avoid waking my family. The hotel staff often tell me, "You are the first person we have seen working here in a long time." My response is always, "Of course! You have to work hard to afford such a beautiful hotel."

Many people might find it crazy to work during a long vacation. They think a vacation should mean completely disconnecting. But my perspective is different. I view my work the same way I view long-distance running: it is a deep passion. All passions come with moments of struggle and moments of profound joy. For me, work is a fulfilling endeavor. Why care about what others think when you are dedicating time to something you truly love?

Recently, I listened to a podcast interview with Nvidia CEO Jensen Huang, and his approach to vacations resonated deeply with me—though he undoubtedly works much harder than I do! He mentioned that when he goes on vacation with his family, the only thing that changes is his view. Instead of looking at the courtyard from his office, he looks at the beach from his hotel room. He is still working the entire time. That is exactly how I operate.

Remote Work Over Vacations

Instead of calling it a "vacation," I prefer to call it "working remotely."

My upcoming schedule is packed: Italy in June and July, France in August for my race, and then potentially the United States in September to help my children settle into school. I travel globally quite often. If you don't disrupt your core working rhythm, this highly mobile lifestyle is actually very manageable.

Whether it is syncing with Asian business hours by working mornings in Europe, or dedicating my afternoons and evenings to work when I am on the US West Coast, I have operated this way for years.

That is all for today. I need to finish packing for my flight tonight.

See you in Italy!