If you had a year to work from anywhere, where would you go? What would you do? What ideas would you want to explore. What skills or personal practices would you want to improve? For me, these are not hypothetical questions.
Regular DKI readers know of my love of travel. I am very fortunate to have been in the position to see the world while working. Since I started the firm in 2020, I’ve done some of my best work from Costa Rica, Peru, Colombia, Argentina, Nicaragua, Thailand, The Philippines, Vietnam, Korea, and half-a-dozen other places. I think there’s something about the friction of dealing with unfamiliar places, languages, food, and cultures that makes me more creative. I’ve tracked this, and I’ve found that I have more interesting thoughts and write more when away from home.
I’ve just completed a deal to rent out my house to a wonderful family for the next year. As of today, I am officially out of my home and on the road until the end of April 2026.
There were a lot of things that went into the decision. Years ago, I’d find that after being on the road for 2-3 weeks, I was typically ready to come home. But I spent six weeks in The Philippines last year. I just returned from two months in Asia and could have easily visited other places before returning. My tastes have changed over time and I now like the longer more-immersive trips.
Plus, while I have a home I love, I spend a lot of time cutting the grass, maintaining equipment, and doing other DIY improvements. I think I’d rather spend my weekends improving my surfing in Portugal, revisiting a historical site in Israel, or experiencing the Bitcoin economy in El Salvador. Any other homeowners reading this who can relate?
Over the past few years, we’ve seen the US economy shift as Gen Z tends to prioritize experiences over goods. I’m excited to spend the year experiencing new ideas, places, and the people who live there. I tend to like renting apartments where the local people live over insulated hotels. If I play my cards right, the DKI interns might make me an honorary member of Gen Z.
Some goals for the year:
Professionally: I want to start working at higher intensity. I think you can often get more done in less time with more focus. I’ve started setting aside time to work on specific tasks, outsourcing more to DKI’s marketing partner, Flying V, and the interns, and have started muting my phone and shutting off notifications.
Personally: I plan to spend more time reading, exercising, and meditating. A year of good work and self-improvement is always a good idea. (OK – the meditating is due to having to deal with the stress of figuring out how to pack for a full year in one bag.)
Locations: I decided to spend the first month in the US visiting people. I handed over the keys to my renters on Thursday and got on the train to NYC where I’m staying with my former partner at Silver Arrow and DKI Advisor, Raji Khabbaz. I’ll have a little over a week here before taking a 9-hour train from Penn Station to Pittsburgh where I have a couple of cousins and a great uncle I haven’t seen in a year. Then, I’m heading to South Florida. Howard Freedland, DKI Advisor and my friend since our first day of nursery school together, lives in Jupiter. We talk almost every day, but I haven’t seen him in person in a few years. There are some DKI clients and subscribers in the West Palm Beach area who I’ll get to meet in person for the first time. You might also see me on a live finance show while I’m in the area.
At the end of May, I plan to head out of the country. Lisbon, Portugal is my first international destination. Side trips to Porto and Morocco, or possibly southern Spain are also possible. I’d like to visit Poland, and plan to return to Israel for the first time since I was 16. When the rainy season ends, I’ll head to Central and South America. I want to see El Salvador and experience the changes since they adopted Bitcoin as currency. Guatemala and Uruguay have been on my short list for too long and I plan to remedy that this year. There are some people I’d love to visit in Argentina and Peru, and Raji and his family are spending Thanksgiving in Cartagena. I might join them there.
For the first time in my life, I have the option to buy one-way plane tickets and see how well a place suits me before deciding how long to stay. It will be interesting to see how well the above “plan” survives contact with the real world. While my main focus will always be investing and the DKI portfolio, I’ll be providing regular updates on interesting experiences along with inspiring and funny photos both here and on X (@Gary_Brode).
As always, I’ll be working and writing along the way, and if you have any questions or comments, reach out at IR@DeepKnowledgeInvesting.com. And please let me know where you’d go and what you would do if you had a year to work from anywhere. Would you spend it all in one place or travel frequently?
