I’ve been coming to San Antonio for various reasons since the mid-2000s. It’s a vibrant, creative city which, like Las Vegas, is often overlooked. It shouldn’t be.
Travel has a way of helping me put my world into perspective in surprising ways. Breaking out of my daily bubble has a surprising way of making me see the world through a different lens.
The biggest breakthroughs in how I see my life and my work have come to me while traveling. When I think about times I’ve had the clearest thinking, when I’ve broken through the biggest mental walls, they have always been when I was somewhere besides home.
I’m not talking about great negotiating successes or big “wins” that come from intentional travel around specific meetings or events. I’m talking about accidental mental breakthroughs completely unrelated to the reason that made me travel in the first place. The team at SHIFT knew that if I was gone for 4+ days there was a good chance I would come back with a completely wild and deeply formed idea.
A few months ago I decided to make a point to travel somewhere “fun” at least once a month. I consider “fun” to be less of a driver in place selection but rather a driver in selecting the longevity of the trip. This month’s it’s Austin & San Antonio, March is St. Louis, April is New Orleans, May is likely going to be New York.
I’ve been to all of those places before, a lot. I’ve done tremendous amounts of work in all three and I’ll be doing some work this time.
But the fun mindset gave me a mental openness to reach out to people I know and those I don’t with casual intent. The trips last a few days and have no specific agenda. The trips allow me to explore cities in ways an intentional trip for a specific meeting wouldn’t. I have meetings, I eat great food, I visit gyms, I sit by fires.
When someone asks if I’m traveling for work or fun I don’t know how to respond. I generally don’t see the world binary terms and travel is no exception.
Some place selections are in reaction to asks from our portfolio or people I know. But instead of assessing whether a meeting is worth the hassle of travel I see the opportunity as a prompt to consider a “fun” trip whose measure of value isn’t determined by the outcome of the meeting.
Considering the geographic spread of our portfolio and of the relationships my past work built, I can visit a lot of places with familiar faces. So that’s what I’m doing.
Thanks to Airbnb I generally stay in places more like home than a hotel. The power of location cannot be overstated.
I’m sure as the year unfolds I’ll visit new places, perhaps some internationally. But it’s most likely that I’ll stick to the US for my monthly “fun” trips. They are mentally easy to schedule and the cities are just familiar enough to not cause mental overload.
First published on February 27, 2016