On Traveling, Letting Go, and Getting Fresh Perspective
?I’m writing this from Logan Airport, waiting to board a flight for a work trip. Traveling has become a regular part of my life—I’ve been finding myself at Logan more frequently than I ever anticipated. And while I’ve developed a solid routine, I’ll admit I have a love-hate relationship with business travel, especially when it falls midweek.
The logistics alone—flights, hotels, rental cars—add a layer of stress to the everyday surprises that come with running an incident-response-based IT business. It often feels like the universe senses when I’m heading to the airport and decides to throw me a curveball. I’ve had employees resign as I was stepping into security, clients experience major site crashes, and new clients insist on urgent onboarding. But, interestingly, more often than not, nothing happens at all while I’m away.
Yet, the mind is insidious. The moment one crisis arises while you’re traveling, your brain starts expecting the next one. It’s like a dog that once found a hot dog under a bush—now, every time you pass that spot, the search is on. As business owners, we have the same impulse. If something went wrong while we were away once, we begin to believe it will always happen, making it harder to let go and trust our teams.
Travel, however, forces an important shift: delegation. You simply can’t be as hands-on when you’re in another state or country. This is a good thing. It forces you to trust your team, create robust processes, and establish clear lines of responsibility. If your business can’t function without you for a few days, that’s a problem—one that travel will expose and help you fix. Stepping away means that you have to be able to trust your team and the foundations you’ve put into place.
I’ve found that stepping away highlights gaps in delegation and operational efficiency. Every time I return, I refine something—whether it's a workflow, an escalation process, or better training for my team. Business owners often wear too many hats; travel makes you take a few off, even if just temporarily.
Beyond delegation, travel provides a necessary break in routine. When you're in the trenches every day, handling similar issues and putting out fires, it’s hard to think creatively or strategize for the future. A change of environment can act as a reset button.
Some of my best ideas—new service offerings, improved internal processes, fresh marketing strategies—have come to me while traveling. When you’re in a new place, the mental white space created allows those ideas that have been simmering in the background to fully emerge.
But here's the key: Ideas are useless without execution. I’ve learned to block out time on my calendar upon returning to integrate the insights I gained while away. Without intentional follow-up, those flashes of inspiration fade back into the everyday grind.
With the rise of remote work, many business owners have the flexibility to work from anywhere—yet few take advantage of it. If you’re constantly in the same place, handling the same tasks, you’re likely missing out on the perspective and creative energy that come from a temporary shift in environment.
It doesn’t have to be a weeklong international trip. Maybe it’s a weekend retreat or a few days working from a different city. The key is to step away, trust your team, and give yourself the space to think beyond the day-to-day.
If you haven’t traveled for work (or just for a change of pace) in a while, consider this your nudge. With the ability to work from anywhere for most people, I encourage everyone to get a trip in for whatever fits your style. Sometimes things being just different enough help push those great ideas out.
Will MacFee is the president of Systems Support Corporation, which provides managed IT services for business in Boston and the South Shore.