There’s something uniquely appealing about a road trip as an entrepreneur. It’s one of the rare moments where you’re forced to step away from your desk, your inbox, and the endless parade of “quick questions” that are never actually quick. But if you do it right, a road trip isn’t just a break from work, it’s an opportunity to think, plan, and even get ahead.
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Of course, that only happens if the trip itself goes smoothly. Otherwise, you’re just a stressed-out founder stranded on the side of the highway Googling, “tow truck near me.”
Here are a few practical (and hard-earned) tips to make sure your next road trip is as productive as it is enjoyable.
Before You Hit the Road: Set Yourself Up for Success
Let’s start with the basics: your vehicle. Nothing derails a road trip faster than poor planning. And yes, realizing two days before departure that you’re overdue for an oil change absolutely counts as poor planning.
Take the time to get your vehicle road-ready well in advance. Top up your fluids, especially windshield washer fluid. If you’ve ever driven through a Canadian winter (or what we generously call “spring”), you know that slush-covered highways can turn your windshield into a Jackson Pollock painting in seconds.
I learned this lesson the hard way. On one particularly memorable trip, my co-founder had to lean out the passenger window with a bottle of water while we were on the highway just to clean the windshield. It was equal parts dangerous, ridiculous, and completely avoidable. We’ve never skipped that step again.
While you’re at it, check your tires. A quick walk around the car can save you hours waiting for roadside assistance. It’s not glamorous, but neither is standing on the shoulder explaining to a client why you’re going to miss a call because of a flat tire.
Fuel Your Body Like You (Claim to) Fuel Your Business
Entrepreneurs love to talk about optimization until it comes to what they eat on the road. Then suddenly it’s all gas station hot dogs and regret.
Packing healthy snacks or a simple lunch is one of the easiest ways to stay energized without unnecessary stops. It also helps you avoid the inevitable crash that comes from fast food and questionable coffee.
Keep it simple: foods that are easy to eat, minimally packaged, and not going to require a full unwrapping ceremony while you’re driving. If it takes two hands, a knife, and your full attention, it’s not road trip food.
Pro tip: peel your fruit in advance. It’s a small step, but it means you’re not trying to wrestle with an orange while merging onto the highway.
Technology: Your Best Friend (Until It Isn’t)
This one seems obvious, but it’s amazing how often it gets overlooked, bring your phone charger. Better yet, plug it in before you even leave the driveway.
A dead phone during a road trip isn’t just inconvenient; it’s a liability. Whether it’s navigation, last minute calls, or a calendar reminder you forgot about, your phone is your mobile office.
Speaking of calls, make sure you’ve downloaded any necessary apps like Zoom or Microsoft Teams ahead of time. These platforms have an uncanny ability to demand updates or installations at the worst possible moment, usually when you’re trying to join a call from a parking lot with questionable cell service.
There’s nothing quite like fumbling with an app download while apologizing to a client and trying not to miss your exit.
Take Breaks (Seriously)
There’s a certain entrepreneurial stubbornness that kicks in during long drives, the idea that you can just power through. After all, you’ve pulled late nights, early mornings, and probably built your business on caffeine and determination. How hard can a few extra hours behind the wheel be?
Harder than you think.
Fatigue sneaks up on you. One minute you’re fine, the next you’re re-reading the same highway sign three times and wondering why your eyes feel like sandpaper. It’s not just uncomfortable, it’s dangerous.
Taking breaks every couple of hours isn’t a luxury; it’s essential. And no, opening the window or turning up the music doesn’t count as a break.
Pull over. Get out of the car. Walk around. Stretch. Grab a coffee or some water. Even 10–15 minutes can reset your focus and make the next leg of the drive significantly safer and more productive.
Turn the Car Into a Rolling Think Tank
One of the most underrated benefits of a road trip is uninterrupted thinking time. No emails. No Slack notifications. No one popping into your office “for a quick minute.”
Just open road and mental space.
My co-founder and I have had some of our best brainstorming sessions in the car. There’s something about the combination of movement and lack of distractions that makes ideas flow more freely.
We always bring a notebook, regardless of who’s driving. Because as great as those ideas feel in the moment, they’re also incredibly easy to forget.
And there’s nothing worse than having a breakthrough idea somewhere between Kingston and Toronto… and then completely losing it by the time you reach your destination.
Write it down. Always.
Learn While You Drive
Look, I enjoy a good music playlist as much as anyone. But there’s only so many times you can listen to the same songs before even your favorite tracks start to feel like background noise.
(And yes, my co-founder would strongly disagree with that statement, especially when it comes to certain 90s boy bands.)
Long drives are a perfect opportunity to learn. Podcasts, audiobooks, industry interviews, there’s no shortage of content that can make you sharper, more informed, and maybe even a little more inspired by the time you arrive.
Download your content ahead of time so you’re not relying on spotty service. Then treat the drive like a mobile classroom.
You might be surprised how much you can absorb over a few hours on the road.
Final Thoughts
A road trip doesn’t have to be a break from productivity; it can be an extension of it. With a little planning and the right mindset, you can turn hours on the road into time that’s safe, healthy, and genuinely valuable.
Make sure your vehicle is ready. Fuel yourself properly. Set up your tech before you need it. Take breaks when your body tells you to. Capture your ideas. And use the time to learn something new.
Because at the end of the day, the goal isn’t just to get from point A to point B.
It’s to arrive better than when you left.
by Kris McCarthy