“I Know You’re on Vacation, But…” – The Reality of Running a Business That Never Clocks Out

Greetings from Las Vegas! I’ve lost count of how many times I’ve heard this phrase in the last few days:

"I know you’re on vacation, but…"

Each time, it’s followed by a question, an urgent request, or a booking inquiry. And I get it—when you’re in a service-based business, especially one centered around travel, people need answers. And never for one second does it escape me that they can get those answers from anywhere on the internet. I’ve built my business around replacing that and work hard to keep it from happening. Clients trust me to guide them through the planning process, find them the best experiences, and troubleshoot when things go wrong.

Add on to this the constant barrage of calls, emails, and texts coming daily from customers and colleagues at my other job—but that’s an entire blog post in itself and is not my story to tell. Yet.

The reality is, even when I’m technically “off,” I’m never really off.

The Challenge of Stepping Away

Owning a business, particularly one still in its growth phase, means every call, text, and email carries weight. I don’t have a massive corporate safety net. There’s no giant customer service team stepping in when I’m out. If I don’t respond, a potential client might move on. A booking could be lost. A time-sensitive travel deal could disappear.

And so, I check my messages. I answer my phone. I send the emails. Not necessarily because I want to, but because I know what’s at stake when I don’t.

The Anxiety of Letting the Inbox Pile Up

Even if I wanted to completely unplug, there’s another layer to this: the anxiety of coming back to a mountain of unread messages.

Most people see vacations as a time to recharge, to disconnect from work. But when you’re an entrepreneur, stepping away for too long means the work doesn’t pause—it just waits for you. And the longer you wait to tackle it, the more overwhelming it gets.

So, I find myself in the constant internal debate: Do I check in now and keep things moving, or do I wait and deal with the flood when I get back?

The Reality of a Growing Business

JMart Travels is still in its early years, and while we’ve had incredible success, we’re not yet at the stage where things run completely without me. That’s the nature of building something from the ground up. It takes time. It takes constant attention. It takes me being available, even when I’d rather be sitting by the pool without my phone in hand.

At the same time, I know that I can’t—and shouldn’t—try to do it all forever. That’s why bringing on help, like my incredible assistant, Lisa, has already been a game-changer. She’s still learning, but even this week, she’s been able to take many things off my plate. And in time, I know she’ll be fully ready to handle more so that I can truly take a step back when needed.

The Future: Blurring the Lines Between Work and Play

Even with all these challenges, I wouldn’t trade what I’m building for anything. Because I know that in time, JMart Travels will reach a point where I don’t have to worry about every call or email. Where I have a strong team in place to keep things running seamlessly. Where I can take a vacation and actually be on vacation.

But at the same time, I’m building something that will allow me to blur the line between work and play in the best possible way. My business isn’t about sitting at a desk all day waiting for the phone to ring or the Inbox to alert me of a new message—it’s about experiencing the world, traveling, and helping others do the same. The long-term vision isn’t about escaping work; it’s about integrating it into a lifestyle I love.

That’s the goal. And I’m getting closer every day.

For now, though… if you see me answering emails poolside, just know—I love what I do. But I also can’t wait for the day when the only thing on my to-do list is ordering another cocktail.