The Vacation Test!

Most business owners and executives think taking time off is the challenge.

It's not.

The real question is whether you've built a business that allows you to step away without everything grinding to a halt.

In this episode, we explore why vacation is one of the greatest leadership tests you'll ever take.

If the thought of being unavailable for a week fills you with anxiety, this conversation isn't really about vacation—it's about trust, delegation, leadership, and the systems you've built.

You'll also discover why disconnecting from work isn't enough. To truly recharge, you have to slow down enough to experience the moments you've worked so hard to create.

In this episode we talk about: 

• Why vacation reveals hidden weaknesses in your business
• The leadership habits that make disconnecting so difficult
• How your example shapes your company's culture around time off
• Why leaders often feel guilty resting
• A simple framework for being fully present on your next vacation
• The one question every leader should ask after returning to work from time off

Did you build your business to create a better life…or have you built a business that keeps you from living it?

If that question makes you a little uncomfortable, then it's one episode you really need to listen too. 

Transcript

SPEAKER_00 0:37

And actually your business forward. So whether you're in the office, on the job site, or just starting your day, grab a cup of coffee and let's jumpstart your week so you can leave better, work smarter, and build a better business. Welcome back to the podcast.

SPEAKER_01 1:02

Today I want to talk about something that probably isn't on your strategic plan. Vacation. Let me ask you a question. When was the last time you were truly gone? Not sitting by the pool answering emails, not just taking one quick call, not checking Slack every hour, I mean completely disconnected. No laptop, no notifications, no constant wondering what's happening back at the office. If the thought of any of that makes you uncomfortable, this is an episode you need to hear. Because one of the greatest leadership tests isn't how well your company performs when you're there, but how well it performs when you're not. Today I want to explore four questions every leader should ask before taking time away. First, let's start with the uncomfortable question. Why can't you disconnect? Most leaders immediately answer with external reasons. My customers need me, my employees depend on me, my company is moving too fast. Maybe that's true, but let's dig just a little deeper. What are you really afraid will happen? Are you afraid something will go wrong? Are you afraid someone will make a decision differently than you would? Or maybe you're afraid they'll discover they don't actually need you for every decision? And that's a difficult thought. Here's another question for you. Do you not trust your team? Or have you simply never equipped them to succeed without you? Those are two very different problems. If your phone has become your security blanket every time you leave the office, the issue probably isn't your vacation. It's your leadership system. If we struggle to disconnect, the next question becomes what is our vacation actually revealing? I want you to take a minute to think about vacation differently. Vacation doesn't create problems, it exposes them. If projects stop, if decisions wait, if employees panic, if customers can't get answers, those problems didn't begin when you boarded the airplane. They were already there. Your absence simply revealed them. Maybe expectations aren't clear. Maybe nobody knows who owns decisions. Or maybe you've become the bottleneck for everything. Maybe your managers have never been given permission to lead. Every vacation becomes an audit of your systems, not your commitment, your systems. One of the greatest compliments your team can give you isn't we couldn't survive without you. It's we handled everything. That statement doesn't diminish your value, it multiplies your impact. Because leadership isn't about making yourself indispensable. It's about building people who no longer need you for every answer. But even when our systems are healthy, many leaders still struggle to disconnect. Why is that? Well, somewhere along the way, many of us started believing that productivity equals worth. The harder we work, the more valuable we become. Rest begins to feel irresponsible. Taking time off feels selfish. Even when we encourage everyone else to do it. Think about the message you're sending. You tell your employees to use their vacation. Then you answer emails from the beach. You tell your managers to unplug, but you join Zoom meetings from your hotel room. People don't follow policies, they follow their leaders. If they never see you disconnect, why would they feel that it's safe for them to disconnect? And guys, I've been here.

SPEAKER_00 6:17

I've done payroll when I was on vacation because my boss expected me to.

SPEAKER_01 6:24

I've taken calls on vacation because my boss expected me to answer. Culture isn't built by what's written in the handbook. It's built by what leaders consistently model. Here's another hard question for you. Have you created a workplace where people are allowed to rest or merely where they're giving permission on paper? And those are not the same thing. But I think there's another lesson here, one that has nothing to do with business and everything to do with life. Those of you that know me know I spend a lot of time traveling. I work so I can travel. And over the years I've learned something. The best moments almost never happen because I rushed to the next destination. They happen because I slowed down long enough to notice where I already was. I think too many leaders spend months planning a vacation. Then they never actually arrive. Their bodies in Italy, but their mind is back at the office. They're standing on a Caribbean beach thinking about next week's meeting. They're watching a sunset while refreshing their inbox. They're physically absent from work, but mentally they never left. So before your next vacation, I want to challenge you to remember one word rest. The R stands for release. Put your phone away and trust the preparation you've already done. The E stands for experience. Notice where you are. Listen to the sounds. Really taste the food. Talk to the people. Be curious. The S stands for slow down. Not every minute needs an agenda. Leave room for wandering. Leave room for wonder. Leave room for doing absolutely nothing. Because sometimes the best moments happened because nothing was scheduled. And the T stands for take it all in. Ask yourself, what surprised me today? What made me smile? What will I remember about this place five years from now? Because memories require attention. And if you never slow down, you won't just miss your vacation. You'll miss your life. And isn't that why you started your business in the first place? Not simply to make a living, but to create a life worth living. So when you return for your next vacation, don't ask what did I miss? Ask what worked without me. Because every problem that surfaced becomes an opportunity to strengthen your business. Every decision your team made without you is evidence they're growing. And every challenge they solved is proof your leadership is multiplying. And that's the goal. Not to become less important, but to become less necessary in the day-to-day. Because that's what great leaders do. They build organizations that are resilient, not dependent. I'll leave you with one last question. Did you build your business to create a better life? Or did you build a business that's keeping you from living it? Thanks for joining me. If this episode hit a little close to home, I encourage you to share it with another leader or business owner who could use their reminder. Because the strongest businesses aren't built by leaders who are always present. They're built by leaders who develop people, create trust, and build systems that allow both the business and its leaders to thrive.

SPEAKER_00 11:32

So until next time, lead with confidence, focus on your people, and let's build a better business.