How to Go on Vacation as a Business Owner or Manager (and Actually Enjoy It)

Today we’re talking about taking a vacation and coming back rested and recharged. I cannot tell you how many of my clients do not know how to do this - or how hard it’s been for me!

I was nervous, stressed out, always needing to work, constantly feeling like I was going to miss an opportunity, or my clients weren’t going to come back, or I had to work because I had to make money. And if I didn't make money, everything was going to fall apart. The only thing that ended up falling apart was my sanity, my energy, and my health. So I had to get honest with myself about it.

“Listen, chick! You’ve got one life to live. How do you want to live it?”

I find it interesting when my clients come to me and say, "I'm nervous about taking time off. I'm anxious about coming back from vacation." My response is, "Of course you are!"

Imagine if you're already feeling stressed out and overwhelmed, and you have a mountain of a to-do list, and you step away from it for a week or two weeks, or maybe it's a day or two. And all you can think about are the messages, the voicemails, the emails, the mountain of responsibility awaiting you when you return.

You can't relax when you're at home because all you're thinking about is that mountain that is waiting for you. So you convince yourself that you need to go and check your email, you just need to go and check Slack, you just need to go and check your voicemail and text messages on your work phone.

Then you fall into THE RABBIT HOLE OF DISTRACTION and before you know it you’ve work a full day while you were supposed to be on vacation.

And then you start comparing and judging yourself. And thus, the cycle continues, and you come back after your "vacation" feeling worse than when you left. You are not rested, not recharged, AND you are beating yourself up on the inside for not handling things how you wanted.

So first, let us all take a deep breath.

Let's use this as an opportunity to forgive ourselves for past violations of our vacation time and the self-punishment that followed. Let’s instead acknowledge that we have not treated ourselves very well. We have not been good stewards of our well-being.

And then we can use this as our opportunity to redefine what vacation is about how we want to feel when we're on vacation and, most importantly, how we want to feel when returning from vacation. For me, vacation is about us taking intentional time away from my day-to-day tasks to have fun, nap and read.

Did you know that a lot of companies have mandatory sabbaticals? For example, in the financial industry, companies have pre-scheduled mandatory time that you step away. Companies use this time as an opportunity to see if there has been any corruption or fraud happening or if processes are breaking down or not as efficient or effective without us. As a manager or business owner, you want to know where you may be creating inefficiencies or gaps.

Breaks and vacations are an integral part of the business. We need to take breaks because we need to see how realistic and reasonable it is without you there. Yes, that's right, you are replaceable. We all can be replaced, but I still think you're special!

We are not robots or machines. Even robots and machines need servicing, updates in software, belts and batteries replaced, or an oiling up!

You should be oiled up on a beach! Doesn't that sound fantastic?!

I also want you to realize and understand the message you send to your team when you don't take breaks. When you don't recharge when you step away and don't honor that time with your family, it says, “you shouldn’t either or I may not value or respect you.” Your actions are just as important as your words and when they don’t line up, it creates distrust.

This is an old story, and you probably have had a stressful situation where you've had a boss who's violated boundaries, who's messaged you while you're away, while you're with family, and you have probably responded. Maybe that was a toxic situation, perhaps it was an emergency. But the reality is we start to categorize everything, every communication as urgent and important, when in fact, it's not. We are allowed to go away and we also need to have boundaries.

Here are some ways I’ve prepped myself for time away from my business:

Make an Agreement with Yourself

When I'm away on vacation, I agree to do the following things:

(I want you to write your own list)

1) I agree to remove social media apps from my phone.

2) I agree not to check work email.

3) I agree to put an out-of-office response on my email.

4) I agree not to schedule client meetings while I'm on vacation. (That's a big one. For me, I'm like... I can squeeze in a session.) No, vacation is vacation.

Ok now that we have our vacation agreements made, here’s are 3 Things to Prep You for Vacay:

1) Let people know well in advance that you will be taking a vacation

2) Create a contingency plan. For example, "In my absence, please get in touch with this person and then that person can then determine if it is an emergency and be clear about what makes an emergency."

An emergency is not when people can't find a file or have trouble with a mail merge. That's what Google is for. It's a beautiful thing.

3) The Night Before, or Right Now, Delete The Apps that Trigger You - A lot of my clients have Slack. Take this app off your phone. There's something about that "ping" sound that elicits a stress response. Anything that alerts you turn it off, or better yet, delete it! We're trying to de-stress you here!


Your time away is also an opportunity to train people to be more autonomous, have more agency, and feel more independent. Ultimately, this is what you want to do as a leader!

Can you believe that going on vacation is leadership training?!

Here is where you can start to delegate away:

As you're preparing for a vacation, you need to put your contingency plan in place. Who's responsible for what in which scenarios?

  1. If you're feeling anxious, use it to find the gaps and areas of concern in your plan.

"Oh, no, this is going to happen! What do they do if I'm not there?!"

Okay, let's imagine that happens. Who's going to do what? Who's going to take on what needs to happen while you're gone?

2. Accept that you cannot do everything, AND you are not meant to do everything.

It's a very inefficient business model to do that. If you were that in demand, you are holding things up, you are the bottleneck. So this is the time to take the lid off the bottle and depressurize.

3. This vacation allows you not just to unplug and recharge but allows your team to see what else they can do.

What else can they take on? What else are they capable of? And if they can't handle it, well then, what's wrong with the process, and what needs to be shifted and changed in the process? If it's not sustainable for you to be away, then we either don't have enough resources, the process is broken, the product is damaged, but we can't mask it. We can't duct tape it and say that it's perfection because that's not true. Once we know the source, we can improve our fix the dysfunction, but not with you in the way!

You deserve to have a break. It is a necessary part of life. So if you're a small business owner, take a break, even if you're just getting your business off the ground.

As a reminder, be proactive. Look for the gaps. If you have a stress response, get curious about it. What is it that you need to figure out? What questions do you need to ask? What resources do you need to build a plan that's outside of you so that you can step away and exhale?

4. Remember to breathe, just breathe.

That's the biggest thing about being on vacation is just to be present, take it in, enjoy the time and capture those memories. I hope you take a break as much as you can because we all need it.