Small Business Owners on Vacation: Is it possible?

Ferien! If it sounds foreign, that’s because it is. And what it means might actually sound even more foreign, especially to my fellow small business owners. Ferien means “vacation” in German. My husband and I spent a week in Germany and the Netherlands in 2020, right before the world shut down. Cheese, beer, windmills, and churches… we saw it all.

If you’re like I was, the idea of small business owners on vacation could cause an immediate spike in heart rate. What if there’s a client emergency? What if my website goes down? What if someone submits an RFP, and I don’t see it and lose out on new business? We are not corporate employees getting three or four weeks of paid time off a year, with someone else running the company while we play.

For small business owners to take a vacation requires stepping away from the business we’ve built from the ground up, and many times, with no one left in charge. The stakes are much, much higher. High stakes are why only 57% of small business owners take vacations. And of those who go on vacation, almost 70% of us check in with work at least once a day.

Does this sound familiar? We need to do better—for our mental health, our relationships, our employees, and our creativity.

So, can small business owners truly “get away”? The answer is yes. But it comes with structure, planning, and boundary-setting. Since my week-long trip to the Netherlands and Germany, I’ve been to Mexico for 10 days with friends and am planning a two-week Mediterranean Cruise in September with my mom and sister. Here’s how you, too, can make this happen.

Stop Making Excuses for Not Getting Away 

My initial answer to considering a vacation was, “I can’t do that.” Or “I can’t afford it.” Or “I can’t afford the time to plan it.” All those reasons are deep-seated in my head, and I know they are incorrect. Now, when I start to feel that way, I change my mindset to “I can’t afford to miss this opportunity.”

The reason for the 2020 trip was that my husband had some work-related training scheduled in Germany. So we approached it as a great opportunity to do something together—and a very inexpensive one at that. We bought my flight and hotels on points and stayed with some friends in the Netherlands. Mexico is close to Texas, and the all-inclusive resorts are pretty inexpensive. The European cruise is not inexpensive… I’m not going to lie. But, it is a gift from my father to his girls. And we intend to enjoy his generosity with this once-in-a-lifetime trip. (That gift is due to my dad’s hard work as a lifelong business owner. And I’ll be taking it with my sister, who is also a business owner.)

These options address the “I can’t afford to go” objection – at least from the financial side. Now… what about the time side?

Communicate Your Time Off 

I start to let people know I will be gone soon after scheduling the trips. Much of the stress associated with small business owners on vacation lies in the unknown. What will happen when I’m gone? Who’s going to do what? Communicating as soon as your plans are set will help you get in front of it.

As soon as I book trips, I start communicating with clients and my team, prepping them for my unavailability. I send the usual email and phone notifications, but I used to take it further and include it in my proposals. For my 2020 trip, all of the business proposals I wrote stated that I would be on vacation during set dates. After 2020, that step was unnecessary as I had stopped working directly with clients, so my team was handling the work.

Your clients are real people, too, who also take vacations. Talk to them. Wrap up projects or postpone projects until you get back. Just don’t let your clients find out you’re on vacation by your out-of-office message.

To Combat Your Vacation Objections, Start by Identifying Your Slow Time.

• When are you free of conferences?
• What projects can be placed on hold?
• How can you do it more cost-effectively?
• Do you or your significant other have a work trip booked that you can add something to the beginning or end of?
• What is holding you back from taking some deserved time off?

Delegate and Automate 

Leaving the office for vacation is the best test of your delegation skills and how well you have implemented automated processes in your business. Can your business still operate without you there? Luckily, mine can. That means my executive assistant still took care of my emails, my team ran our client projects, and my marketing assistant kept up my social media and other content. My bookkeeper runs payroll, so I didn’t need to worry about that either.

If you’re handing off tasks while you’re out, evaluate how they went while you are gone. Maybe that task you delegated during your time off can become someone’s permanent task instead of yours. Essentially, don’t take it back!

When you return, figure out what needs to be fixed before the next trip.

• What didn’t get done while you were away?
• What balls were dropped?
• Use what you have learned to show what gaps need to be filled.

It’s easy to fear that your business will fall apart without you, but if you have established solid processes, your team is prepped for what a true emergency is, and knows how to reach you, things will run just as smoothly as they would if you were there. Trust the process and the team you have assembled. They exist for this reason.

Give Yourself Permission to Check-in with Work 

Some small business owners might actually feel more relaxed on vacation if they are somewhat connected to the office while away. I used to be one of those people. When you first start stepping out, it is OK to check in but put some parameters around your working time. Pick a specific time of day, do what you must, and then be done. If you need reinforcement to help you honor your parameters (besides your significant other telling you to put your phone away), apps exist that can shut off phone distractions. On an iPhone, you can set up different focus settings so you don’t see notifications from work apps unless you purposely go to them. Do what you need to do to respect the boundaries you established.

In 2020, I still applied calendaring to my vacation. (Intentional use of time did not stop when I was out of the office… I am sure this surprises absolutely NO ONE.) I focused on checking in mainly in the mornings, with afternoons and evenings left for fun. Also, I did my work primarily while en route to somewhere, like the eight-hour flight and the train to Frankfurt and Munich. The beauty of virtual workplaces is that you can work from anywhere. I felt I was still on top of it but also on vacation.

But the 2020 vacation was the last time I checked in. In Mexico, I took Slack and my work email off my phone. I purposely planned to separate myself from work. It took almost five days for me to stop dreaming about work. But thereafter, I was truly relaxed. My European cruise has the added advantage that the time zones are so different that checking in and working are much harder. So, I expect to let it go from my brain even sooner.

Relax

Of course, the daily check-ins helped on my first long separation attempt, but I did relax and took time for self-care. My husband and I had a wonderful dinner at a one-Michelin-star restaurant, Schwarzreiter. (It was amazing. And my first official Michelin Star experience.) We took a brewery tour in Munich and saw an attic church and the Anne Frank Museum in Amsterdam. Plus, we enjoyed a day in Leiden, just wandering around the old haunts of our friends who met there.  

Vacation brings a change of pace and a change of daily inputs. It lets your mind think about things you don’t normally think about. For example, seeing history in Europe brings a new perspective that gets the creative side of your mind working. Laying on the beach reading books and getting massages creates a peace that separates you from the day-to-day stress. (I read Where the Crawdads Sing during that vacation, and it’s a great read if you’re looking for something to get your mind off work. Please don’t take business books!) Regardless of your choice of how to get away, a change in pace is true recreation, which is always uplifting.

To make the transition back into the real world much smoother, give yourself a buffer before and after the trip to deal with jetlag, catch up on email, and get your house in order again before diving into work.

Reflect on How You Have Progressed as a Small Business Owner

Most importantly, taking time off gave me time to reflect on being a small business owner. Many wonderful things come with being a small business owner, and I wouldn’t trade it for the world. But those things come at a cost. Some of that cost is that you’re never not working when you’re first starting out. But because we are a virtual business, I am blessed to be able to work anywhere in the world. I am lucky I could work while we went on vacation, as one of the OneLife Mastermind members reminds the group regularly.

But the biggest lesson from my vacations is that I am proud to say that I no longer work in the day-to-day. In 2017, I could not have taken trips like these. I could only take one day off here and there – maybe a long weekend. But for Beyond the Chaos to grow, scale, and be a real business, I needed to get out of the daily minutiae, so I’m not the bottleneck. The 2020 trip was the first step. The Mexico trip was the test. And I’m not the slightest bit worried about the upcoming European cruise.

How do you get to a long vacation? For you, that may mean you’re not the one developing software anymore. You might be writing a marketing plan but not creating the copy or art. Create processes, get the details out of your head, and share them with your team. Your team can execute for you. So take that trip. Or that staycation. You’ve earned it.  Remember, if your business can’t run without you, then you don’t own a business – it owns you.

My team and my processes have Beyond the Chaos humming. Your goal should be a three-week vacation without checking in. That’s the real test. As of now, I could take a three-week vacation, but I would miss my dog too much!

To learn more about establishing a process-driven business and getting to that vacation, read Efficiency Amplified: Driving Business Value. This book, written by Tom Bronson (an exit planner) and me, will show you the path to a true vacation, and it starts with establishing solid operational processes. (Make sure you read the foreword written by our client, Joe Scarpetta of The Scarpetta Group, as he recounts his first three-week vacation.)