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Why Business Owners Need a Vacation (and How to Plan Yours)

Picture this: Work is under control, you’ve got a plan in place to keep plates spinning without you for the week, and you’re finally on an actual work-free getaway. Heck, you’re feeling so free and clear, and you and your family are building vacation memories Hallmark would kill to capture on film.

Wishful thinking, right?

We get it. No matter how badly you need a vacation, it can feel like an impossible dream at any stage of business. Getting away from work takes work—especially when you’re the business owner (aka the chief everything officer). You might worry the whole time that things are falling apart without you or feel like you barely have time to unplug before it’s time to head back from vacation and play catch-up.

But no matter how tricky it is to disconnect from running your business, you need a vacation . . . even if you start with just a day off or long weekend. You are worth the break, your family is worth the extra effort, and your team members are worth the healthy example you set.

So let’s unpack why taking time off is so important and how to plan your getaway so coming back to work feels less crazy. Once you’ve nailed down your vacation strategy, you’ll be set to pack your bags for some well-earned rest and relaxation.

Why You Need to Say, “I Need a Vacation”

3 Keys to Planning Your Vacation Strategy

More Vacation-Time Tips for Business Owners

Why You Need to Say, “I Need a Vacation”

Here’s the hard truth: You need a break. And it’s healthy to admit it. But don’t stop there. Once you’ve said those four powerful words—I need a vacation—you’ve got to make it happen.

Here’s the Debbie Downer side of why breaks are important:

  • Working long hours increases your chance of death from heart disease and stroke.1
  • Middle-aged men who skip annual vacations are more likely to die from cardiovascular causes, including heart attacks.2

That’ll get your attention! But besides being scared straight, you need a vacation for positive reasons like these:

  • You’ll enjoy things that fill your soul. Taking a break from work gives you more time to be with family and friends and enjoy the great outdoors. Why is this a big deal? Because 83% of Americans say being with family and friends gives them the most meaning, and 71% say experiencing nature fills them up.3 So make extra time to watch the sunset with your significant other—feel some sand between your toes while you’re at it.
  • You’ll stir up new ideas, solve nagging problems, and make better decisions. Did you know the windshield wiper was invented because, during a visit to New York, Mary Anderson realized that streetcar drivers were at the mercy of their side windows when it rained?4 She didn’t experience that problem sitting in an office. She was taking a break. And when she returned to her Alabama home, Mary sketched a wiper blade, had a company produce a model, and the rest is windshield-wiper history. Imagine the fresh ideas you’ll come up with  as you refresh your mind and let new creativity flow.

Fun fact: Money expert Dave Ramsey says when he travels to his lake house, he keeps a yellow pad and pen near his tackle box. Then he's ready to jot down new ideas or solutions to problems as they pop into his recharged mind.

  • You’ll grow, and your leaders will grow too. An old Chinese proverb says, “When I hear it I forget it. When I see it I remember it. When I do it I know it.”5  In other words, when your leaders and team members are given the chance to apply new skills and take on more responsibility in your absence, they build confidence and develop their leadership skills.
  • You’ll fine-tune your work processes and systems. Your goal of taking a real vacation is a great motivator for you to get your processes and systems in order. Documenting what you do and how you do it will help you see and fix gaps and see where you can easily delegate. In the end, you’ll have a working guide in place that will make your business stronger.
  • You’ll develop a healthier company culture. When you actually disconnect from work, you give your team permission to enjoy a healthy work-life balance too.
  • You’ll make strides in three of the six Drivers of Business: Personal, People and Plan. Did you notice how we just hit on how time away makes you personally stronger, develops the people on your team, and gives your mind space to dream and plan? Those are three of the six Drivers of Business in the EntreLeadership System (the other three are Purpose, Product and Profit). And as you master these areas, your business naturally grows.

So what are we saying? For the love of your health and the fantastic wins awaiting you, take a vacation from business!

3 Keys to Planning Your Vacation Strategy

There’s no going back now that you have your why. But crafting your vacation strategy is essential to your success. These three tips will help you plan.

1. Prepare your business.

  • Hire people you trust. Building confidence to be away from work starts with building a strong team. You do this by hiring people who align with your core values and operate with a self-employed mentality. What we mean by that is team members who own their work and the good of the company even when no one is watching. Trustworthy team members are ready to take on more responsibilities.
  • Set clear boundaries. No matter how little or how much operations shift during your absence, ensure the people you work closely with know you won't be available to handle certain tasks. Tell your clients and vendors when and how business tasks will get done while you’re away. And if you completely shut down your business while you’re gone, give a “business is closed for vacation” notice weeks in advance. You’ll be amazed how supportive people are when you loop them in early.
  • Use technology. Automate repetitive tasks like invoicing, calendar scheduling and inventory management using software. You can also streamline operations by using automated email responses. The better you communicate when you plan to return and what to do in case of emergency, the more confident others will be in your service to them.

2. Prepare your team (in other words, delegate).

  • Cross-train team members. Great leaders prepare their team members to cover lots of tasks so they can rise to new opportunities when duty calls. This is an important part of delegating with confidence. To grow your business—and to take a break from it—you’ve got to release some things to others who can handle them well. If you’re worried that handing things off to others will be a burden to them, stop. When you trust and elevate high-performing team members, it’s called upskilling, and it actually motivates them more. Just keep tabs on their workload and stress level as you empower them to handle more. And be sure to reward their extra effort.
  • Set clear expectations. Documenting your work and how you get it done gives your team the gift of clarity and sets you all up for a delegation win. If you really want to streamline your workflow, go a step further and identify what work is essential and what’s nonessential while you’re away. For example, preparing payroll for payday is an essential task to delegate or work on in advance. A nonessential task (aka one that can pause until you return) might be your weekly one-on-one meetings.
  • Designate a point person. Who do you trust to handle communication and filter what’s urgent enough to contact you while you’re away? That’s your point person. Identifying them is another critical part of effective delegation. Let your point person know what constitutes a true emergency, and empower only them to reach out to you. One business owner we know tells his team, “Only call in case of fire, flood or blood.” You likely want to add money or legal issues to that list, but the point is, make your boundaries clear.

3. Prepare yourself.

  • Plan well in advance. When you schedule your vacation months in advance, you can block your calendar so nothing gets scheduled while you’re away. Planning far ahead also makes it easier to snag time- and money-saving travel deals and arrange details like pet care, package holds and schedules with your travel buddies.
  • Review finances and contracts. Check upcoming financial obligations like bills to pay and contracts that need to be signed. Also, look over your insurance coverage and make sure your policies are active to avoid surprises if an emergency happens.
  • Disconnect with intentionality. Your vacation goal is to set aside distractions and do things you love with the people you love. Read, go fishing, play with your kids, or take a nap—whatever refreshes you! If unwinding is hard for you, try yoga, prayer or journaling to help you work through distractions and clear your head. Having some time to think will help you pinpoint business and leadership gaps you need to work on when you return. But once you identify them, set them aside and be present where you are.

Related article: Small-Business Success Stories

More Vacation-Time Tips for Business Owners

Ever heard the saying, “Give me six hours to chop down a tree and I’ll spend the first four sharpening the axe”? We’re not suggesting a tree-chopping or axe-throwing vacation—unless that’s your thing. But we are saying that well-crafted time away from work is a sharpening stone that will hone your business.


You probably thought running a business sounded fun—until you realized it would actually run you. Discover the EntreLeadership System—the small-business road map that takes the guesswork out of growth.

Here are some more ideas on how to make your vacation more meaningful:

  • Begin with the end in mind. Visualize what sounds fun and relaxing. Plan your location, time frame and budget around your vacation vision.
  • Share your vacation goals with a few trusted work friends so they can help you disconnect.
  • Start small if you need to. Even one day off makes a difference.
  • Set these boundaries: No phone at dinner, no work talk, and if you have to keep up on emails, set one hour in the morning to send and respond to messages.
  • If you have to make a business call, schedule it in advance and limit the conversation to about 10 minutes.
  • Get an accountability partner (like your spouse) to keep you in check.
  • If you really want an electronics-free vacation, choose a destination with no internet service.
  • Reframe your mindset: Taking this vacation will help you see the gaps in your business so you can make it stronger in the long run.Top of FormBottom of Form

The Bottom Line for Your Vacation

Taking a vacation from your business is an investment in your growth, well-being and the success of your team. So embrace it and have fun! With some great planning, the only care on your mind will be deciding between a poolside nap and a sunset stroll.


What’s Next: Discover Why, When and How to Delegate to Your Team

How do you turn your vacation from a pipe dream into a promise? You delegate the right responsibilities to the right people in the right way. Check out EntreLeadership’s free Delegation course to become a better delegator.

Delegate With Confidence

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Ramsey Solutions

About the author


Ramsey Solutions has been committed to helping people regain control of their money, build wealth, grow their leadership skills, and enhance their lives through personal development since 1992. Millions of people have used our financial advice through 22 books (including 12 national bestsellers) published by Ramsey Press, as well as two syndicated radio shows and 10 podcasts, which have over 17 million weekly listeners. Learn More.

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