5 Things Entrepreneurs Must Do to Ever Get Some Time Off

You may not think you need a vacation but your team might think you're overdue.

learn more about Maria Rapetskaya

By Maria Rapetskaya


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It's a familiar story. You started your business because you wanted to be in better control of your life. You sacrificed time off to build up your company. And now you wonder where that control went as you continue to neglect your hankering for vacation. Or worse, any vacation you do take winds up feeling like the office, just with better scenery and daytime cocktails.

Related: 5 Tips for Maintaining Work-Life Balance, From People Who've Been There

I'm a fellow entrepreneur who, from the start, feared turning into yet another over-worked business owner. Here are the practices I've put in place to successfully prevent this from happening.

1. Strategize and plan accordingly.

You know when your slow times are, and if you don't, start paying attention. This can be done simply by keeping good records of when and how you spend your time. If you have a significant staff, it may be worthwhile to pay attention to their activity cycles. Even with simple spreadsheets you can quickly identify the lulls. This is the best way decide when to plan a getaway.

2. The "lulls" aren't times when things halt.

If you're able to identify a handful of weeks that historically and consistently demand none of your time, you're fortunate. Most of us, however, must accept that our companies are always operating, at some level. And this, too, is okay. It may mean negotiating with your business partner or your right-hand employee. Asking your co-workers, whatever their official designation, to help you get a break in exchange for extra pay or time off is perfectly acceptable. Alternatively, you can put freelance help on standby, or on committed contract, whichever best suits your needs and personality. The point is to use the info you uncover to create contingency plans while you're away. It will prevent you from regressing to those established thought patterns that deny you time off. If you allow yourself to believe it's possible to escape, you'll make it happen.

3. Book the vacation.

You don't wait and see if you're correct about your timing. You don't stall for any reason. Here's why: your entrepreneurial sense of responsibility will continue to trick you if you let it. Let's imagine you decide you'll book one month out. An invitation to bid on a project comes in that same day. You're very likely to avoid any financial commitment to a vacation until you know the status of this bid. This opens the door for plenty of other excuses, including the higher costs of booking last minute. Avoid giving yourself the loophole. Plan, commit and get excited about it. Of course, there's always the option of getting travel insurance for real emergencies.

Related: Adopt These 12 Habits for a Better Work-Life Balance

4. Decide who will be "you" while you're away.

Whether they're staff or a contractor, have a nice long chat with this person about how they prefer to handle your absence. This is a valuable lesson that my executive producer taught me. I always aimed to cover my bases by bringing my laptop and staying on top of my own emails. She, on the other hand, was far more comfortable not relying on me at all once my flight took off. It seemed counter-intuitive to me, but she had a great point. It may be stressful losing the key creative person in the company, but she can manage it based on the situation at hand. I can be on a trek without service for the day, or asleep based on the time difference. She can't wait on my input on time-sensitive decisions, and anything that's not time sensitive can wait because she'll be too busy for it anyway. Despite my genuine desire to be involved, I need to step away, and let her do her thing. I hired her because she's exceptionally competent, organized, trustworthy, responsible… the list goes on. So, with gratitude, I say "See you in two weeks!" Then I make sure to give her the same understanding and courtesy when it comes to her personal life.

Related: Lifestyle Entrepreneurship Is the Ultimate in Work-Life Balance

5. Wrap things up.

Finally, If you have some loose ends you'd like to wrap up, go for it, but don't beat yourself up if you cant' get through the list.

Do what you can and drop the rest on the list for when you return. Make whatever checklists you need to in order for you to feel more comfortable leaving. Go through them with your team, but don't overdo it. You don't want to come across as lacking confidence in people's ability to do their jobs without your presence. Of course, take appropriate measures if things do fall through the cracks, but be fair while you assess the state of affairs on arrival. Do remember you are a critical part of the company. So you can't expect everything to run the same exact way without your presence. Accept this and you stand a much better chance of actually enjoying your time away.

As an entrepreneur, you have the ability to craft the culture of your company. A commitment to quality time away benefits everyone. If you're as fair to your co-workers' vacations as you are to your own, you may find them very willing to help you spend some time on the beach.

Maria Rapetskaya

Founder and Creative Director of Undefined Creative

Maria Rapetskaya is the founder/creative director of Undefined Creative, a boutique agency built on flexibility, low overhead and a special emphasis on good, old-fashioned customer service. Her work includes award-winning creative projects for the NHL, NBCUniversal, Meredith and the United Nations, among others. Rapetskaya is also an outspoken speaker and published writer.

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