Why Business Owners Don’t Like Long Vacations — and How to Change That

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For many business owners, taking a multi-week vacation sounds like torture. Even if you manage to take time away from the company for an extended period, most owners are unable to fully unplug while away. You have to bring the company with you: frequent phone calls, regular emails, and a few hours’ work here or there while the rest of the family enjoys themselves.

The conventional explanation for why business owners do not take uninterrupted time off is that they are Type A control freaks who cannot let go. While a few owners may suffer from workaholism, it is not the most likely candidate.

If you don’t like long vacations, it’s probably not a personality flaw, but rather due to either of two contributing reasons. And both reasons are important to understand if you want to happily exit one day in the future.

Reason #1 – Your Team Is Not Running the Company While You Are Gone

The first major reason owners have bad experiences when taking time away has to do with your team — they are not actually running the business in your absence. We constantly hear business owners bemoan that taking vacation time is frustrating because they return to find an overloaded email inbox and a stack of issues requiring immediate attention.

This is a clear sign your team is not running the company in your absence — rather, they are stockpiling work until you return. You must create a team that is capable of running the company without you for at least a few weeks, including handling your normal responsibilities.

This is not simply to allow you some quality vacation time. If the company cannot run without you, it will be difficult, if not impossible, to achieve commonly-held exit goals: selling the company for a strong price, achieving a smooth succession, and exiting on your own terms. When you return from a vacation, you should return to an empty inbox and a short stack of issues requiring immediate attention.

Reason #2 – You’d Rather Be Working

The second major reason owners often do not take an extended vacation has to do with you — you enjoy what you do so much that being away from your company for a few weeks is simply not fun. You’d rather be working.

By itself, this is a blessing. As the saying goes, "If you love what you do, then you never have to work a day in your life." In the long run, the deep connection and affection business owners feel for their company can become a serious problem. One day you will want to exit — few owners aspire to die at their desk — and when you decide to exit, you will want to have a meaningful and fulfilling life after the company.

But if you cannot happily take even a few weeks away from the business, ask yourself, how will you find engagement and fulfillment once you have permanently exited from the business? Taking a few weeks away from the business gives you small, bite-sized opportunities to do just that.

How to Change This

Taking time away and fully unplugging from the company is critical. Too many owners look back later in life and wish they would have found more time for family and friends. Do not make that mistake.

In addition, taking time away from the company also benefits the business. It gives your leadership/management team a chance to see how well they can perform without you. Removing yourself from the company for a few consecutive weeks stress-tests your people and systems, revealing unforeseen weaknesses and uncovering unknown strengths. Furthermore, time away gives you the chance to explore options and envision plans for your future life after exit.

To catalyze change within your company, evaluate your leadership team. If they are incapable of running the company for at least two weeks without you, you must develop a plan and timetable for how you will cultivate the team that you need.

If you believe your team is capable of handling the company in your absence, take the following steps:

  • Meet with your team and let them know you intend to take a few weeks off and fully unplug while away.
  • Delegate one person to review your mail, email, and phone messages and assign any issues that arise.
  • Tell them you expect them to fully handle all company operations, including your responsibilities.
  • Specify the issues that they should not handle on your behalf but leave for you — it must be a very short list.
  • Instruct them that they are not to contact you while you are out unless for an emergency that they cannot handle. If necessary, describe realistic scenarios that would qualify as an emergency. This, too, should be a short list.
  • Schedule advance meetings with your team for immediately after you return. At these meetings, your team should be prepared to brief you on what happened while you were away, including how the company performed, what significant actions they took, and what issues require your attention.
  • Finally, give your team feedback on how they performed in your absence. Reward strong performance, and provide coaching and training appropriate for any inadequate performance.

To learn more about preparing yourself and your company for exit, schedule a complimentary consultation.

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