The Real Reason Entrepreneurs Don’t Take Vacations

Between 2003 and 2008 my husband Chris and I did the following: moved halfway across the country, had two children, started three businesses and sold one of them. Those years were a blur, but I don’t remember taking a vacation longer than three days.

By the time we were ready to take a “real” vacation — the kind with beaches, Mai Tai’s and massages — the Great Recession was in full swing. It wasn’t until 2012 that we finally cleared our calendar and scheduled a much-needed break. By this time we hadn’t set foot on a beach since our honeymoon.

I remember the first day of that “real” vacation well. I remember sitting on a white-sand beach in Gulf Shores, watching our boys frolic in the waves, trying desperately to relax and not think about business. Far from feeling any sort of bliss, I felt disconnected from the carefree, beach-goer merriment around me.

In that moment I realized something unsettling about myself: I had forgotten how to take a vacation.

Freedom? Not so much

The life of an entrepreneur is filled with irony. You don’t have to own a business for long before you notice the gaps between what you thought versus what you got. One of my favorite entrepreneurial ironies is this: People often list “freedom over my time” as one of the primary reasons they start a business, yet entrepreneurs constantly bemoan how hard it is to step away.

The short-term consequences of not taking a vacation from your business may seem tolerable. Your spouse and children are disappointed, but you’ll make it up to them next year. You won’t get the R&R you know you need, but you can tough it out for now. The long-term impact of not taking time off goes beyond compromised health and relationships: it will decrease the value of your business.

While excuses abound, the real reason entrepreneurs don’t take vacations is because we forget how. Let’s take a look at how this happens.

The 3 stages of vacation amnesia

I’ve noticed — and experienced firsthand — that vacations fall off the business owner’s radar for three different reasons at three different stages in the business life cycle.

Stage One: Financial

During the startup phase vacation plans often get scuttled for financial reasons. These are the bootstrapping months (or years) of business ownership. Budgets are tight both in and outside of the business. Even if you can afford to take a vacation during this stage, the priorities are to conserve cash and focus all of your time and energy on turning a profit.

You skip vacations during these years.

Stage Two: Physical

Once the startup phase is in the rearview mirror, your business enters the survival and growth stage. At this point your reasons for not taking a vacation go from financial to physical. While your business is perking along nicely, your presence is still required for it to run smoothly. The business is experiencing some serious growing pains that probably revolve around your unwillingness to a) hire senior management, and b) delegate. You feel the tension between profitability and sanity. The former takes a hit if you hire talent to help run the business, but the latter will suffer if you don’t.

You manage to take vacations during these years, but you can’t truly unplug from the business.

Stage Three: Mental

Even as the business reaches maturity, some owners still have trouble taking extended time off. With the first two excuses off the table, vacations now represent a mental challenge. Your identity and daily rhythms are so intertwined with your business that it’s just too hard to mentally “check out” and take a vacation. This is often the time when marriages have been stretched to the breaking point, regrets about missed birthdays and soccer games begin to set in, and health issues begin to surface.

You may or may not take vacations during these years, but you find it increasingly difficult to enjoy them.

The link between vacations & value

There’s an additional irony associated with not taking time off. While your justification for skipping vacations may be to protect the profitability of your business, you are actually hurting its value.

When I meet with owners who are considering selling their business, vacations are one of the first things we discuss. On the surface it may seem like a nice conversational ice-breaker. But it’s also a quick way to gauge how attractive the business might be to buyers. Owner dependence has a direct correlation sellability, which in turn affects value. Simply put, if your business can’t run without you then you don’t really own a business, you own a job.

I’ve heard a variety of answers to the vacation question over the years. Not surprisingly, the most successful owners have built an enviable life outside of their business. They take at least four weeks of vacation a year, or more. They visit remote locations where they are completely unreachable for weeks at a time. They split their time between homes (plural!) both here and abroad. These fortunate owners can look forward not only to their next vacation, but a handsome payday when they’re ready to sell the business.

If this sounds like you, then congratulations; you’ve won the great game of business. If not, it’s time to get over vacation amnesia. In addition to the many personal benefits of taking time off, vacations are a litmus test for the health, sustainability and value of your biggest asset: your business.  

Want to build a sellable business that doesn’t rely on you? We’re here to help. Contact us today to get the conversation started.


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