It is not uncommon to hear an entrepreneur make the statement “I’ve worked really hard this year, and I deserve a vacation.  I’m taking my family to the beach for a couple of weeks and completely unhooking from the business."  

But the question is, does a small business owner ever really deserve a vacation...

...or is that mindset a holdover from his or her days as a salaried employee earning 2 weeks of paid vacation a year that he has been told he deserves? 

No one can deny that launching a small business is an onerous task fraught with daily or hourly challenges and stress.  As soon as one tough decision is made, another one crops right up to take its place.  At the end of the day, entrepreneurs often stare with wonderment at the sheer number of decisions they have made throughout the work day.  It’s an impressive list.  But they also know, the next day brings more of the same albeit always different issues.

Many entrepreneurs thrive on the challenge of always being in the hot seat, but at some point, all entrepreneurs suffer burn out – and that’s when the words start tumbling out about “deserving” time away from the constant pressure of making the right decisions. 

No doubt, you have figured out where this is going. Entrepreneurs choose to be hands-on managers of their businesses.  It is their baby, and they’re going to run it the way they want to run it.  Letting go of decision-making is one of the most difficult things an entrepreneur must do be truly successful as a business owner.  If a strong leader suddenly loosens the reins enough to delegate some decision-making, two things happen.  Either the Delegate tries to figure out what the boss would do, or the Delegate uses her own judgement.  In the first instance, it’s highly likely the Delegate has misread the boss, and it’s the wrong decision.  In the second instance, it’s not what the boss would have done, and it’s the wrong decision. 

Entrepreneurs are always eventually faced with this conundrum:  Letting go means decisions are made by others, and they are not the same decisions the owner would have made.  Learning how to delegate responsibility with authority is one of the toughest lessons small business owners have to learn. 

The dictionary defines “deserve” as “to be worthy for some reward or requital”.  When an entrepreneur has learned how to let go of control and effectively delegate decision-making with the authority and responsibility that goes with it, only then are they truly worthy for a reward or requital.

When an entrepreneur learns how to work on their business instead of in their business, that’s when they do actually deserve a vacation.

About the Author(s)

Penny Pompei

Penny Pompei is a serial entrepreneur having launched three of her own businesses in the San Francisco Bay Area and several others in partnership with others throughout the country.  She has relocated to South Florida and is now a volunteer mentor with Palm Beach SCORE and serves as their Chapter Chair.

Chapter Chair and Mentor, Palm Beach SCORE
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