Most entrepreneurs, at one time or the other, have had to move their vacation plans due to a business emergency or they just didn’t have anyone to leave in charge of their affairs while they are away. For most, the few times they have managed to go on vacation, they found they were not able to entirely disconnect from their business. Under these circumstances, the time meant for relaxing becomes even more stressful with no chance of relaxing or recharging.

During the holidays, with all the feasting and family, it’s very easy to skip resting. Holidays can be a triple-threat most often for entrepreneurs as travel and socializing always come with their own stress. However, intentional and conscious rest during the holiday season can be very beneficial for entrepreneurs.

Have it in mind that deep relaxation and some space from work allow for more clarity and creativity. In addition, it is pertinent to allow for a “re-entry” cushion of at least one day upon your return before jumping straight back into your routine. Note that this is very critical if you’ve been away for a long time. Remember to let everyone know of your vacation so they can plan around your absence.

Note that one of your reasons for hiring workers is to have people that can efficiently handle the affairs of your business in your absence. Entrepreneurs who go on vacation regularly return with happier, more positive views of life. Reports have shown that entrepreneurs who take regular vacations have more fulfilling relationships with less friction than those who barely do, as well as fewer heart attacks and lower stress levels.

Possible Reasons Why Many Entrepreneurs are Uncomfortable on a Relaxing Vacation

Truth be told, a lot of entrepreneurs are afraid of taking a break, and this fear stems from these few factors;

1. Business Affairs

According to reports, over 10% of Americans agree that they never get to relax on vacations, while 76% agree that they end up always checking voicemail and email. If there is pressure in the workplace, an entrepreneur may find it difficult to relax and enjoy a vacation.

  1. Financial Concerns

Money plays a very crucial role in travel and vacation as it can limit where you can go, how you get there, where you stay, what you can do, and how much fun you have. Vacations can also be quite expensive and although there are lots of ways to save money on travel, travel is a big expense for most people.

Have it in mind that this extra financial commitment can put a strain on an entrepreneur’s finances, especially if their business is still struggling. This can keep them from relaxing and fully enjoying the vacation.

  1. Unnecessary Commitments

Aside from work responsibilities, other forms of personal commitments may arise, especially during vacations, such as family reunions, meetings with friends, visits, or courtesy trips. Note that all these, if seen as obligatory, can be massively counterproductive, thus making an entrepreneur feel loads of stress even during a vacation.

  1. Negative Thoughts

Note that having adequate free time during the holidays can transcend to over-analyzing each situation, seeing nonexistent faults, and always having negative thoughts. Over time, this practice propels an increase in internal tension and a tendency to believe that situations are more serious than they are. This condition is yet another thing that can make an entrepreneur not enjoy a vacation.

To ensure you don’t fall into this predicament, you need to apply the “thinking stop technique”, which, according to experts, involves stopping negative thoughts that bring about emotional discomfort and replacing them with thoughts that are better and more innovative.

5. Navigating Unfamiliar Experiences and Situations

For entrepreneurs traveling to a new location, you will experience a lot of new things such as new foods, customs, currency, styles of dress, and modes of transportation. Although all these can be quite fascinating, they can also feel crushing or confusing at times. Language barriers can also in some ways add to feelings of culture shock and may propel you to feel isolated or devastated in a new place.

While you can never really be fortified for all the cultural differences, you can do a lot to prepare. There are so many books and online resources about every destination and culture, and acquiring adequate knowledge about a place can make you feel more relaxed once you get there.


Indeed, vacations are very necessary for an entrepreneur. The same way a car needs petrol to continue running, we humans also need to refuel & re-energize ourselves. If not, you will just be too tired to continue at some point. This is never a good feeling for an entrepreneur, especially for the sale of your business. Therefore, it is very necessary to go on a vacation if you feel exhausted, as long as you plan in advance to ensure that work moves ahead.