A woman sitting on a beach chair on the beach reads a book.

How to Take a Vacation as an Entrepreneur

When you start a business, it’s a bit like your child. You don’t want to leave it, and you spend most of your time working on it.

There will come a time, however, when you need a break, and you’ll start dreaming of a vacation.

But how can you take a vacation when you are an entrepreneur? Read on to find out more about how even the busiest business builders can take a vacation. 

Why You Should Take a Vacation

When you began your business, you probably started with the mindset of knowing you would work weekends and holidays if it meant your business would take off. You know that you need to work hard in order to achieve success.

You may also be afraid to take a vacation because you fear you will lose some of the progress you have made with your business. 

While these are both valid reasons not to take a vacation, it has been found in studies that Entrepreneurs frequently burn out faster than regular employees. Burnout is a condition where you become over-stressed, and as a result, your health begins to fall apart. 

If you allow burnout to happen, you will likely need to take some time away from your business in order to recover. Depending on how burned out you are, this could take weeks or months

Taking a vacation every now and then is one of the few ways to prevent burnout. Even taking a short vacation of just 5 days to a week can do wonders for your mental well-being. 

Therefore, while you may be afraid to take a vacation, it’s time to be afraid of what will happen if you don’t take one. For the most part, a client will understand you being gone one week, but if you have to take months off to recover from burnout, you will likely lose far more business. 

You should stop asking why you need vacations as an entrepreneur and start looking at how you can take one in order to preserve your own mental health. 

A checklist in a notebook.
It can be easy for an entrepreneur to take a vacation if they plan in advance.

Steps For Taking a Vacation as an Entrepreneur

Before you pack your bags, know that there are several steps involved with taking a vacation as an entrepreneur. While you may not need them all, you need to take a few to ensure you don’t lose business in your absence.

1. Choose to Travel During the Slow Season

Every business has a slow season. For personal care and shopping businesses, it tends to be after the Christmas holidays in January and February. 

For education-related businesses, the off-season tends to be in the summer, and for marketing, while it depends on the product being marketed, the spring is often the best time to take a break. 

If you are having trouble locating your business’ off-season, then take a look at your accounting and see which month you made the least amount of money. This is the month you should plan your vacation as it will affect your work the least. 

Also, you shouldn’t plan to travel at the beginning or end of the month, as these are the times that typically require the most bookkeeping when it comes to business ownership. Instead, choose a week in the middle of the month so you can bookkeep before and after your trip. 

2. Start Delegating

A major aspect of being able to travel when you have your own business is delegating tasks. While you don’t need to delegate everything, you should take the time to get rid of some of the most meaningless tasks on your plate. 

A great place to start is by hiring a social media manager to handle your socials on a regular basis. You could also look into hiring a bookkeeper to help you with your accounting. 

If you don’t have the funds to hire an employee yet, don’t worry, as delegating can often include automation. Automation is your friend, and you should use it wherever possible, even if it’s just setting up an autoresponder for an email account. 

But, if you are able, you should look at hiring an assistant or manager of sorts to lead employees in your absence. Before you hire anyone, just be sure they exhibit leadership qualities that will help them maintain control in your absence. 

While whoever you hire (or whatever AI you set up) shouldn’t replace you completely, it should bring your company to functionality so you don’t stop earning revenue while you are away. 

3. Move Important Business to Your Phone

While it is always possible to take a vacation as an entrepreneur, you may find that you still need to be available occasionally to handle emergencies. This is typically the case when you can’t hire an employee and must rely on AI.

In this instance, move any urgent business to your phone. Input numbers for suppliers and take the time to set up your work email on your phone. 

Do note that it is not suggested to actually work during your vacation, rather just set up some basics, so you aren’t buying a flight home in the event of an emergency. 

4. Notify Clients in Advance

If you have a manager or assistant handling your business in your absence, there is no need to take this step, but for solo entrepreneurs and freelancers, this is crucial. 

Notify all of your clients that you will be gone at least a month in advance. Any client worth having will understand, and this will give them an opportunity to ask for any urgent work to be completed in the days before you leave. It also gives them an opportunity to place orders in advance.

You should also address any outstanding deadlines in the notification email. For example, if your vacation is March 12-20, and you have a deadline of March 31, let the client know that you still intend to meet that deadline without issue. This will reassure them that you understand the deadline and won’t let your vacation come in the way. 

Even though you are notifying in advance, you can ask the client if they would like a reminder email the day you leave. Sometimes busy clients appreciate this, especially if your company is just one cog in their large machine. 

5. Take Shorter Vacations

Unfortunately, as an entrepreneur, those two to three-week vacations you see friends taking are probably off the table for you. Instead, you should focus on taking the longest vacation possible without disrupting your business. 

The shortest vacation you should take is at least 5 days, as it will take at least this long for you to feel you are on vacation and not just a long weekend. But in general, your business should survive for a week without you.

Remember, just because you own a business doesn’t mean you need to work day and night all year long. You earn your vacations, too, just in a different way than most normal employees.

If you ever question whether or not you are taking too much time off, you should reference the amount of vacation time government employees are given in your area. This will give you a good idea of how much time off your clients can reasonably expect you to take. 

Some entrepreneurs might be able to take more than their local government employees, and this is great, too, just be receptive to clients when they begin voicing concerns about your availability. 

6. Add Days to Business Trips

There may be some businesses, especially during the initial start-up phases, where it seems truly impossible to take time off. In those cases, you should consider adding days to the beginning or end of a business trip to make time for yourself.

For example, if you have to travel to a client meeting in Florida for two days, consider extending your hotel for another 3 and making it a long weekend while you are there. While it may not be as relaxing as the full vacation you planned, it can make a huge difference to your mental health.

Plus, no matter what you may think, your business can be without you for a long weekend. 

7. Buy a Pre-Booked Vacation

Have you ever heard the saying, “I need a vacation from my vacation?” Sometimes, it can be all too true. 

As an entrepreneur, you will spend hours planning for your vacation, whether you are automating, hiring help, or working a little bit ahead. Don’t underestimate how tiring it will be to try and book your vacation on top of this.

It might be a little more expensive, but a pre-booked vacation, even if it is just 5 days, may be necessary to help your vacation work out. This way, you can just pay once, show up at the airport, and allow yourself to be in vacation mode. 

Not to mention that if something goes wrong while you are away, and you need to make a call back to your business, it is much less stressful to do so when you aren’t also trying to get around a foreign country by yourself or book tours somewhere where you don’t speak the language. 

8. Work Ahead

Once you’ve purchased your vacation, notified your clients, and the day you plan to leave approaches, don’t be afraid to work ahead a little bit, so you aren’t bombarded with work when you return.

For example, a few hours spent scheduling social media posts and blog posts can go a long way to lowering your stress level. You can also work to meet deadlines scheduled after your vacation in advance. 

Don’t go too crazy and burn yourself out before your days off, but just keep in mind that you may feel a bit stressed at the amount of work you have when you return from your much-needed vacation. 

9. Have an Emergency Plan

No matter how well you may plan in advance, emergencies happen. You cannot predict them all.

The best course of action is to have a plan if an emergency happens while you are on vacation. It may be as simple as giving a family member the key to your shop (in case an employee is locked out or there is a break in etc.), or you may need to have travel insurance in case you need to end your trip early.

Either way, go into your vacation with a contingency plan in case things may go wrong, then hope that you never have to use it. 

Chairs sit on a deck by the sea on a sunny day.
Having an emergency plan can help your vacation go smoothly. 

How Many Vacations Should an Entrepreneur Take?

The best part about being an entrepreneur is that you are your own boss. This means you can take as many vacations during the year as you would like. 

Of course, if you have a regular business, you can’t just take a vacation any time you please, especially if you are the only employee. But if you have the funds and time, you should take as many vacations as you would like. 

As a general rule, you should plan to take a break from your business twice a year. One study on Insider found that 13-14 days of vacation a year is what is needed to maintain your mental health. This lines up perfectly with taking two one-week vacations from your business a year. 

You will want to spread these vacations out, obviously, but finding your slowest month in the first half of the year and the second half of the year can help you to get in two nice vacations with the least impact on your business. 

Ready For Your First Vacation as an Entrepreneur?

Hopefully, by now, you have realized that even the busiest entrepreneurs can enjoy a vacation. Whether you plan to hire an assistant, work in advance, or simply take a short break working for clients, every entrepreneur deserves a break. 

If you have decided to hire employees to make it possible for you to take your vacation, ensure you know the biggest hiring trends before you begin the selection process. 

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