The Guilt-Free Guide to Vacationing for Entrepreneurs - Craft Your Content

The Guilt-Free Guide to Vacationing for Entrepreneurs

It’s that time of year again. We’ve stuffed our bellies full of turkey with all the trimmings, and now the hustle and bustle of the holiday season is upon us.

You might be thinking about how great it would be to take some well-deserved time off from the daily grind. But can you?

Does simply thinking about taking time off make you break out in a cold sweat, worrying about all the work that won’t get done while you’re offline? Do you feel guilty when you’re not working or at least thinking about your business?

Even though it’s important to keep business operations going, it’s even more important to take a break now and then for your own well-being. Taking care of your mental and physical health is crucial to the success of your business.

The holidays are a difficult time for entrepreneurs to balance taking time off to celebrate the season with their family and friends with preparing and planning for the work year to come. And don’t forget how important it is to finish the current year strong.

Luckily, entrepreneurs can alleviate the guilt of taking time off during the holidays by delegating some tasks and automating others, while also making sure their team members take time off themselves.

Why It’s So Hard to Take Time Off From Work


Entrepreneurs tend to work non-traditional hours. It’s difficult to have a set number of hours to work per day or per week when you are the owner of a startup or a small business. For many entrepreneurs, they’re a one-person or a few-person show. Also, most entrepreneurs love what they do for a living, and it’s hard to take a break from doing something you enjoy!

When emails are coming in fast and furious from staff and customers, it’s up to the entrepreneur to put out any fires as quickly as possible to make sure their business runs smoothly and keeps thriving.

Guilt can also be a big factor keeping entrepreneurs from taking much-needed breaks. You don’t think about your own needs because you feel guilty about not focusing on your business constantly.

But you can’t continue to work all those hours without allowing yourself to take a break and still expect your business to remain successful. Something’s gotta give.

Downtime and vacation time are vital for entrepreneurs; they can refresh your mind, improve productivity, and boost creativity. There are negative effects of continuously working without a break, so it’s important for entrepreneurs to sneak in some downtime when they are unable (or unwilling) to take a full vacation.

What Can Happen if You Don’t Take a Vacation

When it comes to taking vacations, entrepreneurs might think about all the bad stuff that could happen to their business. They might think employees’ productivity could go down if they aren’t there, details could get missed on important projects and potentially send a client packing, or they could miss a big business opportunity if they aren’t available to answer calls.

But what about the effects that not taking a vacation can have on the entrepreneurs themselves? Here are some of the negative effects of failing to take adequate time away from work:

  • Your brain won’t have the downtime it needs to function properly. Just as your body needs rest, so does your mind. Downtime helps ensure that your brain can do the work it needs to do to keep you motivated and attentive.
  • You won’t be as creative. If you take some time off, you might actually be able to come up with new ideas. Giving your brain a rest and refreshing yourself can open up your mind to innovative project ideas.
  • You could snap at your staff. No one wants a miserable boss, so taking some time off can help ensure you’ll maintain a good relationship with your employees.
  • You might make poor decisions. When you’re feeling tired or overwhelmed, you aren’t as clear-headed as when you are well-rested and feel good about your daily workload. Taking a vacation can give you the break you need to keep your mind sharp and ready for making important choices for your business.
  • You won’t be a good leader. A fried boss is a bad boss. Thinking quickly on your feet and coming off as authoritative is important as an entrepreneur. Your staff will follow your lead more effectively if you aren’t foggy-headed and are able to make important decisions quickly.

Entrepreneurs don’t typically think about the consequences of not taking a vacation. But the points mentioned above could affect your business if you’re not careful, so it’s vital that you take a break from time to time to have a healthy mind to make the right choices for your company.

So, you might be convinced that it’s a good idea to take time off, but you’re feeling guilty just thinking about taking a vacation.

Guilt-Schmilt: How To Enjoy a Guilt-Free Vacation


One of two things might happen if you take some time off from work:

  1. The world will implode after the first 24 hours that you have not worked.
  2. Everything will be fine, and your business will keep running smoothly.

I’m fairly certain it won’t be the first option.

It’s understandable that you’d feel guilty about taking time off. After all, your business is like your baby, and you want to take care of its every need. Maybe there’s a sense of responsibility (like you’re raising a child), and you’d feel irresponsible leaving your company unattended … But you need to recharge and relax, and take some time away for the health of your business and yourself.

Here are some tips for how to set yourself up for taking a vacation — without feeling guilty or stressing out.

Take a Short Vacation to Get Started

According to a Funding Circle survey, almost half of small business owners intend to take off fewer than three days during the holidays. And a lot of those people will still check email or even do some work during their time off.

If you are having trouble imagining yourself sprawled out on a beach somewhere sipping (or chugging) piña coladas, start small. Take a half-day off to shop for gifts. Or take off a full day to get rejuvenated and pampered at a spa.

Eventually, you can move on to taking off two days in a row. If, in your absence, the building doesn’t burn down (which it won’t) and all of your clients don’t decide to move on to other companies (which they won’t), you’ll start to feel better about taking longer amounts of time off in the future. You may feel guilty that these terrible things could happen in your absence, but if you keep in mind how important it is for you to take some time away from work so your business is always in a good state, you shouldn’t feel too bad about taking off a couple of days here and there. That way, you’ll eventually get to go on that Mediterranean cruise you’ve been dreaming about.

Or maybe a staycation is the way to go for you, until you stop feeling guilty for long enough to leave the state or country. But no matter which route you choose, downtime is extremely important for busy entrepreneurs.

Planning Is the Key to Stress-Free Time Off

The key to enjoying your time off is to make sure you set up everything ahead of time. Plan, plan, and then plan some more. As Winston Churchill put it, “Let our advance worrying become advance thinking and planning.”

Sure, with access to such advanced technology these days, people can easily work on a plane or while sitting on a beach, as long as they have their laptop or smartphone with them. But in order to truly enjoy your vacation time, you need to “unplug” and not constantly think about work. Clearing your mind will help you feel less stressed about the business you’re leaving in someone else’s hands while you’re away. One way to make clearing your head easier is planning.

Are there some tasks you can get done ahead of time so you won’t have to worry about anyone having to work on them in your absence? Make a list of things you typically do during a work day and see how much of it you can get done before going offline for a few days. Of course, a lot of the daily tasks you complete will still have to get done while you’re out of the office, but you’ll feel better if you can get some other projects done ahead of time.

Planning also comes into play with the vacation itself. According to a 2010 study in Applied Research in Quality of Life, merely thinking about your vacation can make you happy for up to eight weeks before you even take the time off. You can look at your calendar or set an electronic reminder for yourself to keep you feeling excited about the upcoming downtime.

It’s a good idea to plan to either be offline the entire time you’re out of the office or set aside a certain amount of time each day to answer emails or make phone calls. Limit yourself to just one hour and do the work at the same time each day. That way, you set boundaries for yourself while still being able to check in and make sure your staff is handling everything well.

Another way to plan for a stress-free vacation is by discussing with your staff recent conversations you’ve had with clients, so they’re in the loop. This could help them anticipate questions that might be asked or requests that might come in while you’re out of the office. This will ensure you won’t get any anxious phone calls from staff who would be able to respond to clients’ questions if they just had the necessary information at hand.

If you can’t take time off during the holidays, plan to take off during a different time of year. Some businesses are slower during certain times of the year, while other businesses might be booming during those same times. For example, for entrepreneurs with online retail presence, the holidays are likely one of your busiest times of year, so it could be quite difficult to take time off. Then, after Christmas, you might have to deal with potential returns of items purchased during the holiday season.

The important thing to remember is that planning can help you enjoy your vacation and feel good about delegating work to the staff that’s taking care of the day-to-day business issues while you’re away.

Delegating Is a Fine Art That Helps You and Your Employees

You’re the boss. Remember that. You have a staff that you can delegate tasks to, and since you hired them, you know they are more than capable of getting things done in your absence.

Trust them and let them help.

Your employees might actually feel more confident when working on projects while you’re away. It’s not that they don’t need you — because they do.

It’s just that they’ll get a boost of self-confidence if they’re able to manage the workload or complete complex tasks in your stead. That will keep them motivated to continue putting forth the high-quality work that you’ve come to expect. And new leaders could emerge with the added responsibility that you give to your staff in your absence.

According to Forbes, you should delegate a whole project, not just a task. Gasp! I know, it sounds scary.

But your employees will feel more engaged in a project if they can take ownership of it. As mentioned in the previous section about the importance of planning ahead, make sure you include all the necessary details for the project so you don’t set up your employees to fail. Their success is your success.

Pick the right person for the task or project based on their skill set and interests. If someone feels uncomfortable doing a certain task because they don’t have as much experience in that area, you will not feel confident that they will handle things appropriately while you’re away.

If you’ve planned your vacation and know far in advance when you’ll be out of the office, start delegating tasks to certain employees ahead of time. That way, they’ll get practice with dealing with certain aspects of your work, and you’ll feel comfortable that they can handle everything well in your absence.

Automating Tasks to Save Time and Energy

In your day-to-day business operations, you know there is some work that requires forethought and specialized attention to detail, so those items would have to be delegated to other staff in your absence. But there are other tasks that don’t take as much thought and consideration that still need to get done on a daily basis.

Have you ever thought about which of your daily tasks could potentially be automated? There are ways to automate some mundane chores instead of having an employee do them while you’re away.

Set an out-of-office message in your email directing people to contact other staff members about their inquiries.

“If you have a question about ____, please contact [email protected].”

“For ____ issues, please contact [email protected].”

Include a link to Google Calendar or Calendly in your out-of-office email so staff members or external customers can set up a meeting time with you for when you’re back in the office. That way, they won’t have to remember to contact you again, and you can block off your time so no one will try to set up an appointment with you at a time when you’re away.

Think about creating email templates that your employees can fill out when responding to certain categories of emails. You could probably easily come up with this information if you think about the typical emails you answer every day.

You can actually automate emails using Gmail, so they are put into different categories as they come into your inbox. You can also add certain contacts to a VIP list and select a special message tone that you’ll hear on your smartphone when an email comes in from one of the people on that list. Whether you use the Default Inbox setting or a Priority Inbox setting, you can set up notifications to alert you to when certain important messages are received. Organizing these settings a few weeks before you go away is a good idea, as you can “train” Gmail to flag the right messages as “important.”

Automate payroll or accounting-related tasks. Some software can be automated to set up payroll for you to make sure employees get paid even in your absence.

To automatically sort information regarding customer requests, create online forms for specific pages of your website instead of a general comments box. You can include text like, “If you want to learn more about ____, fill out this form.” That way, you can save time by not having to sift through emails to figure out what potential customers are interested in when you get back from vacation.

You can automatically send out social media posts using a program like Hootsuite or HubSpot. If you’ll be out of the office for a week, set up three different tweets or other posts you can send out automatically. That way, you’ll still be in contact with your customer base without having to take time to type them out and send them.

Automating tasks can save time when you get back from vacation, and your employees will thank you for not leaving them with an endless list of boring tasks. Because, after all, employees deserve time off, too.

Giving Employees the Time Off They Deserve

So, the holidays are fast approaching and, of course, everyone wants to take time off. As long as you plan things out, everything should work out smoothly.

Just make sure your employees know that the few days before and after they take time off, they will be busier than usual.

Some companies close up shop the week between Christmas and New Year’s Day, knowing that a lot of staff members will be champing at the bit to put in for that coveted holiday time. Is that a possibility for your company?

Sometimes, it’s not. Companies like Amazon could never close during the holidays because they would lose so much of their business.

Give employees a deadline by which to request time off. If multiple people request the same days, you can use a first come, first served basis. Or you can talk to the staff to see how imperative it is that they have off on those particular days. Would they be willing to work the mornings during certain days if the other employees work the afternoons?

Let employees work from home if you have a main office. It is very easy to work virtually these days, so it shouldn’t be a problem if you trust your employees. Working from home can cut down on commuting time, and maybe they’ll be able to pop into the kitchen every now and then to make sure the Christmas cookies they’re baking for their family party don’t burn.

You can set guidelines around holiday time off. Tell employees that if they don’t work on Christmas Eve, they need to work on New Year’s Eve, and vice versa. If they take off on Thanksgiving and the day after, they can’t also take off both Christmas Eve and Christmas Day. Although you need to compromise with your employees regarding time off, you also have to stick to what your business needs to run smoothly.

Following your guidelines is a slippery slope because you don’t want your employees to resent you for not letting them take time off. That could lead to a lack of productivity and a tense working relationship.

Make sure you don’t make your employees feel bad about requesting or taking time off. If they think you don’t want them to take days off, they will be afraid to ask you for vacation time. They need their downtime, too.

By following a few of the tips above, staff vacation requests can be handled more seamlessly and with less stress for both you and your employees.

Vacation Time, Here I Come!


Entrepreneurs can take time away from their business without it being a detriment to their successful operation. There is no need to feel guilty about taking a vacation — taking time off is a great way to keep our mind and body healthy, and ready for all the good work we do day after day. It’s just a matter of planning as much as possible before taking time off, automating certain tasks, and delegating work to capable and talented staff.

If the boss is happy, the staff is happy — and vice versa. The work environment, as well as the quality of the work produced, will be better when everyone involved gets adequate downtime and vacation time. A business is like a machine — it needs to be well-oiled to make it run at its best, so get out your oil can and plan some much-needed time off.

Happy vacationing, and happy holidays!

About the Author Melissa Lewis Grimm

Melissa Lewis Grimm, ELS, graduated from Millersville University with a Bachelor of Arts degree in English. She has worked as an editor and a marketing manager for a laboratory standards–developing organization, a proofreader for a nursing continuing education provider, and a journal manager for a scientific and medical publishing company. Despite Melissa’s work history, one of her lofty goals is to become a world-famous voiceover talent. Yes, you read that correctly! She loves spending time with her wonderful husband and adorable toddler. She is currently Senior Copy Editor at Craft Your Content.

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