Work hard, play hard. You hear the expression but do you really allow yourself to play? Or in the case of vacation, get away? Often as busy professionals (especially business owners and those who manage a team), we find it unmanageable or problematic to take a vacation. Our calendar gets booked and there is this project and that project; someone is going on vacation or maternity leave, military leave, or you have a lot of staffing holes. So, there is never a good time to take vacation, right? Wrong.

The case for vacation

Vacations are the pause button you didn’t realize how much you needed. In fact, it helps you work more efficiently when you return, fights burnout, and helps your team grow while you are out. Whenever I get away, I see how other businesses are run, come back with new ideas and see my businesses through new lenses. I often have a chance to read and reflect, which I so appreciate. It may seem unnecessary to have a “how to” on taking a vacation, but being a mom of two under 12, business owner for over 13 years, author, professor, and someone who wears a lot of hats, I have found this process to help me actually take time away from the office.

Step 1: Make goals for the vacation

Is the point of the vacation to relax, spend quality time, read, think and plan, make new memories, seek new adventures, visit friends and family or some combination? After making your goals and sticking to them, you can decide whether your trip succeeded or not. You can’t do all of the above on the vacation and if you think so, you will be disappointed when you realize you didn’t. Knowing what you want to get out of it helps you decide where to go and what to do. Make sure whomever else is with you on vacation is on the same page as well (emphasis on this).

Step 2: Plan, plan, plan

There’s a time for spontaneity and there’s a time for planning. Vacations are something you want to plan. This helps on so many levels, including examining when there are fewer conflicts with your work calendar. It helps you to secure the best prices for the trip and coordinate with others who might be vacationing with you. Furthermore, planning not only minimizes stress but it also ensures that you have something concrete to look forward to — science has even proven that the anticipation of a vacation is healthy!

Bonus Tip: Don’t shy away from planning for the most popular vacation windows, like Spring Break or Thanksgiving week. I find that I relax more when I know that most other people are on vacation anyway and that my business is likely slower than at other times of the year.

Step 3: Prepare Your Staff

Once dates are set, inform your team and staff and install a plan for while you are away. Basically, having a job description about everything you do and dividing up the duties while you are out is ideal. If you don’t have that written up, do the best you can and you’ll learn for the next time. Depending on your boundaries and the urgency, you could let your team know that, if necessary, they can contact you.

Step 4: Review the Calendar

Closer to your vacation, go over the calendar to move any meetings, appointments, and/or reassign ownership. If necessary, prepare clients about unavailability, assure them that your team is in office to help and that you have a back-up while out.

Step 5: Set up Auto Replies

Before leaving, update your email and voicemail with an automatic out-of-office reply. Train your team on the messaging while you are out and teach them who will be your replacement. I have noticed that with a trained executive assistant who is experienced with monitoring and responding to my email, my inbox is really manageable when I return.

Step 6: Digitally Unplug

Depending on how much you want to unplug, attempt to avoid social media and news (and Internet access). Try to set boundaries for yourself by setting a specific time each day, while you are away, to check in with the team and to review only urgent emails you need to answer. This will allow you to get the best out of your vacation and will help protect your mental state. For those with difficulty letting go, I suggest visiting a national park or going on a cruise to limit your access to the Internet. Constant connectivity can tempt us to check in with our work duties, which should not be necessary given the out-of-office plan that your staff is implementing.

Step 7: Decompress

Seems obvious, but for many entrepreneurs, our innate sense of drive can be hard to suppress. Take the time to rediscover joy. I schedule a massage the first day or two to help me unwind on a “relax” vacation. When my goal is to read and reflect, I bring several books to choose from and see where my interest is at the moment in deciding which to read. Take photos to remember how much you need vacation. Don’t feel guilty for being away. Focus on what your goals for the trip are and make sure you put in place the parameters to make it successful.

Step 8: Plan the Next Vacation

Planting the seed and even planning your next vacation while you are on vacation is so beneficial because you get spectacular ideas on what you want your next adventure to be. Journal on what could have made your vacation better so you can improve for the next time.

Step 9: Keep Reentry Low Key

Be kind to yourself. Keep your first day or two back home light. Have time to schedule check-ins with key staff and block off work time just to respond to email. Use your newfound clarity to build the life you don’t have to escape from. Value your time away, and encourage your staff and team to have their vacation too. Go forth and vacation!

About the Author: Ruby L. Powers is a board certified immigration attorney and managing partner at Powers Law Group, P.C. She is also a business coach and consultant for Powers Strategy Group. Follow Ruby on LinkedIn or on TikTok at PowersImmigrationLawyer and PowersStrategyGroup.

How To Take a Vacation: For the Entrepreneur Who Never Has the Time