Six Ways to Take the Stress Out of Taking a Vacation as an Entrepreneur



Eight years after leaving my job at a very large multinational company, where my hard earned vacation was plotted and planned, I struggle with taking a vacation as a business owner. Business ownership is something I am grateful for every day. The flexibility of determining my schedule has been life changing. All my fears of miss-ing business suits, morning rush hour, board room meetings, water cooler ex-changes and fancy corporate lunches were, for the most part, unfounded.

But when a business is your own, everything is critically important… all the time. It’s not the same when working for a large corporation, even if you love your job as intensely as I did. This impacts your days and weekends but is particularly stressful when taking vacation. Really taking off can be a struggle.

For most of our vacations the emails still flow, conference calls happen and we are working late night hours to respond to emails throughout the week. Not many out-siders would even know we are on vacation.

Throughout the last several years I found a few things that work to take some of the “stress” out of taking a vacation.

1. Recognize there is no perfect time to be on vacation, and there never will be.
You can count on deadlines shifting, production delays, accountants wanting documents immediately, HR issues, urgent customer meetings, or important in-dustry meetings – all during the time you have planned to be off. Once you accept you will always be missing something important, you are better able to let it go and enjoy.

2. Manage your expectations. Per point one above, there will be times during the week where you will probably have to handle work issues. But keep it to the critical ones only. If you take your computer to the pool, you are not going on the pool. If you don’t leave your phone in the room, you’ll be checking it every 20 minutes. Leave large blocks of time where you don’t have access to your phone or computer- maybe four hours in morning and then three hours through dinner hours. It works incredibly well. I no longer spend my dinner grabbing my phone at every ping. If its there it’s a distraction – period.

3. Manage the expectations of your family and/or friends. A friend recently de-scribed their family vacation as wonderful except “Joe” had to work the entire time. They told the kids “Dad can go, but on this trip has to work. You can’t be disappointed or frustrated. We can cancel, just mom and you go, or we all accept Dad will be with us as much as possible.” The trip goes a lot smoother if partners and kids are prepped for times during a vacation when you simply have to get things done.

4. Conquer issues before you leave. Separate major projects and assign them to someone else to handle. Give as much direction as possible before you leave – really take the time to make sure everything is clear and organized. It sounds easy, but in the flurry of rushing to get things done before you leave it’s hard to give thoughtful direction. Shooting off emails from the airport it is not the way to do it. Block off an hour a day the week before you leave to give organized, detailed summaries in writing and in person. Dedicate time for this — it makes a world of difference.

5. Have a partner or senior manager that can handle most anything in your absence. Having some overlap on major initiatives, accounts and responsibilities helps when you are away. We overlap in almost all areas of the business so we are ready and able to step in when needed. Let them know you are reachable at all times – chances are they won’t need to but a quick ten minute call can resolve so much so quickly! Make sure they, and you, know the call has a limit.

6. Enjoy your vacation!

Being an entrepreneur is so gratifying because you are a master of your own time, which includes being a master of your own time off. Take your vacation time seriously — your family will thank you for it.

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