5 Steps to Take Time Off as an Entrepreneur Without Worrying

Photo by Simon Migaj on Unsplash

Aside from all the decision-making, financial burdens, and day-to-day responsibilities of entrepreneurship, the central dilemma of owning a business comes with the dissonance of trying to manage a healthy work-life balance. You’re fully invested in your organization, so the more work you put in, the more rewards you’re likely to see, and to top it off, you’re more passionate about the work you’re actually doing. The combination leads many entrepreneurs to work heads-down, indefinitely, until the stress of overworking finally catches up to them.

The “easy” solution, of course, is to take time off in the form of occasional mental health days or extended vacations. But those scenarios often backfire — once you’re out of the office, you can’t help but continue to check your email or at least worry about what’s going on back in the real world. Under these conditions, a vacation can wind up more stressful than a normal day of work.

It’s clear that time off is necessary, but only if you can take it without preoccupying yourself with more work. So how can you do that as the committed entrepreneur?

1. Make a Plan

The more intensely you plan your vacation, the more likely you’ll be to follow through on it. Schedule your time off weeks (or even months) in advance, and tell everyone you know in or out of your organization about it. Spreading the information this way will do two things. First, it will subtly prompt you to follow through on your commitments, if for no other reason than to avoid the “aren’t you supposed to be on vacation?” questions. Second, it will help everyone around you develop plans for your absence. For example, one of your partners can start charting out the responsibilities he plans to take over temporarily while you’re gone. Set an expectation that you will be unreachable except for emergencies, and chances are your team will follow those expectations.

2. Delegate or Postpone

For each task, including your ordinary day-to-day tasks as well as emergency situations that might pop up periodically while you’re gone, decide whether to delegate or postpone your action. To delegate your task, designate one of your team members to take it on in your absence. To postpone the task, deem the task “unimportant,” and know that you’ll handle it only once you’ve returned. Delegated tasks require no worry because you’ve left someone qualified in charge of them. Postponed tasks require no worry because they don’t need to be done until you come back. Theoretically, you should have no worrisome tasks left by the end of this process.

3. Disconnect

It’s a simple step, but one we’re all guilty of neglecting. When you’re on vacation, disconnect yourself from the world. Turn off your phone, disconnect your Internet, and try not to turn on any of your gadgets. Doing so could serve as a gateway back into worrying about work — it’s almost unavoidable. If there’s an emergency, someone on your team can mitigate it until you come back or reach you via hotel phone or in person (if it truly is that bad).

4. Establish “Worry Time”

If you find that even while disconnecting, you can’t help but worry about your job, try to refocus your efforts so you only worry about your job for a certain period of time during the day. For example, you could designate 12pm-1pm as your worry time, to check emails and think about what’s going on back at work. But as soon as 1pm hits, you have to pull yourself away from the screen and focus only on enjoying yourself. This compartmentalization strategy doesn’t work for everybody, but if you find yourself worrying no matter what, this can mitigate its effects on your time off.

5. Practice and Scale

Some entrepreneurs will undoubtedly find themselves incapable of taking a truly relaxing, worry-free vacation. They’re natural born worriers, or they care too much about their businesses to let them go, even for a few days. If this sounds like you, practice taking worry-free vacations by starting small and working your way up. Start by only taking a half-day off, following all the rules I mentioned above, and once you’ve become comfortable there, try taking a single day off every once in a while. From there, you can scale to 2-day, 3-day, or even week-long vacations and more. Like anything else, you’ll get better with practice and experience.

With these strategies, you should find it easier to take time away from work without being bogged down with worries. It takes a real effort to disconnect your mind from work, especially in an entrepreneurial role, but if you want to avoid burnout and maximize your potential for happiness and satisfaction, it’s a step you’ll have to take.

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!