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5 Simple Steps To Stress-Free Time Off As A Small Business Owner

Taking time off. What a wonderful concept. Imagine closing down your computer on your last day at work before heading off on vacation, knowing everything is running smoothly and going exactly as it should. Now you're heading to some well-deserved time off where you can truly relax and recharge.

As small business owners, especially solo business owners, it can be really difficult to get to this place. When you're in your first year or two of business, taking time off can seem like something totally unachievable. It's hard to imagine your business continuing and not falling apart if you're not there.

While some of us want to scale and some of us want to keep it just us in our business, learning to take time away is essential because it does allow us to recharge, gain perspective, and offers time for just thinking. Sometimes when we are busy in the day-to-day, it can also be hard to step back and look at the bigger picture.

In this post, we are going to talk about the 5 step process I take for every vacation and period of time off I schedule that has helped me go from being super frazzled and stressed out to recently, having the most relaxed vacation I've had in awhile, where my business continued to run, even while I wasn't there.

Step 1: Plan your vacation

This probably is obvious, but I'm not just talking about booking your flights and hotels and calling it a day. I've found that best practice is to plan for time off at least 30 days ahead of time or more. If your time off is going to be longer, planning further ahead can be helpful. Planning ahead allows you the space you need to think about what needs to get done prior, and also gives you time to let your clients know you're going away.

Next, you're going to block out the time on your calendar. My most recent vacation to the beach was planned for 1 week, so I blocked out the entire week. This was helpful because when it came to scheduling clients, I knew I couldn't schedule anyone that week.

Step 2: What to do prior to your time off

Now that you have your time off blocked out in your schedule, it's time to do a brain dump and figure out what needs to get done before you leave.

  • Do you have any projects that need to be finished?

  • Do you have any fulfillment for clients that needs to be completed?

  • Are you planning to bring on new clients or customers before your vacation, or wait until after?

  • When are you going to let your current clients know that you'll be away?

  • Do you have a packing list? (pro tip -- I always work off of a packing list I made several years ago -- that way I don't have to think about what to bring, I just check things off and know I have everything!)

Once you have your list, you're going to start to organize it. I find it helpful to go through and prioritize it by what absolutely needs to get done, what I can pass off, what can wait until I return, and what doesn't actually need to get done. A simple way to remember: do, delegate, defer, or delete. Mark everything as you see fit.

Next, another pro tip, take off the day before you're scheduled to leave for your vacation or time off. This is extremely helpful in making sure you have time to tie up loose ends and get travel ready if needed. I've tried working the day of me leaving, and it usually just ends up being stressful and sweaty 🥵️

Last thing to do in planning out what to do at this stage, open up your calendar and start to block off time to complete the "do" items on your action list.

Step 3: What to do once you return from your time off

Before you leave, I would also recommend taking off 1-2 days on the back end of your time off to give yourself a small grace period in getting back into the swing of things. This will give you plenty of time to check in on where your business is, check in with any clients or your assistant, respond to any messages, and generally just get back into work mode without having to rush. I don't typically schedule client appointments on this first day back, so I can make sure my head is clear and ready to go once I do start working with clients again.

I also like to give myself the full week as a grace period to catch up. I've found it's been a little difficult to get motivated to start large projects the week I get back from vacation, so I usually plan for it to just be client appointments, catch up work, busy work, small tasks, etc. If there are any big projects coming up, I will make sure they aren't scheduled to start until the week after I get back from time off.

Step 4: Decide what you're going to do during your time off

This is where we start to get into the boundaries discussion! The most important thing I want you to remember when it comes to boundaries is that you're the only one in charge of your boundaries and the only one who can decide on them.

Some people might tell you that you need to be completely turned off while on vacation, and if that aligns with you, that's totally fine.

For me, it stresses me out to be completely turned off and leave a bunch of unread messages in my inbox. It creates what I call "open loops" (a term I got from David Allen in Getting Things Done) in my brain, and that feels chaotic. I worry about them and then don't enjoy my time.

So how I typically handle things is I will set partial boundaries. I keep myself available for text messages from clients and answer them whenever I have a moment. That feels easy to me and like not a big deal.

What I don't answer are emails and social media messages. I set up an app called AppBlock that keeps me from opening these apps on my phone and helps me implement those boundaries.

Lastly, I keep a list handy on my phone so that if I have any ideas on vacation or any tasks come up, I can jot them down in a trusty app or list, therefore "closing the loop" and giving myself permission to address them at a later date. For this, I use TickTick and Google Keep.

Step 5: Set it all up

Now that you have an understanding of what to do before, during, and after your time off, set aside some time now to go through the steps and outline your plan. Plug it into your calendar and task list or planner so that you're ready to enjoy some well-deserved time away from being a successful CEO!


Looking for more help? Come join us in the Facebook group here where healthcare entrepreneurs just like you are learning how to navigate being successful new business owners!

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