How To Take a REAL Vacation When You Work for Yourself

Jun 13, 2022

(Art Credit: Karen Fischer)

When you work for yourself, by yourself, “time off” can be a bit of a paradox — you can be much more flexible about having “time off” day-to-day, but it can be hard to take extended time off to truly unplug. If you’re doing hourly work, the money stops when you stop working. If you’re doing more retainer or flat rate work, you feel obligated to be there for your clients ALL the time.

No matter how you structure your work, even the thought of completely unplugging can be stressful when you think about the mountain of emails and tasks waiting for you when you plug back in.

For solopreneurs particularly, it can be tricky to completely unplug when you are a one-person show, and you don’t have anyone to cover for you when you’re gone. There are ways that solopreneurs can take REAL vacations (the kind where your out-of-office message is actually on), but it takes some intentional planning. Here are a few helpful tips for planning a vacation that can help relieve the stress of unplugging.

Structure your work so that vacations are possible

This is more of a business model strategy than a vacation strategy. When you initiate work with a client, price yourself so that you’re building in “PTO” just like anyone else. If you’re hourly, you’ve slightly padded your rates to account for time off, and if it is a flat rate, you’ve structured it so it is about deliverables delivered and goals met, not time spent.

You also need to set clear boundaries with your clients from the beginning about when you are and are not available, whether that’s daily “hours,” the fact that you only work four days a week, or take one week off a month in the summer. This helps you ensure that you’re selecting clients who respect your non-work time from the get-go.

Designate a contact

Making sure you have the right person on deck who can run point while you are out is crucial. For solopreneurs, this might seem impossible, but you have to think outside the box. Reach out to each of your clients to let them know you are out of town and, if possible, designate an internal contact who knows the project and can handle requests while you are out. You could also consider teaming up with a fellow freelancer to help guide a project while you are out. Most solopreneurs I know would be happy to do this on an “I-scratch-your-back” basis instead of charging for it.

Master the out of office message

Many solopreneurs I know don’t turn out out-of-office messages because they’re worried about not being responsive or losing potential work if a new client contacts them. This goes back to the point above about working for people who respect your non-work time — if a potential client sees your out-of-office message as a liability, they’re likely not the type of person you want to work for. With that said, I get it; when opportunity knocks, you want to be there to answer the door. This is where the clear out-of-office message comes in.

Use your out-of-office message to appeal to all audiences:

  • Existing clients: Let them know who to reach out to, whether your designated internal contact or your solopreneur buddy who’s watching your back.
  • Potential new clients: Let them know that you’ll get back to them by a specific date, and if it is urgent, they can reach out directly to you via phone or text.
  • Everyone else: I’ll get to you when I get to you…

One other thing to consider here is your “if this is urgent” caveat. Really consider whether or not you need this. If you want to unplug completely, then put your trust in your planning and backup, and just let folks know that you will get back to them when you return.

Schedule specific check-ins (if necessary)

If you will be gone for an extended time and/or have urgent project needs during your vacation, be strategic about scheduling specific times when you will check in via phone or email. You can make sure that your clients and colleagues are aware of this and even put it in your out-of-office message. That way, you don’t have to be checking your email constantly.

Filter your email

Email filters are super handy and underused. I get so many things in my inbox that are not urgent, like blogs, newsletters, news updates, etc. You can set up automatic filters that will put these things into a subfolder as they come in. When you get back to your inbox, you will only see your messages from clients and colleagues. This is also an excellent tool for everyday inbox management.

Take an extra day on both sides

Block off the whole day before you leave for vacation to tie up loose ends and get everything settled for you to be gone. I am also a huge proponent of taking an extra day after a vacation to regroup and get back into regular life. This is not an extra day to go through your inbox but a day to do laundry, go to the store and get your brain back into regular-life mode. Make sure your out-of-office message reflects these extra days, that way, if you need to, you can still check and respond to emails on those days, but no one is expecting you to.


Solopreneurs, you work HARD and deserve to take dedicated time off. I hope you use these strategies to make it happen.

Sarah Duran

I started Fruition Initiatives to help people and organizations reach their highest potential. I design and lead projects for organizations and help businesses refine systems and processes.