How to Take a Vacation (For Freelancers & Small Business Owners)

“I took a vacation!” My friend exclaimed yesterday.

“And I only had to deal with 3 client emergencies!” they proudly proclaimed.

This is madness.

Vacation is for Unplugging and Recharging.

Most small business owners and freelancers have NEVER taken an unplugged vacation away from work.

Fact: I’ve created almost all of my business innovations while AWAY from my business.

Examples of Value I Created For My Biz While Unplugged:

  • I was the first of my WordPress dev colleagues to create a pre-paid hourly billing system (now they all do it).  Thought of that while on paternity leave from my own biz and implemented immediately upon return.
  • I invented our customer portal for tracking hours and communicating progress to customers over Christmas vacation.  Implemented immediately upon returning to work in the new year.

No better time than the present!

Here’s how you can take your dream vacation…or just some time unplugged from your business.

If you check email once on your vacation, you have missed the point.

If you answer one business-related phone call, you have failed miserably.

Small Business Owners & Freelancers Don’t Take Unplugged Vacations.

Find a friend who owns their own business and ask them, “When’s the last time you went a week unplugged from your business?”

“Never,” they’ll reply.

This is the norm. 

And it’s stupid.

Because taking unplugged vacations is one of the few benefits of owning your own business!

Thankfully, the mechanics of taking an unplugged vacation away from your business are simple!

So simple that even I can do it!

How to Take 2 Weeks Off Starting Today

Did you know it’s possible to take 2 weeks off, starting today?

It is.

Step 1: Just Go.

Close your laptop, turn off your phone, go home, pack up, and go somewhere for 2 weeks where there’s no cellphone signal.  (Boundary Waters, Grand Tetons, Quebec City, etc.)

That’s it.  One. Single. Step.

The benefits of the vacation will be exponentially-greater than the costs.

Some bad things might happen, and that’s okay.

Don’t have any money for a fancy vacation?  No problem! 

Just turn off your phone and internet for 2 weeks and enjoy the sights in your home town, re-introduce yourself to family & friends, read The House At Pooh Corner, take long poops, you get the idea.

Turn off push notifications on your phone, email, voicemail, Slack, Google, etc.

At this point, your lizard brain is puking out excuses and what-ifs. 

That’s okay – that’s its job.

Next we’ll deal with the nay-sayers in your own body.

Conquer Your Excuses and “What-ifs”:

Divide a piece of paper into three columns:

  • In the first column, write down all of the things that could go wrong should your attempt fail. Think of the most terrible things possible.
  • In the second column, determine ways that you can mitigate the possibility of each of those bad consequences from happening.
  • In the third column, think of how you would recover from each of the scenarios you imagined and wrote in the first column.

(Thanks @Tim Ferris)

Step 2: Debrief Upon Return

Now that you’ve taken your first unplugged vacation, I guarantee you’ll want to do it again.

It didn’t go perfectly this time, and that’s okay and expected. 

Nobody hits a home run the first time.

You’ll experience exponential improvements next time.

  • How did it feel to take 2 weeks unplugged and away from work?
  • Did you have any relapses and check email or do business phone calls?  Why? 
  • What would you change about your vacation location, process, etc.?
  • What issues popped up that you need to address before next vacation? (You lost Customer X, Customer Y is pissed off, you didn’t pay the bill for Z, etc.)
  • Create processes and plug holes in your existing processes to address the things that went wrong.
  • What was your goal going into the vacation?  Did you meet that goal?  Why not?
  • What expectations would you have set differently with customers?
  • Would outsourcing some work to freelancers have helped?

Step 3: Plan Your Next Vacation

Now you have a better idea of what you want out of your vacation, so take a few minutes and block off a couple of weeks for your next vacation!

Only 3 Benefits To Owning a Business

Remember, there are only 3 benefits to owning your own business.  You get to decide:

  1. When you work.
  2. Where you work.
  3. With whom you work.

Now Go forth and take that vacation!


p.s. If you are unwilling to do the above, consider working a full-time job where they force you to take vacation.  I won’t judge.

Toby Cryns

Toby Cryns is a freelance CTO and WordPress Guru. He also writes for