The Ins and Outs: How Business Owners Work on Vacation

How business owners work on vacation

Truth: Business owners need vacations more than probably anybody.

Second Truth: That is because we literally can never take vacations, haha. What even are weekends?

So if I want to have a weekend getaway, the truth is my work is going to follow me there. It’s just how this whole “entrepreneur” thing goes.

Work on Vacation

Even on my Honeymoon to Barcelona, my Vacation Guilt was heavy. In that post I explained it so well:

“The thought slipped into my head that I’ve just worked for months on a project that can be unraveled by a 10-day trip.”

Yeesh, that sentence alone is enough to convince me to never take vacations again.

my location independent careerBut honestly those memories of sippin’ sangria in a new city with my hubby are just too good to ax out of my life — and so now I have some surefire ways to make sure my business doesn’t crumble while I juggle work on vacation:

Start early.

I want to specify that I am NOT an early riser, so this is actually a huge sacrifice for me. Lee is generally up by 6am while I can sleep in ALL morning, especially on vacation.

I usually sleep right through Lee’s entire morning routine: watching the morning news, breakfast, shower. Like magic, that’s the perfect time to get sh*t done! (who knew?)

St Louis Trip work on vacationThis past weekend I was able to seriously practice what I’m preachin’. Lee & I took a weekend trip to St. Louis and we stayed at Seven Gables Inn, a quiet & quaint inn right in Downtown Clayton.

And with a small plate of breakfast & coffee by my side, I was able to Start Early without missing out on anything touristy we had planned.

Stay somewhere that is beautifully inspiring.

Truth is, setting is everything & motivation while on vacation is LOW. Being in a boxed hotel is just not an option because frankly, I’m going to want the get the Freak outta there as soon as possible.

I knew our hotel had a gorgeous courtyard & that very spot was the main reason I booked this hotel — when I was squirming to get out of my room, I headed down there and enjoyed my coffee outside. It was PERFECT.

Seven Gables Inn work on Vacation

work on vacation in st louis

seven gables inn courtyard st louis

This fit so seamlessly into our day because work became part of the destination (and we didn’t feel locked up in our room, huge bonus!)

Use downtime wisely.

I’m absolutely guilty of the black-hole-effect of checking my phone for a quick email & never looking up again. It doesn’t really bother me but it annoys THE HELL out of Lee, haha.

So I try (Yeah I’m just saying “try”) to keep this bad habit to a minimum by smashing it all into designated downtime.

how to work on vacation

I find car rides between activities the best time to get all this necessary evil outta my vacation life. Because car rides have a definitive beginning and end, so once we arrive I AM DONE.

Take My Word for It: If I don’t squeeze all of my check-ins into downtime & instead try to casually do it all throughout the day, I end up with one grumpy husband.

Maybe for you it’s during nap time or the 30 minutes you’re killing before dinner reservations. Whatever. Just plan ahead of time when you think you’re going to have to make some calls or follow up on 10 emails etc… & do it when you guys are literally doing nothing.

Communication, baby!

FYI, whoever you’re traveling with is going to definitely feel the effects of you bringing your work into their vacation. It’s definitely not an easy thing to balance, and I’m super conscious of making sure Lee is having a great time (and his beer glass is ALWAYS full!)

But besides getting him drunk, setting expectations at the beginning is pretty important.

It’s as simple as, “I have a phone call with a client until 10:30, then I’m all yours” …or the one he dreads the most, “FYI you’ll be taking my picture today & it will take 20 minutes.” (as seen in action below)

Weekend Getaway in St. Louis

how to work on vacation

weekend getawate st louis

It’s pretty simple, but outlining the day for everyone who will be affected by your work schedule is a pretty big deal.

So these are the In’s and Out’s of Balancing Work on Vacation:

  • Start Early
  • Make the Work the Destination
  • Use Downtime Wisely
  • Communicate your Expectations
*I want to give a very special thanks to Seven Gables Inn in Clayton, MO for the room accommodations & the perfect setting for a relaxing AND productive weekend!

What do you struggle with the most when it comes to balancing work on vacation?


Want to join my crew of positive, creative entrepreneurs that will help coach you as you build your business? We’d love to have you! Click here to join:

Business Coaching for women entrepreneurs

  • Olivia Tennant

    I try to pre-schedule as much as I possibly can anytime I know I have a busy weekend, a trip, or friends coming to visit me. That usually takes a lot of the pressure off!

    Olivia | Prep Essentials

    • Absolutely — weekends are so busy especially this time of year, & I HATE making people wait around for me while I work! It’s the worst feeling

  • Aliza Strachan

    I can definitely attest that the black-hole-effect is real because I get sucked into my phone so easily when I intend on just doing one thing! But, that is such a great tip to stick to checking email during car rides and down time. This is such a helpful post!

    xx Aliza

  • Johanna

    I can relate to this. I have a very hard time disconnecting on vacation and then I deeply regret it after.