Working While Vacationing

One Entrepreneur’s Journey Up a Mountain

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Catskills — the view from Hunter Mountain

I just got home a few hours ago from a week on a mountain in upstate New York. My husband and I never vacation alone — it is always something family or holiday-related. Which is not a bad thing at all! We just wanted to see if we could tolerate each other for a whole week together 24/7.

Turns out we can, so that’s nice.

Before we left Brooklyn, I made sure to do as much as possible the week before. All the blogs and articles and projects that would be due while we were gone.

I spoke to each client individually and let them know I’d be out of town, though sporadically available by email.

I still worked at least an hour a day while we were gone. And I consider that a win! That is about what I was anticipating. I have a few daily or weekly tasks that I knew I would do while I was away.

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I love horseback riding & got to gallop!

The resort had excellent wifi and we had basically no cell service anywhere else. The week was blissfully, amazingly quiet and serene.

We were in a ski resort in the off-season, so we basically had the entire place to ourselves!

We were in Hunter and saw all Hunter and Tannersville had to offer, had some great food, and visited places like Kaaterskill Falls, which we hiked to on two occasions from two different directions. We went to Hudson, NY and were up close and personal with the Hudson River and a local ramen place that was awesome. We went to Woodstock for their Halloween festivities — talk about a town that takes holidays seriously! We went to Cooperstown for the National Baseball Hall of Fame and Oneonta to visit a cousin and have amazing soup. We even went horseback riding.

It was a lovely week.

I also worked while we were gone. I did social media posts for the week for one client, edited part of a book for another, and managed book reviewers for a third.

I ended up sitting in my car in Hudson, NY while taking a client call for half an hour, feverishly scribbling notes in my tiny purse-sized notebook, discussing their needs and my pricing and timing.

I spoke to another freelance writer via text while sitting at dinner one night, needing to know his availability to work on a 3-month project and work with me.

I had a client let me know she needs to pause for November and December and resume work in January.

I edited another 30 pages of a client’s book, whose deadline is fast approaching.

I woke up every morning and checked my work email and responded to anything I needed to before starting our day.

And now, we are home.

It was a lovely vacation and even though it was peppered with some work here and there, that didn’t detract from my thorough enjoyment of hanging out with my husband and exploring somewhere we’ve never been and watching Stranger Things season 2 at night.

I prepared as much as possible and did minimal work while we were gone, which didn’t interfere with vacationing. I feel like this was my most successful vacation since becoming an entrepreneur!

How do you deal with vacations and traveling when you’re an entrepreneur or freelancer? Do you work while traveling or not at all? How do you let your clients know? Share your tips!

Written by

Entrepreneur, writer, editor, book coach, cat lover, weirdo, optimist. Author of “Write. Get Paid. Repeat.” & “Concept to Conclusion.” jyssicaschwartz.com

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