A Working Vacation- Does it “Work”?

Ah, the week after Spring Break. The snow is almost melted and the temperature has been above freezing for two whole days now. Lucky for us, we got to go someplace warmer recently. We spent the past week in Louisville, Kentucky and had a pretty great time. As the title suggests, it was a working vacation for both of us.

USITT, a well-known theatre conference, was taking place there at the time and my department was pushing me to go. Due to the conference’s enormous scale, it is not my favorite thing to attend, but I begrudgingly did it. I invited Mr. Sweetspot to tag along, since the trip was mostly paid for (I get $1250 of travel money from work). As he’s a traveling teaching artist, he organized a workshop to teach on our final day there, so it quickly became a business trip for both of us. But we wanted to have some fun as well…

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Did it work? Absolutely. The caveat? During a working vacation, you will not be able to excel at working, or at vacationing. You just have to accept that. As soon as you get excited networking with colleagues, you’re running late for a dinner reservation. The moment you discover a cool street you’d like to wander down, you have to return to conduct portfolio reviews. Your last night in town you might need to review your workshop materials instead of heading out on the town. You certainly get to experience a new place, but it’s not the same as if you were just visiting. The pace is also very different- by combining these two events you’re always in “go” mode, so while very fun, I wouldn’t describe this getaway as relaxing.

What did we get to do? A bit of everything… but mostly vegan food and bourbon. Who knew Louisville has so many epically delicious vegan options (I think most people know about the bourbon)?! Mr. SS got to do an aerial acts class in a circus craft studio. I took baths every day (we don’t have a working tub at the homestead). We wandered around downtown and got to see two shows at the Humana Festival. We even got to visit Big Bertha at Marvelous Mystery. But every day, we also had to work.

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In that case, why do it? Obviously, if you can, a non-working vacation is the way to go. You will have all of the fun, none of the obligations. But yes, if money is an object, then this kind of travel might just be right for you. While we did not live frugally during that week (in fact I’d estimate we spent ~$100 each of the 3 days, with an extra ~$50 on travel days) this still adds up to a five day vacation for less than $500. And to us, that was absolutely worth it, especially since Mr. SS earned a little money with his workshop.

A Cat Cafe!

Some things to consider:

  • Do some research. There are conferences/workshops/seminars in all kinds of locations. Are any of them a place you’d like to visit? Justify why this is THE BEST opportunity for you (I got to go to Vegas that way).
  • Understand what will and won’t be paid for. Does your company cap the amount of money you can spend? Can you calculate a per diem or do you need food receipts? Can you take your own car and claim mileage or does it make sense to rent a car if you’re driving?
  • Are you at a place where you can afford to not put your all into a conference (or whatever opportunity you’re pursuing)? You can’t give 100% and still have a vacation. You can tell yourself that, but recognize that it’s a lie.
  • If you’re not going alone, do your fellow travelers recognize that you will need to work, and might not be able to go to a leisurely brunch or stay out late?
  • Do you think the working vacation model will make you happy? Trust your gut. For me, it meets the intersections of frugality and a desire to travel. It lets me enjoy myself, knowing that I’m living large while traveling on the cheap.

Have you had a successful working vacation? How do you feel about the idea?

2 thoughts on “A Working Vacation- Does it “Work”?

  1. Costa Rica FIRE says:

    I love work-cations though I agree you may not feel like you get enough of either work or vacation. I like it b/c I find that I can do more of each all around because of the flexibility with scheduling and financing (i.e., piggybacking off of work expenses). I also appreciate just working or just vacation, but a work-cation every couple of months is great. I plan to spend November in Costa Rica for NaNoWriMo (National Novel Writing Month).


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