What the Ice Cream Road Race Taught Me about a Work-Free Vacation

Like many leaders, I don’t completely stop working while on vacation. It’s partly the nature of entrepreneurship and running a small company. There are just certain things that can’t wait, nor is there someone else to do them. I also pride myself personally on being responsive, particularly to customers, so will check in just to make sure nothing urgent has emerged. Finally, vacation does have some good chunks of free time, particularly early mornings, to catch up on organizational things you just never seem to have time for. While I’m sure updating your computer software sounds like a terrible way to spend a vacation morning, it feels great to me to check it off the list.

I’m also very aware that my entire team watches what I do on vacation and it sets a tone. Therefore, I try not to be visibly online very much. I try not to send emails or slacks. But then something unexpected comes up and despite best efforts, I find myself on the phone with the team while also in line for the Log Flume ride. I try to surreptitiously sign documents from the Chicken Shack. I once took an investor call while standing between sand dunes to block out the beach noise. I sneak work in, like eating marshmallows after midnight.

This week however, I learned about another pitfall of doing this type of work while on vacation. It joins the nearly twenty other reasons that you should consider a “work-free” vacation. As we go into this heavy August vacation season, I share this story primarily as a “don’t do what I just did” cautionary tale.

This week, we had a big deliverable due to a customer. It required a lot of decisions and collaboration across three teams. I was also scheduled to be on vacation for a few days on the west coast, three hours behind the team. The result is that we were working somewhat asynchronously over Slack, leaving messages for each other, comments on documents, but not actually speaking live. Finally, I realized that we really need to talk and so said “let’s convene in the morning” at 8:30am ET. But note that I said this at a time on the west coast when everyone on the east coast was likely already asleep.

So I got up a few minutes before the call, logged on and saw a note from one of my team members that said he had been scheduled to be out for a few hours with his family for their annual town Ice Cream Road Race, but he could skip to do the call. I could see he was online. “Did you go to the road race?” I asked, crossing my fingers that he said yes. “I didn’t”, he responded with “slightly smiling face” emoji. “Do you still have time to get there? If yes, GO! There are other times we can talk today.” He responded immediately that he could still make it and he sprinted off to join everyone for the race. He was the last person to register, but he made it.

My effort to get work done at vacation times that worked for me, combined with the pitfalls of asynchronous communication and time zone differences had almost led to someone I care about missing a planned family/community event to do a call that didn’t even need to be done then. While I immensely appreciate his dedication and sensitivity to my schedule, I’m extremely relieved that he didn’t miss the race for it. It’s those small events missed or sacrifices that accumulate over time and lead to burnout and frustration.

I can think back to times at WeSpire where entire vacations were cancelled to be able to hit deliverables. Despite the mythology of the “sleep on the floor and take no vacation” requirements to be a great startup, I don’t think we were a better, stronger company at that time. It strikes me that a strong, well-run company is one where everyone works hard, but also intelligently. You can run the Ice Cream Road Race that morning and just work later that evening (as long as your vacationing leader isn’t dive-bombing everyone’s schedule to work around hers). If something isn’t going as planned, you are willing to ask people to step up and do more, but also to have tough conversations with customers when you are at capacity. You plan for and take vacations, and work-free vacations are feasible (even if personally the idea is still a bit unfathomable).

So as you head out to your vacation, challenge yourself to increase your number of work-free days, even if, like me, it might be going from none to one. However, when and if you do work, don’t just be sensitive about the tone you are setting. Be sensitive to the pitfalls of asynchronous communication and time-zone differences. Do your best to not blow up everyone’s schedule to accommodate yours. Finally, make sure the quality of what you do doesn’t suffer due to not having the right amount of time to do it. Something might be better left until you return, refreshed and recharged, to tackle it.

Quote of the Week: “It is a good thing for everyone who can possibly do so to get away at least once a year for a change of scene. I do not want to get into the position of not being able to see the forest because of the thickness of the trees.”

Franklin D. Roosevelt

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PS: While on the theme of work-free vacations, we will be taking a vacation from Saturday Spark for the rest of August. We encourage you to check out some of the posts you may have missed by visiting our blog and we will see you back in September!

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