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How to Take a Better Working Vacation Than Donald Trump Did

August 20, 2017, 1:00 PM UTC

I’m an executive involved with businesses around the world, and I manage clients in time zones that seamlessly link day and night for me. Today, though, I’m on vacation. I’m also writing this article. This morning I had a conference call with a colleague who is on a family vacation. We are trying to ‘finish up’ some things so they won’t be waiting for us when we get back from vacation. Yes, we are working on vacation to make sure we won’t have so much work to do when we are done vacationing.

That’s the recursive, complicated, and often vexing relationship many people have with the concept of vacation. There are many theories about American cultural norms that suggest why we are so uncomfortable as a nation with the concept of leisure. We wear the badge of BUSY everywhere we go, we mark social standing by how in demand we are, and we seem enamored with the idea of being indispensable. The very idea that life in the office will continue without us is stressful, and vacation is supposed to reduce stress, not increase it, and so we find ourselves in a bind.

Meanwhile, we are told that it is important to have time away and to recharge if we want to be at our best, which of course we desperately want to be. So when we do vacation, we do it like champions! Some of us do planning and logistics that would rival a campaign to lay siege to a castle. I have been known to make a PowerPoint in support of a family trip, and once made a project plan to make sure everything went perfectly.

So vacation is a challenging paradox that even U.S. presidents cannot escape. Since World War II, presidents have engaged in a highly connected vacation model, never far from the constant information flow from Washington, D.C. In fact, some of our most iconic images of presidents have occurred during these stretches away—we see John F. Kennedy sailing, George W. Bush clearing brush at his ranch, Barack Obama with his family, and Donald Trump on the golf course. In the same day, world events happen, and presidents respond to them. In truth, that isn’t a terrible model for many people. Sure, we don’t have to worry about global meltdowns and domestic challenges the way a president does, but we have our own challenges and crises to manage that can feel just as looming.

We call this compromise a working vacation, and it can take many different shapes. For many of my colleagues and for me, vacation days are best spent following early morning calls to check in. Then I can relax and enjoy the rest of the day, knowing that I’ll have an hour or so in the evening to myself to get ‘caught up’ again. It provides the balance of feeling connected and needed with spending time doing something other than work for most of the day. That can feel like a win in many situations. The reality is that a working vacation is an acceptable alternative to feeling stressed about what’s happening while we are trying to have quality time away from work.

If you fall in this category, I have a few suggestions that might help make the experience a bit more restorative:

  1. Be practical. Don’t expect to multi-task during lunch at Disney World. Block off your schedule for times when you are with friends and family and can’t be distracted. Remember, a working vacation is about staying reasonably caught up while ALSO taking chunks of time away. You need to do both.
  2. Let your colleagues and clients know that you are taking some time off and that you will only be checking in periodically. That will give you some breathing room when something shows up in your notifications.
  3. Start small and be fully present when you do agree to do something, even if it is only for 30 minutes. Resist the compulsion to check your phone while your child waits for you to buy ice cream. Consider these small blocks of downtime training for bigger ones to come.
  4. Do what works for you. When people accusingly ask why you can’t just disconnect, don’t get defensive. Just smile and say, “This is what is best for me right now” and leave it at that. If they persist, try, “I guess you are better at vacation than me” and let it go. You don’t have to defend yourself to anyone.


I’m sure there are people who think I’m crazy to advocate for a working vacation. I get that. I acknowledge all the reasons why people should be able to step away for extended periods of time. Meanwhile, I’m finishing up this article and going to go spend the rest of the day enjoying family time, without my phone. I’ll be back online tonight staying caught up enough that I can relax again tomorrow. And that’s okay—I don’t have to be the best vacationer out there. I just have to find what works for me right now, and you can do the same.

Julie Williamson, PhD is chief growth enabler with Karrikins Group and coauthor of Matter: Move Beyond the Competition, Create More Value, and Become the Obvious Choice.