A Busy Executive's Vacation Survival Guide

By Jessica Wishart

In a previous post, I outlined the business case for spending that week at the beach or in the mountains vacation2guilt-free this summer. Understanding what the benefits are is one thing, but for many of us, the experience of going on vacation can yield less than desirable results. How many of us have crammed so much work into the week before vacation that we have to spend the first part of the vacation recovering instead of relaxing? What about those of us who “take a vacation” but cling to our phones, taking calls and answering emails, so that our vacation is actually just working from an exotic location? How about that first day when you return to the office and see 500 emails and a calendar full of meetings and feel those vacation benefits slip away only to be replaced by a sense of dread? 

Taking a truly restorative vacation takes commitment. According to Claudio Fernández-Aráoz, "we must approach our vacations with the same tenacity as we do our vocations, and use them to come back to the office better than before." For those of you who are committed to taking the time, I’ve compiled the best expert advice I could find on what to do before, during and after your vacation to maximize those benefits and avoid the scenarios I mentioned above. I hope you enjoy!

Before Your Vacation

  • Give yourself permission to leave: If you truly believe that everything depends on you and the doors to your business will close if you are gone for a week, then even if you do manage to get away, you won’t be feeling very relaxed while you’re gone. According to Scott Edinger, "For many of us, our work is such a vital part of our lives that we have a distorted view of our own importance. When we take a step back and change our perspective, we give ourselves permission to not be indispensible for a time. Odds are, the world will be okay if you’re out for a week or so."
  • Plan your vacation in advance: Planning your trip and daydreaming about activities you’ve planned is part of the fun of taking a vacation. Plus, your vacation will be far more relaxing if you don’t leave things to chance. As Fernández-Aráoz points out, "Seamless air travel, nice accommodations, guaranteed restaurant and tour bookings—all of these will make your time off more productive and enjoyable."
  • Don’t try to cram everything in before you go: In order to start your vacation with the energy to enjoy yourself and your loved ones, Edinger suggests expending no more than your normal amount of energy or hours the week before you leave for vacation. Alexandra Samuel agrees, adding that it can be helpful to leave some projects that you enjoy doing unfinished before a vacation. Make a note of where you left off, and then you’ll have something that’s not too painful to return to when you get back.
  • Make sure you’re covered: Think about things that have to happen while you’re gone. If you can set up anything automated (like prescheduling blog or social media posts to go out while you’re away), do that. For everything else, make sure you have a coworker designated to handle situations as they come up. Try to anticipate any likely scenarios, and write instructions for how to handle them (“If the website crashes, call this number” or “If a client calls for this problem, handle it this way”).
  • Plan for your return to work: Samuel suggests triaging your priority list before you leave; "Make a short priority list of what you actually need or want to tackle in the week or two after vacation, and annotate that list with where you’ll start with each one.” She also recommends blocking off time on your calendar your first week back so you’ll have some built-in buffers to catch up rather than coming back to a calendar full of back-to-back meetings.
  • Set up out of office messages on your email and voicemail: Samuel even suggests giving yourself a breather when you return by extending the time you’ll be unavailable for a few days after you’re back. That way, people won’t be expecting to hear from you first thing Monday morning, and they’ll be pleasantly surprised if you get back to them sooner than they anticipated.

During Your Vacation

  • Pick the right destination: Shawn Achor cites that "vacations result in higher levels of happiness and energy" when you go further away from your home city. Fernández-Aráoz advises choosing a peaceful, naturally beautiful spot to foster creativity and inspiration.
  • Get to know new people: Achor recommends interacting with a host or a guide who is knowledgeable about your destination. Fernández-Aráoz suggests that meeting interesting, different people is a critical part of vacations because “The world’s most productive people are deeply curious and collaborative and constantly seek out new acquaintances and allies – even when they’re on vacation."
  • Get moving: This is especially important if your job keeps you behind a desk all day, according to Fernández-Aráoz. Of course, vacation time is for relaxing poolside and going to the spa, but for maximum benefit be sure to also work in some time for hiking, swimming, walking, exploring, playing, and otherwise enjoying the opportunity to reap the benefits of physical activity.
  • Don’t be afraid to spend money for the experience: While material things rarely hold up over time, meaningful experiences last forever. In addition to the wonderful memories, your perspective and sense of self can be expanded and your productivity and well-being can improve making the vacation truly priceless. According to Fernández-Aráoz, "quality vacations are one of the highest-return investments you can make."
  • Establish and stick to rules for checking in: Many experts feel strongly that the only way to have a rejuvenating vacation is to completely unplug. But, the mere idea of going for days at a time without at least checking in on work is enough to give some executives a panic attack (the opposite of the intended effect of vacation time.) So, if unplugging completely is simply not in the cards for you, Edinger recommends a compromise: "the idea is not to forbid contact with work but to establish clear ground rules about when you will engage in it, with the explicit recognition that when you’re engaged in work you really aren’t on vacation, you really are at work.” Setting aside a few specific days and times to check in and limiting yourself only to those times can help you balance the need for minimizing your anxiety about what’s happening back at work with taking the critically important time to disengage.

After Your Vacation

  • Stick to the plan: Here’s where hopefully your good planning before vacation will help you out. Keep those times blocked on your calendar to help you catch up. Use the notes you made for yourself to ease back into finishing those projects that you left for yourself (hopefully the ones you enjoy doing).
  • Keep a communication buffer: Samuel suggests we wait a day or two to turn off our email auto-responder "so your colleagues and clients don’t expect an instant response” while you are getting back into the swing of things. She also recommends leaving your interoffice chat and social media channels offline for the first few days so that you aren’t flooded with communication. This way, you actually stand a chance at catching up with the emails and calls you missed while you were away.
  • Triage communication: When you sit down to tackle that inbox, immediately delete (or file for much later) any blog notifications, promotions, or other non-essential communications. From there, come up with a system that works for you. Maybe you go down the list and reply to all client emails first before reading any internal messages. Or maybe you just start with anything that came from your manager. You might also take advantage of tags or other inbox organization tools to help you respond to what’s most urgent now without forgetting to come back to those other messages when you have time.
  • Catch up: You may want to plan on having lunch with a coworker the first day back so you can hear the updates on what you missed in person. Keep this casual; choose someone to debrief with that you enjoy spending time with, and this will help you reconnect and get back in the groove. Another great way to catch up on what you missed while you were out is to review your teams’ Rhythm dashboards; you can quickly scan for the status colors and read comments on priorities that are important to you so that you’ll have a clear idea of what happened while you were gone.
  • Do what you can to enjoy the return to work: The transition back to work can be painful, and that only gets worse if we have a negative attitude about it. Samuel suggests trying to "Make work fun. Put your first week back to good use by doing neglected tasks you actually enjoy.” She also suggests using a new Spotify playlist or Pandora station to help you enjoy the process of catching up on mundane tasks.

Now that you are armed with tips for how to take that vacation and enjoy it without all the frenzy before and after, I hope you will find yourself smiling as you set aside a week’s worth of blog post emails from us upon your triumphant return from a truly remarkable vacation!

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Jessica Wishart


Photo Credit: iStock by Getty Images