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THE INC. LIFE

You Need a Vacation: Here’s How to Make Sure You Can Take One

Taking time off is mostly a mental challenge, not a business one.

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BY Carrie McKeegan - 09 Aug 2018

You Need a Vacation: Here's How to Make Sure You Can Take One

PHOTO CREDIT: Getty Images

With the summer vacation months come endless streams of smiling, swimsuit-clad Facebook photos, and stories of long, lazy, sunny days on the beach or by the pool. But for many of us who run businesses, this time of year--the time when we want (and need!) to log off for a week or two--can also be riddled with anxiety at leaving work behind. In my experience, the biggest issue CEOs have with taking time off is a mental one. Usually, the issue is more about being able to rest, relax, and trust your team, and not that the business will actually fall apart without constant observation. Here are some tips to make sure you feel comfortable taking time off and stay that way while you are away.

1. Book two transition days: one the day before your vacation starts, and one for your first day back in the office.

Have you ever sent a "last email" from the airplane as you're taking off for your vacation? I have, and it's miserably stressful. To ensure that doesn't happen, use a buffer day. The day before your vacation, block out a completely open day with no meetings on your calendar and no big priorities. Use this day to hand off any last-minute items on your to-do list, clear out your email inbox, and get super organized for when you return. Inevitably, a few last-minute tasks will pop up, but at least you will have time allotted to handle them.

Similarly, do not book meetings for your first day back in the office. Allow a transition day following your return as well. If you don't, you won't have time to get back up to speed before you kick off in full gear again, and you will feel like you need to catch up on emails before your first day back at work.

Explain this approach to your team, so they understand what these days are about and don't think you're working on your first (and last!) day of vacation.

2. Appoint a deputy for anything that arises that doesn't have a natural owner.

For most of us, assigning one deputy for everything is impractical and unnecessary. However, it's good to have a point person who is the team's go-to for any unanticipated needs that arise while you are away. Chances are, nothing will come up. But if something does, then you know it's covered and won't slip through the cracks.

3. Set up an automatic out-of-office message.

This sounds obvious, but most people don't do it. Many of us believe that always being available is a sign of devotion, and that turning on an out-of-office message signals to the world that we are not serious about our business. This is nonsense! For one thing, setting up an out-of-office message, even if you're still checking messages, allows you to ignore all non-critical messaging and avoid the "I am so sorry I didn't reply to your email..." messages when you return. For another, setting an out-of-office message indicates not that you lack devotion, but that you are organized, value work/life balance, and trust your team. It's a simple, but powerful, way to unplug.

4. Give your deputy a way to contact you if there's a true business emergency.

The first step to giving yourself permission to step away entirely is to feel confident that if something genuinely does come up while you are away, your team knows how to contact you. Ideally, you want this to be through an alternate channel than where you receive all your usual correspondence; otherwise, you will need to open your email inbox to look for those notices and needlessly be stressed by the number of messages coming in.

What I do: I give my deputy my personal email address and tell her to use it if anything critical arises. And then I put an out-of-office message on my business email with my deputy as the point of contact, and let her determine if anything needs to be brought to my attention (in 10 years, this has happened only five or six times).

5. Stack the deck in your favor.

Before you take time off, do a few things:

  • About two weeks before you leave, send a reminder to your team about your upcoming vacation and ask them to consider where they may need your input in advance. Send a similar note a few days before. Put the responsibility onto your team for anticipating anything that might come up. That way, anything that can be avoided, will be.
  • Devote some deep thinking time to outlining what projects will likely be worked on over the time you are off, and identify those that need your involvement. If there is anything that you think really needs your attention, consider pushing back the timeframe. In most cases, this isn't necessary (your team is capable of handling it 99 percent of the time!), but if there's a genuine exception, don't plan to work "a little" while you are off--just shift the timing.

6. This should go without saying, but doesn't: don't work!

If you can't let work go for a week for your own sanity, do it for your team's sake. If you work while you are on holiday, that's a direct message to your team that they should too! All of us need time to rest and recharge, and CEOs are no different. Give yourself the same thing you'd give to your best friend or one of your team members: permission to enjoy the holiday without any worries about business.

As the CEO, it's key that you genuinely don't work while on vacation. What might seem to be a fairly innocuous email here and there can really derail your business and home life. Convinced? Go get your bathing suit (and out-of-office message) ready!

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