7 Steps to a Great Vacation: How to Take A Full Month Off Work (Without Cheating)

Have you had a real break this year?

If you ask most leaders, the answer is no. Sure, they took time off, but they kept checking email, answering texts, solving problems or being on call ‘just in case’. So it was really a cheater vacation (trust me, I’ve taken my share of those too).

But you never really rest when that happens.

Recently I went one step further and asked leaders whether they’d ever taken a full month off work with no cheating.

Of the several thousand who responded, 81% said no…they never had.  In addition, it seems more than a few of the 19% who had were teachers, where time off is simply given each summer.

The reality? So many leaders never take a break.

And what’s that doing to us?

According to a 2021 Deloitte study, 82% of senior leaders regularly finish work feeling emotionally and physically exhausted. 59% say they are unable to relax or pause activity. 49% have trouble sleeping at night.

The problem is that leaders who never take a break eventually end up breaking.

My Recent Experiment: A Full Month Off (No Cheating)

This year, for really the first time, I took a full month off. No cheating.

It broke a long standing track record of taking vacation but doing an hour of email every morning, checking in with the team, make a few decisions and responding to urgent matters or ‘crises’.

I’ve also done working vacations to finish books or big projects—working in the morning and ‘relaxing’ in the afternoon or evening. After several attempts at that over the years, I finally concluded that working vacations don’t work. You end up not doing great work or getting real rest.

So this year, I decided to take a full month off with no cheating. No checking email every morning (or any morning), no calls with the team, and zero decisions. The team ran everything.

The results? We prepped well enough that the team wasn’t overburdened, I was off, and we had a record month. On most dials in the company, we broke records. I didn’t make a single decision or intervention.

Enough people asked me to explain how it happened that I want to walk you through the exact process I used to help you take a real break the next time you’re off.

Whether that’s a week, two weeks, a month or longer, following the seven steps below can help set you up for success.

To get to the place where you take a month off, you have to move from what I call Level One of leadership to Level Two or Level Three.

Here’s a brief explanation of the Three Levels of Leadership.

The Three Levels of Leadership

From my perspective, there are three levels of leadership any leader or organization operate at. Each phase is more of an approach to leadership than it is a phase of leadership. While every organization passes through Level One, many get stuck there and never move on to Level Two. Even fewer ever make it to Level Three.

Level One: Nothing Runs Without You

If you operate at Level One leadership, you’re the linchpin…nothing runs without you. Leave or step out for a week and everything falls apart. Which is why leaders who operate at Level One never get time off.

If you operate at Level One of leadership, even if you have a team, they’re not equipped or empowered to make decisions or solve problems without you.

Every start up falls into this category at least for a season. But sadly, so do so many other organizations, even organizations that have been around for years or decades.

 Through your inability or unwillingness to delegate, build systems or equip your team, you are involved in virtually everything, and as a result, can’t take a break.

Level Two: Things Run Without You

Some leaders do lead themselves and their organization to Level Two where things run without the senior leader.

That happens by working on systems, clarifying mission, vision, values and operating systems. And honestly, it happens when leaders finally trust their teams enough to let them make pivotal decisions.

As a result, you can take a real break, and things actually run just fine without you!

Level Three: Things Grow Without You

Only a few leaders ever get to this level, but when they do, it’s powerful for everyone involved. Your team is equipped, the strategy and systems are clear, and your leaders are so empowered that things not only run when you’re not there, they grow.

Apple is an example of a company that made it to Level Three. Note that this did not happen after Steve Job’s first exit from the company in 1985, when Apple almost didn’t survive without him. But the time he returned to Apple in 1997, he was a different leader and led it to become the behemoth it is today, even almost a decade after his death.

Disney, Walmart and even Twitter all grew after their founders died or were fired (Twitter).

Level Three is hard work, but you can get there. The church I founded did, and we’re working on the same for my company now, despite the fact that I want to do this for decades longer (that’s another post for another day. Curious? I teach a session on the three levels of leadership here.)

7 Steps That Will Let You Take A Full Month Off Work

Obviously, if you’re at Level One leadership, a full month off won’t work. But you can start building the systems and equipping your team now so you can take a few complete days off, or week off, or two weeks off by next summer.

Keep at it, and you could take a month off.

To take a real break with no cheating, here are seven steps:

1. Resolve you won’t work

At the end of the day, you need to decide whether you’re in. I’m my own worst enemy when it comes to breaking vacation rules.

Like many founders, I love what I do and feel a deep sense of ownership. So it’s easy to work. You probably feel the same way.

You might experience productivity shame the first time you slow down (here are four other emotions you might feel if you decide to be totally off).

Often you don’t need an enemy to interrupt your vacation. You have one: it’s you.

2. Prepare your team

Don’t just bail and dump everything on your team. Get ready months in advance.

At the beginning of the year in my company, we started working on the systems we need in our company for everyone (not just me) to take some real time off this year. That means making sure our procedures were clear, that everyone had someone to ‘cover’ for them in key areas (we’re a small team) and that no one was going to be overwhelmed because someone else was off.

Essentially, we worked for months on moving from a Level One organization to a Level Two organization. Most of my team has been with the company for less than three years. We were able to hit Level Two this year.

You can do a week off if you’re Level One by arranging people to cover for you.

It will be impossible to take a full month off unless you’re at Level Two.

3. Set ground rules for contact

You’re probably thinking, “Well Carey this is great theory, but what if my team really needs me or I need them?”

Fair question.

I’d suggest setting ground rules for contact.

We didn’t get that technical, but essentially told my team they were in charge of everything and to text or call if there was a ‘nuclear emergency’—a term they could define for themselves. I also told them I wasn’t worried—I trusted them.

Not surprisingly, there was no real nuclear emergency.

Did I ever check in?  So, full disclosure yes—briefly. Here’s when and how:

  • One team member decided to take a job with another organization and texted to see if I had time to talk so he could share that. I happily did that.
  • Another staff member had her first day back with us and I gave her a quick call to welcome her back.
  • I had two other very brief conversations with team members, one that was an FYI and another because my EA had been on the job less than two months. I called in to see how she was. Neither call was really necessary. All were fun.

Total combined time invested: less than 60 minutes. Also please note: I made no decisions or interventions.

You can use your own judgment, but I don’t think of that sixty minute total investment as cheating.

Regardless, you need ground rules. My guess is your team is far more capable than you give them credit for.

4. Craft a clear (and kind) auto-responder

So how do you set up your non-team members to know you’re away?

My guess is many of the requests that come from outside your team happen via email. Most of mine do.

With Slack and Asana being used mostly for internal communication, it was email that would provide the biggest challenge. I decided to let my assistant process my inbox while I was away. In addition, I set up this auto-responder (feel free to cut, paste and adapt for your next break).

Subject: On summer break

Hi!

Thanks for your email. I’m on summer break and as a result will be completely offline from June 30th – August 3rd.

My EA, Carly, is handling this email and can tend to anything urgent while I’m gone

In the meantime, if your request is for me personally, do you mind re-sending it after August 3rd? I’d be happy to look at it then.

Trying to practice what I preach and come back with a very full tank for the launch of my next book, At Your Best on September 14th.

Let’s catch up in August!

Carey

An auto-responder like this is both clear and effective. It tells people not only am I not in, but I won’t be sorting through 1000 emails when I get back. In other words, hit me up then if it still matters….

So….how many emails did I have when I got back that needed my attention? Ready? Eight. That’s right, 8.

Normally, even on my private email account I process 30-50 emails a day. So do the math, you would have expected maybe a thousand emails over 30 days.

Nope, eight remained. It was ten minutes work. Similarly, Slack and other channels took about ten minutes each to catch up on. Throw in a 30 minute debrief with my assistant, and I was caught up in an hour.

Which means…what? Well, apparently I do a lot of busy work that doesn’t really matter that much.

But wait, you say, you must have been slammed with people emailing you as soon as you got back with their requests. Actually, only one person re-emailed me. One.

The lesson: most of what seems urgent in a day isn’t that urgent. And most of what seems important well, might not be. That’s what happens at Level 2 and Level 3 of leadership. Your team handles the big decisions. And you lead and guide. And in my case, write.

5. Remove work apps from your phone

As you prepare to leave, remove key work apps from your phone.

I deleted Gmail entirely, and moved other apps so they wouldn’t tempt me. I also left my laptop in my office so I wasn’t tempted to cheat, and didn’t bring it with me when we travelled.

If you bring work with you when you’re on vacation, you’ll work. If you don’t, you probably won’t.

6. Figure out what to do with texts

With email, laptops, and work apps dealt with, what about the trickiest of all ‘contact’ points: your cell phone?

To begin with, I’m old school with my cell phone number. Not that many people have it, and those who do are generally respectful people.

Even so, what do you do with people who text you about work rather than email?

It’s a bit clunky, but you can set up an auto-responder for your text messages too. Here’s how.

I crafted a much short autoresponder for my messages than for email, but the glitch is that it only works if you tell you’re phone you’re driving, which means you can’t access anything else on your phone.

In the end, I only used it a few days (because I was using my phone to find restaurants, check the weather and do other fun things).

Which left me deciding not to respond at all to outside work-related texts.  That’s not an easy call for me, but like email, if it really mattered, I knew people would text me back.

7. Ensure the rest of your team gets a real vacation too

It’s one thing for the boss to get a break. it’s another thing for the entire team to be able to also take time off.

Entrepreneurs and leaders can too often expect their staff to be available when they’re on vacation because, well, that’s how the boss operates. I’ve been guilty of this too often in the past, and that’s just not fair.

If you start working ahead toward becoming a Level Two organization, you can create a structure and system that allows everyone to take time off without having to check in or work while they’re off.

The principle here is simple: whether it’s taking a full week, two weeks or longer off, your team should be able to enjoy the same rest you get. (By the way…as a company are consedering a no-limit vacation policy like Netflix…stay tuned for a podcast episode about that soon with Erin Meyer who co-wrote No Rules Rules with Netflix founder Reed Hastings).

The Result?

The result of a full month off? Well, that’s another blog post but let’s just say it was amazing.

And the team? Because we prepared so careful, no one felt more stress during July (I asked them to tell me the truth…they did…and they’re reading this).

The only thing to note is we did hustle harder in June, recording extra podcast episodes ahead of time so July would move ahead as normal, and I wrote three extra posts ahead of time so I’d have some new content on my website. Other than that, it was business as usual.

And…of course, we had a record-setting month in so many ways.

Becoming a Level 3 organization at my company may be more than possible, as we experienced when the church I led for 20 years moved to Level 3, allowing me to hand it off to my successor who only made it bigger and better.

What Do You Want? 

Wish it was possible for you?

In many ways this year was a systems test of many things, including the principles I share in my brand new book which is available for pre-order now: At Your Best: How to Get Time, Energy and Priorities Working In Your Favor

These principles, implemented over time, are helping all of us on the team reclaim margin at work and in life, and live in a way today that’s helping us thrive tomorrow. I’d love to help you do the same.

If you pre-order now, you’ll get a full video masterclass free of charge along with early access to some bonus resources. You can start the Masterclass today before the book comes out.

Check it out and get the book, Masterclass and bonuses here.

What Helps You?

What strategies help you and your team get real time off?

Scroll down and leave a comment!

7 Steps to a Great Vacation: How to Take A Full Month Off Work (Without Cheating)

5 Comments

  1. keith.duff on September 13, 2021 at 8:15 am

    In regards to auto reply for text messages, there are some great options that don’t just work when driving. I know that’s true on Android and I assume on iOS also.

    With risk of sounding like an app spammer, one that had worked great for me is from http://www.lemiapps.com. And there are probably many others too.

    Often these apps have to be loaded directly rather than through app stores to overcome some of the build in restrictions of iOS and Android.

    It’s kind of funny – Google and Apple say they want us to disconnect sometime and find a healthier use of their devices – then they fail to include auto reply options in their messaging apps and try to block other app developers from doing the same!

  2. Jonathan on August 16, 2021 at 8:05 am

    Carey, I’m glad you were able to take 5 weeks off. I did something similar this summer. I wrestled with what to do with text messages as well. Ultimately, I purchased a pre-paid sim card for the month. I inserted it into my primary phone and took the sim card out of my phone and put it in a borrowed phone. I wanted to be able to still access all of my contacts and other apps on my phone. I only gave my temporary number to family members and left the borrowed phone at home with an auto-reply for text and a voicemail greeting informing people I was on vacation. This was the key for me to be able to fully disengage for the 5 weeks. Thanks for encouraging leaders to do this!

    • Carey Nieuwhof on August 16, 2021 at 8:07 am

      Really great idea. A few people I know are also getting two phones…one for work, the other for personal where only a few have their number. Considering that.

  3. Eduardo on August 16, 2021 at 5:02 am

    Really helpful – but how can you have time off when you don’t have a team? For example, a private doctor, without a nurse or secretary?

    • Carey Nieuwhof on August 16, 2021 at 5:30 am

      Hi Eduardo. I think that’s a great question. I have lots of medical friends and, while it’s not my area of expertise, I see many of them shut down their practice for one to three at a time to enjoy a break. One couple—both docs—took a year off work and traveled around the world with their kids.

      They shut down the office, don’t schedule appointments and work with the hospital to ensure they are not on call. Seems to work great for them.

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