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 a 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. This 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.

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


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!


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.


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