How my bad habit sabotaged productivity for my team

680 360 David DeWolf

Over the past 12 years of my career, I have ruined vacations for nearly an entire generation of my employees. Like it or not, as leaders, people watch, and emulate, what we do. To say the least, my vacation habits have not been the best example.

A Journey to Self Awareness

Three years ago, my wife, Teresa, and I took a trip to St. Lucia to celebrate our 15th anniversary. I committed, for that trip, to leave my laptop at home and turn off my phone once I landed on the island. This simple promise made the trip one of the most refreshing periods of my career. When I returned to work, my mind was sharp and I had a fresh perspective. I saw my productivity improve, significantly.

While I must admit that I have largely slipped back into old habits, I remain fascinated by the growing research on the value of vacation and rest. Books like Rest, When, and Deep Work have impacted my working style and changed how I think about productivity. Most importantly, they reinforced the lesson I learned while in St. Lucia – a true vacation far and away benefits my work much more than workaholism.

This past summer my journey came to a crossroads. Noticing that my productivity and effectiveness were suffering, I decided to take a one-week hiatus, which I dubbed my “Staycation.” During this week, I logged out of work completely, including email, from Friday evening through the following Friday. And, once again, I found myself refreshed, recharged, and ready to go.

Two things struck me as I returned:

  1. The number of people that noticed that I was offline and truly checked out was significant.
  2. The number of people who were on vacation when I returned that were still appearing for meetings, writing emails, or, “checking in” was also significant.

The brutal reality hit me. Despite my vocal support for folks spending time with their families, unlimited time off and flex schedules, my decade of workaholism set the expectation that “truly checking out” isn’t how you get ahead.

Creating a System for Success

Given this reality, I’m resetting expectations within our company to ensure that everyone benefits from proper rest. Here are three things I’m committing to:

1. Lead by example

Rest is important. It’s essential that I demonstrate that you can both be a high performer and get some downtime.

To do this, I’m going to:

  • Hold myself accountable to taking 2 week-long vacations, during which I truly check out, every year. I’m not sure I can remember a year over my entire career in which I’ve had more than a single physical, never mind mental vacation. That changes now.
  • Stay committed to embracing the weekend. Two weeks ago, I started being more deliberate about how I use my weekend for rest, relaxation and fun. I’m going to keep that rhythm going and make sure that I do what I can to remove any mental distractions while I’m with my family.
  • Keep using “Inbox Pause.”  I’ve started using this tool to delay new emails during my “down time” to make sure that I don’t get pulled back in to work by the allure of new information. By pausing the receipt of email on the weekend, for example, I’m able to more aptly pull away.

2. Settings explicit expectations with my team

I need to be more observant about folks who are working during their time off. Ensuring that my team knows that I actually expect high performers to take the time they need to recharge their batteries is essential. I need to set explicit expectations and promote a culture of hard work and deliberate rest.

3. Create systems that reinforce the expectation

As a company, we must develop guidelines that will empower employees and promote healthy behavior. Here are my ideas:

  • Plan for adequate backup coverage during vacation times. Tell not only that person, but also your teammates and clients.
  • Log out of email, Mattermost or Slack, and other communications mediums while away. Try to let go of the temptation to “check in“ in order to stay in the loop or prevent a pile-up of work. If you’ve delegated (whether up, down, or to the side) responsibly, you shouldn’t have a pile of work when you return.
  • Consider using an autoresponder and filter to automatically delete emails while you are out. This will prevent you from experiencing the dreaded flooded inbox on the day you get back and keep things moving while you’re away. Here’s the out-of-office responder that I used (and borrowed from Michael Hyatt).

Thanks for your email.

I will be of the office and offline the week of <date>.

During this time I will not be checking this email account – at all.

If you have something urgent, please contact my assistant, Cheryl, at <email redacted>.

Please note: During this time I will be deleting all messages as they arrive, using Gmail’s filter function. Why? So I don’t return to an inbox full of messages that have already been resolved. And, so I am not tempted to check email while I am gone. 😉

If for some reason your issue is not resolved before I return, please re-send your message after <date>.


As a certified workaholic and stereotypical entrepreneur, I LOVE what I do. In most cases, this is a good thing. When it comes to getting the appropriate rest and time away, let’s just say I’m still learning.