Hoop logo
Join The Waitlist

Get Early Access to Hoop

Make better decisions faster without meetings

Passport? Check. Slack? Disconnect! How To Build Healthier Vacation Habits

All work and no play? Here are practical tips for taking a truly work free vacation.

When was the last time you truly disconnected when on vacation?

The answer might be “never” if you’re in a leadership position. The purpose of a vacation is to step away from daily responsibilities at work and get recharged. Yet, most Americans aren’t able to disconnect because of our pervasive always-on work culture. While healthy cultures encourage vacation, I don’t know many people, especially founders, executives, and people managers in the knowledge economy who feel like they have permission to not check email, Slack, or be generally available while on vacation.

Research shows all the benefits to health and productivity from taking time to  disconnect. With burnout at all time highs, leaders especially need to take care to be mentally and physically prepared for the next crazy moment in what feels like challenge after challenge. As a founder of a startup that’s building a healthy work culture from the beginning, I decided to put myself to the test and see what it would take to disconnect European style for an upcoming vacation.

Here’s what I did, and what you can too to reap all the benefits of a 100% work free vacation, to come back energized and excited for the next challenge.

No ego, amigo

Recently, I met a CEO who was complaining about his meeting load. He mentioned an upcoming vacation, so I said what a great opportunity that would be for him to reassess where he was needed most at his fast growing company. After the vacation, I caught up with him and all he could talk about was being on the phone nonstop during his trip. He was almost bragging about it! Instead of enjoying the tropical sunshine with his family, he chose to be stuck in his hotel room, dealing with some minutiae he felt was more important. He wore it as almost a badge of honor. I recognized that I did not want that to be me.

Often, people perpetuate destructive work practices because it makes them feel important. They may not even realize they are doing it! Having self awareness can really help here.

People often feel like they can’t disconnect because their contributions are crucial to their team’s success. Guess what? They probably aren’t as groundbreaking as we think. 

Early in my career as a manager, I recognized that becoming a bottleneck was often a self serving phenomenon. If I could empower my team to do great work without me, I was doing my job and allowing myself the opportunity to do other things that upskilled my own career. 

A vacation is a great opportunity to check your ego at the door. Invest in trusting your team and invest in your own long term success by taking a break. 

A Peloton devotee, I’m a big fan of trainer Jess Sim’s phrase “No ego, amigo.” She mentions this during workouts as a reminder to lift the right amount of weight vs what she, as a pro, is lifting. I’ve come to use this phrase as a mantra at work when it’s time to admit I don’t know something, could use help from others, or can trust my teammates to make great decisions in my absence. Taking the time to fully disconnect means saying “No ego, amigo” and empowering your team to get things done without your input.

Don’t be like the CEO mentioned earlier, undermining his vacation in favor of putting out the latest work fire. Use the tips ahead to get the most out of your vacation and come back as a stronger operator to an empowered team.

How to do it:

  • Ahead of vacation, reiterate to your teammates that you’re going to be completely unavailable 
  • Make sure everyone knows what to do when you’re out
  • Reiterate that your absence should not slow work down. People are often afraid to move forward without approval from their manager. Mention that you’ll applaud good decision making that doesn’t require your approval.

Plan ahead

A piece of advice a mentor shared ahead of my first maternity leave years ago was to make a document of everything on my plate, and make a plan for what would happen to projects I was leading with my upcoming leave. It turns out, this is standard advice, and there’s a reason for it.

Anyone who’s been on a successful leave of absence knows the value planning ahead can bring both for colleagues and for an easier return. This should also be the case for vacation!

For my upcoming vacation, I started a list of responsibilities well ahead of my planned absence, and as the date drew nearer, I added more details to make sure my absence did not delay any projects. This is typically where someone might be called on a vacation to step in “in case of emergency.”

How to do it:

  • Start a document double the amount of time before your leave starts. If you’re planning to be out for a week, start the document two weeks ahead of time.
  • Make a note every time you find people waiting on you for something
  • A week ahead of your vacation, start sharing out the doc to those who will be affected so they can ask questions and get insights ahead of your absence
  • It seems like a lot of planning, but it’s worth it both for your colleagues to be empowered in your absence, and for you to have peace of mind
Visiting a tiny, family owned winery in Northern Spain

Distribute decision rights

The last thing you want from going on vacation is for work to stall. And yet, it often does because people’s roles, responsibilities and decision rights are not clear, causing ambiguity and chaos. Decision rights are literally that: making it clear who makes the call on any given decision. Understanding this concept, and being able to distribute your own decision rights makes a big difference in disconnecting without guilt.

For my upcoming vacation, I made a list of all the areas where I would typically make a call, and wrote down who on my team would make those decisions in my absence. 

The other maybe tougher thing is to accept that decisions will be made without your input, and you have to respect those decisions. My cofounder Brian made a couple of game time decisions while I was out on things where I had delegated my decision rights. Were the decisions he made exactly the same as what I would’ve done? No. Were they great decisions? Yes, and the experience also helped us deepen our respect and understanding for each other’s roles.

How to do it:

  • In your working document, make a list of all the areas where you’re the decision maker, and specify who makes the decision in your absence.
  • Try to be as specific and comprehensive as you can to prevent delays in your absence
  • Communicate to your team that you are 100% comfortable with the people you’ve delegated decision rights to. This is also a cultural shift that reinforces the trust and confidence in the team.

No single point of failure

As a remotely distributed tech company, we’ve made the decision to operate mostly asynchronously. As a result, we’ve set up processes where bottlenecks can be avoided by making information readily available to those who search without needing to ping another human for answers. 

In the case of a vacation, this might mean information granting access to tooling where an admin typically has to add someone to a tool. 

A vacation is a great test to make sure a team can pass the famous “bus test.” I wish someone would come up with a better analogy here, but the common idea is that if someone on the team got hit with a bus, would the company still function? A way less morbid version is, can we still log into all of our systems if any one person is out?

How to do it:

  • Use a shared password manager to make sure everyone who needs to has access to important systems. We use 1Password.
  • Do a test run ahead of a vacation and make sure admin access is granted to more than one person.

Erase FOMO with a culture of documentation

Much has been said about FOMO, but not enough about JOMO or the “joy of missing out.” To truly be present on a vacation, you have to mentally accept that you’re going to miss things, maybe important things as an opportunity cost for disconnecting. That’s ok. The whole point of building a team is to trust and empower your team.

It takes a few days (actually research shows more like a week) to get into true vacation mode because of all the mental detritus and reminders going off in your head. During this vacation, we had an important investor meeting while I was hiking a beautiful trail. I felt bad for missing it, but took a deep breath and realized the whole benefit of being in nature was to be present. When I got back, I read my cofounders’ notes and appreciated them.

To be able to work asynchronously, companies need to adopt a culture of documentation. At Hoop, we document takeaways from every meeting and do most of our other collaboration in tools  like Twist and Notion. As a result, anyone not present can catch up without needing to ping someone else or schedule a “catch up” meeting.

How to do it:

  • Recognize you’re going to miss things. Take some deep breaths and tell yourself that’s ok.
  • Reframe the vacation not as a guilty pleasure but as an investment in yourself both personally and professionally.
  • Use the vacation as an opportunity to assess where documentation can be leveraged to help reduce a reliance on chat and meetings to collaborate.

Turn off the apps

A frequent social media acolyte, I can’t trust myself not to silence “Screen Time” when I’ve reached the end of my 30 minute allowed allotment. I know that to be able to disconnect, I have to delete my apps. All of them. For this vacation, I deleted:

  • Slack
  • Twist
  • Front
  • Notion
  • Instagram
  • Twitter
  • LinkedIn

Basically, all the worst offenders of where my trigger fingers lead me if there’s a minute or two of quiet. I was surprised by how addicted I was, but also how quickly I became more happy with not having these apps at my fingertips. I found myself thinking more openly and creatively, and feeling more calm overall.

When I got back from vacation, I slowly added these apps back in and am now much more careful about how much attention I give each. This is a similar process that James Clear shared in his book entitled Digital Minimalism. A vacation is a great opportunity to reset the relationship with constant dings, notifications and distractions.

How to do it:

  • If you have self control, you could just turn off all notifications from these apps.
  • If you’re like me and can’t trust yourself not to check (ie you’re human), just delete the apps. 
  • You can always download them when you’re back.

Reap the benefits

After a week away, I came back feeling creatively refreshed. Here were some other unforeseen benefits:

  • Increased empathy for my team because of all they did while I was out
  • Team’s increased empathy for my contributions
  • Clearer insights into our biggest problems because not bogged down by minutiae
  • Fresh slate to instill and practice better habits
  • Insights from reading notes vs being in the moment

This summer, we all have the opportunity to make a choice: will the next vacation force us to evaluate better practices? Or will we continue to check Slack, but in a more tropical location. 

Given the state of mental health in the workplace and my own experience, I recommend the former.

Let's fix the way we work.

Thank you! You're on the list!
Oops! Something went wrong...