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Why You Should Take That Vacation

How living the "virtuous cycle" can impact all aspects of your life, especially your work.

It’s August. Most of Europe is on vacation for the month. Are you? Probably not.

Tweet comparing European versus American out of office replies
What's the deal, America? Take that time off!

There’s plenty of data to support the fact that vacation is good for the individual, team, and company. In fact, truly unplugging does wonders for creativity and innovation, which is the engine of our modern economy. Yet, too many of us struggle to actually take a vacation. Why is that? Maybe the issue runs deeper than simply taking vacation.

Starting a new company is an opportunity to reevaluate norms, establish values and align on practices. It’s an exciting time to challenge assumptions and create the foundation for the type of company people will be proud to join.

This is exactly what we did at our very first offsite last spring. While talking through the kind of company we wanted to create, we ended up aligning on an idea we’re internally calling “the virtuous cycle.”

Brian and family atop Mt. Tam by San Francisco

What is the virtuous cycle?

As pre-work for our offsite, we individually thought through our own values and what the values of our new startup might be. We thought through how we could continue to grow professionally, lead meaningful personal lives outside of work and build something to improve people’s lives using all the lessons we learned at Trello.

We realized that when we felt fulfilled outside of work, we were the most productive in our work. When we did well at work, we brought positives vibes to our family lives. And we were the most productive when we had the freedom and space to be creative.

Life could be a virtuous cycle where the different parts of our selves don’t have to struggle for balance, and instead contribute to a meaningful whole.

The big opportunity ahead is to give companies the tools they need to create space for employees to be creative and to do their best work. People need the space to reach a flow state without sacrificing the benefits of real-time collaboration. Practices and processes are starting to appear to help with this, but the tools need to be part of the equation, too, and that’s where we come in.

The virtuous cycle in practice

As a founding team of three, we’ve been living these ideals while building this company. We’re experimenting with tooling and practices to make sure we don’t fall into old, hyper synchronous habits. We’ve learned some interesting things along the way:

  • Sync time is important - We’re social creatures and working totally async didn’t fit our personalities. We look forward to seeing each other’s faces but are thoughtful about how we use our sync time. Sync time is for making human connections and for burstiness.
  • Constraints breed intentionality - We have limited “core hours” daily for when we are available for synchronous communication whether that’s meetings, Slack or feedback in point products. Since our sync time is limited, we are highly intentional about how we use it. For example, research shows group brainstorming is a waste of time. If the goal of a meeting is to come up with something creative, we brainstorm individually asynchronously and come together to discuss
  • Async everything else - Outside of core hours, we have the freedom to do our work when it’s best for us. This requires trust, boundaries, and clearly communicated goals. We’ve been critical of the tools we use, and are experimenting with what fits our team best.
  • Prioritizing health and happiness - Modern work makes you feel like there is a tradeoff between work and your personal life. But you can’t pour from an empty cup. Prioritizing exercise (and other personally beneficial activities) in the context of better work performance helps those things not go by the wayside. We shouldn’t have to feel guilty for taking care of ourselves. It’s essential to being able to give fully to your professional life.
Stella and her family exploring Miami by boat.

Some surprising takeaways from living the virtuous cycle

It sounds great on paper, but in practice it takes discipline to give yourself permission to break old habits. For example, there are great mental unlocks that come from….

  • Not feeling like you need to constantly check Slack, email, etc.
  • Giving yourself permission to work when you’re feeling the most inspired, regardless of what time of day or night it is.
  • Trusting your teammates to do their work where, when, and how they say they will and holding them accountable to it.
  • Offering async alternatives to external sync time requests.

Back to vacations

If vacations are essential to unlocking more creativity, how can we empower ourselves and teammates to get the most out of vacations?

Invest in tools and processes that reduce anxiety pre, during and post vacation — people don’t get the benefits of vacation when they’re constantly checking email. Creating a culture where employees have the freedom to unplug is critical. Essentially, people should be able to step away and know that things will be taken care of in their absence. Some tactical examples:

  • Documenting processes for who does what when someone is away eliminates the single point of failure. At Front, executives delegate their inboxes while on vacation, so even the CEO can disconnect.
  • Taking important decisions and announcements out of Slack is crucial. Use chat for what it’s meant to be: an ephemeral dialogue and not the canonical place for info.
  • Document important takeaways and decisions that happen in meetings.

Take the damn vacation - Especially if you’re a manager or in a position of power, give yourself and others permission to step away and recharge by practicing what you preach. I know, it’s hard! But if you feel the need to justify the vacation, refer to all the research on how impactful it can be. Some tips:

  • Even if you’re not traveling for vacation, give yourself an opportunity to disconnect and discover all the things you have never discovered in your community.
  • A busy executive friend takes a week off per quarter, and puts that time in their calendar at the start of the calendar year so their team is aware when they will be out.

Come back to calm - If you know that day to day stuff that comes up will be handled while you’re out, you can come back to high signal, important info that actually requires your attention. You can declare Slack bankruptcy (shift-esc for the uninitiated)! You can avoid the dreaded “day to dig out” scenario and skip to the stuff that actually needs your attention, rather than digging for needles.

  • Designate chat as truly ephemeral, meaning no crucial, high signal info only lives there. Create dedicated places where people know to look specifically for important info. This can be email, an async communications tool like Twist or Basecamp, or something else.

Have a great vacation! 🌴

Justin and his family on a ski trip in Colorado

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