The power and importance of vacation planning in executive leadership

Versie Dortch

Planning your vacations with the same rigor and diligence you’d apply to any other project can make you a more effective leader and set an example for your teams.

Man enjoying a staycation at the backyard under an umbrella, EPS 8 vector illustration

Image: Aleutie/Getty Images/iStockphoto

I blocked an hour a few weeks ago to do my quarterly vacation planning, carefully mapping out the various trips I wanted to take with family and friends. These ranged from somewhat elaborate beach trips to a couple of nights in a tent with the family at a local state park. I blocked my calendar for anything with a 50% certainty and added any trip-related items to my task list, from booking hotels to making sure I had the right gear for a camping trip.

SEE: Juggling remote work with kids’ education is a mammoth task. Here’s how employers can help (free PDF) (TechRepublic)

This might seem like a rather elaborate and overly structured process for what should be a fun and relaxing activity. However, vacation is such an essential part of my life that I put in the same diligence in making sure it is successful as I would any other “mission-critical” aspect of my work. For too many of us, vacation is taking that last week of the fiscal year “off” to “do some chores around the house but available for calls as needed.” In this scenario, we’re essentially lying to ourselves that we’re taking vacation days that would otherwise go unused or performing some bogus ritual that supposedly demonstrates that we’re “too important” to be away from the office.

The average individual would loathe throwing away 2% of their annual, pre-tax salary, yet we do exactly this when we throw away a week or two of paid vacation time. Not only is this decision fiscally foolish but it also wastes an opportunity to rest, recharge and be a better leader and overall individual when you return.

Add quarterly vacation planning to your routine

Each year, take the time to block 60-90 minutes each quarter to review and plan your vacation. Treat this time as a top priority, on par with any other major strategic project or planning session and an activity that requires all of your attention and focus. Between these sessions, keep a running list of vacation ideas, that can be as simple as a Post-It note or two, or a categorized list in your preferred planning tool, broken down by family trips versus trips with your partner or whatever other criteria you prefer.

SEE: Leadership tips: How to stay focused and craft a happier worldview (TechRepublic) 

During your planning time, allocate your big vacations and block the time in your calendar. If you’re a parent, you’re likely subject to the school calendar and may be able to easily map out weeklong family getaways the moment the school calendar is published. If you’re someone without constraint, try to map out and block about 20% of your vacation each quarter and take the time to secure it on your calendar and any other planning tools your company uses. Keep a 5% reserve for unplanned events or spontaneous long weekends, but the goal is to plan and block the majority of your vacation time.

I’ve found the simple act of putting an electronic stake in the ground and blocking time on the calendar makes it far more difficult to defer vacation or fall into the mode of assuming you’ll get to using it eventually. A lack of vacation discipline often results in finding yourself with a few weeks left in the year and a full vacation bank.

Plan the break, and don’t break the plan

It’s perfectly fine to block time away from the office, even without a final destination or elaborate plan in mind for how you’ll use it. However, too many people fall into the trap of a staycation that’s basically rebranded working from home. There’s nothing wrong with the staycation concept, as long as you have a plan for how you’ll use that time and stick to it. I’ve taken multiple breaks during COVID where I don’t physically go anywhere, but I will spend the time to plan the key projects and activities I’m doing in advance. Leading up to my staycation, I make sure I have all the materials and days planned, and I’ll intentionally put my work laptop and other tools away to mentally commit to taking a break from work even though I’m still in my “workplace.”

SEE: Let go of perfection: Don’t waste time on projects that won’t yield much result (TechRepublic) 

If you find little joy in vacation planning, engage friends and family, pay a digital or old-fashioned travel agent or expand your definition of vacation to include anything from exploring a new hobby to taking a focused week to start a new workout program without the distractions of work.

Almost every study that’s come out during the last 18 months has indicated increased stress, employee burnout and frustration. The simple act of diligently planning your vacation might seem like it dampens the fun of a break. However, it’s cheap insurance to preserve a valuable and necessary part of your job. Demonstrating that you take vacation seriously is also a chance to lead by example, and ensure your staff realizes that they too should take advantage of the time allotted to rest, recharge, and come back with new perspectives.

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