Plan Your Work Like You Plan Your Vacation – Here’s Why

Business Travel

Have you ever spent hours on TripAdvisor or Expedia just dreaming about vacation? I certainly have. And when it comes time to actually plan a vacation, I am meticulous and deliberate in my planning. A 2010 study showed that people derive more relaxation from planning a vacation than from actually being on vacation, and I tend to agree. Scouring the internet for the best seafood shack on the beaches of Sardinia or the most authentic jazz club to visit in New Orleans, makes me feel like I’m already there. We also know that lack of planning can lead to vacations running hilariously awry.

The question is, why not bring that same energy that we invest in vacation planning to business planning? Well, you may answer, “Because work is one thing and vacation is another.” But let’s think a bit more about this conundrum. I would argue that we can and should plan our work like we plan our vacation, and that you can derive some major benefits from doing so.

Plan for Your Destination

When you are thinking about a vacation, you work up a lot of questions planning for the destination. Where do I/we want to go? What are the most important things to see and do once we get there? What are the pros and cons of this destination? Plenty of online resources provide guidance for planning a trip, and they all revolve around the cost-benefit relationship of choosing a particular destination.

In the same way, you should strategically plan your work. Whether for you, your team, or your company, thinking about short and long-term objectives should be approached with the same enthusiasm and energy you bring to vacation planning. What’s the value of developing strategic goals if you’re not energized about where you’re going? Approach your planning with a sense of purpose and adventure, and it will motivate those planning with you.

Know Who’s Going on the Trip with You

When I travel, significant beach time is almost always part of the game plan. I love having the opportunity to take in some sun, listen to the waves, and unplug from everything. For some family members, seeing the major sights at a given destination is an absolute priority. When you’re planning a trip, you obviously need to take in what will make you and them feel fulfilled. Any parent will tell you that you must take in each family member’s priorities as you plan, otherwise the vacation could be a complete disaster.

In the same way, who are you taking with you on the trip as you plan your next business steps? Bringing energy and enthusiasm to a strategic planning process is all well and good, but you have to consider the people going on this journey with you. To extend the metaphor, are they beach people or sightseeing people? What is going to nourish their intellect and interests in the planning process? All companies are working to retain employees, so we must think about how we keep our employees engaged and motivated. Sure, they’re all getting paid, but with record numbers of people quitting their jobs, we’ve got to think about making the task fulfilling for each member of the team.

Develop a Roadmap

Once you’ve set up a basic plan for your trip, your mind immediately shifts to “the hows.” How do we get there? How do we transfer from Point A to Point B? And of course, how will we pay for it? If you have ever been to a Disney property, you know that the question of “How to Do Disney” is critical for how your vacation will turn out.

Planning for your work or business doesn’t stop when you decide on a destination. Even before you are done determining goals, the question of “what is actionable” pops up. No doubt, many strategic plans (and vacations!) have failed because the action plan that followed was not effectively thought through. As with the strategic plan itself, the action plan that follows works best if you incorporate others who will be going on the journey with you.

Plan for Rain

There’s no greater truism about vacation planning than “plan for rain.” That childlike wonder a person has when they first see a beach in Hawaii can dissipate just as quickly as it appeared when the clouds turn as black as the sand. When you plan your vacation, you’ve got to make contingency plans.

Just as you do with vacation, you’ve got to plan for rain in your business as well. You and your team may have developed the best strategic plan with a brilliant action plan to boot, and if you published it in February 2020, we know full well that your plans have changed since then. There are plenty of traps in strategic planning that you need to be aware of, but the greatest is developing a plan that is not responsive to changes in your business, the market, or the world in general. Plan for rain, my friends.

In conclusion, how your vacation – and by extension, your business – unfolds is largely up to your planning. The energy and enthusiasm you bring to the process will be infectious for everyone else involved. As Rabbi Julius Gordon wrote, “Traveling may be one of two things – an experience we shall always remember, or an experience which, alas, we shall never forget.” On your next trip, you get to determine where you go, how you get there, and who’s coming along for the ride. In the same way, you should take some time to plan your business like a vacation, and the trip for you and your company will be sweeter.


Written by Zach Benson.

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