The other day, my team and I were in the boardroom for our weekly meeting. Since we have a few new faces in the office this summer, we started with an ice-breaker question – the ever-popular, “If you could vacation anywhere in the world, where would it be?” One team member told us of her dream vacation – travelling cross-country in the US – which was actually about to take place in a few weeks.
It suddenly struck me – her vacation was incredibly entrepreneurial in spirit. She had a dream, and she was making the dream a reality.
Of course, she shot a knowing look across the table to me without missing a beat. “You know,” she mentioned. “You should probably think about taking a break, too.” They all nodded.
“I’m too busy!” I blurted out, but then I immediately realized it had been over a year since my family took our trip to Disney. My team was right. It was about time I took a break. I know it’s important, but it’s incredibly difficult to take a break as an entrepreneur – especially when you’re growing a critical part of your business (as we are).
But that’s exactly why I need to take a break. An entrepreneur runs on inspiration, on a proactive spirit, on doing enjoyable tasks (whenever possible). Those are all things that can happen on a vacation, if you plan it right. And it got me thinking – how does an entrepreneur make the most of a vacation?
The key is to play to your strengths. You can take a full break from your business and use it to your competitive advantage. The following are some ways an entrepreneur can use his/her personality traits to make their vacation a productive one.
1) Plan It Out
Convince and Convert reported a recent Applied Research in Quality of Life study that found that “the largest boost in happiness comes from the simple act of planning a vacation. In the study, the effect of vacation anticipation boosted happiness for eight weeks.”
Of course, you can plan to do as much or as little as fits your personality. For some, it might be “Monday through Friday, sit on the beach for four hours clearing my mind;” for others, it might be a planned schedule with every day fully lined out – even where to eat at what times (which is what my family’s vacation to Disney World was like last year). Whatever the plans are, make sure you actually plan it out. If you’re a person who needs a lot of “down time” to recharge, put that in your vacation schedule. If you need a lot of excitement, make time for it. If you tend to find all your relaxation undone by the return travel and unpacking after a vacation, plan a shorter trip with a couple of extra days off afterwards to transition back to “real life.”
As you’re planning, there are a couple of things to keep in mind. Perhaps the most obvious is that the internet and your smartphone are tools for your vacationing pleasure. Convince and Convert recently ran a fantastic article on the importance of planning a vacation for a person’s happiness (see above quote), complete with 46 tools to utilize – from Pinterest to Foodspotting to TripIt. (Then, once you plan it all out, leave your smartphone in the hotel so you don’t get distracted, but more on this later in the post.)
The other thing to keep in mind is a great principle from Laura Vanderkam’s book, 168 Hours. Vanderkam talks at length about thinking of your week in terms of 168 hours, instead of seven 24-hour “chunks.” When you look at your week from that perspective, you find – as the subtitle says – that “you have more time than you think.” Jonathan H. Liu of Wired says, “Our natural rhythm and our schedules are often made up of weeks more than individual days, and 168 hours seems like a lot more to play with and is a bit more flexible than a single day.” This book would be a great read either before vacation (to help make the most of your rest) or during vacation (to help rethink your schedule when you return).
2) Get Creative
As an entrepreneur, you thrive on creative energy; why not make your vacation as creative as possible? This could mean a variety of things, but the bottom line is the same (and you know this old, standby phrase): Think outside the box.
Can you vacation somewhere off-the-beaten-path? Maybe find something unusual to do, even at a typical vacation spot? Take an afternoon to do something you’ve never done before?
Whatever it is, make sure it personally gets YOUR creative juices flowing. Katie Shea, co-founder of NYC startup CitySlips, said in a recent interview with Inc. Magazine that she and her partner try to work in “mini-vacations” throughout the year. Even a day can make a huge difference because, as she says, “It’s hard to be creative sitting in an office all day.”
3) Do What You Enjoy
Why do we, as entrepreneurs, start our own businesses instead of working for someone else? It would probably be easier to work for an established company, but it’s just not as much fun. The reality is that you’ve got to spend your life doing what you enjoy, and that means a very different life for the entrepreneur.
Take this principle on your vacation. Don’t settle, but – like my employee – find a way to make your dream vacation a reality. It might take a few years (or decades), but with careful planning, you can (just like your startup) make it happen.
4) Really and Truly Get Away
You know what this means, right? This means no smartphones, no e-mail, and no sneaking back to the hotel with your iPad. It means going to dinner without a piece of technology sitting out of the table next to you. It means really disconnecting from your work, if only for a week or two.
I know it seems extreme, especially when you’re running a business, but it will have a greater impact on your business. First, your employees will witness your ability to fully enjoy life apart from your work, and see the positive impact when you return. It also helps them grow as professionals, as they learn to take on more responsibility without you there. This will make them more productive, and more valuable to your company. Second, your business will improve because of the vacation’s impact on you personally. Michael Alter of Inc. Magazine says:
“Going back to work fully energized not only boosts your productivity but also clarifies your thinking and priorities. […] You’ll be surprised how your perspective changes after a good vacation. Besides seeing things in a different light, you may realize that what you thought was an urgent priority is actually a minor concern. When you’re not under the gun to make a decision, you can think from a viewpoint that, in my experience, leads to the best solution.”
You’ll be rested. You’ll have more ideas. You’ll be excited to be back, and invest greater energy into your work.
So, as I wish Karen a great roadtrip across the country, I remind myself of the need to take some time off – for myself as an entrepreneur, a business leader, and mostly, as a family man. This year, I’m looking forward to low-key (in comparison to Disney) mini-vacations to Hershey Park and NYC. Then, if all goes well (and the vacations do indeed boost my productivity), maybe we’ll take a little break to Jamaica in the fall.
- What are your vacation plans this summer?
- What was the most “productive” vacation you ever went on – meaning, what “recharged” you the most to make you more productive when you came back to work?




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