4 Business Lessons I Learned from 10 Days on Vacation


My husband Brady and I recently returned from ten days in Costa Rica – sans kids! – celebrating our 10th wedding anniversary. We’d been saving up slowly for over THREE YEARS to make it happen, and we had a fantastic time while seeing and doing things we’d never have the chance to see or do here in Pennsylvania. We hung out with huge iguanas and tiny tree frogs, hiked through rain forests, explored small towns, and spent some time just relaxing and reading by the water.


Although it was a 99% work-free trip, there were actually some great lessons to be had from our experiences, both for life in general and business in particular.


So even if you can’t get away to a tropical country at the moment, you can take advantage of what I learned!


Lesson 1: When in doubt about trying something new…
Go for it!

Throughout our trip, we had opportunities to go on various types of excursions – rain forest hikes, horseback riding, kayaking, snorkeling, and more.


I had never given any thought to some of these activities, such as riding ATVs, but that one struck me as something interesting and fun. On a whim, we signed up – and we had an awesome time! I laughed riotously while learning to drive ours, as I practically crashed into trees or caused Brady to fall off the back (that throttle takes some getting used to). We rode through a huge palm tree plantation, had one of the best meals of our trip at a simple ranch, and hiked through the forest to swim at the base of a waterfall. I’m so glad we did it!


On the other  hand, we also had a chance to go parasailing – which I’ve always wanted to do – and we ended up not doing it. It was a little pricey, a little scary, we wanted to relax on the beach…I’m shaking my head at myself even as I type this! What nonsense! We totally should have taken that chance while we had it – and now that I’m regretting it, I know I can use that regret as motivation the next time I have the chance to go parasailing. There is NO WAY I’m going to miss out on it again!


Bottom line:

When a cool opportunity comes along, let yourself go for it. Don’t let fear talk you out of what you know you want to do! As I seem to learn over and over (and over) again, the only way to eliminate a fear is to do the thing that scares you.


Lesson 2: “Do nothing.”

I’m one of those people who tries to fill every minute of every hour of every day with something useful or productive. I always dream about being able to relax and take some time doing something enjoyable (or nothing at all!), but somehow it never seems to happen.


So I was really looking forward to getting some downtime in Costa Rica, relaxing by the pool, enjoying fruity cocktails, and sleeping in the sun.


And yet, once we got there, I found myself not wanting to “waste” our time by just hanging out on the beach! I kept feeling like we needed to cram in another excursion, or spend time speaking with locals (in Spanish, of course), or exploring another town.


On the other hand, whenever we were out on an activity, I kept thinking, “Man, I can’t wait to be able to just hang out by the pool and relax.” Hilarious!


Luckily, I caught myself engaging in contradictory thoughts pretty early on, and was able to snap out of it and allow myself to do nothing but relax, lie in the sun, read for pleasure, and just generally unwind.


And I’m sooo grateful that I did! For once, I wasn’t worried about “wasting time doing nothing.” Instead, I realized that taking time to relax and unwind IS doing something productive, in and of itself, because it truly refreshed me, filled me with gratitude, and left me feeling rested and ready for the next adventure.


Bottom line:

Work your butt off, yes, but make sure you regularly take time to rest and recharge your batteries – and I don’t just mean getting 5 or 6 hours of sleep at night. I mean taking pure, unadulterated YOU time and NOT feeling guilty or unproductive. Remind yourself that relaxing and unwinding will ultimately help you to be MORE productive when you get back to work.


And instead of feeling guilty, just enjoy the sensation of taking a breather and doing something that relaxes you – whether it’s reading for fun, taking a nap, enjoying a long talk with a friend, or watching the sun set. And most important, really soak yourself in gratitude for being able to do so.


Lesson 3: Prepare in advance – then be flexible and roll with the punches.

Hi, my name is Jenn (Hi, Jenn.) and I’m a plan-aholic.


It’s true. Ask anyone. I LOVE the planning stages of anything, whether it’s a work venture, a house project, or a family goal. And no, vacations are most certainly NOT exempt!


But this time, I resisted my natural urge to schedule every minute and get a plan set in stone. Instead, my husband and I read through the excursion descriptions on the plane, marked off the ones that looked intriguing, and played everything by ear, booking our activities along the way.


This kept us from feeling harried or overscheduled, and let us discover new opportunities that we didn’t know about in advance. We ended up not doing a couple of the activities we’d considered, and found others that turned out to be some of our most memorable experiences.


Plus, having a mindset of being flexible and rolling with the punches was hugely helpful. When things went a little awry – like getting lost in a big city at dusk and having to navigate unidentified streets in the dark – we remained calm and didn’t sweat it. When an activity we wanted to book was full, we quickly adopted a new game plan and enjoyed some beautiful time relaxing by the pool and getting a good night’s rest, then went on the excursion early the next morning.


This “no worries” attitude cut down on any stress and allowed us to enjoy our trip and all the fun things we got to do.


Bottom line:

Plan and prepare in business and life, but cultivate a mindset of flexibility so that you can easily adapt to new circumstances and take advantage of cool opportunities as they come up!


Lesson 4: Make the best of a crappy situation.

I have a tendency to beat myself up over any decision that results in a less-than-ideal outcome. This happened on our last morning in Costa Rica – our transportation to the airport was scheduled to pick us up four hours (FOUR!) before our flight time. I kept thinking I should call and change it, but I reasoned that the airport might be super busy, and it could take us a long time to get through security and the international departure procedures.


Well, it took us all of 15 minutes before we were at our gate – and we still had over three hours until our boarding time! We sat in a food court, got coffee, and did some reading, but I kept stewing to myself about how I should have called to change the time, thinking that we could have spent the morning lying by the pool getting some last-minute sun, taking our time to pack up instead of hurrying, or even visiting a nearby art museum.


Instead, we were stuck inside a windowless section of the airport, wasting time. Grrr.


After a while (and some nudging from Brady), I managed to let myself off the hook. Yes, I could have changed the time and we could have done those things, but who’s to say that the airport wouldn’t have been more crowded later in the day? And did I really think I wouldn’t have spent all morning stressing out about my decision to delay getting to the airport? Plus, there was some work I wanted to get done that I hadn’t touched in ten days – sitting in the airport with wi-fi access and a nice big surface with lots of room for my laptop, mouse, and coffee meant that I could get a jump on it, rather than waiting another day.


So I let go of my regret and made the best of my situation, and I was so much more relaxed and happier that way! Plus, I got some great work done, which made me feel productive and accomplished and proud of using my time in a smart way.


Bottom line:

Getting mired in regret and beating yourself over the head about past decisions doesn’t help you AT ALL. Instead, work on accepting your current situation and finding a way to turn it into a positive.


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So am I the only one to get some business insights on vacation? Tell me I’m not alone! Have you ever learned a great business lesson in a totally non-business environment? What was it? Or, can you relate to what I mentioned about being a chronic planner and over-achiever? How do you let yourself unwind and relax? Share in the comments below!

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  1. Maya

    Another title for number 4 is Let Yourself Off the Hook. You will make a mistake or two in your lifetime. Forgive yourself the big and the small.

    1. Jenn

      Looking at my example, totally true! I hadn’t thought about it that way. Awesome insight! At the same time, I think “make the best of a crappy situation” still holds true as well – when life gives you lemons and all that. :) Thanks for commenting!

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