Everything You Need to Do -- and Not Do -- to Enjoy Your Best Vacation Ever

Everything You Need to Do -- and Not Do -- to Enjoy Your Best Vacation Ever
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Every year my wife and I take at least one international trip, no matter how busy we are at work. It’s a non-negotiable for us. This year, we spent a couple of weeks in Spain. And while I was fired up to experience the Saint John Festival in Barcelona, the beaches and pintxos of San Sebastian, and the palaces and museums of Madrid, I found myself a bit anxious perparing for the trip -- but perhaps for different reasons than you’d think.

I wasn't anxious about leaving my company and team behind. SnackNation would be just fine thanks to the fantastic management team we’ve been able to build at our company. I was anxious to make sure that this vacation was as rewarding and rejuvenating as my company, my team and I need it to be.

You see, I’ve found that vacations are often misunderstood, underutilized and massively underrated in the business world. Vacations can and should be massively valuable -- not just for the person taking the vacation, but for the team that person is a part of back home.

The worst thing isn’t not taking a vacation. The worst thing is taking a vacation that sucks. A vacation that doesn’t inspire new thoughts. A vacation that doesn’t rejuvenate your mind, body and soul. A vacation that makes you feel that you shouldn’t have taken it in the first place.

Related: How to Vacation Like a Boss

I’ve found that vacations are riddled with unlocked potential and hidden value that most people, especially busy entrepreneurs, fail to uncover. Vacations can be one of the best tools to gain new perspectives, recharge the mind and body, make lasting connections and spur your creativity. (And of course, be ridiculously fun, slightly wild and bring out your inner child!)

Ideally, you should come back from your vacation in a better place than when you left. This is always my top vacation goal. That’s what I deserve, and it’s what my team expects. To ensure that I’m maximizing the transformative potential of any vacation, I’ve learned that I need to avoid the following mistakes that I’ve made in the past. Recognizing and avoiding these pitfalls allows my vacation anxiety to vanish.

Going in with the wrong mindset.

One of the first mistakes people make happens long before they step foot on a plane or even book a flight. For a lot of people, the whole notion of what a vacation should be is wrong from the start. Vacations aren’t a mere escape from your daily routine. When thoughtfully planned and mindfully experienced, vacations are a time of discovery, rejuvenation and a chance to stimulate your brain.

Leaving without a specific intention.

Most people leave for vacation without something they want to “figure out” in their head -- which is a major mistake if you want to maximize the potential for growth and development in your trip. Vacations are a time when maximum clarity should shine through, so go into it with a problem supplanted onto your subconscious and await the magic that will help you figure it out.

Planning too much.

Other than leaving without setting an objective, I actually think it’s difficult to plan too little. The real pitfall is in planning too much. While you don’t want your vacation to be a free for all, you also don’t want to pack your days with rigid planning and eliminate the spontaneity that will drive many of your most meaningful experiences.

Forgetting what works at home.

It’s a mistake to forget that the things that make you happy, cognizant and centered at home will also make you happy on vacation. For me, this is exercising. For others, it might be yoga, meditation or twenty minutes of creative writing in the morning. It’s true, vacations are meant to be a way to step outside of your routine, but you can still adapt the things you know work for you at home and take them with you.

Related: 3 Reasons Every Entrepreneur Needs to Take Vacation Time


While vacations should be a time when you allow yourself to enjoy the many amazing pleasures in life, don’t use vacation as an excuse to indulge to the extreme throughout your entire trip. When you drink and eat too much, especially at the end of your trip, you’ll come back back hungover, sluggish and feeling worse about yourself than when you left. This sabotages your ability to feel rejuvenated and refreshed. I’m a big believer that moments of excess allow us to deal with the deadening effects of moderation, but the key word here is moments.

Being too inhibited.

On the flip side, you also want to avoid the other extreme. Keep in mind that the whole point is to be free enough to step outside your daily life and into the learning, betterment and rejuvenation zone. Certainly don’t get stuck answering emails. Make sure to plan one thing every day that you wouldn’t do in your normal course of life. After all, vacations are meant to be explorations!

Forgetting to reflect.

You need to allow time for reflection before and after your journey to help identify your objectives, and evaluate whether or not you achieved them. Journaling is a fantastic way to compare your state of mind before and after your journey, and gauge how effective your vacation was.

Coming back to work too soon.

I’m a big believer that you should give yourself one free day at home after your vacation before you have to go back to work. Don’t come back on a Sunday night and go back to work on a Monday morning. You need one day to resettle and prepare.

So, in a nutshell, that’s what a lot of people get wrong. But how do we combat these tendencies?

Below are some of the travel tips I’ve developed over the last several years of thinking about the things I do to make sure I get the most value out of my vacations. Keep in mind that while most should apply to you, some may not. Take my example as a framework and tailor it to fit your specific needs.

Here are six things I do before, during and after my vacations:

1. I mentally prepare.

I make it a point to dedicate the travel day before my first full vacation day to mentally preparing myself to have the best vacation ever. This way, when I land, I am already on vacation, as opposed to getting off the plane, checking my email and needing three or four days to fully get into vacation mode. That's a major a waste of precious time.

Related: The Secret to Increased Productivity: Taking Time Off

2. I front load indulgences.

I always focus the last third of my vacation on wellness, so even if I party or eat and drink a bunch of unhealthy stuff early in my vacation, it isn’t how I end the trip. Definitely don’t get on the plane back home hungover.

3. I workout every day.

I find it funny how people are always surprised that I workout while on vacation. To me, it just makes sense. I want to come back feeling better than when I left. But perhaps more importantly, I want to maximize enjoyment every day when I’m on vacation. One of the major reasons I exercise is to feel great and to be mentally acute. Without exercise, I’m noticeably fatigued and foggy; it’s night and day for me. Why would I want to feel that way on vacation?  And by the way, this doesn’t mean I’m running on a treadmill every day --long city walks, mountain hikes and ocean swims count as physical activity.

4. I read like I’m a philosopher.

I believe vacation is a time to expand my mind and think differently, so rather than just attempt to think differently on my own, I allow others to give me new or updated thoughts that I can revel in. Reading produces real-life magic for me, especially when I’m away from home. And I prefer to read books that are a bit different than what I’d read at home -- and sometimes a bit out there. I like material that really helps expand my mind and gets me out of any mental ruts I’m in (regardless if I know I’m in one or not).

5. I focus on human connection.

On vacation, I purposely go out of my way to connect with people on an even deeper level than usual. I focus on being fully present with every waiter, every guest I meet in the pool or on the chairlift, or with the hotel attendants. I aim to be interested in absolutely everyone and try to learn things I’d usually take for granted or perhaps not notice because I was too busy focusing on other things. Of course, this includes my wife and/or family and friends I’m vacationing with as well. They’re my first priority.

6. I allow for serendipity.

Outside of my overarching objectives, I give myself permission to go with the flow and do things I otherwise wouldn’t. Fall asleep in the middle of the day because I feel like it. Have a glass of champagne when I want because I can. Write on a completely obscure and weird topic because my heart tells me to. These are the things that can only happen on vacation, and where the most magic can occur.

If vacations for you are purely an escape from your everyday life, the vacation is not going to help. In fact, you’re just going to come home feeling worse than when you left. I’m not saying you should not be massively excited and jacked-up about your vacation. I’m saying you should be excited because vacations are essential to your betterment, are super fun and allow you to be a more ideal version of yourself. 

If you’re living your days for your next vacation, understand that the vacation likely won’t solve your issues. Spend your next vacation 100 percent focused on getting more clarity on key issues in life or perhaps getting closer to understanding your purpose or something else deeply meaningful in your life. Whatever you do, don’t get stuck on the vicious bad vacation treadmill where your holidays just repeat over and over with no measurable additive or long-term benefit to your life. 

Your time is precious and your vacations are super precious. Demand more from them. Once you do, you’ll find that you and everyone else -- including your boss or business partner -- will be more excited for them to arrive. And even more importantly, you’ll find yourself finding more vacation in your every day life.