Why Is My Vacation Self Cooler Than I Am? [Traveling Guide]

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The Other Me

I have a close friend in LA who has also been a travel buddy of mine over the years. Let’s call her Chrissy to protect the not entirely innocent.

Our vacation exploits are legendary (to us), and we’ve always joked that when we’re out of town, we turn into two entirely different people: Vacation Sherry and Vacation Chrissy.

Vacation Sherry and Vacation Chrissy are up for anything.

They have closed clubs in Cabo San Lucas and then partied with the staff on the beach until dawn. They’ve had expensive dinners with international gentlemen and then ditched them. They like to go skinny dipping, but never on nude beaches.

Who are these people?! And where do they disappear to when vacation is over?

I’ve ruminated over this fact through the years. And I don’t think we’re the only people that suffer from this travel-induced schizoid personality.

So I have to ask you a serious question now. Is your vacation self cooler than you are?

The Four Pillars of Keeping the Vacation Self Alive

Yes, I’m forced to admit my Vacation Self is far cooler than my normal self. And it’s not just because she likes to party. When I sat down to think about it, I realized there are a lot of things I admire about Vacation Sherry.

  • She goes with the flow.
  • She tries things she’s afraid of.
  • She talks to EVERYONE.
  • She laughs at disasters.
  • She doesn’t mind losing a little sleep.
  • She’s observant.
  • She hardly ever checks the time.
  • She’s playful.
  • She likes to get lost.
  • And she has a general devil may care attitude.

Wow, I like this girl. Now, why can’t I be more like her?

The answer is, I think I CAN be more like her. It just takes a little practice. That’s why I came up with the Four Pillars of Keeping The Vacation Self Alive.

My goal? Take a few pages from this cool girl’s playbook and keep her alive all year long instead of two weeks a year.

Are you up for the challenge?

Pillar #1: Have Some Balls. Try New Stuff.

One thing I admire about Vacation Sherry is that she loves to get out of her comfort zone and try new things.

At home, I have definite opinions about what I do and don’t like, what I will and will not do. But as soon as I’m on vacation, I ignore those opinions and strike out into uncharted territory.

This is how I ended up canyoneering even though I’m afraid of heights.

It’s why I eat things like guacamole with grasshoppers. Not as bad as I thought it would be.

It’s why I’ve accepted rides from strangers. (Okay, not always advisable.)

Do I have to be on vacation to get out of my comfort zone and try new things? No. Would it enrich my life if I tried new things more often? Most definitely.

And it’s not like you have to pick up an extreme sport. Or eat bugs. Even trying a little something new can enrich your life and help keep your vacation self alive.

Take a new route to work. Try something you don’t like. Order a latte instead of a cappuccino.

Whatever. Just break the routine!

Pillar #2: Keep Your Head Up.

In our day to day lives, we often have our heads down and noses to the grindstone. Stuck in our routine, it’s like we barely see the world around us.

I definitely suffer from this syndrome at times. But not on vacation. I literally keep my head up and my senses open as I try to soak up everything around me because it’s all new to me.

I look at the details of interesting buildings. Listen to birds’ songs. Close my eyes and feel the breeze on my skin. I people-watch.

So why do we forget to really SEE the world around us when we’re not on vacation? No two days are exactly alike if you’re paying attention. And if you want to experience new things, you have to be open to them.

What it all boils down to is practicing mindfulness. Staying present and paying attention. Easier said than done.

But even if you try to drop all the mental noise for five minutes a day and look around it could help. Then maybe you could go 10. 15. You know where I’m going.

Just try to be more like Buddha for a couple of minutes a day. I wonder where HE went on vacation?

Pillar #3: Keep Going. Keep Flowing.


In my home environment, I am a notorious control freak. Yep, I like to run a tight ship. But not Vacation Sherry. She knows there are things in life that are out of her hands and accepts it. Not only that, she makes the best of it.

When caught on top of a mountain in a storm of biblical proportions, she didn’t complain. She just jumped in and tried to save the fire with the rest of her fellow campers.

When her taxi broke down in the middle of nowhere in Mexico, she started laughing. Then Vacation Chrissy started laughing. Then the cabbie started laughing. My vacation self has a strange sense of humor. But it’s better than crying.

Detour on a road trip? No problem. She likes the scenic route.

When you’re on vacation, everything seems like an adventure, so why get annoyed? And while it may be hard to see life’s surprises and inconveniences as an invitation to something different and exciting, I’ve got to try.

Otherwise, Vacation Sherry may disappear off the map.

The next time I get annoyed at everyday life, I’m going to try the laughing Buddha exercise.

It’s literally just forcing yourself to laugh. Which generally turns into real laughter, loosens you up and helps put things in perspective.

It’s also good for your health.

Pillar #4: Remember the Adventure is Over Soon.

If there’s one thing that Vacation Sherry is highly aware of, it’s that her time is limited. In 10 days to 2 weeks, the adventure is over.

On vacation, there’s no putting things off. You’re going to see that castle today because tomorrow you’re in another country.

Yes, you take the ride down the rapids right now because on Monday you’ll be surfing the internet at your desk job.

None of us like to face it, but our time on this planet is FINITE. I’m not trying to be dark or depressing here. But the fact is, nobody really lives life to the fullest unless they accept the fact that it doesn’t last forever.

This is really the pillar that wraps it all up. It’s why our vacation selves are often ballsier, more mindful, and more easy-going. It’s also why my vacation self smiles more, talks to strangers and sometimes acts like a kid.

If you’re only going to exercise one of the pillars, this is it.

This is one of the more challenging/scary exercises, but it’s worth it. Just sit down once every month or two with a notebook. Now write down 5 things you would like to do or be if you knew your adventure was over in a couple of weeks.

You might be surprised at what comes up.

Happy 2020. Let’s All Stay On Vacation.

Well, friends, I hope you find my Tao of The Vacation Self a little bit helpful. We’ve got another 52 weeks ahead of us soon. And probably only about 10 days of actual free time.

I  know I’m going to try my hardest to keep Vacation Sherry out and about instead of packed away waiting for my next trip.

I wish you and your vacation selves the happiest of New Years. May you enjoy life and never part paths. After all, you’re so much cooler together. Let’s try to make it a 365-day adventure!

Sherry De Alba

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