I Need to Take a Vacation From My Vacation Before I Even Go on Vacation
preparing to relax is the most stressful experience
One of the biggest regrets of my life is a vacation we took a few years.
Yep, I regret a vacation.
We decided to add a few days in San Sebastian onto our trip to Portugal. It was a dream for me to visit arguably the most foodie city in Europe.
Better believe I was going to make sure it was the best. trip. ever.
I watched and rewatched Anthony Bourdain’s Parts Unknown episode to get the lay of the land.
Conducted exhaustive research. Reached out to people for recommendations.
Spent hours deciding where to stay. More hours picking restaurants.
Meticulously plotted possible places on a shared Google Map.
And compiled a detailed itinerary for our 36 hours.
Planned it all out perfectly. What could go wrong?
There were no delayed and diverted flights, lost luggage or illness.
It’s far worse.
This is the tale of how I literally exhausted myself trying to set up the perfect conditions for not being exhausted. You know, because it was VACATION!
It was supposed to be fun. But I project managed the shit out of it.
When we finally got there, I was hella jet-lagged. Hungry and overwhelmed.
I absolutely, completely, utterly shut-down. Terrified of making the wrong choice. Of not eating at the right place.
My expectations got the better of me. I desperately didn’t want to miss out on anything.
I had spent so much time in my every day life preparing to live the vacation stories I’d tell later that I ended up not being able to appreciate it at all.
This is where things get a little spicy. Just picture your mom saying, “We don’t talk about things like that in front of polite company.” Here, we emphatically do.
Vacations are no longer experiences to be had.
They’re things we plan to do.
Literally, we ask each other, “Do you have any vacations planned this year?”
Really gotta make it a “thing.”
It’s like we can't relax until we know that we’ve had a heavy-hand in controlling every teeny-tiny thing now that might prevent us from relaxing in the future.
“We're not just going on vacation! We're trying to maximize the experience and control happiness itself. Because we’re happiest when we’re on vacation! Don’t you want to be happy?”
Our anxiety about having a semblance of control is masquerading as preparedness. Which I think stems from a place of scarcity. We only have so many days to take off. Only so many opportunities to go on vacation. We gotta make the most of them!
(Does not apply to anyone in European countries who holiday like it’s their job. Because it is literally built into their job).
So we thoroughly prepare.
You aren’t taking a week off from work. That’s what, like 5 PTO days?
In reality, this one vacation is going to require more like a grand total of 63 days of your life. Days of talking about it. More days deciding to plan it.
Then the meaty planning beings. Days of pre-vacation to-do lists, research doom scrolls and rabbit holes, spreadsheets and packing lists. And more hours of deciding what to actually pack knowing that you will convince yourself to bring shit you think you might need but absolutely never do.
Not to mention the work required to actually take time off work. The whole performative song and dance of “getting ahead” and then pretending that someone else will do your job on top of theirs. You put together lengthy out-of-office documentation capturing endless details about everything you do so that someone else can step in for you. They won’t. Nothing will happen. Cool. More time on the backend for you to play catch-up.
Just add it to the pile.
Fan those anxiety flames about whether all the time, stress, worry and energy you’re putting in now will actually optimize your future relaxation.
But it’s worth it, right? Because if we plan it out now, then we can just show up and fully and completely unwind, let go and enjoy.
Don’t fuck it up like I did.
Hope you enjoyed the conversation - thanks for reading!
If you could go on an all-expenses-paid, done-for-you trip anywhere in the world, where would you go and why?