Why I Let a Stranger Choose Where I Was Going on Vacation

And How Consumer Research Predicted That I Would

Originally posted on Medium on September 8, 2019

Pre-Sunrise at Red Rocks Amphitheatre

My trip to some unknown destination happened because I was tired. I was tired of overthinking and over-planning. I was tired of searching for and tracking flights in Google. I was tired of browsing for places to stay and calculating what would be the best deal. I wanted to think less and just go.

My friend told me about Pack Up + Go, a travel agency that plans entire 3-day trips for its customers. The catch? The destination is a surprise. We decided to go for it. We took a survey about our travel preferences, selected a budget, picked a date to leave, and paid. And then we waited.

Then, on an early morning in August I opened a large white envelope from Pack Up + Go, and saw a warning printed on the cover page to not look at the rest of what was in the envelope until the day of the trip. I obliged and returned the papers into the envelope, wanting to preserve the surprise the way it was meant to be. On the day of my departure, I made my way past the first page and saw printed in big, bright, bubbly words,

“You’re going to Denver!”.

I’m going to Denver, I thought. I didn’t have time for the words to sink in — a few minutes later, I was on my way to the airport, catching a flight to Denver that had been arranged and checked in for me.

When I had told people that I would be going on a trip and that a company was planning it all for me, the first thing they asked was where I was going. “I don’t know,” I would say, pausing a beat. “It’s a surprise”. Responses ranged from “I don’t like that”, to “Can you pay more to find out where you’re going?”, and “So what made you want to do this?”. At the time, I didn’t really know why, other than “Why not?”.

Now, nearly a month later, I’ve reflected on what led me to decide to go on this vacation and what I gained from it. This trip allowed me to:

1. Take a Low Commitment Micro-cation

I love traveling, but due to resource limitations (time and money, mainly) it can be difficult to take time off for a long trip to some exotic location. Recently, I’ve found that I’ve been booking more frequent, shorter trips for things like friends’ weddings, ease of getting away, and budget reasons. I also have more of these trips to look forward to, instead of having to wait longer for a break.

According to the 2019 Vacation Confidence Index released by Allianz Global Assistance, 57% of Americans did not take a leisure trip longer than four nights in the last year. Some of the reasons for taking these “micro-cations” in lieu of longer trips include preferring to take more frequent shorter trips than fewer longer trips (26 percent) and not wanting to spend money on longer trips (19 percent).

Whatever the motivation, many other travelers are also jumping on this trend as well, prompting Travel + Leisure to ask, “Are Micro-cations the Newest Millennial Travel Trend?”

2. It Forced Me to Narrow Down My Options

When you were a kid, did you ever close your eyes, spin a globe, and then point at a random spot on the globe? You’d open your eyes, lift your finger off of whatever location you chose, and that’s where you’d be “going”. This kind of felt like that.

Before my friend recommended Pack Up + Go, we were tossing around suggestions about where we should go and when. These discussions always seemed to increase our options instead of narrowing them down. It looked like our trip was heading towards the dreaded “We Should Totally Meet Up Sometime And Then Never Do” territory until Pack Up + Go was presented as an option. It felt freeing to cross that item (“Decide where to go on a trip”) off my to-do list.

We live in world with many choices and that extends to our travel options. And studies have shown that the more choice doesn’t necessarily make us happier.

Once we were on the trip, my friend and I only stuck to recommendations that came in our trip packet (also included in the white envelope that announced our destination). This wasn’t done consciously but it felt so good to be unchained from Yelp reviews, trying to find the best restaurant to go to, the best things to do, the best anything. There was no FOMO when I wasn’t even aware of all the options.

3. It Saved Me Time Which Would Have Been Spent Planning

Planning vacation takes time and energy. I planned a bachelorette party for 11 women once. The stress of it, plus working full-time, and having other normal life commitments, led to me getting an ocular migraine while in the drive-thru at In ‘n Out and swearing to myself that I would never plan a trip for 11 people again. I can’t enjoy this burger if I die, I thought to myself as blind spots appeared in my field of vision, blinking furiously like pixels on a malfunctioning computer screen. This isn’t worth it.

It turns out I’m not alone in my thinking. As Olga Khazan writes in her article “Give Up on Work-Life Balance” in The Atlantic:

“Constant pressure in my profession has made me go to great lengths to minimize how much labor I perform outside of work. I once made my boyfriend pay me for the hours I spent booking flights and hotels for our vacation.”

Planning a vacation is work. Work that I don’t get paid for and turns out, would gladly pay someone else to do.

4. It Took The Pressure Off Me to Have a Good Time

Pico Iyer writes about “The Unexpected Joys of a Trip to Nowhere” in National Geographic and mentions that one of the benefits of a trip he didn’t plan for is

“that it’s cleansed of the most dangerous kind of luggage, expectation.”

Expectations can be big. Even if they start off small, they can keep expanding if unchecked. I freed up some space in the carry-on luggage of my mind to bring home souvenirs of the memory kind.

A problem that I personally struggle with is that when I plan a trip, I feel responsible for everything. If someone’s not having a good time, then I’m not having a good time. Once I left everything up to Pack Up + Go, something shifted. I was responsible for nothing. I didn’t even worry about not having a good time myself. I didn’t even care if it met my expectations because I had none. I felt lighter and more carefree. I was the self-actualized version of Amy Poehler’s character in Wine Country.

It was the small things, like landing at the airport after only getting a few hours of sleep the night before. I realized I needed coffee and the line at Caribou Coffee in the terminal was long. Whereas before, I would have bolted from the airport away from the crowds to fully enjoy my destination, I was weirdly OK not fully “maximizing” my trip hours.

I became open to down time instead of dragging myself out during my mid-afternoon slump, determined to see everything because I was on vacation, not necessarily because I wanted to. My friend and I were on the same page and discovered the series “Typewriter” on Netflix. We had a lot of fun freaking ourselves out in our hotel room and I don’t regret it for a moment.

5. It Gave Me an Experience I Would Remember

In case you haven’t heard, Millennials (and every other generation, actually) are all about experiences now. Writes Blake Morgan in Forbes:

“People want to experience all that life has to offer, and since acquiring things no longer dictates your class or status in life, millennials are simply enjoying experiences over things, access over ownership.”

We reach for experiences now, the novelty of stuff wearing off sooner and sooner. We lust over yoga retreats to Bali, discovered on Instagram, imagining ourselves swinging on a giant swing overlooking the jungle.

Did I have a great experience? Yes. I remember watching the sunrise from just outside Red Rocks Amphitheatre. I remember grabbing drinks at the hotel bar, curling up in a comfy chair in front of the fireplace, and having deep conversations. I remember our Uber driver casually mentioning his spirit guide, a chicken hawk. I remember googling “chicken hawk” and being disappointed that it didn’t look like how I pictured it. Honestly, I just remember how good I felt. In the lead up to the trip, I enjoyed the thrill of anticipation and none of the stress of planning. During the trip, I wasn’t thinking about what I was doing next. I was simply in the moment.

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Ultimately, this trip reminded me of the joys of traveling. I was able to enjoy my time without having to take care of all the work normally associated with making a fun time happen. While I’m not sure if I’ll do this again, Pack Up + Go showed me that another way of travel that is possible. And that if you don’t want to do something, you can always pay someone to do it for you.

Sonya Shen is a San Francisco Bay Area-based qualitative researcher who loves to travel. You can find her at linkedin.com/in/sonyashen.