Hey there,

I hope you are enjoying the holiday season.

Here’s what I have for your this week:

• One big thing. If your memories are unreliable, how well do you anticipate what you will enjoy in the future?

• You have to check this out. Lessons on hoarding (life).

• Tools & Tech. Unearthing flight deals.

Let’s get started.

1️⃣ ONE BIG THING

Rose-colored distortions.

I grew up in the 70s in Miami.

Driving around town, we’d listen to FM radio (93.9 Love 94, 105.9 WAXY). I have distinct memories of song lyrics that confused me. They seemed simple, but my young brain was baffled. Somehow, I still remember them.

One was 50 Ways to Leave Your Lover. It’s a great song for kids.

Slip out the back, Jack. Make a new plan, Stan. You don't need to be coy, Roy. You just listen to me.

Easy enough. But I wondered: Why do they need a sneaky plan to leave their lovers? What’s a lover?

Another was Dreams, by Fleetwood Mac.

Thunder only happens when it's rainin'… players only love you when they're playin'.

The thunder part made sense. But why did musicians only love you when they’re playing? It felt like an early, uncomfortable insight into duplicity.

In the 80s, there was more country music around the house (99.9 KISS). A new genre, similar confusion. A country song I didn’t fully understand was Rose-Colored Glasses, a classic from John Conlee (YouTube, Spotify).

I don't know why I keep on believin' you need me
When you proved so many times that it ain't true
And I can't find one good reason for stayin'
Maybe my leavin' would be the best for you

But these rose-colored glasses
That I'm lookin' through
Show only the beauty
'Cause they hide all the truth

And they let me hold on to the good times, good lines
The ones I used to hear when I held you
And they keep me from feelin' so cheated, defeated
When reflections in your eyes show me a fool

Back then, I didn’t think too much about the heart-wrenching dynamic of this song. I was confused about the actual glasses. All this sorrow from glasses?

Misremembering past experiences.

Last week, I described how memories are (incompletely) constructed by the remembering self. Every experience is not stored forever. Instead, we retain memories of the most emotionally intense moments (the peak) and the final moments of an experience (the end), and we organize them in a story structure.

That means a lot is left out. One of the primary things our memory storage system leaves out is negative emotional experiences.

This is a well-documented phenomenon called rosy retrospection, a cognitive bias that causes you to remember the past more positively than you actually experienced it.

And they let me hold on to the good times, good lines
The ones I used to hear when I held you

Misremembering the past as rosier than you actually experienced it can, in fact, help you in the present.

In my newsletter Dancing on the Edge of Failure, I described my experience doing hard things—running a series of longer-distance trail races. My memory of these events regularly pays dividends. I know I can overcome challenges. Training and seeing results give me positive vibes of personal growth. I feel satisfied that I spent big chunks of the last year doing meaningful things.

For the above to happen, it really helps not to fully relive the low points from past events. One of the earliest studies on rosy retrospection found that a month after completing a three-week bicycle trip, cyclists remembered the experience as more enjoyable than they had perceived during the journey.

It is not that you don’t remember the low points. Instead, they lose their negative emotional salience and become subsumed as part of a larger, positive narrative that gives structure to your memory.

My trail race memories are a story of training to get ready, feeling the energy at the start of the race, fighting off persistent pain in my legs and feet, crossing the finish line, and eating Oreos and drinking a strawberry soda with others (maybe I am the only one that had that delectable combo).

If I had broken my ankle at Mile 12 and had to be carried out of the woods to the nearest hospital, that would have become the story. One that no glasses could improve.

It is going to be a rosy holiday.

Perhaps you took some time off work this week to visit friends or family. Maybe you just returned.

How much did you enjoy it?

According to our friends in the vacation research department, if you are on your trip right now or just returned, your answer is likely to be, “Not as well as I anticipated.”

When planning such trips, you generally anticipate they will be positive. “It will be great for the kids to spend time with their cousins." “I only have so many more chances to bake pies with my mother.” "Seeing everyone's faces as they open their presents will be wonderful."

But your rose-colored glasses do not just blur your memories; they also lend a rosy tint to your expectations of future events. The exact mechanisms that create rosy retrospection also produce rosy prospection.

Through several studies, our researchers found that people’s reported enjoyment during a trip is consistently lower than their anticipated enjoyment. They surmise three reasons for this discrepancy.

The first is unexpected disappointment in the discrepancy between what is expected and what actually occurs. In one study, “only 5% of participants anticipated in their narratives that they might feel disappointed during the experience; however, well over half experienced disappointment between what they expected and what in fact occurred.”

Perhaps no lived reality can compete with the buzz and glow of anticipation. Some people say, “Anticipation is greater than realization.”

The second is unimagined distractions. As you imagined the feeling of connection while baking pies in the kitchen with your mother, you failed to picture the beads of sweat running down your cheek because your mother refuses to set the A/C below 78. Or your rising irritation from your uncle’s new dog that won’t stop barking.

Your fantasies about your next beach holiday don’t have litter on the beach, persistent hawkers selling sunglasses, or sleepless sunburned nights.

The first verse of Fleetwood Mac’s Dreams nails this concept:

Now here you go again
You say you want your freedom
Well, who am I to keep you down? 
It's only right that you should
Play the way you feel it
But listen carefully
To the sound of your loneliness

I'll admit I have absolutely anticipated freedom without listening carefully to the sound of loneliness.

The third is loss of control. Anticipation is all your own. In your imagined future, you’ll call the shots. You’ll pick the restaurants and who to invite. You’ll plan for the beach on Thursday since it will be less crowded. During your actual vacation, your control slips away. The restaurant is closed for renovations. It rains on Thursday.

Here's Carly Simon getting this idea precisely right in her 1971 song Anticipation:

And tomorrow we might not be together
I'm no prophet and I don't know nature's ways
So I'll try and see into your eyes right now
And stay right here 'cause these are the good old days

Unexpected disappointment, unimagined distractions, and undesired loss of control all conspire to make our actual experiences less enjoyable than we expected them to be as we gazed into the future with our rose-colored glasses.

Rosy retrospection to the rescue.

The good news? As we now know, rosy retrospection will save us.

And it won’t take long.

The rosy-view researchers found, “Negative thoughts about the vacation are not anticipated nor are they remembered, even as soon as a week later.”

One week!

Now we have a better feel for how ole John Conlee never learned:

I don't know why I keep on believin' you need me
When you proved so many times that it ain't true

Here, we have an insight into the dangers of rose-colored glasses: they leave us with fond memories but continually lead us astray as we plan for the future.

It turns out there are even more hidden traps undermining our future planning. I’ll dig into those next week.

A P.S. confession: I was today years old when I realized “players only love you when they're playin'“ probably isnt about musicians.

That’s it for today. And for this year.

Thank you for reading,