This article is adapted from Ted's Smart Thinking podcast Episode 389: Your Greatest Hits.
Last week I stood in a record store in St. Louis called Euclid, digging through the recent arrivals bin the way I always do when I travel. That is my ritual. New city, new record store, straight to the used section. I keep a running list in my phone of 45s and original pressings I have been hunting for years, and I love finding a little treasure that means something to me. In Joshua Tree, it was a 45 of The Edge from U2. It is framed in my office now.
But in St. Louis, I picked up something I was not hunting for at all. John Denver’s Greatest Hits. Green cover, mountains in the background, round rim glasses, that hat. And just like that, I was back in third grade.
My parents bought me a record player for Christmas the year I was in third grade. When you are eight years old, you do not have your own record collection, so you get what your family no longer wants. My parents had come of age in the sixties and had just discovered the eight track player, which turns out to be about the least cool piece of technology ever invented. So I inherited a stack of scratched up Beatles, Rolling Stones, Blood Sweat and Tears, Four Tops, and a lot of Motown that had somehow survived the dorms of UW Stevens Point in the late sixties.
My whole childhood ran on a soundtrack. My mom played music constantly. My dad did too. So did my aunts and uncles, and my brothers and I used to sleep over at my Aunt Marsha’s upper flat in Milwaukee, where she and my uncle had a massive record collection full of seventies singer songwriter records and, strangely, a lot of southern rock.
One night my Uncle Lee found me going through their stacks and asked if I liked any of the records. He told me something I still carry with me forty five years later. He said, “If you like an artist, Teddy, but do not know much about them, always get their greatest hits. That way you really get to know them before you buy too many other records. And if they do not have a greatest hits record, they are too new and nobody knows much about them yet.”
That night my aunt handed me a stack of records to take home, and right on top was John Denver’s Greatest Hits. She told me why she loved him. The trip she took to the Rocky Mountains because of him. The time in West Virginia. Why she loved the name Annie. I played that record over and over in elementary school and never once got tired of it.
Here is what I have figured out as an adult. A greatest hits album only works because it is short. An artist’s full catalog can take you eighteen hours to listen to. John Denver’s greatest hits takes thirty nine minutes and thirty six seconds. That is the whole point. It gets you to the heart of who someone is fast, without drowning you in everything else.
Now think about the people you lead, teach, coach, or love. Most of us never get the greatest hits version of anyone. We get the noisy, scattered, eighteen hour catalog version of their lives, filled with static and half remembered details. We rarely stop to help people, or ourselves, pull out the nine or ten songs that actually define us.
And when we do reflect, we usually reflect on the wrong things. We think about the macro stuff. Titles. Salaries. Records broken. The things we assume would impress that fourth grade version of ourselves sitting across the table. But that is not what actually makes a life great. The real greatest hits are quieter than that.
Here is the exercise. I use the rule of three. Three prompts, three answers each, which gives you a nine song greatest hits album for a person. Simple enough to do in a meeting, powerful enough to change how a team sees each other.
I recently asked a group to reflect on their personal, professional, and family and friends greatest hits from one summer. People pulled out their phones and started scrolling through photos and calendars just to remember everything that had happened. Several told me afterward that they had so many good things happen that they could not narrow it down to three. What a problem to have. Life moves fast, and if you are not paying attention, you miss it.
Since then I have built out a whole library of greatest hits prompts you can use with your team, your students, or yourself. A few of my favorites:
Relationships and Connections: Three mentors who saw potential in you before you saw it yourself. Three acts of unexpected kindness that shifted your outlook. Three conversations that changed how you view the world.
Resilience and Hard Won Growth: Three failures that turned out to be blessings in disguise. Three moments you stood up for your values when silence would have been easier. Three seasons of uncertainty where you quietly found your footing.
Courage: Three leaps of faith into the completely unknown. Three decisions you are proud of, no matter how others judged them. Three boundaries you set that reclaimed your time or your self respect.
For CliftonStrengths Coaching (Executing): Three chaotic situations you organized and restored to order. Three long term goals you pursued with relentless focus. Three promises you kept when keeping them cost you something.
For the Classroom: Three times you were a loyal friend when someone genuinely needed support. Three awkward or embarrassing moments that felt huge then but make you laugh now. Three times you resisted peer pressure or stood up for someone being left out.
Have people reflect silently first, then shuffle around and share. The connections and the empathy that come out of it are real, because people finally get to see the greatest hits version of each other instead of the scattered, chaotic full catalog.
Here is what I want you to do this week. Build a greatest hits journal. Same two prompts every week, plus one new one. Do it for yourself. Do it with your students. Do it with your team. By the end of the year you will have a full box set of who you have become and what you have overcome.
Buffalos run straight into the storm because they know the storm does not last forever. And when it passes, they do not just walk away from it. They turn around, reflect on it, and add it to the collection. That is what I want for you. Not just surviving your storms, but turning them into songs on your own greatest hits album.
So this week, list the teams or individuals in your life who would benefit from this exercise. Then answer it for yourself. What are your three greatest hits from this past week?
Because here is the truth. Somewhere out there is a version of you in third grade, watching you right now, and you are about to give that kid a pretty good album to listen to.