Forget Spotify Wrapped. Try This Instead.

This time of year is interesting. We are swimming in retrospectives. Your flight count for the year. Hotels stayed. LinkedIn interactions. Spotify Wrapped. There’s a plethora of retros telling sometimes fun, sometimes depressing stories about how your year went.

One retrospective practice that caught my attention comes from Eugene, Oregon.

I’ve really enjoyed the culture Dan Lanning has built as the head coach of Oregon. Recently, I watched him break down something interesting about how they operate—and it ties directly into this season of self-reflection.

After every game, Oregon players write essays documenting areas where they could improve. Not just verbal debriefs—written self-assessments. They evaluate what they did well, where they fell short, and where they are mentally. Then they share these with their coaches. Lanning reads each one personally.

As he puts it: “Self-awareness is something I’m really big on. If you can identify a problem within yourself before a coach tells you, then you have a better chance of solving that problem.”

This isn’t just for players. Every coach. Every staff member. Everyone has an improvement plan. One thing they must get better at.

It struck me how relevant this is to what we do.

It’s one thing to have someone else tell you facts about your reality. It’s another thing entirely to critique yourself, look for areas to improve, and then share that with your support system—the people positioned to actually help you.

Our industry sits on a foundation of coaching and supporting people. Regular people walking through life who raise their hand seeking assistance, outsourcing some function of their lives.

As the value of financial advice continues to evolve, we have more opportunities for creative dialogue around the things in our clients’ lives that could be improving.

Try this: Ask your clients an open-ended question as they look ahead to 2026. “What are the areas of your life you wish would improve?”

The direction they take that question is only limited by their imagination. It’ll speak volumes about where their minds and hearts are. And then you can figure out how to better lend advice in the framework of where they want to go.

I’m sure there will be answers that won’t have direct ties to financial planning, but the opportunity to state these things out loud? That’s where transformation starts. We need to be facilitating that.

This works internally too. In one-on-ones with your team, ask them to write down the answer to this: “Who do you want to be at work this next year? Where do you think your department could be when 2027 comes around? What process do you want to improve?”

To create a culture where this works the best, you’ll have to withhold judgement about their ideas. Use their responses as a way to gain insight into what matters most to your team members.

It’s important to not shame anyone for a bad performance during this process. If you can communicate that imperfection will always be a part of our lives in one hand and the concept that everyone’s working to improve in the other, you can build a fundamentally healthier culture.

I’m seeing this at Oregon. If you’re already doing this, I’d love to hear about how it’s going. If not, maybe it’s time to start.

Consistency over time breeds excellence. Progress is transformative when it’s built day by day.

And here’s my encouragement for you: consider doing this for your personal life. Write down your answers. Who do you want to be next year? What do you need to start doing now to become that? How do you want to grow? Then share it with someone who’s likeminded and can speak truth into your life.

We are in a process improvement business. We should always be working to get better—taking accountability for our performance on the field. Whether your field is client meetings, building technology, helping people get more out of what they’ve invested in, or navigating family, finances, and behavior.

If we become healthier versions of ourselves through increased self-awareness, think about the impact we can actually make.

This isn’t a New Year’s resolution list. It’s way more practical. It’s a real way to improve your outcomes in the year ahead.

Have a great weekend.

– Jud