I wish you all the joy and love during this season (and every season, really).

If you follow this newsletter closely, you’ll know I’m a big fan of reflection. This time of year is really when I go the deepest on my own personal reflection and all aspects of my life.

Next week, I’ll share some of my reflections, and then I’ll share some forward-looking thoughts.

But today, I thought we could start with the HOW. My process. Tips and tricks.

But first, why?

I think it’s obvious, but I’ll use the analogy of how the best sports teams “review game film.”

If you’re not familiar with that term, the best sports teams and players in the world commonly watch the entire game the day after they play it.

They look at what went well and what could be better. They learn from it.

The point is you will learn and be better by doing some sort of reflection.

One other benefit: it provides closure and a sort of clean break to the year. For example, if I complete my reflection today, I can chill with nothing on my mind for a few days.

It’s a powerful tactic, and I encourage anyone to practice daily, weekly, monthly, quarterly, and, of course, annual reflection.

I use YearCompass (it’s free!). It’s beefy but has tons of helpful prompts. And I’ve done it for a few years now, so it’s a helpful reference point.

Here are my major tips for nailing this process:

Yes, it’s obvious. But it’s also the place most people get stuck. Holidays can be a busy, unstructured time.

I think you probably need 4-5 hours total over 2-3 days.

If you’re struggling, here’s a text you can copy and paste to your spouse or friend: “Honey, I really would like to take a few hours to reflect on my year. It will make me better for myself, you, and all facets of my life. Can you help me make it happen?”

They’ll become your discipline buddy or just cover for you, or maybe do it with you!!

The first hour is data gathering. What did you do this year? It’s a bit tedious but actually helpful. A lot happens in a year!

Then take a break. Then two hours of reflections.

Then a break. Then forward-looking.

5 hours to recap 8,760 hours! I think it’s worth it.

YearCompass gives a great set of categories:

• Personal Life, Family

• Career/Studied

• Friends/Community

• Relaxation, Hobbies, Creativity

• Physical Health, Fitness

• Mental Health, Self-Knowledge

Here’s an even more detailed list a coach gave me:

• Health & Fitness

• Intellectual Life

• Creativity

• Emotional Life

• Character

• Giving

• Spirituality

• Love & Romance

• Parenting

• Social Life

• Finances

• Career

• Lifestyle

I like the specific callouts around Love/Romance, Finances, and Spirituality. The first two especially take up a lot of people’s bandwidth, and they often don’t realize it!

Being comprehensive is important because most people have a tendency to compartmentalize their lives to their own detriment.

Why is it a detriment? Because we are one whole person. And even if you think you’ve mastered it, issues always bleed.

For example, if you’re having a tough time with your spouse, it can be hard to show up as a great CEO.

Or if you lost money in the stock market, maybe you’ll be making more conservative decisions for your startup.

In fact, once I do this comprehensively, I usually notice patterns that connect things I didn’t see before.

Let’s face it. We get so used to putting on a show for our clients, employees, family, and friends that it becomes natural to spin things.

This is a private document for an audience of one.

And as the saying goes, “the biggest lies we tell are the ones we tell ourselves.”

So this is your chance to stop that pattern and be really honest with yourself. What were your biggest challenges? Where did you come up short? What learnings did you have?

And don’t forget part of being honest (a lot of folks struggle with) is seeing the good! Where did you crush it? What great decision did you make?

Soak it all in.

So there you have it. Make time. Be comprehensive and be honest. The YearCompass is a great guide with a ton of helpful questions. Use it.

Bonus:

One of the most important questions that keeps coming up for me in the last days of the year: What am I leaving behind?

We get so focused on doing more. Adding more.

Here’s my challenge: what thoughts, stories, situations, people, etc are you leaving behind and letting go of in 2026?

I’ll be thinking about that, and I hope you do too!

Happy holidays.

jesse