11 Questions to Ask Yourself at Year End
Take a moment before 2026 begins and reflect a bit. It will provide unmatched clarity.
In light of the holidays, I have a short and sweet one for you today. (Don’t worry, I’ll be back with part 3 of the Business Pillars series next week…)
But before diving in, I hope 2025 was a great year for you. I hope your relationships thrived, your professional pursuits were successful, and you made strides toward building the life you want to live.
I also hope your mind, body, and soul are healthier and more content than they were last year.
And if not, I wish you these things in 2026.
Which brings me to today’s newsletter topic: an annual reflection exercise.
I ask myself these 11 questions at the end of each year. And, to give credit where it’s due, they’re an amalgamation of Michael Girdley’s and Michael Hyatt’s concepts, with a smidge of other “thought leaders” thrown in. I didn’t make any of them up. I didn’t need to.
Let me encourage you to pour a cup of coffee in the still morning hours of your holiday and spend an hour or two journaling your answers to these questions.
If you’re like me, you’ll stumble upon some real gems that can make 2026 your “best year yet.”
Here we go:
What were your biggest “wins” of 2025? (Feel free to break these into a few different professional and personal silos.)
What were your biggest “losses” of 2025?
What would you say is your life’s purpose?
What do you wish you had more of in your life?
What drives you today? What are you most passionate about?
If you “stopped” today (retired, died, moved to Costa Rica, and lived on the beach), have you accomplished “enough?”
Are the best things in your life ahead of you or behind you? Why do you think this?
What factors from 2025 do you think caused you to answer #7 the way you did? What do you want to keep, start, or stop in 2026 as a result of this?
What were your three most significant learning experiences from 2025?
What is keeping you from taking your company or profession to the next level in 2026?
What is the most critical thing you can accomplish in 2026?
Wrap Up
Sometimes we avoid tough questions because, deep down, we’re afraid of the answers.
Let me encourage you to face these questions head-on, even if they feel uncomfortable at first read.
You can’t control everything in 2026. Heck, you can’t control much at all. But you can control the clarity of your direction and your actions toward building the life you want. Let’s get after it.
Thanks for reading this post. I appreciate you. In return, please share this with those you know who may be interested.
Free Guide: 🧠 Build Your 2026 Business Plan Using AI
I just released my full framework for building a 2026 Playbook: a simple, AI-assisted process to help you plan the year ahead in hours, not days.
If you lead a business or team, this is the exact tool I use every October to clarify goals, align strategy, and make next year’s planning effortless.
Things I've Enjoyed Lately: I’ve shared a ton about EO (Entrepreneurs’ Organization) in this newsletter over the last few years. And I’ve really been enjoying the new EO Forum I launched with nine others back in April. It’s been a true blessing. Getting to spend time with such high-caliber individuals and be real and raw with each other has been incredibly meaningful. I love doing life with them.