Why looking back honestly is the best way to plan what’s next
Every year, I set goals.
I’ll be the first to admit I have an overcomplicated way of thinking about my year. You don’t need to do it my way. Do what works for you. The point is to choose a path that leads you toward the life you want in 2026.
For me, it starts simply: grab a notebook and review the year you just lived.
Let the Calendar Tell the Truth
I start by going through my calendar. It’s full of reminders: who I spent time with, the places I’ve been, and the work and projects I’ve been part of.
If you live in the digital world, your calendar doesn’t lie.
It turns out to be a fantastic journal prompt. By the end of it, you get a very honest picture of whether you’re content with how you spent your time.
I’m often surprised. Misfit backpacking trips. Books I forgot I read. Progress, or lack thereof, on fitness goals. It’s all there in black and white.
Review the Photos (Even If You’re Not a Photographer)
Next, I review the pictures on my phone, month by month.
Trust me, I am no photographer. But the photos show where I’ve been and who I’ve spent time with, and that’s incredibly satisfying. It’s another lens on the same truth: how you actually lived your year.
Revisit Your Goals (Not to Judge, To Learn)
Then I review my annual goals.
My goals are usually inspired by categories from a great book called The Dream Manager. I’ve kept notebooks for more than ten years now, so most years I’ve set intentions around health and fitness, relationships, travel, hobbies, or finances.
I don’t try to cover everything. I usually pick three or four categories.
This year, my focus was on doing my best across a handful of areas:
Travel: Florida and backpacking trips
Smartphone habits: I’m failing at this one. It’s hard to set the phone aside, even with a lockbox.
Daily reflection: What did I do today? What can I learn from it? How can I do better tomorrow?
Reading and meditation: Nailed it.
Scaling Outside Insights and Placers: A lot to celebrate and a lot to improve.
Health at 57: I’m not climbing Rainier these days. I’m defining what exercise, eating, and self-care look like for this stage of life. We’ll call this one a work in progress at best.
Six goals are too many. That’s my max. Five would have been better.
Lesson learned.
The Life List: The Story of the Dash
I also keep what I call a life list.
It’s essentially the question: What do you want on your tombstone?
That might sound morbid, but it isn’t to me. It’s about the dash, the time between when you’re born and when you’re gone.
Each year, I review that list and ask whether I’m spending my time in ways that align with my values, and whether anything meaningful needs to show up in my plans for the year ahead.
Reflection Before Direction
This is my prep work. My time of evaluation. My self-reflection.
Reflection turns experience into direction.
To know where you’re going, you have to know where you’ve been.
This is my way of reminding myself what I did well, what I did right, and what I actually accomplished during the year. Those are easy things to forget if you don’t stop to look.
With that clarity, setting goals for next year becomes easier. I can do more of what I enjoyed, adjust what didn’t work, and move forward with intention.
That’s how I think about the year ahead: by first honoring the one I just lived.
A Simple Next Step
If you haven’t done it yet, take an hour this week to review your year. Look at your calendar. Scroll through your photos. Revisit the goals you set. Reflection is how experience turns into direction, and direction is how you earn what comes next.
Until next time, friends,
Chris
If you enjoyed this article, I recommend reading these past Outside Insights posts:
What Thousands of Conversations Reinforced This Year
The Quiet Power of the Pause: A Thanksgiving Strategy
Relationships Are Your Real Resume
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