Hey Time Dorks,
Connor here.
Back in December, we hosted a free workshop on annual reviews. If you missed it, I’ve put the recording back up. It’s not too late to reflect on 2025 and gain clarity for 2026!
I first got into the habit of reflection through practicing the fourth step of the Make Time framework, “Reflect.”
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Taking daily notes helped me understand which tactics were working and which weren’t, so I could fine-tune my approach along the way. We like to say you should be a scientist in your own life: plot out your own experiments, observe what happens, and adjust based on results.
Not only is this an effective way to learn and iterate, I’ve personally found it removes a lot of the guilt and self-criticism that self-development can bring. When I fail to make time for my Highlight, or get sucked into the Infinity Pool of my inbox, I don’t berate myself for being weak-willed or lazy. I just observe what happened, go back to the book, find a tactic to try, and give it a go.
Daily notes showed me what wasn’t working. But to spot bigger patterns (the stuff that really matters), I needed to zoom out.
That’s where monthly reviews come in.
Something to Try: Monthly Reviews
At the end of each month, I set aside 30 minutes to reflect on what mattered, what I learned, and where I want to focus next.
I like to think of it as leaving breadcrumbs for my future self.
Every month, I try to capture:
- A few highlights and lowlights
- Fun memories worth keeping
- Any lessons learned
Then when December rolls around, my annual review practically writes itself. I have a clear sense of what mattered, what worked, and where I want to go next.
Why monthly?
To understand where monthly reviews fit, it helps to see the full picture. You can think of these like different zoom levels on a map:
- Daily notes are tactical: How focused was I? Where was my energy? Did the tactics I tried today work?
- Weekly reviews zoom out: What was important this week? What progress did I make? What do I want to focus on next week?
- Monthly reviews reveal patterns: I might notice “I had more energy the weeks I exercised three times” or “my best creative work happened on Tuesday mornings.” These insights only emerge when you zoom out far enough to see the month as a whole.
Plus, monthly reviews give me space to savor the good stuff. I like to skim my weekly notes, scroll through my photos, and appreciate the special moments. Truthfully, I’m often surprised by how many moments I’d already forgotten. Taking time to reflect helps me shift from a mindset of ‘what’s next?’ to one of gratitude.
Monthly reviews serve me in two ways.
- Reflection — I learn from reviewing what actually happened
- Direction — It gives me a clearer sense of what I want to do going forward
How to do it: Keep it simple
In the past, I tried to create elaborate, in-depth review systems. They never lasted. Especially after I had my first child, I realized: if it’s not simple, I won’t do it.
So here’s what works:
- Time-box it: 30 minutes is plenty. Sometimes 15-20 is all I have. Other times, I’m enjoying it and spend an hour. That’s fine too.
- Use a few core questions (see below)
- Don’t overthink it: The goal is reflection, not perfection
My process (bonus tip)
Last year, I stumbled onto something that changed my monthly reviews: talking to AI while walking.
Here’s how I do it:
- I go for a walk (research shows walking is better for creativity and thinking)
- I talk through each of my questions out loud to my LLM (Claude at the moment)
- I ask if it has any follow-up questions that would be helpful
- Then I take that conversation and drop it into my notes app (Evernote)
I can do this while running an errand or walking to work. Then I take that output and spend time writing to deepen the reflection and insights.
My Core Questions
What moments stood out this month?
- List 3-4 highlights
What didn’t go so well?
- List 3-4 lowlights
What did I learn about myself or life?
- List any lessons learned
What do I want to focus on next month?
- What’s one big thing I want to prioritize? What can I let go of to make space for this?
Additional Questions (if you have time)
What was the best thing I read, watched, or listened to?
- List out books, films, podcasts, or anything else that inspired you
Which photos caputed special moments?
- Star a few favorites in your photos app (I use Google Photos) to create an annual “best of” album
Who did I really enjoy spending time with? Who do I want to see more of next month?
- List people you enjoyed spending time with and who you want to see more of
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If any of this resonates, or you give this tactic a try, I’d love to hear from you.
Thanks for reading.
— Connor
P.S. If you enjoyed this and want to go deeper, my Inner Operating System program includes a complete review ladder: daily notes, weekly reviews, monthly reviews, and annual reflections. Learn more here.
