I started this week intending to use GenAI to “enhance” my personal annual review—a personal practice, not a workplace performance review. After testing several prompts across four email accounts and multiple notes and task apps, I hit a wall: the more I “optimized,” the less meaning I found. AI made both recall and insight harder, and my review felt…performative. The real irony? When I saw the gaps in what AI returned from my prompts, I could immediately see the larger, more important lessons that were missing. That’s why I won’t use AI next time—at least not until after I’ve done my reflection first.
If something truly mattered, a simple skim of my calendar and a glance at email sent over the course of each month was enough to jog my memory. No prompt required.
In the frenzy to use AI for everything (heaven forbid we miss a “peak”), I found myself chasing the best prompt instead of the real lessons. After ~25 minutes across two LLMs, I had questionable data and fewer insights. That’s when I stopped and felt instantly relieved.
AI-driven recall is not the same as knowing what matters. We forget it’s ok, even beneficial, to let most things fade so the signal stands out.
The problem: data over meaning
GGenAI excels at retrieval, but annual reviews are about interpretation. When the tech leads, the review feels hollow, maximizing recall at the expense of insight. I ended up with a meaning-less list, not clearer lessons upon which to reflect and grow.
Signs you’re in the trap:
- You feel pressure to “cover everything” instead of deciding what mattered.
- You spend more time engineering prompts than writing.
- Your output is exhaustive but emotionally flat.
The case for forgetting
There’s a lot that happens in 365 days. The point isn’t to catalog it all; it’s to extract the 20% that generates 80% of your lessons. What sticks—without technology—often matters most.
Signals to let something go:
- It doesn’t make your heart sing or stir a strong feeling (positive or negative).
- You can’t name a consequence: “What changed because of it?”
A better question for annual reviews
What good reasons—beyond fear—do you have for not changing everything in your life?
I love this question! Annual reviews often default to optimized lists: more goals, more tools, more tweaks. What if you used the question above to test your biggest commitments—work, relationships, personal growth? If you can’t defend what you’re doing with an objectively compelling reason, change it. Choose paths and activities that energize you and expand your impact.
We’re here to live life fully. Annual reviews are a spot-check to assess how well our daily actions match our aspirational intentions.
What meaning surfaced for me
- Time with friends—eating, laughing, being ridiculous.
- Workshops and presentations that felt exceptionally rewarding.
- Personal joy: making gifts; new forms of exercise and meditation.
These endured without AI and barely showed up in my calendar or inbox. The act of reflecting—not the artifact—is the value. Let your highlights be your compass for what to change in the year ahead.
A workflow for personal annual reviews
I love technology, but in this case, I advocate an “AI optional” approach—and only after personal reflection. Here’s the path that worked after I stopped editing prompts:
- Start with why: Why do your personal review? What is the purpose? What three questions do you want to explore?
- Skim your apps: Flip month-by-month through your calendar, email sent, notes apps, and anywhere else you’re likely to see signs of the joy (and struggle) of the past year.
- Jot notes: Go old-school with pen and paper. Connect words that emerge. Doodle. Play with ideas as a new 20/20 perspective on your year emerges. If one or more themes emerge, make a note.
- Reflect and write: Create new meaning from past experiences, celebrate accomplishments and the distance you’ve traveled from your former self to the person you are today. Then, connect what you’ve learned to your Future Self: State what you’ll bring forward in actionable ways in the year ahead.
- Optional AI: Depending on how much you’ve written, consider using AI to tidy language or review for other strands or themes that you might consider. (If privacy is a concern, skip AI—or use a local, private model when available.)
Actionable: a 30-minute annual review ritual
- Set a 30-minute timer. Sit quietly for 2 minutes. Close your eyes and take 3 deep, clearing breaths. Allow two peaks and two valleys from the past year to come into your consciousness immediately. Write why you’re doing this review at all. What do you want to learn or see?
- Skim your main calendar and one inbox/sent mail; add any events that trigger a strong feeling (+/-).
- Time-box it. Decide in advance what apps you’ll check and for how long.
- Answer this question with brutal honesty: What would happen if I changed everything in my life? Let this lead you toward where to show up more fully yourself, without excuses.
- Revisit periodically. Note how you, your understanding, and your commitments evolve.
The takeaway
Annual reviews aren’t about perfect recall; they’re about us becoming more fully ourselves and sharing that with the world. This starts and ends with meaning. If you must, invite AI after you’ve contributed the very human art of reflection first. Choose growth. Change everything you can’t credibly defend continuing to do—and embrace that change with conviction! Set a timer. Move forward. Watch what happens next…