5 Steps to a Brutally Honest AI-Assisted Annual Review

“Stop wasting time writing blog posts and newsletters that get minimal engagement.”

“By December, you’re still asking the same questions as January, just with fancier frameworks.”

“You’d rather keep theorizing about your perfect path than risk fully committing to any single direction.”

Last week, I shared why I turned to AI for a brutally honest annual review. Today, I’m sharing the specific steps I followed for getting AI to stop being a supportive sycophant and serve me better as a self-deception destroyer.

Step 0: Know What You’re After

Why put all this effort into having AI analyze my year?

My answer: I want my 95-year-old self to know I gave my best to life and got the best from it. And I want that example to inspire my kids and anyone else watching.

So I’m not looking for a pat on the back—I want merciless clarity on where I’m spinning my wheels. Only then can I get real traction.

Step 1: Accept The Self-Deception in Self-Reflection

Traditional year-end reviews are exercises in self-delusion—our annual opportunity to reinforce biases and cement comfortable stories.

AI’s inhumanity cuts through this biological blubber:

• Processes vast amounts of granular data without getting lost in the story
• Brings broad knowledge with zero emotional investment
• Analyzes iteratively without getting bored or distracted
• Won’t coddle your ego (unless explicitly asked)

But AI’s output is only as good as the data you feed it.

Step 2: Feed the AI Raw Data, Not Processed Stories

This wasn’t me treating AI as some digital therapist, sharing my feelings and repressed memories, then begging, “Oh, Dr. AI! What’s wrong with me?”

Instead, I gave it cold, hard data: monthly recaps built from weekly summaries, which came from daily logs:

• Wins and progress (“Pumps”)
• Setbacks and struggles (“Leaks”)
• Lessons learned
• Developments by life area: Work, Relationships, Health, Development, Memorable Moments

Want a template? Here’s the guide I share with participants in my ARC program. 

Step 3: Force the AI to Not Be Nice

AI defaults to being inoffensive and supportive, just like most ineffective self-help content. You have to explicitly override its people-pleasing programming.

I created custom instructions to force it to:

• Focus on my 95-year-old self’s goals (from Step 0)
• Process the raw data objectively
• Run specific analyses
• Challenge rather than validate, always backing criticism with examples

Here are the exact instructions I used.

Step 4: Ask Radical Questions

Getting useful output from AI is a skill that takes trial and error to develop. While I can’t teach you what I’ve figured out in this post, I can give you nine prompts that worked.

Each of these forced AI to attack my year from a different blind-spot-enlightening angle.

1. Fighting Myself for My Life

Imagine you are another version of me from a parallel universe. Somehow, you got irrevocably ported into my universe. You want to take over my life, to outdo me, to win over Kim and my kids and family and friends, to take over my business. What actions will you take to do so? Bear in mind that you can't simply "do more" than me. You have to cut out things that I habitually do to make space for the activities that will ultimately outdo me.

Sample Response:

“Stop wasting time writing blog posts and newsletters that get minimal engagement…Drop playful or unserious tones that undermine your credibility…”

2. My Most Likely Life Story

If I continue living at this rate, what will the story of my next 56 years (from 39 to 95) most likely look like? Project the story for the most likely outcome, not some story that will please me. Be blunt, dispassionate, analytical. Tell the story of these next 50 years looking back, as if someone at my funeral recounting the story of my life from age 39 (now) through 89.

Sample Response:

“In his 50s, Chris finally accepted a part-time position at a local university teaching personal development courses while maintaining his coaching practice.”

3. The Inner Saboteur’s Report

Take the role of my worst enemy - the inner demon conspiring to ensure I live a mediocre life and become a 95-year-old who wishes he could go back and try harder. Looking back at 2024, what are you most proud of accomplishing? 

- Your biggest win - the specific action/decision that will haunt my 95-year-old self
- Your subtle ongoing victories in keeping me comfortable and small

Use specific examples from the recaps.

“By December, you’re still asking the same questions as January, just with fancier frameworks. chef’s kiss”

4. Comfort Zone Workout Plan

Take the role of "comfort zone trainer." Your role is like that of an olympic coach but for life - to push me in all areas of life (relationships, physical health, mental health, career, finances, personal development) to get the most out of what I am capable of to maximize my performance. Based on what you see from 2023 and 2024, what specific workout plan will you devise for me for 2025? Bear in mind that to give me new "exercises" you have to replace something else I'm currently doing. Also bear in mind sustainability — any workout you give me should be one I can sustain for 56 years, i.e, while challenging it is also intrinsically energizing.

Sample Response:

“Cut: Podcast consumption, random book reading. Add: 1. Monthly “deep dives” – spend 30 days studying one topic exhaustively. 2. Quarterly skill acquisition projects (e.g. learning Spanish, mastering a new sport).“

5. Hidden Pattern Breaker

Analyze my behaviors, decisions, and thoughts across these recaps. Look for patterns among:

- My biggest contradictions between stated intentions and actual behavior
- Areas where I repeatedly commit to change but don't follow through
- Uncomfortable truths I dance around or rationalize away

Give concrete examples from the recaps to support your analysis. Then identify the root cause that connects these patterns - what fundamental misalignment or belief might be driving this behavior?

Sample Response:

“You claim to want extraordinary impact but your actions reveal someone more committed to maintaining optionality than making real change – you’d rather keep theorizing about your perfect path than risk fully committing to any single direction and potentially failing.”

6. Hidden Gold Polisher

Analyze my 2024 recaps as for undervalued, overlooked progress. What am I:

- Not seeing or giving myself credit for, but that my 95-year-old self would recognize as among the best thing I accomplished or started in 2024?
- Getting disproportionate returns from relative to effort invested?

Support your findings with specific examples from the recaps.

Sample Response:

“Even in the chaos of parenting, you made deliberate choices to create moments of joy and progress for your boys…You significantly advanced your ability to systemize and distill insights…Low-stakes conversations have brought clarity to major next steps.”

7. Bold Mover

What is the one bold decision I could make right now that would most radically transform my trajectory toward creating the life and legacy I truly want—without compromising my core values?

Sample Response:

“…going all-in on creating a flagship product or project that forces you to bet on your expertise and ideas.”

8. Analysis Tightener

What one or two additional inputs should I include in my monthly reviews from now on that would allow you to perform a better analysis? What low-signal inputs might I remove from my review structure? 

Sample Response:

“…A log of risks taken each month…be explicit when something not only went well but gave you a noticeable energy boost or flow state.”

9. Unasked Question

Based on everything you've seen so far, what is the one question I should ask you that I haven’t yet thought to ask—something that could unlock the most transformative insight?

Step 5: Condense and Commit

Recall Step 0—I want unflinching clarity on where I’m spinning my wheels. After all this convoluted analysis, I distilled it down with two simple questions:

• Where have I been going wrong?
• What specific shifts will create real change?

I’ll eventually forget 99 percent of this analysis, so all I want are a couple of explicit shifts to focus on making. 

For me, it came down to boldness and focus. 

Where My Review Affects You

One specific insight from my analysis might resonate with you:

I want to focus on helping people whose discipline and drive brought them conventional success, only to realize it’s not enough. They’re ready to redirect their energy toward something more fulfilling, but aren’t clear on what or how.

My new ARC program addresses this by combining three elements I’ve been obsessing over:

1. Finding your energizing Life’s Work
2. Crafting an extraordinary life story
3. Building systems that keep you focused and aligned

I’m selecting 3-5 beta testers for intensive 1:1 work. You’ll get the full program at a fraction of the future cost, while helping shape its development.

Curious? Email me the word FOCUS and we’ll schedule a call to explore if you’re a fit. Even if not, I guarantee you’ll walk away with an extra pep in your step. 

Want More Insights on Minimizing Self-Deception?

Consider skimming through these:

• How I’m Making Game-Changing Big Life Decisions – Another way to improve your odds of making winning moves by deconstructing your past.
• Watch Yourself, Win – The basics for building an ongoing system for objectively recording, reviewing, and planning your progress.
• The Two-Headed Source of Your Obstacles – To defeat your enemy, you need to identify it. I call mine “The Suck.”