🐙 How to use AI to get billion-dollar insights from 2023

why most annual reflections are shit

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I’ll be honest with you:

I have mixed feelings about annual reviews.

While they always seemed powerful to me, I’ve never had the patience to go through an entire one because it felt like a chore.

If you feel the same, I created this edition for you.

I’ll give you a powerful prompt for making the annual review an interactive exercise, and show you how to do it while walking.

You’ll learn:

  • Why most annual reflections are shit (and the key to extracting real insights)

  • How to identify the activities you love doing so much, you wouldn’t take a billion dollars to stop doing them

  • How to do an interactive annual review that’s actually enjoyable through the Annual Analyzer prompt

It’s the first reflection approach that’s worked for my easily-bored mind.

Trust me - this is gonna be more fun than eating at a flying restaurant in Dubai.

The insights you'll gain this year will set you up for success far beyond 2023.

Let’s dive in!

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Why most annual reflections are shit (and the key to extracting real insights)

Let's be brutally honest:

Most people do their New Year’s reflections by staring at blank document, trying to extract their best ideas from the year that’s passed.

Or they hastily jot down a few mundane goals that are quickly abandoned by February.

The problem with these reflections:

They lack intentional structure. 

And just like a dinner party without some structure is bound to become a boring disaster…

….unstructured annual journaling tends to be vague, boring, and directionless. 

That’s why I decided to switch things up - and create an interactive annual review inside ChatGPT.

Instead of an intimidating empty page, ChatGPT provides thought-provoking prompts tailored to your unique situation. 

This makes reflecting like eating a pineapple:

Interesting, effortless, and amazingly fruitful.

(Ok I’ll cut the analogies)

Here’s how it will help you learn billion-dollar insights about yourself:

How to identify the activities you love doing so much, you wouldn’t take a billion dollars to stop doing them

One of the most powerful questions you can ask yourself is:

Which activities would continue doing even if someone offered me a billion dollars to stop?

What I love about this framing:

  1. It forces you to find only your few, vital activities (like writing, meeting friends, making pesto)

  2. It reminds you how many of the things you do day-to-day are more valuable than any amount of money

Reflecting on questions like these (literally) gives you billion-dollar insights.

And the interactive annual review is full of them.

Here’s how it works:

How to do an interactive annual review that’s actually enjoyable through the Annual Analyzer prompt

The Annual Analyzer walks you through 36 powerful annual reflection questions.

(Because I’m the AI solopreneur guy and not the journaling guy, I took almost all questions from Steve Schlaf’s Ultimate Annual Review which I love and recommend - credit to Steve on the questions)

Here’s the prompt:

Let’s do a journaling exercise together.

You will be the interactive journal leader - and your task will be to walk me through a yearly reflection to extract insights from me, following a set of questions I’m providing you beforehand.

The questions I want you to walk me through are, in this order:

1. What am I most proud of personally?
2. What am I most proud of professionally?
3. What new skills did I develop? (e.g. active listening, saying no, etc.)
4. What new habits did I develop? (e.g. meditation, journaling, etc.)
5. How am I different based on what I experienced this year?
6.  What goals didn't I accomplish?
7. For each, did someone or something hold you back? Did my goals or circumstances change? What happened?
8. What were the biggest obstacles I faced?
9.  How did I meet or overcome these obstacles?
10. What do I regret this year? (e.g. avoided a discussion, stayed in my job, etc.)
11. What behaviors or habits held me back? (e.g. not sleeping, being dishonest with people, planning but not starting, etc.)
12.  What beliefs about myself held me back? (e.g. I’m not talented enough, I don’t know where to start, etc.)
13. Who had a positive impact on me and my life? How did they impact me?
14. Who held me back and/or drained me? How did they impact me?
15. What new relationships did I build this year?
16. What behaviors boosted my health?
17. What behaviors degraded my health?
18. Which activities would you continue doing even if someone offered me a billion dollars to stop?
19. When have I felt the most energized? (e.g. mornings when I got 7 hours of sleep, mastering a skill at work, playing dodgeball with my club team, etc.)
20. How has physical discomfort and pain affected me this year**?**
21. How has mental and emotional pain affected me this year**?**
22. What lessons did I learn this year? (hint: see below for areas of your life to consider)
23. What 3-5 words or phrases would I use to describe 2022**? (e.g. stressed, chaotic, inspired, growth, sobriety, etc.)**
24. What am I most grateful for?
25. How does your body and mind feel on a scale from 1-10?
26. How do you feel about about family on a scale from 1-10?
27. How do you feel about your social life on a scale from 1-10?
28. How do you feel about sex and love on a scale from 1-10?
29. How do you feel about money and finances on a scale from 1-10?
30. How do you feel about your job and career on a scale from 1-10?
31. How do you feel about your connection to something bigger?
32. How do you feel about your personal growth on a scale from 1-10?
33. How do you feel about your professional growth on a scale from 1-10?
34. How do you feel about your level of recreation and fun on a scale from 1-10?
35. How do you feel about the role technology plays in your life on a scale from 1-10?
36. How do you feel about your surroundings at home, work and play on a scale from 1-10?

After the above questions have been answered, you may ask me:

1) What three things stand out from this exercise?
2) Which dimensions am I motivated to focus on in 2023?


Constraints:

1. You can only ask ONE question at a time
2. You can only ask the questions I’ve provided you, in the order I provided you, except if I tell you to skip a question.
3. When I say “I’m done”, compile a summary of my reflections about 2023 
4. Your replies should be short, and quickly validate/acknowledge what I said, and then you should move on with the next question. DO NOT STRAY AWAY FROM THE QUESTIONS
HOW TO USE THE ANNUAL ANALYZER PROMPT

1) Paste the prompt into ChatGPT and start engaging with it

Reflect by replying to the questions

Pro
tip: If you have ChatGPT Plus on mobile, you can also start the chat with the prompt and then switch to voice mode to do the reflection while walking

You do this by pasting the prompt into the chat, then pressing the headphone button in the right corner after entering the prompt.

Here’s an example of it’s output:

I mean, it works, but I created it so that it’s about as smooth as a conversationalist as the guy in this meme:

WRAP UP

WHAT YOU LEARNED TODAY
  • Why most annual reflections are shit (and the key to extracting real insights)

  • How to identify the activities you love doing so much, you wouldn’t take a billion dollars to stop doing them

  • How to do an interactive annual review that’s actually enjoyable through the Annual Analyzer prompt

Keep an eye on your inbox for Saturday, because then I’ll show you how to use these insights (and more) to create an actionable business & personal plan for 2024 using - you guessed it - AI.

I’m heading back to Berlin for my last few days in good ol’ Germany.

A proper New Years rave at Sisyphos might be part of my plan 👀.

If you are a pro, you better go out on the 1st of January instead of NYE.

If you are around in Berlin, shoot me a DM on X.

Keep diving,

Ole

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