If you know me, you know I’m a lifelong learner and committed to self-improvement. I look for ways to improve and do it more quickly. Well, today I discovered one and wanted to share it with you.

I would love to see others do this and share their learnings. If you try this, please share!!

Over the years, journaling has been one of my go-to tools for reflection. My journals are organized Google docs filled with hundreds of pages of observations, musings, and lessons from both my personal and professional life: all original, highly personalized content. While the process has been invaluable, I’ve often found it toilsome to sift through all that content to extract actionable insights.

That changed this morning when I discovered a way to leverage AI, specifically Google Gemini, to analyze over a decade of my journal entries. It's super simple. The results have been transformative, revealing patterns, connections, and opportunities I might never have identified on my own. The results have also been incredibly validating, which surprised me. It’s an experience I’m excited to share because it could help you uncover your own hidden gems, too. Oh, and since the content is specifically my own I didn't get fortune teller-like platitudes and generalizations LLMs often produce, but precise and personalized insights.

The Challenge: Too Much Information, Too Little Clarity

Like many professionals, I use journaling for:

Processing Experiences: Decompressing after a challenging day or project.
Capturing Observations: Noting team dynamics, management styles, and technical trends.
Documenting Lessons Learned: Reflecting on successes, failures, and key takeaways.
Covering My Ass: Sometimes, in certain environments, you need a paper trail.

The problem? Over the past decade, these reflections became scattered across hundreds of pages in Google docs, making it difficult to connect the dots and identify recurring patterns. Manually reviewing everything felt time-consuming and inefficient.

The Breakthrough: AI-Powered Analysis with Google Gemini

That's where Google Gemini came in. By feeding my journal entries into Gemini, I was able to:

Identify Key Themes and Patterns: Gemini quickly extracted recurring themes related to leadership, management, technical challenges, and personal growth.
Uncover Hidden Connections: AI helped me connect seemingly disparate entries, revealing underlying patterns in my thinking and behavior.
Isolate Novel Discoveries: Gemini pinpointed unique insights and observations that I might have otherwise missed.
Organize Insights into Actionable Categories: AI helped me structure my learnings into practical categories, such as leadership styles, team dynamics, and technical best practices.

Examples of Insights Gemini Unlocked

Here are a few specific examples of how Gemini helped me extract valuable insights from my journaling:

Leadership Style: Gemini identified a recurring theme in my reflections: the importance of leading through influence ("changing hearts and minds") rather than direct command-and-control. By analyzing numerous entries about team interactions and management approaches, Gemini highlighted the effectiveness of fostering a supportive team culture, delegating effectively, and promoting open communication. It also highlighted my style of deeply focusing on the power of observation. Sit back and watch. Try not to get over your skis. It's so informative.
Technical Debt Management: Analyzing my reflections on various projects revealed a clear pattern: the negative impact of mismanaging technical debt. Gemini highlighted the long-term consequences of prioritizing short-term fixes over sustainable solutions, reinforcing the importance of addressing technical debt proactively. Moreover, "patching" and "bandaids" were often worse than just ripping the bandaid off and doing it right. Repeatedly, getting it right before moving on is critical.
The Impact of "Saboteurs": This isn's a term I coined, but it's incredibly powerful. I had identified things that got in the way of good teams, good leadership, and good outcomes, but I had not identified them as consistently recurring patterns that could be analyzed and actively addressed across a number of contexts. Gemini was able to point these patterns out and let me know the common thread running through them.

Informing My Approach to Leadership

Using Gemini to analyze my journaling has had a profound impact on my approach to understanding my strengths and weaknesses in technical leadership and management:

More Focused on Intentional Culture Shaping: I always start with culture first. Why? When trying to make changes on a new, inherited team, one on which I didn't have full street cred, those changes could lack buy-in from those responsible for executing the tasks. The outcomes vary considerably from success to passive aggressive refusals and malicious compliance. More than once, this effort has paid off: shaping a strong culture pays incredible dividends that money literally couldn't buy (story for a later time).
Greater Emphasis on Execution and Strategic Planning: I focus on aligning ideas with disciplined execution and addressing technical debt proactively. It helped me identify the gulf between idea and execution. Happily, I got better at execution throughout the years.
Clearer Understanding of Team Dynamics: I'm more attuned to team interactions, communication patterns, and individual motivations. I'm also more attuned to myself.
More Deliberate in Mentorship and Feedback: This includes giving and receiving feedback across multiple levels.

Give it a Shot!

If you're a journaler (or have similar content) on your own path to self improvement, looking to unlock deeper insights, I highly recommend using AI to explore what you have locked away. Here's what I did in just a few minutes. I'd love for you to give this a shot and share what you've found!

Choose an AI Tool: Explore tools like Google Gemini, ChatGPT, Claude, etc, which offer features for text analysis, theme extraction, and pattern recognition. I chose Gemini b/c my original content was in Google docs already and Gemini can natively read that. When prompting Gemini just "@-mention" the content (folder, files, file) for processing. You can upload documents to OpenAI (ChatGPT) and Claude and others. Chose what works best for you.
Consolidate Your Journal Entries: Gather your journal entries into a digital format that can be easily analyzed by AI. I just concatenated all of my google docs into a single one that I analyzed with Gemini. This is essentially a RAG task, so gathering the content in one source to present to the LLM was necessary.
Analyze the Text: Explore the features offered by your chosen AI tool and experiment with different analysis techniques to find what works best for you. Don't just ask for a summary. Ask a variety of powerful questions, like: (1) What important observations did I make? (2) What novel discoveries did I make? (3) What were the most impactful discoveries I made? (4) How can I best leverage my experience as outlined here to easily propel my technical consultancy to success? (5) What did I miss? (6) Where can I improve? etc, etc.
Focus on Actionable Insights: Don't just passively review the AI's findings. Actively seek out concrete steps you can take to apply your learnings to your work and life.

Conclusion:

Oh, and since the content is specifically my own I didn't get fortune teller-like platitudes and generalizations LLMs often produce, but precise and personalized insights.

Combining journaling with the power of AI has been a game-changer for my personal and professional growth. It's allowed me to unlock hidden insights, connect the dots between disparate experiences, and develop a more intentional and effective approach to leadership and management. I'll be taking some time to review the insights in depth and likely turn this into a series of blog posts or articles. If you're looking to take your self-reflection to the next level, I encourage you to give it a try.

Do you use journaling or AI for self-reflection? Share your experiences and insights in the comments! What tools or techniques do you find most helpful?

I hope this helps and can't wait to see what you share.

Cheers!

Unlocking Leadership Insights