For ten years I have used Google Keep to serve several key functions in my life. While I do still bookmark pages in Chrome, they quickly become unwieldy, and Keep serves as my repository of "important" pages I want to remember. Tagging helps me keep them in buckets, of sorts. Checklists for shutting down the house in Door County or Downers Grove, To-Do lists, restaurant lists, shopping lists and more are quick to create, duplicate and re-use. I also often jot poetry or story ideas as they occur.
With over 1800 entries, my thoughts about Bookmarks in Chrome being unwieldy might be inaccurate, but Keep is a treasure chest that I wanted to mine with the help of AI.
My query:
Thinking like an expert personal coach with extensive experience helping Fortune 500 C-suite executive retirees plan their next chapter in retirement in their 50's, knowing that cycling, writing and photography are passions, review my 5+ years of Google Keep notes in the attached document. The "More List" found within it is important as that is a brainstorm of things I enjoy that I want more of in my retirement life.What are the Top 5 themes you find, what are hidden opportunities for growth and learning, and overall insights can you make about me based on this review. I use Keep as a way to bookmark items to return to, a way to keep checklists, and sometimes a way to capture snippets of poetry. It is how I capture what comes to me online.
Help me increase the things I want more of and present an actionable plan for "better living" based on your review. The deliverables for this are:
1. An executive summary
2. A detailed review of findings
3. Discussion of these findings
Full disclosure: I wasn't a Fortune 500 C-suite, my VP job was in a small privately-held company, but I wanted professional "help". I wanted the notes to be analyzed with a bit more gravitas I suppose. So indulge me my delusions of grandeur. Still, with 7 patents, over 1 million miles of travel, and work in 20 countries revolutionizing how vision is tested, I should be permitted a small delusion.
Before I retired, as I journaled and worked through the process of determining if it was time to exit and my thoughts and emotions about it, I created a list of things I wanted more of in my life. My "More List". So that I have it everywhere, the list is in Keep and has things as simple as s'mores, dogs, convertibles, cycling and about 20 things I love, many of which were pushed to the periphery in my career and constant travel. These are the North Star of what I want out of retirement, and there is friction internally:
I'm not doing better doing the things I profess to want more of.
I tried Claude, ChatGPT, Gemini, and Grok. Grok, largely because I've not spent much time with it, and the others because I'm a daily user. The results, interestingly, were similar. I don't have a clear favorite. Often I prefer Claude for its depth and clarity. Claude knows me best as I've provided it the clearest picture, but in this case ChatGPT states it most clearly and right upfront:
You Are Quietly Reconstructing an Identity Around Creativity This is the dominant theme by far. Not creativity as productivity. Creativity as identity.
I think if this blog is any indication, that is definitely work in progress.
I decided to do a bit of meta analysis of the results and took all 4 of the "answers" and provided them back to Grok to review. Why Grok? I wanted a referee that I don't have history with. I feel the answers it returned were solid.
Analyzing where they agree:
Claim Creative Identity Publicly and Shift to Output: Stop collecting; start completing and sharing
Permission and Receiving: Grant yourself permission to spend time/energy/joy on the “More List” without earning it.
Refreshingly, "There is remarkably little “bad” advice— all outputs are thoughtful and well-calibrated." Phew!
Looking at the concrete advice for a daily plan:
- Morning ritual (30–60 min protected): Writing/poetry/journaling (Modern Wisdom prompts) + tactile start (coffee ritual, bread shaping, calligraphy). No screens first. This is going to be the hardest. I always start my day with coffee and the Wall Street Journal.
- One micro-action: Short walk with Gus, poem snippet, or photo. The smallest action I can take to move me forward - alright - let's go!
- Evening wind-down: Sensory pleasure (fire, drink, music, reading) + brief gratitude/reflection. I do enjoy a drink and a book. I can do this!
- Track aliveness/joy (1–10) simply Honestly, I like this. I had a friend that would call out "joy" when she discovered it, so this resonates!
As I said in my post Kevin Butler and the Temple of Doom Scrolling I need to stop defaulting to picking up the phone and scrolling. I'm trying harder to read more, but protecting my creative output, not asking permission to work on the projects that I want to nurture needs to be a priority as June approaches. 2026 is nearly half done and I have little output to show for it save these posts. Consider this a step to that future.
Note: If you'd like to try this yourself, export your Google Keep to a Google Doc, save the resulting document as a docx, upload to the various AI, use my query edited to your own passions and your own "More" list, and see what returns. I don't believe you'll be disappointed. Let me know in the comments what you discover!
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