For years, I’ve known intellectually that my best days aren’t my busiest days. That sustainable productivity requires balancing multiple priorities. That beating myself up about not accomplishing “enough” is counterproductive.

But knowing something intellectually and remembering it when you need to are very different things.

So a couple of months ago I started trying something different to help me better understand how I spend my time, what works, and what doesn’t. I wanted to

• Capture what I was actually doing across multiple areas
• Track not just activities but impact and how I felt
• Mine the data for insights about what was actually working

A long time ago, I tried tracking my time in 15 minute increments, which was helpful, but a lot of work. At DuckDuckGo I used to keep a list of what I’d done for the week and then outside of work I mainly used Trello. But then I only got the dopamine hit of the checkbox for finishing things – not all the effort that went into them.

The Solution: A Spreadsheet

I set up a spreadsheet.

• One tab per week – easy to review without drowning in data
• Columns for categories: Adulting, Human Being, Development, Promotion, Revenue, Twill, DDG (while relevant)
• Two assessment columns: Daily impact rating and overall vibe, color coded (green/yellow/red).
• Color coding: I also highlighted high-impact activities in green.
• Keep it open: I left it in a browser tab and jotted things down as they happened

The key was making it easy. I wasn’t timing anything precisely or categorizing every minute. Just capturing: “What did I do today? Did it matter? How did I feel?”

After a month, I had enough data to start asking bigger questions about what was working overall and what was not.

The AI Analysis

I fed my spreadsheet to Claude and asked it to analyze my patterns over the past month. What came back was a thorough, personalized report that I would never produce myself. First because of the time, and secondly because I’m inclined to be overly harsh on myself for what I accomplish – and what I don’t.

This is one of the core ways I use AI: to give me faster and more detailed feedback loops.

The feedback tends to be very positive, which is why real data matters—it keeps the AI grounded. It also tends to be generic, which is why identifying a process that works for me first, then using AI to give feedback and iterate, works better than asking for generic suggestions.

But when you combine genuine data with AI analysis, something useful happens. Here are some of the insights I got from Claude’s analysis.

The High-Impact Day Formula

Claude identified patterns in my color-coded days. It turns out my best days share these characteristics:

• 2-3 categories active (not all six—trying to do everything leads to feeling scattered)
• 1 significant accomplishment I can point to
• Mix of strategic + tactical work (both vision and execution)
• Human Being time included (exercise, relationship time)
• Clear assessment at end of day of what I achieved

This was validating. My instinct to prioritize exercise and quality time with my partner isn’t “nice to have”, it’s foundational.

Wins + Opportunities

Claude validated me as someone who:

But also (accurately) called out that I would benefit from:

⚠️ More deliberate planning (light vs. focus days)
⚠️ Increased development investment
⚠️ Recovery time after intense periods
⚠️ Clearer daily priorities to reduce “busy but unclear” feeling

The Core Insight

I’m pretty sure I already knew this, I just forget when focused on all the things I haven’t done (yet). I hope that building a structured way to give myself a regular reminder is not just good for my productivity – but also for my mental wellbeing.

My best days aren’t when I work most, but when I have clarity about what matters, make visible progress, and maintain my human being practices.

This felt particularly important to pay attention to as I navigate a transition from a structured and meeting heavy work environment to a more portfolio setup, but honestly most of the same insights probably would have been true 6 or 12 months ago.

Rinse and Repeat

The nice thing about this system, was I could use the insights and feed the data back in a week later. Claude was encouraging about my progress, which was nice – I tend to start the week a little overwhelmed by everything I want to accomplish and it helped me ground myself in what I am capable of.

After taking the feedback, I managed to have a week as a person that:

• Works hard without sacrificing relationships
• Rests intentionally without guilt
• Acknowledges challenges without catastrophizing
• Celebrates progress without waiting for perfection
• Maintains systems without being rigid

Obviously I still had things I can do better (specifically: spending more time on development). But for one week later – a busy one! – that was pretty great progress. This solidified the Monday morning ritual – run the spreadsheet through and ask “how did I do?” and “what can I learn?”

Failing

I live for the validation, but a few weeks later I took a long weekend and missed the Monday ritual. By Friday, I was toast. I ran the spreadsheet through Claude, and it brought the Real Talk^TM. Pointing out that I had:

• Sprinted through the week before the long weekend.
• Not actually rested – had a hectic (but fun!) weekend away.
• Came back and tried to jump back to full capacity whilst noting myself “discombobulated and tired”.
• Missed my physical anchors (no yoga or spin).

Claude ordered me to stop and rest, and I obeyed. It was a good call – I managed a nice afternoon reading a novel before spending the entire weekend sick.

I know this is a pattern I have. That I push myself to “earn” a break by getting everything I would have done in that time around it. It’s destructive. But the good thing is that the failing enforced the value of this ritual more than any succeeding would have done.

Try It Yourself

If you’re curious about your own patterns:

1. Pick 5-7 categories that matter to your life (work projects, learning, relationships, health, etc.)
2. Create a simple spreadsheet with these as columns.
3. Add an overall impact and overall vibe columns to capture how you feel about how the day went.
4. For 2-4 weeks, jot down what you do each day.
5. Use color for an easy visual emphasis.
6. Feed it to an AI and ask for patterns – note that in your prompting you’ll likely need to be explicit about the color coding and what it means.

Maybe you’ll learn something new, or maybe – like me – you’ll be reminded of the things you know but forget when you’re stressed. Either way, I hope it’s useful.

If you try this, I’d love to hear what you discover. What patterns emerged? What surprised you?