Personal Board Update #9: Measuring Fulfillment
Personal Board of Advisors,
Over the past 7 years I've written around 2,500 journal entries, tracking everything from "moments I pushed through something difficult" to days I "felt connected". While the metrics and broader questions shift every 6-12 month, one consistent question that keeps coming up is "what drives my sense of fulfillment?".
In 2021 I started tracking fulfillment and it feels like I'm finally getting close to the level of insights that I was hoping for back then. I've been meaning to write more on this topic, but for now, let's zoom in on fulfillment this past quarter.
Side note: no big ask for Q3. Mikayla and I are planning our wedding and I'm loving Anthropic - learning a lot!
Current approach to measuring fulfillment
In my first 2026 personal board update, I shared my (current) approach to measuring fulfillment.
In short, I spent around 4 years monitoring how my subjective feeling of fulfillment correlates with a variety of metrics. The factors that seems to have the highest correlation are writing, staying focused on my top priority, learning something meaningful, and connecting with people important to me.
So, for each of these categories I give myself a score of 1-10 that day. For writing I give myself a score of 0 if I write for under 15 minutes, 5 if I write for 15-30 minutes, and 10 if I write for over 30 minutes.
The other scores I currently track relate to health. These metrics - sleep, diet, workout, and meditation - are more objective: based on time asleep, calories, whether or not I worked out, and time spent meditating.
Each of the health scores and fulfillment scores contribute to a different percentage of my overall health and fulfillment scores:
Which then factor into a broader well-being score.
See the chart below for the past ~6 months (Trending upwards on all fronts!)
Mini discoveries this past quarter
Whenever I get less sleep, I end up compensating with meditating longer.
I started to become much more intentional with my Saturdays. My average fulfillment jumped from ~6.7 -> 8.1 for Saturdays this quarter.
My diet is slowly improving - 27% of days were 250+ calories over budget vs 31% in Q1. I also have 45% of days under or at budget compared to 35% in Q1.
I've started to write much less these past few months. I've been spending more time learning or reading when I have time.
Now, the issue with tracking everything is that it's difficult to capture the more special, fun, or magical moments.
So I created bonuses.
Bonuses are an automatic + 5 or 10 points (5% or 10% boost on that day's fulfillment score). Bonuses can be for any reason, but I need to write in the reason.
The most common factors for bonus scores include spending time with people I love, meaningful experiences, and times I've pushed myself.
On days with a bonus, my learning score runs almost a full standard deviation higher than on days I don't have a bonus.
Some other fun learnings:
- Wednesday is my best day. Core and Learning both peak, and it's where my time from alarm to getting up is the lowest (16.5 min).
- Days with long drives are the highest indicator of a bad day (across nearly all metrics).
While daily level of tracking has become a helpful forcing function for me to slow down and reflect each day, I think a more meaningful understanding of my fulfillment will come from tracking metrics at a weekly, monthly, and quarterly level.
Hoping to have some more baked out thoughts on this soon.
In the meantime, hope you have a wonderful rest of the summer.
Until next quarter,
David