Measured Well-Being: My Personal Development OKRs

I wanted to be a better person, but I didn’t know how to. And the desire to figure it out usually came in waves, always cresting with global periods of renewal—spring, Passover, Easter, Christmas, and, of course, New Year’s—before crashing down.

I played this game for years, confident I was completing some sort of personal development but never sure if I had obtained “it.” And never sticking with it long enough to find out. At least 18 years, to be exact. Because every New Year’s Eve since I was 16, I have played the same album that came out in 2003.

The first track on Death Cab for Cutie’s album Transatlanticism is a song titled “The New Year.” It starts like this:

So this is the new year
And I don’t feel any different
The clanking of crystal
Explosions off in the distance

So this is the new year
And I have no resolutions
For self-assigned penance
For problems with easy solutions

I remember Transatlanticism came out when I was 16 because the same year that a friend burned me a copy of the new Death Cab CD, I became fascinated by songs that had hidden messages when played backward.

I had read about the secret messages in Queen’s “Another One Bites the Dust” and The Beatles’ “Revolution #9.” I checked Audacity to see if Death Cab for Cutie, who got their name from The Beatles’ movie Magical Mystery Tour, had also been inspired to encode a backward message.

They hadn’t.

But something about the album captured my attention from the start. I added it to my roster of songs or albums that mention a date or time I play on that date or time every year. Like “Tune-Up #1” from “Rent” on December 24th, 9 pm, Eastern Standard Time. Or the musical “Parade” on Memorial Day. But those always felt schticky, whereas the earnest poise of Death Cab’s “The New Year” haunted me every December 31st. Like I was in Derry, Maine, after Pennywise’s latest 27-year slumber was about to end.


2020 felt like that year more than any other. Like everyone else, I went through it. My wife and I packed our bags in March and fled New Jersey to escape our 700-square-foot condo and a Covid-19 curfew that kept creeping up earlier and earlier. Once at my parents’ house in Minnesota, we came down with it.

After a nomadic summer, we returned to our condo and realized that it no longer felt like “home.” We put it on the market and sold it without any clear idea where we would end up. On our second drive back to my parents that year, we hit a deer in Pennsylvania and totaled our car. Luckily, we were all okay. But it was a wake-up call for me—a brush with death.

Lucky to survive this.

In my head, a quote by Marcus Aurelius from my Stoic practiced floated to the top:

“Don’t behave as if you are destined to live forever. What’s fated hangs over you. As long as you live and while you can, become good now.”

I liked the quote because it did not infer “badness,” only that there are areas for improvement. For being “better.” But it was November, and the idea was out of season, so I let it exist under me. Like an ancient cosmic force that inhabited a sewer system. That was until December 31st, 2020, when I put Transatlanticism on like some Ritual of Chüd. But this time, for whatever reason, I listened to the lyrics for the first time. I had heard them backward and forward for so many years, but all at once, it hit me.

I could name all my problems but could not name their easy solutions. And that’s why I didn’t feel good.

Earlier in the fall, after reading Stephen King’s writing memoir, I realized part of his success is that he knows how to set goals. I turned his goals into writing OKRs (Objectives and Key Results) for myself. While ultimately, that OKR got pushed another quarter (which is okay), I concluded on New Year’s Eve that the reason I never felt like I was a good person was that I never identified what that is to me.

Because of my work with John Doerr’s “Measure What Matters”, I knew that OKRs were, to quote myself, “a vaccine against fuzzy thinking—and fuzzy execution.” I needed something to point to, a mission for my life outside the egoic tendencies that generally plague or hinder us when we decide to be better. I no longer needed perfection. I wrote this mission statement for my life:

To grow my health, wealth, and mind every day by not having to be perfect but good.

It was not only drawn from the ancient wisdom of Marcus Aurelius, who himself wrote it down in his immortal book, Meditations, while living in a pandemic but also Voltaire and John Steinbeck:

“And now that you don’t have to be perfect, you can be good.” — John Steinbeck, “East of Eden”

“Perfect is the enemy of good.” — Voltaire

Writing My Personal Development OKRs

So, what are the attributes of a good person? Having obtained the rank of Eagle Scout in the Boy Scouts of America, the Scout Law popped into my head, which goes, “A Scout is trustworthy, loyal, helpful, friendly, courteous, kind, obedient, cheerful, thrifty, brave, clean, and reverent.”

I narrowed these twelve adjectives into five OKR buckets of financial, well-being, digital well-being, work, and writing OKRs. I figured out what I wanted out of each of these things and what success with that looked like. Instead of saying, “I want to use my cell phone less,” I figured out why that was important to “being good.” And what using my cell phone less actually meant. For example:

Objective (O): Use technology intentionally and never out of boredom or habit to stay as present at all times.

With this objective, this goal, I could draw a straight line to my life’s mission. I could make the shift, as Eckhart Tolle writes in “A New Earth”, from “thinking to awareness.”

These are what the key results in becoming more aware of my technology use are to me:

Key Result 1 (KR1): No cell phone use in bed, while watching shows, or walking outside.
Key Result 2 (KR2): Keep daily social media use below one hour.
Key Result 3 (KR3): Stop playing Pokemon Showdown.

(Pokemon Showdown is a Pokemon battle simulator that, my wife will attest, was my go-to procrastination platform.)

It’s that simple. And I did that with every other part of my life. And, at the end of the quarter, March 31st, I would grade them in a simple, stoplight fashion: green meaning I delivered, yellow that I made progress, and red that I failed to make progress.

I’m a little early, but I had a chance today to look over where I was. To finally know if I was on track to “be good.”

So, here are all my personal development OKRs and how I did for the first three months of 2021:

I’m pleased with the progress I’ve made. Am I a better person for it? I’m not sure. But it’s working for me and, and as Dan Harris quotes David Axelrod in “10% Happier”, “All we can do is everything we can do.” And as I draft my personal development OKRs for the next quarter, I now know exactly where I need to focus.

Goal Setting & OKRs

OKRs for Writers (And Creatives)

I’ve been working on my current manuscript for months now. It’s coming along in stop and go motion like learning to drive stick for the first time. Sometimes, everything clicks and aligns, and I can get some movement, if not distance, for a very urgent meeting. Other times, I stall because life obstacles keep getting in the way. The impulsive thing to do is to slam on the breaks when you think you’re going to crash.

The items on the list of why I don’t have time to write for myself is long. I could list them all, but a modified Stoic maxim comes to mind. “Waste no more time arguing about what a good writer should be; just be one.”

Alternate History Historical Fiction

Legally White: A 1908 Court Case Reversal

In January 1908, a trial in Minnesota decided whether John Svan, an outspoken activist and socialist from Finland, could become a naturalized United States citizen or not. At the time, citizenship was legally defined only for “Whites” and “Blacks.”

A district prosecutor maintained that Finnish immigrants were Mongol, or “Yellow,” and thus not eligible for citizenship due to the Chinese Exclusion Act.

Svan eventually won his court case, legally proving that Finnish people were White.

Here’s my take on what would have happened if John Svan had lost his court case to become “legally White”—only adding to the conversation of where the concept of “supremacy” is coming from if “whiteness” is purely a construct.


Tend To Your Night Garden

There’s a story about death and rebirth you probably haven’t heard.

It comes from a rarely-remembered Greek myth about a soldier named Auxentius and the trickster goddess Eris, who, after instigating the Trojan War, was upset that nobody remembered to honor her once it was over.


The Millennial Joads

While my wife, Belinda, and I were packing our car to go to Minnesota and escape the coronavirus outbreak in New York, she turned to me and asked, “Aren’t you thinking what’s it going to be like when we get there?”


Kill, F*ck, or Marry: A Buttigieg or a Dilettante?

A recruiter called me a dilettante at 8 a.m. on a Monday after I had already been up for two hours working on a time-sensitive deliverable for a client before I had to shower and head into the city for my full-time job.