My crystal anniversary and OKRs

Goal-setting in my personal life

In this edition

• Stuff you might like

• My crystal anniversary and OKRs [expanded version of LinkedIn post]

Stuff you might like

I came across this blog post that is nominally about deciding whether/when to quit, but it (together with some of the linked pieces) is really a masterclass on how to make decisions in an environment of uncertainty. This para sums it up:

When you realize you cannot know which scenario you’re in [the 2 scenarios being persistence leading to success vs failure], you realize that the job is to find out which one it is as quickly as possible, which means to cease your dithering, make a strong decision, keep your eyes open, try to measure what’s happening as objectively as possible, hope for [the scenario leading to success], but allow for [the scenario leading to failure], to not feel guilty if you guessed wrong, and not feel cocky if you guessed right. [emphasis original]

Conventional wisdom seems to be that AI will lead to widespread job loss and/or depressed wages, and I’ve thought that too. But Noah Smith argues that it is very possible that humans will continue to have lots of high-paying jobs, thanks to the operation of comparative advantages. His argument is premised on some critical assumptions that may not hold up, but it certainly made me pause and think twice.

My crystal anniversary and OKRs

Today is my 15th (crystal) wedding anniversary. 💑

[we took this picture at the Changi Airport Terminal 2 Flap Pix installation, with my wife and I facing sideways - obviously the installation works much better for one person looking straight into the camera]*

We don’t do a big celebration anymore, although we just had a nice dinner out. 🍽️ But just because we don’t celebrate, doesn’t mean we don’t care.

I’ve occasionally thought about what would be most important to me at the end of my life. This line of thinking started last year, after I attended the wake for an old classmate, and resurfaced after a recent wake for a former co-worker. 🕊️ It forces you to think deeply about what’s truly important.

🌟 My top priority would be for my wife to feel genuinely happy 😊 to have spent her life with me.

Then it occurred to me that it might be fun to apply a planning process 😛 (yes it is a weird idea of fun, especially since I never enjoyed annual planning), so this is what I did:

🥅 Start by defining the ideal outcome (see above).

📝 Develop the strategy (essentially a set of coordinated actions) to make the ideal outcome a reality. My strategy (for at least the next 12-18 months) is to create as many powerful shared memories as possible, while minimizing the number of negative moments. 📝

🎯 Translate that set of coordinated actions into 3-5 objectives.

📈 Define 3-5 key results to measure progress towards each objectives. In doing so, the KRs should ideally be input (not output/lagging) metrics, and most if not all KRs should have some sort of quality guardrail.

I have come up with 3 OKRs so far, here’s one of them (specific values omitted):

✅ Objective 1: Create many opportunities for powerful shared memories

🌍 Key Result 1: Take at least XX trips together every year. We’ve taken 1 so far, with 2 more already planned.

🎆 Key Result 2: Each longer trip (>5 days) should include at least one “hero” experience, i.e. something that can result in unique and/or intense memories, typically some sort of novel activity or extreme sport, or something animal-related, or a stunning outdoor landscape. I had shared earlier about our trip to Tasmania — the “hero” experience would’ve been the training flights that we didn’t get to do, but our experience with the wombat checked that box.

💕 Key Result 3: Spend at least XX hours of downtime together every day, bonus points if it’s with our cats 🐱

🗓️ Key Result 4 (which is more of a guardrail): Commit only to things that maintain my flexible schedule

(I recognize that the KRs are not necessarily SMART.)

Objective 2 is still WIP, but will probably be around expressing my love for my wife (using the love languages framework). Objective 3 is about achieving a balanced and low-stress lifestyle, which I’ve realized helps me show up better for my wife.

What I’ve not yet done, is decide on a review process and cadence. I don’t quite see myself doing a QBR on this every quarter…

I initially did this for amusement, but I realised the process would enable me to hold myself accountable for making progress towards my most important priority. It’s also allowed me to identify and fill gaps that I might otherwise have overlooked.

I can’t possibly be the only person who applies planning and OKR processes to their personal life! Let me know if you’ve done this.

I’m also curious to hear what other people might pick as their most important priorities at their end of lives, and how they are working to create those outcomes.

In the meantime, here’s to many more non-celebratory wedding anniversary dinners! 🥂💖