Newsletter: Objective Paradox

The one where I highlighted some parts from the first four chapters of the book "Why Greatness Cannot be Planned"

I recalled a casual Slack conversation December 2022 with Sam of

The Forcing Function

about my ideal day. It’s one with practicing snowboard for half the day and the other half doing work. I liked that so much I put it as a target in my Twitter profile.

I took 3 weeks off in February to try that out and it was glorious. I met 3 customer deadlines while I was learning to snowboard in Japan. On top of that, I still had extra time to reflect on my lifestyle and my goals because you cannot really do too much in cold winter in a country where you don’t speak the language.

Learning to snowboard at my 4th attempt (I failed on 3 previous shorter trips) plus hitting some work output goals while still serving my end users and 99% of them not realizing my physical absence is mind-blowing. All the words in books like 4 Hour Work Week pale in comparison with one meaningful, real experience.

Long story short, I will heavily refactor my lifestyle moving forwards and that includes this newsletter as well. I haven’t settled on the details yet, but one thing for sure is, I’m not going to maintain a weekly cadence for its own sake.

I will have more to say about this trip and the reflections I got out of it in future updates.

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One other thing I got out of this trip is I got more time to read carefully the books on my list. And one book that I really deep-dived into is Why Greatness Cannot Be Planned: The Myth of the Objective by Joel Lehman and Kenneth O. Stanley.

I've enjoyed literature that extolled the merits of real, detailed planning like the Peter Drucker’s Effective Executive and books on OKRs. However, at the back of my mind, there’s always something bugging me about such literature.

Why Greatness has been on my to-read list for a super long time, and I finally was able to take the time to read it. I regret not reading it sooner.

It elegantly and rigorously articulated that nagging feeling I’ve had all this while. Since I published my Dirty Work piece, I’ve been finding ways to practice what I preach.

I’ve always liked to hit multiple goals with a single move (the proverbial one stone killing n birds), since

• the snowboard February trip has influenced me to take a more deliberate, less frequent approach to my newsletter,

• I wanted to strengthen myself to have more stamina for Dirty Work,

• and I wanted to be more deliberate about integrating and practicing lessons from really good books I read into my life

my essay for this week is a highlights-and-commentary post on the first four chapters of the book.

Notes on Objective Paradox Part I: Think In Search Space

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Elsewhere on the internet

Cedric Chin @ejames_c

I feel like I vanished into a hole for my judo experiment, skipped doing my New Year’s resolutions in favour of more training, and now, coming out on the other side, I feel totally discombobulated. Like, bank runs and AI are a thing now?

Vanishing into holes to reconfigure yourself as a person is highly underrated. My Feb snowboard trip was my personal vanishing hole.

Huge pockets of empty time where you exercise a great amount of autonomy is the new luxury item.

Dave Anderson @scarletinked

2. Valuable work experience. It's crucial for being a successful business content creator. Without it, you can't add value by communicating your knowledge. How can you build this experience? Get a job, make a startup, invest your time.

This echoes some of my own nascent thoughts about this newsletter. Given the rise of ChatGPT and similar tech, there will be more bland and generic content churned out.

Increasingly, differentiators like:

• Quality of the output (writing/video) in non-formulaic ways,

• hard-to-fake signals like receipts,

• tight fit between creator-topic-audience

are going to be even more so going forward.

Thank you for your subscription to my newsletter.

As always, I wish you and your family good health and good fortune.