You'll notice things look a little different this week.
While I was recovering, I reviewed all of your survey feedback (thank you!) and spent some time thinking about what I actually want this newsletter to be.
Three years in, it was time to simplify. But not to shorten. I was surprised how many of you wanted to keep it "as is" with all the ideas, quotes, and fun finds.
But I wanted each section to have a clearer purpose — and for the whole thing to feel more like mine. Not just a collection of links, but a point of view.
Here's the new structure:
- What I'm Writing — an essay of mine, a post from the Filament blog, or some musings on LinkedIn
- My Favorite Find — the one idea I can't stop thinking about
- Worth Your Time — four more ideas that earned their spot
- This Week's Question — one question worth asking your team (or yourself)
- Random Things for Smart People — because not everything has to be workplace related
- Words of Wisdom — borrowed brilliance to close us out
Let's see how it feels
What I'm Writing:
Two weeks ago, I wrote about retiring 10% at a time. Here's an excerpt:
I'm not retiring. But I'm starting to practice.
Beginning this year, I'm taking two random days off each month. Not vacation. Not sick days. Retirement days. Two days a month is roughly 10% of my working time.
The honest truth is I've never been retired before, and I don't know anyone who does it particularly well. So I'm hoping to learn now, while I still have the energy and curiosity to figure it out.
The guilt is real, by the way. But I've watched too many people sprint to a finish line only to arrive too exhausted or too sick to enjoy what they'd been running toward.
I'd rather practice now.
My Favorite Find:
I read hundreds of blogs and dozens of newsletters every week, and I always find more ideas than I can share. This week, I really loved Addy Omani's reflection on the lessons learned from fourteen years at Google. Some are software developer specific, but most will resonate no matter what you do, including:
Being right is cheap:
Getting to right together is the real work.
You can win every technical argument and lose the project. I’ve watched brilliant engineers accrue silent resentment by always being the smartest person in the room. The cost shows up later as “mysterious execution issues” and “strange resistance.”
The skill isn’t being right. It’s entering discussions to align on the problem, creating space for others, and remaining skeptical of your own certainty.
Most “slow” teams are actually misaligned teams.
When a project drags, the instinct is to blame execution: people aren’t working hard enough, the technology is wrong, there aren’t enough engineers. Usually none of that is the real problem.
In large companies, teams are your unit of concurrency, but coordination costs grow geometrically as teams multiply. Most slowness is actually alignment failure - people building the wrong things, or the right things in incompatible ways.
Novelty is a loan you repay in outages, hiring, and cognitive overhead.
Treat your technology choices like an organization with a small “innovation token” budget. Spend one each time you adopt something materially non-standard. You can’t afford many.
The punchline isn’t “never innovate.” It’s “innovate only where you’re uniquely paid to innovate.” Everything else should default to boring, because boring has known failure modes.
The “best tool for the job” is often the “least-worst tool across many jobs”-because operating a zoo becomes the real tax.
More Thinking Worth Your Time:
To explore the impact of friends at work, KPMG has conducted Workplace Friendship research. Their latest results showedworkplace friendships:
- Workplace friendships are valued at 20% salary premium
- 57% of people would take a job with salary 10% below market value if it offered close work friendships (vs a role with 10% over market salary but no friendships)
- Three-quarters of workers say that financial constraints prevent them from socialising with colleagues outside of work
- 87% say friendship-enabling cultures are crucial for retention
There's nothing "just" about "just hopping on a call."
Your colleague asks you a reasonable question. You could take 5 minutes to write a cogent reply. You have everything you need to reply well. Multiple teammates would benefit from reading your reply. But instead, you say, “Let’s hop on a call.”
When you say this, sometimes what you really mean is: “I don’t want to do the work of clarifying my own thinking. And I believe it’ll be easier to think out loud and answer in a live conversation.”
My response to you is: I do not want to hop on a call because you are too lazy to write a cogent message. If you don’t want to invest 10 minutes to write a reply to a reasonable question, why should I listen (with no 1.5x button) as you meander in real time? GTFO.
There’s nothing “just” about “just hopping on a call.”
We're judging our decisions all wrong:
“Resulting” is (Annie) Duke’s term for judging a decision’s quality by its outcome. A good decision can lead to a bad outcome (and vice versa) because of factors outside your control.
When you overfit decision quality to outcome quality, you risk repeating errors that preceded a lucky good outcome and avoiding good decisions that didn’t work out due to bad luck.
Are you trapped in a Prison of Rightness?
What actually hurt was the feeling of resistance to being wrong, the cognitive dissonance between who I was at my outermost and innermost layers — a feeling that would build and build for as long as the dissonance was maintained.
Being wrong, and saying so, is by contrast liberating — like your mind is tangled up in a very complicated knot of stories and anxieties, but by pulling out just the right thread, the whole thing falls apart.
Acknowledging what is true is so much cleaner, psychologically, than maintaining everything necessary to avoid acknowledging it. Feynman famously said, “you must not fool yourself, and you are the easiest person to fool,” but I think I disagree. Fooling yourself takes work.
This Week's Question:
Ask each of your team members: What are you stuck on?
Posing the “stuck” question communicates that feeling challenged is not an experience that needs to be hidden or feared. It’s expected. That perspective is useful because it fosters resilience. It’s much easier to weather adversity when we anticipate being tested. In contrast, when struggle arrives unexpectedly, it shakes our confidence and leads us to question our abilities.
Random Things for Smart People
- One difference between animated chipmunks Chip ’n’ Dale is that Chip has one tooth and Dale has two.
- How do they get the bubbles in Champagne?
- Defending adverbs
- Rock Paper Scissors Strategies
- The ultimate guide to dinner parties
Words of Wisdom
The real problem is not whether machines think but whether men do. — B.F. Skinner
Even spontaneity gets better with practice. – Rick Rubin
Leadership is disappointing people at a rate they can absorb. – Claire Hughes Johnson
Persistence is the runway that gives your talent time to take off. – Barry Demp
Working smart isn't the opposite of working hard. It's the result of working hard. – Shane Parrish