Essential reading for product builders—part 1

7 timeless essays you likely haven’t read but should

Jul 15, 2025

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For something a little different, I’m going to share seven essays that have had the most impact on my product career—that you likely haven’t read.

There’s so much content flying at us these days, it’s hard to separate the “this sounds so smart!” from the “this is genuinely correct, helpful, and timeless.” The essays below are ones I find myself quoting from, sharing with people, and coming back to most often, even though most are decades old.

“The thing I’ve tried to do the last few years is ‘barbell’ my inputs. I basically read things that are either up to this minute or things that are timeless. I’m trying to not read anything that’s from yesterday through to like 10 years ago.” —Marc Andreessen

Note that this isn’t an exhaustive list. And I’m not including books—yet. This post is the beginning of an essential and timeless reading library meant specifically for product leaders.

I’d love your help building out this list. What’s missing? Let me know in the comments. Bonus points for sharing the impact it had on your career/life, and more bonus points for sharing stuff people may not have heard of. 👇

1. Who’s Got the Monkey?, by William Oncken, Jr., and Donald L. Wass

“Let us imagine that a manager is walking down the hall and that he notices one of his subordinates, Jones, coming his way. When the two meet, Jones greets the manager with, ‘Good morning. By the way, we’ve got a problem. You see. . . .’ As Jones continues, the manager recognizes in this problem the two characteristics common to all the problems his subordinates gratuitously bring to his attention. Namely, the manager knows (a) enough to get involved, but (b) not enough to make the on-the-spot decision expected of him. Eventually, the manager says, ‘So glad you brought this up. I’m in a rush right now. Meanwhile, let me think about it, and I’ll let you know.’ Then he and Jones part company.
Let us analyze what just happened. Before the two of them met, on whose back was the ‘monkey’? The subordinate’s. After they parted, on whose back was it? The manager’s. Subordinate-imposed time begins the moment a monkey successfully leaps from the back of a subordinate to the back of his or her superior and does not end until the monkey is returned to its proper owner for care and feeding.
In accepting the monkey, the manager has voluntarily assumed a position subordinate to his subordinate. That is, he has allowed Jones to make him her subordinate by doing two things a subordinate is generally expected to do for a boss—the manager has accepted a responsibility from his subordinate, and the manager has promised her a progress report.
The subordinate, to make sure the manager does not miss this point, will later stick her head in the manager’s office and cheerily query, ‘How’s it coming?’ (This is called supervision.) Or let us imagine in concluding a conference with Johnson, another subordinate, the manager’s parting words are, ‘Fine. Send me a memo on that.’
Let us analyze this one. The monkey is now on the subordinate’s back because the next move is his, but it is poised for a leap. Watch that monkey. Johnson dutifully writes the requested memo and drops it in his out-basket. Shortly thereafter, the manager plucks it from his in-basket and reads it. Whose move is it now? The manager’s. If he does not make that move soon, he will get a follow-up memo from the subordinate. (This is another form of supervision.) The longer the manager delays, the more frustrated the subordinate will become (he’ll be spinning his wheels) and the more guilty the manager will feel (his backlog of subordinate-imposed time will be mounting).”

2. On agency, by Henrik Karlsson

“Last year, when I talked about learning ‘how to handle being sentenced to freedom,’ a phrase I borrowed from Sartre, I meant roughly what people these days call ‘cultivating high agency.’ But I need to define my words, since some ways the phrase high agency is used feel foreign to me, and depressing.
Agency, as I see it, is an amalgamation of two skills, or mental dispositions: autonomy and efficacy.
Agency requires the capacity to formulate autonomous goals in life—the capacity to dig inside and figure out what wants to happen through you, no matter how strange or wrong it seems to others. In other words, it requires autonomy (which was what I was getting at when I said ‘authentically, and responsibly’).
Agency also requires the ability and willingness to pursue those goals. It requires the ‘will to know,’ the drive to see reality as it is, so you can manipulate it deftly and solve the problems you want to solve, instead of fooling yourself that certain problems are ‘unsolvable.’ In other words, efficacy (‘handle it effectively’).
Or phrased negatively, the opposite of agency can mean one of two things. Either (1) doing what you are ‘supposed to do,’ playing social games that do not align with what, on reflection, seems valuable to you and/or (2) being passive or ineffective in the face of problems (assuming your problems can’t be solved, that someone else should solve them, or working on things that do not in a meaningful way address the problem).
Agency is often framed as a hard-edged, type-A, aggressive approach. But over the last year, as I’ve been thinking about writing this essay, I’ve talked to a lot of highly agentic people, and I’ve read biographies about and interviews with people whose agency I admire and . . . hard-edged does not fit what I’ve seen. Often, agency is almost gentle—an attunement to the world and the self, a feeling out the details of reality, and a finding of the path of least resistance. There is sometimes considerable force involved, hard work, but it is like the force of a river being pulled toward the sea.”

3. On building good taste, by Ira Glass

(Technically this isn’t an essay, but who cares.)

“All of us who do creative work, we get into it because we have good taste. But it’s like there is this gap. For the first couple years that you’re making stuff, what you’re making isn’t so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.
But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you’re making is kind of a disappointment to you. A lot of people never get past that phase. They quit.
Everybody I know who does interesting, creative work went through years where they had really good taste and they could tell that what they were making wasn’t as good as they wanted it to be. They knew it fell short. Everybody goes through that.
And if you are just starting out or if you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you’re going to finish one story. It is only by going through a volume of work that you’re going to catch up and close that gap. And the work you’re making will be as good as your ambitions.
I took longer to figure out how to do this than anyone I’ve ever met. It takes a while. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.”

4. Strategies for learning, by Andy Masley

“Pretending to learn feels good. Actual learning often feels bad. A lot of people are just pretending to learn (memorizing passwords) when they think they’re learning. [. . .]
A lot of people read whole books just for the feeling of being the type of person who reads them, and retain no actual information about the world.
Avoiding playing pretend during your valuable learning time is important and psychologically difficult. A lot of people’s learning is limited by their insecurities and need for their social status to be reinforced. It often feels amazing to pretend to learn things, and unpleasant to actually learn. People are drawn to activities that make them feel high status, and repelled from activities that make them feel low status.”

5. If your product is great, it doesn’t need to be good, by Paul Buchheit

“I believe this ‘more features = better’ mindset is at the root of the misjudgment, and is also the reason why so many otherwise smart people are bad at product design (e.g. most open source projects). If a MacBook with OSX and no keyboard were really the right product, then Microsoft would have already succeeded with their tablet computer years ago. Copying the mistakes of a failed product isn’t a great formula for success.
What’s the right approach to new products? Pick three key attributes or features, get those things very, very right, and then forget about everything else. Those three attributes define the fundamental essence and value of the product—the rest is noise. For example, the original iPod was: (1) small enough to fit in your pocket, (2) had enough storage to hold many hours of music and (3) easy to sync with your Mac (most hardware companies can’t make software, so I bet the others got this wrong). That’s it—no wireless, no ability to edit playlists on the device, no support for Ogg—nothing but the essentials, well executed.
We took a similar approach when launching Gmail. It was fast, stored all of your email (back when 4MB quotas were the norm), and had an innovative interface based on conversations and search. The secondary and tertiary features were minimal or absent. There was no ‘rich text’ composer. The original address book was implemented in two days and did almost nothing (the engineer doing the work originally wanted to spend five days on it, but I talked him down to two since I never use that feature anyway). Of course those other features can be added or improved later on (and Gmail has certainly improved a lot since launch), but if the basic product isn’t compelling, adding more features won’t save it.
By focusing on only a few core features in the first version, you are forced to find the true essence and value of the product. If your product needs ‘everything’ in order to be good, then it’s probably not very innovative (though it might be a nice upgrade to an existing product). Put another way, if your product is great, it doesn’t need to be good.”