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The art of the pivot, part 2: How, why and when to pivot
The art of the pivot, part 2: How, why and when to pivot
people mix up two very different types of pivots and that it’s important to differentiate which path you’re on: Ideation pivots: This is when an early-stage startup changes its idea before having a fully formed product or meaningful traction. These pivots are easy to make, normally happen quickly after launch, and the new idea is often completely unrelated to the previous one. For example, Brex went from VR headsets to business banking, Retool went from Venmo for the U.K. to a no-code internal tools app, and Okta went from reliability monitoring to identity management all in under three months. YouTube changed direction from a dating site to a video streaming platform in less than a week. Hard pivots: This is when a company with a live product and real users/customers changes direction. In these cases, you are truly “pivoting”—keeping one element of the previous idea and doubling down on it. For example, Instagram stripped down its check-in app and went all in on its photo-sharing feature, Slack on its internal chat tool, and Loom on its screen recording feature. Occasionally a pivot is a mix of the two (i.e. you’re pivoting multiple times over 1+ years), but generally, when you’re following the advice below, make sure you’re clear on which category you’re in.
When looking at the data, a few interesting trends emerged: Ideation pivots generally happen within three months of launching your original idea. Note, a launch at this stage is typically just telling a bunch of your friends and colleagues about it. Hard pivots generally happen within two years after launch, and most around the one-year mark. I suspect the small number of companies that took longer regret not changing course earlier.
ou should have a hard conversation with your co-founder around the three-month mark, and depending on how it’s going (see below), either re-commit or change the idea. Then schedule a yearly check-in. If things are clicking, full speed ahead. If things feel meh, at least spend a few days talking about other potential directions.
Brex: “We applied to YC with this VR idea, which, looking back, it was pretty bad, but at the time we thought it was great. And within YC, we were like, ‘Yeah, we don’t even know where to start to build this.’” —Henrique Dubugras, co-founder and CEO
·lennysnewsletter.com·
The art of the pivot, part 2: How, why and when to pivot
Perfectionism is optimizing at the wrong scale | Hacker News discussion
Perfectionism is optimizing at the wrong scale | Hacker News discussion
The thing I most worry about using anti-perfectionism arguments is that it begs a vision in the first place—perfectionism requires an idea of what's perfect. Projects suffer from a lack of real hypotheses. Fine, just build. But if you're cutting something important to others by calling it too perfect, can you define the goal (not just the ingredients)? We tend to justify these things by saying, we'll iterate. Much like perfectionism can always be criticized, iteration can theoretically always make a thing better. Iteration is not vision and strategy, it's nearly the reverse, it hedges vision and strategy. This is a slightly different point, but when we say we don't need this extra security or that UX performance, you're setting a ceiling on the people who are passionate about them. Those things really do have limits (no illusions!), but you're not just cutting corners, you're cutting specific corners. That's a company's culture. Being accused of perfectionism justifiably leads to upset that the company doesn't care about security or users. Yeah, maybe it's limited to this one project, but often not.
Perfection can be the enemy of the good. It's that it's not a particularly a helpful critique. To use the article’s concept, it’s the wrong scale. It might be helpful to an individual in a performance review, but it doesn’t say why X is unnecessary in this project or at this company. Little is added to the discussion until I describe X relative to the goal. Perfectionism is indeed good to avoid—it's basically defined as a bad thing by being "too". But the better conversation says how X falls short on certain measuring sticks. At the very least it actually engages X in the X discussion. Perfectionism is more of a critique of the person.
It takes effort to understand the person's idea enough to engage it, but more importantly it takes work that was supposed to (but might not) have gone into developing good projects or goals in the first place. Projects well-formed enough to create constraints for themselves.
I agree with the thesis of this article but I actually think the point would be better made if we switch from talking about optimizing to talking about satisficing[1]. Simply put, satisficing is searching for a solution that meets a particular threshold for acceptability, and then stopping. My personal high-level strategy for success is one of continual iterative satisficing. The iterative part means that once I have met an acceptability criterion, I am free to either move on to something else, or raise my bar for acceptability and search again. I never worry about whether a solution is optimal, though, only if it is good enough. I think that this is what many people are really doing when they say they are "optimizing", but using the term "optimzing" leads to confusion, because satisficing solutions are by definition non-optimal (except by luck), and some people (especially the young, in my experience) seem to feel compelled to actually optimize, leading to unnecessary perfectionism.
Perfectionism is sort of polarizing, and a lot of product manager / CEO types see it as the enemy. In certain contexts it might be, but in others “perfectionism” translates to “building the foundation flawlessly with the downstream dependencies in mind to minimize future tech debt.” Of course, a lot of managers prefer to pretend that tech debt doesn’t exist but that’s just because they don’t think they can pay it off in time before their team gets cut for not producing any value because they were so busy paying off tech debt.
kthejoker2 3 months ago | prev | next [–] Not sure you can talk about perfectionism without clarifying between "healthy" perfectionism and "unhealthy" perfectionism. Both exist, but often people are thinking of one or the other when discussing perfectionism, and it creates cognitive dissonance when two people thinking of the two different modes are singing perfectionism's praises or denouncing its practice.
looking at these comments, it seems perfectionism is ill-defined. it seems to be positive - perfectionism is not giving up, it is excellence, it is beyond mediocre. it also seems to be negative - it is going too far, it is avoiding/procrastinating, it is self-defeating. I wonder what the perfect definition would be?
·news.ycombinator.com·
Perfectionism is optimizing at the wrong scale | Hacker News discussion
The Complex Problem Of Lying For Jobs — Ludicity
The Complex Problem Of Lying For Jobs — Ludicity

Claude summary: Key takeaway Lying on job applications is pervasive in the tech industry due to systemic issues, but it creates an "Infinite Lie Vortex" that erodes integrity and job satisfaction. While honesty may limit short-term opportunities, it's crucial for long-term career fulfillment and ethical work environments.

Summary

  • The author responds to Nat Bennett's article against lying in job interviews, acknowledging its validity while exploring the nuances of the issue.
  • Most people in the tech industry are already lying or misrepresenting themselves on their CVs and in interviews, often through "technically true" statements.
  • The job market is flooded with candidates who are "cosplaying" at engineering, making it difficult for honest, competent individuals to compete.
  • Many employers and interviewers are not seriously engaged in engineering and overlook actual competence in favor of congratulatory conversation and superficial criteria
  • Most tech projects are "default dead," making it challenging for honest candidates to present impressive achievements without embellishment.
  • The author suggests that escaping the "Infinite Lie Vortex" requires building financial security, maintaining low expenses, and cultivating relationships with like-minded professionals.
  • Honesty in job applications may limit short-term opportunities but leads to more fulfilling and ethical work environments in the long run.
  • The author shares personal experiences of navigating the tech job market, including instances of misrepresentation and the challenges of maintaining integrity.
  • The piece concludes with a satirical, honest version of the author's CV, highlighting the absurdity of common resume claims and the value of authenticity.
  • Throughout the article, the author maintains a cynical, humorous tone while addressing serious issues in the tech industry's hiring practices and work culture.
  • The author emphasizes the importance of self-awareness, continuous learning, and valuing personal integrity over financial gain or status.
If your model is "it's okay to lie if I've been lied to" then we're all knee deep in bullshit forever and can never escape Transaction Cost Hell.
Do I agree that entering The Infinite Lie Vortex is wise or good for you spiritually? No, not at all, just look at what it's called.
it is very common practice on the job market to have a CV that obfuscates the reality of your contribution at previous workplaces. Putting aside whether you're a professional web developer because you got paid $20 by your uncle to fix some HTML, the issue with lying lies in the intent behind it. If you have a good idea of what impression you are leaving your interlocutor with, and you are crafting statements such that the image in their head does not map to reality, then you are lying.
Unfortunately thanks to our dear leader's masterful consummation of toxicity and incompetence, the truth of the matter is that: They left their previous job due to burnout related to extensive bullying, which future employers would like to know because they would prefer to blacklist everyone involved to minimize their chances of getting the bad actor. Everyone involved thinks that they were the victim, and an employer does not have access to my direct observations, so this is not even an unreasonable strategy All their projects were failures through no fault of their own, in a market where everyone has "successfully designed and implemented" their data governance initiatives, as indicated previously
What I am trying to say is that I currently believe that there are not enough employers who will appreciate honesty and competence for a strategy of honesty to reliably pay your rent. My concern, with regards to Nat's original article, is that the industry is so primed with nonsense that we effectively have two industries. We have a real engineering market, where people are fairly serious and gather in small conclaves (only two of which I have seen, and one of those was through a blog reader's introduction), and then a gigantic field of people that are cosplaying at engineering. The real market is large in absolute terms, but tiny relative to the number of candidates and companies out there. The fake market is all people that haven't cultivated the discipline to engineer but nonetheless want software engineering salaries and clout.
There are some companies where your interviewer is going to be a reasonable person, and there you can be totally honest. For example, it is a good thing to admit that the last project didn't go that well, because the kind of person that sees the industry for what it is, and who doesn't endorse bullshit, and who works on themselves diligently - that person is going to hear your honesty, and is probably reasonably good at detecting when candidates are revealing just enough fake problems to fake honesty, and then they will hire you. You will both put down your weapons and embrace. This is very rare. A strategy that is based on assuming this happens if you keep repeatedly engaging with random companies on the market is overwhelmingly going to result in a long, long search. For the most part, you will be engaged in a twisted, adversarial game with actors who will relentlessly try to do things like make you say a number first in case you say one that's too low.
Suffice it to say that, if you grin in just the right way and keep a straight face, there is a large class of person that will hear you say "Hah, you know, I'm just reflecting on how nice it is to be in a room full of people who are asking the right questions after all my other terrible interviews." and then they will shake your hand even as they shatter the other one patting themselves on the back at Mach 10. I know, I know, it sounds like that doesn't work but it absolutely does.
Neil Gaiman On Lying People get hired because, somehow, they get hired. In my case I did something which these days would be easy to check, and would get me into trouble, and when I started out, in those pre-internet days, seemed like a sensible career strategy: when I was asked by editors who I'd worked for, I lied. I listed a handful of magazines that sounded likely, and I sounded confident, and I got jobs. I then made it a point of honour to have written something for each of the magazines I'd listed to get that first job, so that I hadn't actually lied, I'd just been chronologically challenged... You get work however you get work.
Nat Bennett, of Start Of This Article fame, writes: If you want to be the kind of person who walks away from your job when you're asked to do something that doesn't fit your values, you need to save money. You need to maintain low fixed expenses. Acting with integrity – or whatever it is that you value – mostly isn't about making the right decision in the moment. It's mostly about the decisions that you make leading up to that moment, that prepare you to be able to make the decision that you feel is right.
As a rough rule, if I've let my relationship with a job deteriorate to the point that I must leave, I have already waited way too long, and will be forced to move to another place that is similarly upsetting.
And that is, of course, what had gradually happened. I very painfully navigated the immigration process, trimmed my expenses, found a position that is frequently silly but tolerable for extended periods of time, and started looking for work before the new gig, mostly the same as the last gig, became unbearable. Everything other than the immigration process was burnout induced, so I can't claim that it was a clever strategy, but the net effect is that I kept sacrificing things at the altar of Being Okay With Less, and now I am in an apartment so small that I think I almost fractured my little toe banging it on the side of my bed frame, but I have the luxury of not lying.
If I had to write down what a potential exit pathway looks like, it might be: Find a job even if you must navigate the Vortex, and it doesn't matter if it's bad because there's a grace period where your brain is not soaking up the local brand of madness, i.e, when you don't even understand the local politics yet Meet good programmers that appreciate things like mindfulness in your local area - you're going to have to figure out how to do this one Repeat Step 1 and Step 2 on a loop, building yourself up as a person, engineer, and friend, until someone who knows you for you hires you based on your personality and values, rather than "I have seven years doing bullshit in React that clearly should have been ten raw HTML pages served off one Django server"
A CEO here told me that he asks people to self-evaluate their skill on a scale of 1 to 10, but he actually has solid measures. You're at 10 at Python if you're a core maintainer. 9 if you speak at major international conferences, etc. On that scale, I'm a 4, or maybe a 5 on my best day ever, and that's the sad truth. We'll get there one day.
I will always hate writing code that moves the overall product further from Quality. I'll write a basic feature and take shortcuts, but not the kind that we are going to build on top of, which is unattractive to employers because sacrificing the long-term health of a product is a big part of status laundering.
The only piece of software I've written that is unambiguously helpful is this dumb hack that I used to cut up episodes of the Glass Cannon Podcast into one minute segments so that my skip track button on my underwater headphones is now a janky fast forward one minute button. It took me like ten minutes to write, and is my greatest pride.
Have I actually worked with Google? My CV says so, but guess what, not quite! I worked on one project where the money came from Google, but we really had one call with one guy who said we were probably on track, which we definitely were not!
Did I salvage a A$1.2M project? Technically yes, but only because I forced the previous developer to actually give us his code before he quit! This is not replicable, and then the whole engineering team quit over a mandatory return to office, so the application never shipped!
Did I save a half million dollars in Snowflake expenses? CV says yes, reality says I can only repeat that trick if someone decided to set another pile of money on fire and hand me the fire extinguisher! Did I really receive departmental recognition for this? Yes, but only in that they gave me A$30 and a pat on the head and told me that a raise wasn't on the table.
Was I the most highly paid senior engineer at that company? Yes, but only because I had insider information that four people quit in the same week, and used that to negotiate a 20% raise over the next highest salary - the decision was based around executive KPIs, not my competence!
·ludic.mataroa.blog·
The Complex Problem Of Lying For Jobs — Ludicity
When To Do What You Love
When To Do What You Love
People pay you for doing what they want, not what you want. But there's an obvious exception: when you both want the same thing. For example, if you love football, and you're good enough at it, you can get paid a lot to play it.
it's clear that Bill Gates truly loved running a software company. He didn't just love programming, which a lot of people do. He loved writing software for customers. That is a very strange taste indeed, but if you have it, you can make a lot by indulging it.
If you want to make a really huge amount of money — hundreds of millions or even billions of dollars — it turns out to be very useful to work on what interests you the most. The reason is not the extra motivation you get from doing this, but that the way to make a really large amount of money is to start a startup, and working on what interests you is an excellent way to discover startup ideas.
Many if not most of the biggest startups began as projects the founders were doing for fun. Apple, Google, and Facebook all began that way. Why is this pattern so common? Because the best ideas tend to be such outliers that you'd overlook them if you were consciously looking for ways to make money.
there's something like a midwit peak for making money. If you don't need to make much, you can work on whatever you're most interested in; if you want to become moderately rich, you can't usually afford to; but if you want to become super rich, and you're young and good at technology, working on what you're most interested in becomes a good idea again.
When you have trouble choosing between following your interests and making money, it's never because you have complete knowledge of yourself and of the types of work you're choosing between, and the options are perfectly balanced. When you can't decide which path to take, it's almost always due to ignorance. In fact you're usually suffering from three kinds of ignorance simultaneously: you don't know what makes you happy, what the various kinds of work are really like, or how well you could do them
Don't wait till the end of college to figure out what to work on. Don't even wait for internships during college. You don't necessarily need a job doing x in order to work on x; often you can just start doing it in some form yourself. And since figuring out what to work on is a problem that could take years to solve, the sooner you start, the better.
You'll become like whoever you work with. Do you want to become like these people?
If you choose a kind of work mainly for how well it pays, you'll be surrounded by other people who chose it for the same reason, and that will make it even more soul-sucking than it seems from the outside. Whereas if you choose work you're genuinely interested in, you'll be surrounded mostly by other people who are genuinely interested in it, and that will make it extra inspiring
The less sure you are about what to do, the more important it is to choose options that give you more options in the future. I call this "staying upwind." If you're unsure whether to major in math or economics, for example, choose math; math is upwind of economics in the sense that it will be easier to switch later from math to economics than from economics to math
The root of great work is a sort of ambitious curiosity, and you can't manufacture that.
·paulgraham.com·
When To Do What You Love
Tennis Explains Everything - The Atlantic
Tennis Explains Everything - The Atlantic
Tennis is an elegant and simple sport. Players stand on opposite sides of a rectangle, divided by a net that can’t be crossed. The gameplay is full of invisible geometry: Viewers might trace parabolas, angles, and lines depending on how the players move and where they hit the ball. It’s an ideal representation of conflict, a perfect stage for pitting one competitor against another, so it’s no wonder that the game comes to stand in for all sorts of different things off the court.
The “Battle of Sexes” match in 1973, between Billie Jean King and then-retired Bobby Riggs, has since been mythologized as a turning point for women’s sports. If the social allegory of the Ashe-Graeber match was subtextual, the one in this spectacle—which ended in a decisive victory for King over the cartoonishly chauvinistic Riggs—was glaringly explicit. At a time when women’s liberation was becoming a force that threw all sorts of conventions into question, and plenty of people were for or against the gains of the movement, seeing the debate represented by a game of tennis surely had a comforting appeal. For those with more regressive beliefs, rooting for Bobby was certainly easier than really articulating a justification for maintaining massive pay disparities between men and women, both within and outside of professional tennis.
Within their love triangle, tension arises with the dawning recognition that in a one-on-one sport, there’s always another person who doesn’t have a place on the court. Save for the night they meet, when Tashi induces Art and Patrick to kiss each other for her entertainment, the three of them rarely engage with one another at the same time: Someone is always watching from the stands, whether literally or metaphorically.
During Patrick and Tashi’s brief romance, a post-coital conversation seamlessly transitions into a discussion about Patrick’s poor performance as a pro, and eventually becomes a referendum on why their relationship doesn’t work. Confused, and trying to make sense of it all as their banter swiftly changes definitions, Patrick asks: “Are we still talking about tennis?” “We’re always talking about tennis,” Tashi replies. Frustrated, Patrick tersely retorts: “Can we not?”
As the linguists George Lakoff and Mark Johnson argue in their 1980 book,Metaphors We Live By, “Our ordinary conceptual system, in terms of which we both think and act, is fundamentally metaphorical in nature.” In other words, we’re always talking about things in terms of other things—even if it’s not always as obvious as it is in Challengers. Metaphors are more than just a poetic device; they’re fundamental to the way language is structured.
No matter what issue is at stake, or how grand it may be, it can always be reduced to an individual’s performance on the court.
While Patrick is still dating Tashi, and Art is transparently trying to steal his best friend’s girl, Patrick playfully accuses Art of playing “percentage tennis”—a patient strategy of hitting low-risk shots and waiting for your opponent to mess up
Art asks for Tashi’s permission to retire once the season is over. Art knows that this would be the end of their professional relationship—he would no longer be able to play dutiful pupil to Tashi. But it might also be the end of whatever spark animated their love in the first place, as you can’t play “good fucking tennis” in retirement. Tashi says she will leave Art if he doesn’t beat Patrick in the final. Tired of playing, but unable to escape the game, Art curls up in his wife’s lap and cries.
·archive.is·
Tennis Explains Everything - The Atlantic
Build tools around workflows, not workflows around tools | thesephist.com
Build tools around workflows, not workflows around tools | thesephist.com
Building your own productivity tools that conform to your unique workflows and mental models is more effective than using mass-market tools and bending your workflows to fit them
My biggest benefit from writing my own tool set is that I can build the tools that exactly conform to my workflows, rather than constructing my workflows around the tools available to me. This means the tools can truly be an extension of the way my brain thinks and organizes information about the world around me.
I think it’s easy to underestimate the extent to which our tools can constrain our thinking, if the way they work goes against the way we work. Conversely, great tools that parallel our minds can multiply our creativity and productivity, by removing the invisible friction of translating between our mental models and the models around which the tools are built.
I don’t think everyone needs to go out and build their own productivity tools from the ground-up. But I do think that it’s important to think of the tools you use to organize your life as extensions of your mind and yourself, rather than trivial utilities to fill the gaps in your life.
·thesephist.com·
Build tools around workflows, not workflows around tools | thesephist.com
Productive Procrastination
Productive Procrastination
I do a pretty good job of channeling my procrastination into adjacent creative tasks which, in the end, influence, shape, and improve the chunks of work I do complete. And that looks like productivity from the outside. But trust me, from the inside, it usually just feels like avoidance and procrastination. But I’ve learned to accept that’s the cost of doing the kind of work I feel good at, so I let it be what it is.
The particularly nice thing about coding is that it offers many little “wins”: I get a function working, I figure out a piece of design
“Can’t face work? Then cultivate some side projects — and channel your work-avoidance into fun opportunities to learn” and once you’re done, you’ll 1) have something productive to show for it, and 2) be much more fit, rested, and ready to tackle that project at work. In other words: rather than fight your penchant for procrastination, work with it. It’s a judo move: don’t fight your enemy, use its momentum against it for your benefit.
·blog.jim-nielsen.com·
Productive Procrastination
The most hated workplace software on the planet
The most hated workplace software on the planet
LinkedIn, Reddit, and Blind abound with enraged job applicants and employees sharing tales of how difficult it is to book paid leave, how Kafkaesque it is to file an expense, how nerve-racking it is to close out a project. "I simply hate Workday. Fuck them and those who insist on using it for recruitment," one Reddit user wrote. "Everything is non-intuitive, so even the simplest tasks leave me scratching my head," wrote another. "Keeping notes on index cards would be more effective." Every HR professional and hiring manager I spoke with — whose lives are supposedly made easier by Workday — described Workday with a sense of cosmic exasperation.
If candidates hate Workday, if employees hate Workday, if HR people and managers processing and assessing those candidates and employees through Workday hate Workday — if Workday is the most annoying part of so many workers' workdays — how is Workday everywhere? How did a software provider so widely loathed become a mainstay of the modern workplace?
This is a saying in systems thinking: The purpose of a system is what it does (POSIWID), not what it fails to do. And the reality is that what Workday — and its many despised competitors — does for organizations is far more important than the anguish it causes everyone else.
In 1988, PeopleSoft, backed by IBM, built the first fully fledged Human Resources Information System. In 2004, Oracle acquired PeopleSoft for $10.3 billion. One of its founders, David Duffield, then started a new company that upgraded PeopleSoft's model to near limitless cloud-based storage — giving birth to Workday, the intractable nepo baby of HR software.
Workday is indifferent to our suffering in a job hunt, because we aren't Workday's clients, companies are. And these companies — from AT&T to Bank of America to Teladoc — have little incentive to care about your application experience, because if you didn't get the job, you're not their responsibility. For a company hiring and onboarding on a global scale, it is simply easier to screen fewer candidates if the result is still a single hire.
A search on a job board can return hundreds of listings for in-house Workday consultants: IT and engineering professionals hired to fix the software promising to fix processes.
For recruiters, Workday also lacks basic user-interface flexibility. When you promise ease-of-use and simplicity, you must deliver on the most basic user interactions. And yet: Sometimes searching for a candidate, or locating a candidate's status feels impossible. This happens outside of recruiting, too, where locating or attaching a boss's email to approve an expense sheet is complicated by the process, not streamlined. Bureaucratic hell is always about one person's ease coming at the cost of someone else's frustration, time wasted, and busy work. Workday makes no exceptions.
Workday touts its ability to track employee performance by collecting data and marking results, but it is employees who must spend time inputting this data. A creative director at a Fortune 500 company told me how in less than two years his company went "from annual reviews to twice-annual reviews to quarterly reviews to quarterly reviews plus separate twice-annual reviews." At each interval higher-ups pressed HR for more data, because they wanted what they'd paid for with Workday: more work product. With a press of a button, HR could provide that, but the entire company suffered thousands more hours of busy work. Automation made it too easy to do too much. (Workday's "customers choose the frequency at which they conduct reviews, not Workday," said the spokesperson.)
At the scale of a large company, this is simply too much work to expect a few people to do and far too user-specific to expect automation to handle well. It's why Workday can be the worst while still allowing that Paychex is the worst, Paycom is the worst, Paycor is the worst, and Dayforce is the worst. "HR software sucking" is a big tent.
Workday finds itself between enshittification steps two and three. The platform once made things faster, simpler for workers. But today it abuses workers by cutting corners on job-application and reimbursement procedures. In the process, it provides the value of a one-stop HR shop to its paying customers. It seems it's only a matter of time before Workday and its competitors try to split the difference and cut those same corners with the accounts that pay their bills.
Workday reveals what's important to the people who run Fortune 500 companies: easily and conveniently distributing busy work across large workforces. This is done with the arbitrary and perfunctory performance of work tasks (like excessive reviews) and with the throttling of momentum by making finance and HR tasks difficult. If your expenses and reimbursements are difficult to file, that's OK, because the people above you don't actually care if you get reimbursed. If it takes applicants 128% longer to apply, the people who implemented Workday don't really care. Throttling applicants is perhaps not intentional, but it's good for the company.
·businessinsider.com·
The most hated workplace software on the planet
How Perplexity builds product
How Perplexity builds product
inside look at how Perplexity builds product—which to me feels like what the future of product development will look like for many companies:AI-first: They’ve been asking AI questions about every step of the company-building process, including “How do I launch a product?” Employees are encouraged to ask AI before bothering colleagues.Organized like slime mold: They optimize for minimizing coordination costs by parallelizing as much of each project as possible.Small teams: Their typical team is two to three people. Their AI-generated (highly rated) podcast was built and is run by just one person.Few managers: They hire self-driven ICs and actively avoid hiring people who are strongest at guiding other people’s work.A prediction for the future: Johnny said, “If I had to guess, technical PMs or engineers with product taste will become the most valuable people at a company over time.”
Typical projects we work on only have one or two people on it. The hardest projects have three or four people, max. For example, our podcast is built by one person end to end. He’s a brand designer, but he does audio engineering and he’s doing all kinds of research to figure out how to build the most interactive and interesting podcast. I don’t think a PM has stepped into that process at any point.
We leverage product management most when there’s a really difficult decision that branches into many directions, and for more involved projects.
The hardest, and most important, part of the PM’s job is having taste around use cases. With AI, there are way too many possible use cases that you could work on. So the PM has to step in and make a branching qualitative decision based on the data, user research, and so on.
a big problem with AI is how you prioritize between more productivity-based use cases versus the engaging chatbot-type use cases.
we look foremost for flexibility and initiative. The ability to build constructively in a limited-resource environment (potentially having to wear several hats) is the most important to us.
We look for strong ICs with clear quantitative impacts on users rather than within their company. If I see the terms “Agile expert” or “scrum master” in the resume, it’s probably not going to be a great fit.
My goal is to structure teams around minimizing “coordination headwind,” as described by Alex Komoroske in this deck on seeing organizations as slime mold. The rough idea is that coordination costs (caused by uncertainty and disagreements) increase with scale, and adding managers doesn’t improve things. People’s incentives become misaligned. People tend to lie to their manager, who lies to their manager. And if you want to talk to someone in another part of the org, you have to go up two levels and down two levels, asking everyone along the way.
Instead, what you want to do is keep the overall goals aligned, and parallelize projects that point toward this goal by sharing reusable guides and processes.
Perplexity has existed for less than two years, and things are changing so quickly in AI that it’s hard to commit beyond that. We create quarterly plans. Within quarters, we try to keep plans stable within a product roadmap. The roadmap has a few large projects that everyone is aware of, along with small tasks that we shift around as priorities change.
Each week we have a kickoff meeting where everyone sets high-level expectations for their week. We have a culture of setting 75% weekly goals: everyone identifies their top priority for the week and tries to hit 75% of that by the end of the week. Just a few bullet points to make sure priorities are clear during the week.
All objectives are measurable, either in terms of quantifiable thresholds or Boolean “was X completed or not.” Our objectives are very aggressive, and often at the end of the quarter we only end up completing 70% in one direction or another. The remaining 30% helps identify gaps in prioritization and staffing.
At the beginning of each project, there is a quick kickoff for alignment, and afterward, iteration occurs in an asynchronous fashion, without constraints or review processes. When individuals feel ready for feedback on designs, implementation, or final product, they share it in Slack, and other members of the team give honest and constructive feedback. Iteration happens organically as needed, and the product doesn’t get launched until it gains internal traction via dogfooding.
all teams share common top-level metrics while A/B testing within their layer of the stack. Because the product can shift so quickly, we want to avoid political issues where anyone’s identity is bound to any given component of the product.
We’ve found that when teams don’t have a PM, team members take on the PM responsibilities, like adjusting scope, making user-facing decisions, and trusting their own taste.
What’s your primary tool for task management, and bug tracking?Linear. For AI products, the line between tasks, bugs, and projects becomes blurred, but we’ve found many concepts in Linear, like Leads, Triage, Sizing, etc., to be extremely important. A favorite feature of mine is auto-archiving—if a task hasn’t been mentioned in a while, chances are it’s not actually important.The primary tool we use to store sources of truth like roadmaps and milestone planning is Notion. We use Notion during development for design docs and RFCs, and afterward for documentation, postmortems, and historical records. Putting thoughts on paper (documenting chain-of-thought) leads to much clearer decision-making, and makes it easier to align async and avoid meetings.Unwrap.ai is a tool we’ve also recently introduced to consolidate, document, and quantify qualitative feedback. Because of the nature of AI, many issues are not always deterministic enough to classify as bugs. Unwrap groups individual pieces of feedback into more concrete themes and areas of improvement.
High-level objectives and directions come top-down, but a large amount of new ideas are floated bottom-up. We believe strongly that engineering and design should have ownership over ideas and details, especially for an AI product where the constraints are not known until ideas are turned into code and mock-ups.
Big challenges today revolve around scaling from our current size to the next level, both on the hiring side and in execution and planning. We don’t want to lose our core identity of working in a very flat and collaborative environment. Even small decisions, like how to organize Slack and Linear, can be tough to scale. Trying to stay transparent and scale the number of channels and projects without causing notifications to explode is something we’re currently trying to figure out.
·lennysnewsletter.com·
How Perplexity builds product
Accepting Your Potential with ADHD - everyonehasamnesia on Tumblr
Accepting Your Potential with ADHD - everyonehasamnesia on Tumblr
I was so used to hearing from teachers and family that if I just didn’t procrastinate and worked all the time, I could do anything! I had all this potential I wasn’t living up to! And that’s true, as far as it goes, but that’s like saying if Usain Bolt just kept going he could be the fastest marathon runner in the world. Why does he stop at the end of the race??
Now, I’ve found that I do need to work on not procrastinating. Not because the product is better, even, but because it’s better for my mental health and physical health to not have a full, sweating, panicked breakdown over every task even if the task itself turns out excellently. It’s a shitty way to live! You feel bad ALL the time! And I don’t deserve to live like that anymore.
I don’t have an ocean of productivity and accomplishments inside of me that I could easily, effortlessly access if I just sat down 8 hours a day and worked. There’s no fucking way. That’s not real. It’s an illusion. It’s fine not to live up to an illusion.
·tumblr.com·
Accepting Your Potential with ADHD - everyonehasamnesia on Tumblr
Yes! And...
Yes! And...
Missed context - Because you’re not a full-time employee (even if you’re working 5 days a week) you may not be included on all-hands emails, announcements and so on and so you always have to work hard to gain the full context of a client. Tightly scripting a performance doesn’t leave room for new contexts to emerge during the performance. Instead there should always be room for new context to emerge and get integrated into the performance in real-time. Missed feedback - It’s not uncommon as a consultant to be the most proficient powerpoint user in the org (or at least your portion of the org). This has benefits but it also has the unintended consequence of making everything you touch look “finished”. And finished work gets very different feedback from people than raw materials and thinking. So sometimes it’s important to un-design and un-polish your work, to invite people onto the stage to co-create the performance - this way you ensure that you get the appropriate feedback.
“thinking on your feet” is about the balance between deflecting decisions for further analysis and providing the answer there and then.
learning to provide an answer that you believe in but leaves room for revision later is key. The real game that’s being played here is not one of being right or wrong - it’s the executive asking two questions at once - firstly “how much do you know?” and secondly “can you improv?” to understand how useful you’re going to be in the theatre of work.
There’s a fine line between reacting to a situation in the room and bullshitting. As a consultant this is especially hard to avoid. Your default mode of operating is the liminal space between industries, businesses and markets. A few times a year I’m forced to learn something new from scratch. This forces us to work in spaces where we’re often the least knowledgeable about a specific business (even if we are experts in the industry… And sometimes we’re experts at a discipline but neither knowledgeable about the business or the industry).
·tomcritchlow.com·
Yes! And...
101 Additional Advices
101 Additional Advices
Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.
Try to define yourself by what you love and embrace, rather than what you hate and refuse.
Where you live—what city, what country—has more impact on your well being than any other factor. Where you live is one of the few things in your life you can choose and change.
Once a month take a different route home, enter your house by a different door, and sit in a different chair at dinner. No ruts.
Every now and then throw a memorable party. The price will be steep, but long afterwards you will remember the party, whereas you won’t remember how much is in your checking account.
Most arguments are not really about the argument, so most arguments can’t be won by arguing.
invent your own definition of success. Shoot your arrows first and then paint a bull’s eye around where they land. You’re the winner!
There should be at least one thing in your life you enjoy despite being no good at it. This is your play time, which will keep you young. Never apologize for it.
You have 5 minutes to act on a new idea before it disappears from your mind.
The patience you need for big things, is developed by your patience with the little things.
When you are stuck or overwhelmed, focus on the smallest possible thing that moves your project forward.
For steady satisfaction, work on improving your worst days, rather than your best days.
Your decisions will become wiser when you consider these three words: “…and then what?” for each choice.
If possible, every room should be constructed to provide light from two sides.  Rooms with light from only one side are used less often, so when you have a choice, go with light from two sides.
There is a profound difference between thinking less of yourself (not useful), and thinking of yourself less (better).
Always ask yourself: what would change my mind?
Becoming one-of-a-kind is not a solo job. Paradoxically you need everyone else in the world to help make you unique.
If you need emergency help from a bystander, command them what to do. By giving them an assignment, you transform them from bewildered bystander to a responsible assistant.
The most common mistake we make is to do a great job on an unimportant task.
Don’t work for a company you would not invest money in, because when you are working you are investing the most valuable thing you have: your time.
Fail forward. Failing is not a disgrace if you keep failing better.
Do not cling to a mistake just because you spent a lot of time making it.
For small tasks the best way to get ready is to do it immediately.
What others want from you is mostly to be seen. Let others know you see them.
When you try something new, don’t think of it as a matter of success / failure, but as success / learning to succeed.
use your honesty as a gift not as a weapon. Your honesty should benefit others.
A good sign that you are doing the kind of work you should be doing is that you enjoy the tedious parts that other people find tortuous.
Celebrating the success of others costs you nothing, and increases the happiness of everyone, including you.
To tell a good story, you must reveal a surprise; otherwise it is just a report.
a long horizon allows you to compound small advances into quite large achievements.
Often ideas are rejected because of the tone of voice they are wrapped in. Humility covers many blemishes.
When you are right, you are learning nothing.
Very small things accumulate until they define your larger life. Carefully choose your everyday things.
If you are impressed with someone’s work, you should tell them, but even better, tell their boss.
Humility is mostly about being very honest about how much you owe to luck.
·kk.org·
101 Additional Advices
Flow state - Why fragmented thinking is worse than any interruption
Flow state - Why fragmented thinking is worse than any interruption
Both arts and athletics involve a lot of deft physical movement, and I could see why professionals in those fields would benefit from learning to resist overthinking so they can “just do it.”  Almost every profession involves some need for focus, however, so you can see why, over time, the idea of a flow state breached its original limits. Now, “flow state” has all sorts of associations—some scientific, some folk, and some a mix of both. For many, the term has just become a dressed-up version of focusing.
A 2023 study found, for example, that there is a huge range of barriers to flow—many of which aren’t just interruptions from coworkers. They categorized these as situational barriers, such as interruptions and distractions; personal barriers, such as the work being too challenging or not challenging enough; and interpersonal barriers, such as poor management and poor team dynamics.
A 2018 study found, in addition, that the most disruptive interruptions aren’t external—they’re internal. 81% of the participants predicted internal interruptions would be worse, but they were wrong. “Self-interruptions,” the researchers wrote, “make task switching and interruptions more disruptive by negatively impacting the length of the suspension period and the number of nested interruptions.”
But because no one literally interrupted your work, you might be unaware of the costs of that rote, mundane work. You might even castigate yourself over the day for not getting the work done: You fought for a distraction-free day, got it, and you have nothing to show for it. It can feel bad.
a seemingly individual problem, staying focused, is often downstream from an organizational problem.
·blog.stackblitz.com·
Flow state - Why fragmented thinking is worse than any interruption
Seeking Calmness: Stop Drifting
Seeking Calmness: Stop Drifting
I think a lot of folks feel like you should be doing these certain things like writing the great American novel or reading the 100 Greatest Movies of All-Time when in actuality these are achievements that have no real guarantee of happiness. Unless you are truly enjoying those journeys, there is no reason to set upon them.
I don't think there is anything wrong with having hopes and dreams, but I do feel that maybe we allow those things to be excuses for not living a content life. I also think at times we hold onto old dreams that no longer serve us, instead of focusing on something new and more applicable to your current situation.
adulthood wasn't full of Ferraris and mansions, and I found out rather quickly that I wasn't going to save anyone, because I was struggling to save myself.
·brandonwrites.xyz·
Seeking Calmness: Stop Drifting
Don’t Give Advice, Be Useful
Don’t Give Advice, Be Useful
on being a good consultant and advisor
resist the urge to add immediate value. Instead we have to hold space for a more vulnerable, honest and open relationship with our client - to allow them to open up more fully and to work on things that are useful, even if not in scope.
While giving advice can help you be seen as knowledgeable, it doesn’t necessarily build trust.
“You should…” It’s a simple sounding phrase but it gets you in trouble more often than not. It’s problematic for two reasons: it assumes a control of client resources and it’s too prescriptive in form
We typically don’t have a complete view of everything that the company is working on, we don’t have a detailed understanding of how long things actually take or the full range of dependencies required for them.
Example: working with a client where I wanted to re-design a landing page on their site to improve it. Unfortunately I was under-estimating the number of people who need to be involved since the landing pages were still owned by the product team and are technically part of the same codebase as the full tech product. So a “small” change required detailed security scrutiny and QA before going live. Making “simple” changes was not in fact simple at all here.
Example: working with the NYTimes cooking team I suggested that they should re-tag their content. This kind of “you should…” recommendation seemed straightforward but neglected the political considerations - the team had just spent 6-figures on re-tagging all their recipes - so to ask for further budget to re-do a task they had just done would lose them face internally. A “straightforward” change that actually carried a bunch of political baggage.
Some other types of complexity that you might be under-estimating with regards resource allocation: Regulation/compliance complexity - which either prevents you even doing your recommendation or makes it slower. Technical complexity - while something might be technically easy, doing it with the client’s existing technology might be hard. Data complexity - a simple seeming request on the surface (make a landing page for every neighborhood) might actually depend on a robust, maintained data set that doesn’t yet exist. Maintenance complexity - even if the initial request to create something or do something is not resource intensive, it might come with an implicit agreement to continue to maintain it - expanding the resources allocated. Production complexity - where what you’re proposing isn’t that expensive or resource intensive to do, but the client (for whatever reason) has a higher quality threshold, making the recommendation more expensive/slower/harder than you anticipated. Narrative complexity - where what you’re recommending seems reasonable but either the company has tried it before, or a competitor has tried it before or there’s a general sense that “this doesn’t work”. Which can make your recommendation extremely hard to actually get done.
When we say “You should…” we’re essentially offering a problem diagnosis AND a solution at the same time. The consequence of this is that we’re essentially asking the client to accept or reject both together.
most of your work would be more effective at actually changing clients if you stopped to clearly separate the diagnosis from the solution.
if you’re asking “You should…” to the client, stop and examine if you’ve properly defined the situation and provided evidence for the problem, to help the client deeply internalize the problem and win over the necessary stakeholders before you propose any kind of solution.
A good mental exercise to ensure you’re doing the work here is to ask yourself: what happens if the client takes no action? What is the consequence of the current trajectory, or the null case of no investment?
By showing what’s possible, clients are able to feel more invested in designing the solution with you, rather than just being told what to do.
clients deeply appreciate you clearly separating out expert opinion and judgment from evidence-based analysis.
A good process for the advisor to follow is: Give them their options Give them an education about their options (including enough discussion for them to consider each option in depth) Give them a recommendation Let them choose
Taking a collaborative stance with your client is powerful. There are many aspects of consulting that are almost combative by nature - like pointing out problems the client has (that the client was complicit in creating!).
I find in my own work that senior executives are often blocked by some inability to see what’s actually going on - and that telling them is useless! Instead you need to help them see it for themselves.
Because of their distance from the day to day work, senior executives are especially prone to replacing some version of reality with a compressed narrative. And when this compressed narrative is wrong in some key way you need to return to first principles to show them (not tell them!).
Your sense of “what’s going on” with a client is intermediated by your point of contact and it turns out that your client is an unreliable narrator.
When a client comes to you asking for a “content strategy” or support “hiring a VP marketing” it all seems so straightforward, rational and well defined. But as you unpack the layers of the onion you begin to realize why it’s been so hard for the client to help themselves. And that’s when the emotional and political complexity of the problem starts to come into view.
if the work is done effectively, it requires that the consultant be both involved enough in the dynamics so as to experience their impact and detached enough so as to analyze what is transpiring. These demands make imperative the use of oneself as tool.
always work on the next most useful thing. This mantra helps remind me that consulting isn’t about being right, it’s about being useful.
I delivered what I think is good quality work with a deeply researched and evidence-based 66-page strategy for producing content and…. Nothing happened? They were happy enough with the work product but it didn’t lead to any material change in their strategy or an ongoing consulting relationship. In hindsight the key mistake here was not asking myself enough what the next most useful thing was. I think if I’d been more honest about what would add value and show momentum for the client it would have been either a) condensed one or two slide summary of the content opportunity for their fundraising deck and/or b) supporting their VP marketing recruitment effort.
Either you’re telling the client “draw some circles” and the client is frustrated the advice is too basic and high level. Or you’re telling the client to “draw the rest of the fucking owl” and are ignoring the detailed reality of the situation and the limitations of teams, resources and capabilities.
Or worse, the client asked you for help drawing owls but what they’re really doing is painting a woodland scene…
Think about this image next time a client comes to you for help drawing owls - your first response shouldn’t be “Oh, that’s easy, first you draw some circles”, it should be “Show me how your owls look today. What do you think is holding you back from drawing better owls? And why is drawing owls important to you right now?”
Remember - it’s about adopting a collaborative, trusted stance with clients. And that might require resisting your initial urge to give advice. Instead you need to listen to the full emotional and political situation and then work with the client to re-examine reality in new and surprising ways. Always work on the next most useful thing. And that doesn’t always involve doing what the client asked for.
·tomcritchlow.com·
Don’t Give Advice, Be Useful