Don't Chase the Fake Rabbit: A Meta Product Leader's Guide to a 60-Year PM Career

Singhal, who says he coaches hundreds of people through career forks and takes a few "911 calls" every week, begins with the early-career mistake he sees most: short-term thinking. A disliked boss, a slow company or hard shipping conditions probably exist at most places you could move to, so lateral moves are by definition not forward moves. His remedy is to treat your career as a product and work backward from the end state.

That is why his newsletter and podcast are called The Skip: think about the job after next, or your boss's boss's job, and decide whether your current role serves it. If the aim is to found a company one day, staying put and learning to handle ambiguity may be the right call. He also sees people fuse career and promotion, asking how to speed a promotion by six months, when promotion is just the company's system for recognizing progress and should serve a longer arc.

Rachitsky asks about collecting prestigious logos. Singhal says label-chasing feels shallow to builders, and he prefers a diverse set of experiences: pre-product-market-fit, scaling, internal and external problems, consumer and B2B. For executives, though, big-tech experience matters, because companies hire them for expertise at scale. He prefers the term "MAGMA" to FAANG, and says that if you are brought in to take a company to the next level, you need to have seen that level before.

Singhal describes a decade of blitzscaling in which strong distribution platforms let companies grow in 18 months what once took ten years, producing a wave of unicorns. Then the music stopped when zero interest rates ended. He sees a pocket of heavily funded private companies that aren't laying off or raising but are still searching for their next product, while comparable public companies are worth 10% or less of their former value.

His fear is that many tech workers are joining or staying at these firms expecting equity payouts that won't come, and that boards will pull back this year. A company with 300 people and multi-billion-dollar expectations that is still seeking product-market fit, he says, is not going to get there. His test: are customers pulling you in with a "sucking sound", or are you still looking for it, and is the valuation in the hundreds of millions or more?

Founders can recap, reset or restart, but employees essentially have to start a new four-year investment. If half or more of your pay is equity that may be worthless, he asks, would you accept a half pay cut? He says pull is the clearest sign of product-market fit, citing OpenAI's pull even without massive revenue. Reasons to stay include a once-in-a-career executive role or genuine loyalty, but "fear of finding another job is a bad reason".

Asked for his top advice for early-career PMs, Singhal says to become world-class at one kind of product ambiguity as early as possible. He lists being a great crafter, handling market ambiguity, handling organizational ambiguity, being a domain expert (such as in ML or hardware), being a team expert who manages managers, and growth. A PM meets all of these, but should pick one lane.

The second goal is having a story for your next employer. In interviews he often hears candidates describe early jobs where things simply happened, and he wants to know what they learned and did. Borrowing from Amazon's press-release-first approach, he suggests thinking about the story and skill first, then planning your day-to-day and review cycles around it.

Singhal offers four common blockers. First, no one advocates for you, whether manager or promotion committee, in which case you may need a new project, manager or company. Second, the next role simply doesn't exist, which is more common now that hypergrowth hiring has stopped. Third, impatience, especially among high performers used to annual promotions who find that senior roles take longer to absorb because impact lags.

The fourth, which he says covers around half the cases, is a real development area. The manager may not see it, but the promotion committee does, and the person either refuses to hear it or says "this is who I am". Rachitsky summarizes the four and asks how someone can tell whether they are truly doing great or just unrecognized.

Singhal's answer is to get real feedback rather than formal feedback; at scaled companies the two often differ dramatically. That means strong listening skills, triangulating among people who see you often and rarely, and creating safety so no one fears retaliation. He praises Jules Walter for repeating feedback back better than the giver said it, and suggests managers publicly credit the person who gave them feedback, so others see it is rewarded.

Singhal says the biggest surprise future historians will find about early tech is how long the industry thought it was fine not to train managers. Being a good coder or PM does not mean you know how to teach others, which he likens to assuming that someone who can make a car knows how to build the factory. He says podcasts like Lenny's may be more meaningful than most L&D departments.

For first-time managers, he offers two points. One is to share the steering wheel: not divide and conquer, not teach-to-ride-a-bike and let go, but more like a motorcycle sidecar where you are attached and give counsel. The second is that organizational power is not earned authority, so you must be invited in like a vampire at the threshold.

Concretely, he asks a new report what he can help with, and if the answer is "I don't need you", he accepts it, since anything more would backfire. When they eventually need help he is in the sidecar, and once invited he picks one or two areas to partner on. The shared theme is invitation, specificity and shared responsibility.

On the senior IC path, Singhal says it is more acute now because management used to be the way to drive expansion, and with growth slowing there is less need for it. He calls the IC track "one of the best things" to happen to the industry, since many managers were promoted early without being taught. He imagines a hiring manager preferring an IC who has mastered a market or organizational ambiguity over someone who briefly managed two people.

He thinks the tracks are still "tender" and not yet set in cement, but expects them to solidify within six to nine months. Engineering and design already have this split, and he sees PM's lack of it as a long-standing bug. He hopes "builder" and "IC" will become synonymous, because many PMs look at their manager's job and see only docs and headcount justification.

To help new managers learn, he says training is weak and self-service is improving, but community is the answer: a safe, authentic place to share best practices. He built a CPO community, which began in the pandemic with about half a dozen people on WhatsApp and Zoom, and has grown to 28 members. He worries that scaling is the enemy of trust, so it remains for mid-to-late-stage product leaders.

For late-career leaders, Singhal borrows a phrase from a therapist, "the shadows of superpowers". What got you here isn't what gets you to the next level, and a strength used with the same tools can become a weakness. His example is a great collaborator who has collaborated as long as people agreed with them, but now struggles when asked to be opinionated with senior people outside their function.

He lists pairings such as growth experts who struggle to innovate, storytellers who avoid details, taste-makers who rarely introduce change, and great listeners who are weak at deciding. Sometimes in a 30-minute conversation he can guess a leader's development area because it is the shadow of their identity. You don't need a coach, he says, but you must listen to contradictory feedback and go through the "discard pile" of feedback you previously dismissed.

Singhal says his own superpower as an entrepreneur was making decisive calls from small amounts of information, and as an executive he had to hold opinions loosely and make sure everyone had context. He resisted at first, until he asked what if his critics were right, given he would work for 30 more years. A trusted peer's feedback was the linchpin.

Singhal says a story rarely told is that many people who have made it struggle with mental health, partly because it is a "luxury problem" that feels awkward to raise. He splits a career into acts: learning and building the car, building the factory, and then act three. With careers possibly lasting 60 years or more, someone 30 years in is only halfway, yet people often succeed and then become lost.

He tells the story of greyhound tracks in the Midwest, where dogs were motivated by a fake rabbit, and a dog that accidentally caught it would never run again because there was nothing next. Likewise, people fixate on becoming a VP or founding a company and don't plan what comes after. Without a new North Star, he warns, people may keep working with nothing else to do, create conflict, or fall into bad habits.

Rachitsky says he felt this after selling his startup to Airbnb, and Singhal calls his move into content creation a new North Star. He sees two broad categories: scaling economics, or giving, which Eastern philosophies treat as an end state of happiness. His own act three, he says, is coaching and lifting others, and making it scale authentically is "a product problem".

In the lightning round, Singhal recommends Crossing the Chasm by Geoffrey Moore and Leadership and Self-Deception, a short audio book about a person stuck in a box of their own mindset. He agrees with Rachitsky that product people should learn more from marketing, calling it the language of connecting products with people. His favorite interview question asks what conventional wisdom the candidate thinks is inaccurate, since it pulls people out of rehearsed answers.

His recent product pick is the Arc browser, and he enjoys seeing a smaller team innovate on a mature product. A small change that helped his team was treating the meeting operating system as a product: his team is on "version seven", revised every 90 days with feedback along the way. He says rebooting meetings is a good first move for new leaders because it works even with low context, and his order is process, then people, then product, then strategy.

For his final career tip, he says to make sure that the story you will tell about today's work is meaningful for your skip job. Write down what problem you solved, skill you built and headwind you faced, using "I" rather than "we". If the story is weak, change it. He points listeners to The Skip podcast and Substack newsletter, and to LinkedIn and Twitter for feedback.