The Skip: Career as a Product
Plan for the job after next, not the next job — and treat promotion as a means, not the goal.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 5
- Confidence
- 94%
Nikhyl Singhal argues most career decisions are made from short-term irritation (bad boss, slow shipping) which produces lateral moves that feel like progress but aren't. Instead, treat your career the way you'd treat a product: define the end state, then reverse-engineer the versions. The unit of planning is 'the skip' — not your next job or your boss's job, but the job two steps out, your boss's boss's job. Every current decision gets evaluated as being in service of that.
Origin
Singhal's own framing, developed across ~15 years of coaching hundreds of PMs and CPOs through 'forks in the road'; it is the reason he named his newsletter and podcast 'The Skip'.
Core principles
- 01Lateral moves are by definition not forward moves — the complaints that drive them exist at nearly every company.
- 02A career is a product: define the great version first, then break it into v1, v2, v3.
- 03Promotion is a company's internal system for recognising forward motion; it is short-term and should be in service of the long-term arc, not the arc itself.
- 04Diversity of experience (pre-PMF, smoke-to-fire, fire-to-scale; inside-the-building and outside-the-building problems; consumer and B2B) makes you a better builder than logo collection does.
- 05Chasing brand-name logos as a bet on the next job — rather than as a source of building experience — leads to sadness.
How to run it
- 1
Name the end state
Write down what a 'great product' version of your career looks like at the end — found a company, run product at scale, become a domain authority. Be concrete enough that you could describe it to someone else.
Pro tip If your only stated goal is a title or a number, it's a rabbit, not an end state — see the Act Three / North Star framework.
- 2
Identify the skip job, not the next job
Work backwards one level past the obvious. Not your boss's job — your boss's boss's job. Not the next role — the one after it. Name that role explicitly.
- 3
Test every current option against the skip job
For any decision (stay, move, take a project), ask: does this build the experiences and story the skip job requires? Frequently the answer is 'grind it out and stay' — learning to deal with ambiguity is often the missing input.
Watch out A move driven by 'I dislike my boss' or 'it's too hard to ship here' is a short-term filter. Those statements are usually true at the destination too.
- 4
Reframe promotion as a subordinate question
When you want a career conversation, don't collapse it into 'how do I get promoted in 18 months instead of 24'. Ask instead what the promotion is in service of. If the honest answer is 'so I can leave', the real conversation is about the skip job.
Pro tip Useful diagnostic question to ask yourself or a report: 'the promotion is in service of what?'
- 5
Deliberately collect diverse building experiences
Sequence roles so you see the whole movie in different frames: pre-product-market-fit, smoke turning into fire, and fire turned into something great. Mix inside-the-building (organizational) problems with outside-the-building (market) problems, and consumer with B2B.
Pro tip For executive roles specifically, having operated at a company that has already scaled to millions or billions of users is a real endorsement — it's very hard to be hired to take a company to a phase you've never lived through.
In the wild
Someone tells Singhal they eventually want to found a company. Rather than optimising their next move for title or comp, he has them treat founding as the skip job, then ask what the current job and the next job must teach in service of it — which often means staying put and learning to operate through ambiguity rather than leaving for a cleaner-looking role.
→ The decision flips from 'leave because this is frustrating' to 'stay because the frustration is the curriculum'.
Singhal repeatedly meets people who say 'as soon as I get promoted, I'm going to leave.' He responds by asking what the promotion is in service of, which reveals the conversation was never about promotion at all.
→ The discussion converts from a short-term levelling negotiation into a long-term career arc conversation.
Common mistakes
Confusing career with promotion
Promotion is a company-specific, short-horizon system with levels, processes and decision makers. Treating it as the career goal produces impatient, company-shaped decisions instead of arc-shaped ones.
Logo collection as strategy
Accumulating famous employers because you think it improves your odds at the next job is 'in service of some future dream that is not build oriented' — it feels shallow to builders and correlates with unhappiness.
Moving on a push, not a pull
Leaving because of a bad manager or slow shipping is a lateral move dressed as progress; those conditions are present at most destinations.
Is it for you?
Best for
Individual contributors and mid-career operators (especially PMs) who feel stuck, are weighing an offer, or keep optimising for the next promotion without a longer arc
Not ideal for
Someone in genuine crisis — a toxic or unsafe environment, or an ex-growth company where the opportunity cost is already compounding — where exiting fast beats arc-planning
From the transcript
“lateral moves are by definition not forward moves”
“work backwards from your end State almost think of career as a product”
“not the next job but the one after it maybe think about not your boss's job but your boss's boss's job”
“the more diverse career you have the better Builder you are”
From the episode
Building a long and meaningful career
Nikhyl Singhal (Meta, Google)