Plan Your Skip Move, Not Your Next Move

TL;DR

• In a stable market, optimise for your next role. In an exponential market, optimise for the role two hops away, because the next one is a stepping stone whose shape you cannot forecast.
• The skip-move framing makes lateral or downward title changes rational, when they'd look irrational under a next-move framing. The 2026 career ladder rewards skill-stack recency, not title continuity.
• I took the skip-move bet myself: CPO scope to solo builder to a senior manager role, trading title stability for skill-stack relevance. The math only works if you measure on the job after next.

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Career advice is built around a simple optimisation: what role do I take next, and will it make me more valuable for the one after? The unspoken assumption in that advice is that the market you're optimising for in five years looks like the market you're optimising for today. Stable markets let you think one move ahead, because the role two moves ahead will resemble the first one.

AI-era markets do not stay still long enough for that to work. The role two moves ahead in 2026 is not a bigger version of the role one move ahead. It is a different role, shaped by tools and operating models that barely exist yet, in organisations that have not yet been designed. Optimising for the visible next job, the way traditional career advice suggests, systematically under-serves the invisible job after.

The fix is a reframe: stop planning your next move, and plan your skip move.

Why the skip frame works when the next frame doesn't

The standard career planning exercise looks like this: I'm a Senior PM now. The next rung is Principal or Group PM. I'll take the role that best positions me for that rung. I'll optimise for visibility, scope, and proximity to the promotion decision-makers.

That exercise is sound when the Principal or Group PM job will look recognisably like the job senior PMs currently below them are climbing toward. It breaks when the shape of the Principal PM role is itself changing. In 2026, the Principal PM role in a leading AI-native company doesn't look like the Principal PM role at a big-tech incumbent from 2022. Same title, different work, different skill requirements, different compensation band.

If you plan your next move against the 2022 version of the role, you end up positioned well for a job that is being quietly retired. If you plan your next move against the 2028 version of the Principal PM role, which is the one that actually matters for your career, you have to reach further out, and the shape of that role is harder to see with single-step thinking.

The skip frame forces a different question: what will the 2029 version of the senior role I want look like, and what move today actually positions me for it? The answer is often surprising. It's often not the next-rung promotion. It's often a sideways move into a company operating at the frontier. Sometimes it's a title cut to a role with materially more hands-on work. Occasionally it's leaving the ladder entirely for eighteen months to build something.

None of these decisions look rational under next-move framing. All of them can look rational under skip-move framing.

The moves that only make sense as skip moves

Four patterns I've watched operate this way in the last two years:

The title cut for the tool stack. A senior PM at a 2,000-person company takes an IC role at a 30-person AI-native startup. The title drops two levels. The compensation drops maybe 20%. The scope drops from managing multiple products to owning one feature area. Under next-move planning, this move is self-sabotaging. Under skip-move planning, it's the only move that rebuilds the skill stack against the 2028 version of the senior PM role. Eighteen months later, that operator interviews as a peer to Principals and Directors at frontier companies who were hired externally at twice the previous comp.

The regressive-looking founder pivot. A Group PM leaves a great job to build something that doesn't work. Twelve months later, they've shut down the project and are looking for a next role. On paper, a lost year. In practice, a year of skill-stack reconstruction (shipping, evals, tool fluency, unit-economics reasoning) that the next company values more than the Group PM resume line it replaced. The skip move was always to frontier builder skill, not to another Group PM seat.

The lateral into a strategic dead-end. A VP takes a role running an AI-native team that isn't yet connected to the core business. It's smaller than their previous VP role. It looks like a lateral at best, a demotion at worst. Eighteen months later, when the AI-native work becomes the core business, that VP is the one running the company's most important function, and every peer who stayed in the bigger-looking job is being reorged under them.

The out-of-industry reset. An enterprise SaaS PM takes a role at a property tech, legaltech, or healthcare company they know nothing about. The vertical pivot is dismissed by peers ("you're going backwards into a small market"). Two years later, they have domain depth plus AI-native skills, a combination that is absurdly scarce and absurdly well-compensated. The skip move was always to domain-plus-AI, and the next move looked lateral.

In every pattern, the move that looked regressive under single-step planning was the one that moved the operator closest to the skip role. The ones who passed on the move, because their current employer counter-offered or because their spouse or board disapproved or because their ego defended the title they held, ended up with rising compensation for a declining skill stack.

My own skip-move bet

I took this bet in the last two years and I'm still in the middle of it, so the ledger isn't closed. The shape of the bet is worth describing anyway.

My previous seat, Director of Product at Cotality, was a strong role by most measures: eight products, thousands of enterprise seats across Tier 1 banks, a $70M P&L, clear promotion path to CPO or VP. Under next-move planning, the rational play was to keep accumulating scope, move to CPO internally or at a comparable enterprise, and compound the seniority.

I left instead to build two AI-native vertical SaaS products as a solo operator. On paper, that's a drop in title from Director to founder-who-is-also-everyone, with no compensation guarantee. The reasons I published at the time were framed around building real things rather than strategising about them. The underlying career bet was skip-move thinking: the role I actually want in 2028 is one where AI product leadership means shipping AI products, and the fastest way to rebuild the skill stack against that role is to do the shipping myself.

The next step I'm making now, toward a Senior Manager AI role, also looks lateral or regressive under old framing. The title is one step down from where I was. The scope is more focused. The company is mid-market, not enterprise. Under next-move planning, none of that is obviously optimal. Under skip-move planning, the combination (hands-on AI work, smaller scope I can influence end-to-end, an AI-native mandate) is what positions me for the CPO or VP role I'd actually want to hold in the 2028 market, not the 2022 one.

The bet might not pay off. Skip moves don't come with guarantees. But the career outcome I'd regret most is having spent 2024–2026 accumulating scope in a role whose value the market was actively repricing down. Measured against the job after next, the skip-frame decisions look obvious. Measured against the job next, they look strange.

How to actually run the exercise

The skip-move frame isn't hard to apply. It's hard to believe.

Three practical steps:

Describe the role you'd want in 2029, in enough detail that you could interview for it. Not the title. The daily work. The tools you'd use. The skill stack the hiring manager would test you against. The kind of company that would be hiring for it. If you can't describe the work concretely, the skip frame won't work, and you need to spend time in frontier companies until you can.

Audit the skill delta between your current stack and the 2029 role. Honest audit. Most senior operators discover the delta is larger than they'd admit. The gap usually spans three dimensions: tool fluency, domain depth, and operating-model fluency (shipping cycles, eval practice, cost reasoning, team composition). The delta is the brief for the skip move.

Identify the next move that closes the biggest chunk of the delta. Often this isn't the next-rung promotion at your current company. Often it's a sideways or downward move that puts you inside the operating model of the 2029 role. The promotion at your current employer might feel irresistible. That's the signal to look at it carefully, because the promotion is the move that optimises for your current track, and the skip move usually requires stepping off it.

The exercise is easy to describe and hard to execute because everyone around you is running next-move planning. Your manager wants you to take the next promotion because it benefits their team. Your recruiter wants you to take the higher title because it's easier to sell. Your family wants the stable compensation curve. Skip-move thinking is structurally countercultural inside the systems that reward next-move thinking. That is exactly why the move that results from it is usually high-return: the market is under-pricing it because most people can't bring themselves to make it.

The risk profile

Skip moves carry more downside than next moves on average. That's the whole point. The higher variance is precisely why the expected value is higher, once you weight for the tail where the next-move strategy leaves you stranded on a declining skill stack.

Two risks worth naming:

The move that looked like a skip move was actually just a bad lateral. Some sideways moves reset your career without rebuilding your skill stack. The diagnostic: does the new role actually put you in the operating model of the role two hops away? If yes, it's a skip move. If no, it's a lateral for lateral's sake and the career cost is real. The audit-the-delta step exists specifically to avoid this failure mode.

The forecast for 2029 turns out to be wrong. Markets surprise. The AI trajectory could stall, plateau, or bend in a direction no one predicted. If that happens, the traditional-career operators will come out ahead, and the skip-move operators will have spent years building for a version of the market that didn't arrive. This is a real risk, and I don't have a satisfying answer for it. The partial answer is that even a wrong-forecast skip move usually rebuilds judgment and taste that compound in any market, while a right-forecast next move only pays off if the forecast holds.

The choice is ultimately between taking larger bets on a clearer long-horizon view versus taking smaller bets on a clearer short-horizon view. In slow markets, the second strategy dominates. In fast markets, it usually doesn't. The last eighteen months of AI-market repricing have been fast enough to bend the tradeoff noticeably toward the first.

The question to ask your 2029 self

Career decisions compound more than people realise. A single decision to stay in a comfortable role for an extra eighteen months can be the decision that closes off the skip role entirely, because by the time you leave, the next wave of operators has already filled it from the companies building the skill stack you delayed acquiring.

The practical discipline is to check every major decision against a simple question: will your 2029 self thank you for this move, or will your 2029 self wish you'd taken the harder one?

Most of the time, the harder move is the skip move. The next move is the one your 2026 self prefers. The skip move is the one your 2029 self needs you to make.

Ship something soon and become the builder version of yourself. Those are the two most reliable skip moves in the current market. Neither of them looks rational if you're planning your next move. Both of them look obvious if you're planning the one after.

Frequently Asked Questions

Isn't this just "take a risk" dressed up as a framework?

No. The skip-move frame is a specific decision rule: evaluate career moves against the role two hops away rather than the one hop away. The rule doesn't tell you to take bigger risks; it tells you to use a longer-horizon reference point, which often (but not always) makes a higher-variance move the rational one. Some skip moves are low-risk. Some next moves are high-risk. The frame just changes what you're optimising against.

How long a horizon is a "skip move"?

Depends on market speed. In AI product work in 2026, two hops ahead is roughly 3–5 years. In slower-moving industries, it could be 7–10. The test is whether the shape of the role two hops ahead is already diverging from the shape of the role one hop ahead; if yes, the skip frame is needed, if no, next-move planning still works.

Doesn't this justify every bad career decision as "a skip move"?

It can, if you let it. The discipline is in the audit: does the move actually put you inside the operating model of the role you're aiming for? If it doesn't, it's not a skip move, it's just a lateral move dressed up in framework language. The two failure modes are staying put when you should have moved, and moving for motion's sake. The frame is designed to correct the first. It requires honesty to avoid the second.

What if my current role actually is the skip move?

Then you're one of the lucky ones, and the planning exercise just confirmed it. A subset of current roles, especially roles at frontier AI companies with daily hands-on work, are already positioned for the 2029 market. If the audit shows your current role closes most of the skill delta, stay. The skip frame is about identifying when to move, not about moving for its own sake.

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Related: The Skills That Got You Promoted Are the Ones Making You Obsolete and Stop Reading About AI. Start Shipping With It.