The Skip Job Strategy
Plan two career moves ahead to position yourself for the role being built right now
The Skip Job Strategy reframes career planning around the 'skip job' — the role you want two moves from now, not one. Instead of asking 'what's the best job I can get today?' you ask 'what positions me for where this industry is heading?' In a period of rapid transformation like the current AI transition, this distinction is critical. The framework requires two disciplines: ego release — accepting lateral or smaller roles if they put you on the right trajectory — and long-term orientation — tolerating short-term sacrifice for skip-destination payoff. Named by Nikhyl Singhal, it became the organizing principle of his professional community 'The Skip.'
- The best career advice is always about the move after next, not the next move
- In periods of rapid change, title and level are poor proxies for long-term positioning
- Ego is the primary enemy of the skip — accepting smaller roles to reach the right future is a power move
- The cream rises once you are on the right boat — skills and leadership compound after the transition
- Pace and urgency matter in transition windows; treat this period like year one of a new relationship
- Staying current is more valuable than staying senior in a transforming field
- Map the 2–3 year industry trajectoryResearch where your field is heading: which roles are growing, which are contracting, and what skills will command premium compensation. Use hiring data, industry reports, and conversations with people already operating in that future.Pro tipLook for 'dandelion seed' roles — positions where people with broad judgment and strong communication are being seeded into new industries as change agents. These are often where skip jobs live.
- Define your skip job concretelyWrite a one-paragraph description of the role you want two career moves from now — not one. Include the type of company, scope of the role, skills required, and the world in which it exists.Pro tipThe skip job should feel slightly out of reach today. If you could take it right now without any change, it is not a skip — it is just the next job.
- Score current opportunities for skip alignmentFor every role you are actively considering, ask whether it puts you on the path to your skip job. Rate each option and deprioritize those that optimize for today at the cost of tomorrow's positioning.WarningA high salary or prestigious title at a company that will be disrupted in two years is an anti-skip move. Weigh trajectory over current compensation whenever you have the financial runway to do so.
- Release ego around level and titleActively consider roles that are lateral, smaller, or adjacent to your current seniority if they place you in the environment where your skip job will emerge. Reframe this explicitly as strategic positioning, not a step back.Pro tipAsk: 'Would the version of me who has the skip job think this move was smart?' If yes, take it regardless of how it looks on a resume today.WarningThe single biggest skip killer is the statement 'I would only consider roles at my current level or above.' This is the ego trap that strands professionals in contracting roles.
- Commit to a 'new relationship' paceTreat this transition window like the first year of a new relationship or new job — bring maximum energy, stay obsessively current, and make time for skill-building even if it means disappointing others in the short term.Pro tipThe professionals who increase their pace before they are forced to have far more options than those who wait until disruption hits them directly.
- Stay on the skip path through the tunnelAcknowledge that the transition period is exhausting and uncomfortable — that is expected and unavoidable. Maintain focus on the skip destination and trust that skills and leadership compound once you reach the new world on the other side.Pro tipFind community with others going through the same tunnel. Shared exhaustion becomes 'smiling exhaustion' and is far more sustainable than navigating the transition alone.
Nikhyl Singhal named his entire professional community 'The Skip' around this framework. The community centers on helping product leaders think past their next job and toward the one after — especially during the AI transition. Every interaction, matching decision, and piece of content is filtered through the skip lens.
Nikhyl predicts that PMs who master AI tools first will be seeded into non-tech industries — HVAC firms, schools, PE-backed companies — as change agents. A PM who takes a hands-on IC role at an AI-native company today is on the skip path toward a VP-level change-agent role in a traditional industry within 18 months.
Designers whose pixel-production work is being automated apply the skip strategy by identifying their skip job as a senior PM or Head of Product role. They accept a hybrid PM/design role today, build PM skills using AI tools, and reach that destination within two years rather than defending a contracting design title.
Created by Nikhyl Singhal, former VP at Google and Meta, as the organizing philosophy for his professional community 'The Skip.' Singhal built the concept around the observation that the best career advice always centers on the move after next — particularly critical during rapid industry transitions. Shared in depth on Lenny's Podcast.