The Skip — Plan the Move After Next
Optimize career decisions for the job two moves out, not the next job.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 3
- Confidence
- 85%
Singhal's naming philosophy for his community and its core career heuristic: the best career advice is never about your next move but the move after it — the 'skip.' In the AI transition, this means enduring an uncomfortable, possibly smaller near-term move to guarantee that your skip opportunity (a premier builder role, high comp, real relevance) stays open once the industry re-stabilizes.
Origin
Nikhyl Singhal's founding concept for his 'Skip' community, podcast, and newsletter; he named everything 'Skip' precisely because of this two-moves-ahead lens on careers.
Core principles
- 01Evaluate an opportunity by what it sets up two moves from now, not by its immediate title or comp.
- 02In a period of rapid change, staying modern is worth more than staying senior.
- 03Swallowing ego short-term is an investment that protects the long-term 'skip' payoff.
- 04Once the industry re-stabilizes, 'the cream rises to the top' — so the near-term goal is to arrive current, not to arrive high-ranked.
How to run it
- 1
Name your skip opportunity
Define the role two moves out that you actually want — e.g., a premier builder job with high salary and real relevance in the post-transition industry.
Pro tip Ask 'what's the skip job? what's the skip opportunity?' rather than 'what's the best job available now?'
- 2
Swallow your ego on the next move
Be willing to take a lateral or even smaller role if it keeps you hands-on and current. Refuse to gate yourself with 'I was an XYZ leader, I'll only consider that level.'
Pro tip Staying hands-on is now a necessity, not just in vogue — an egoless, current operator beats a senior-but-stale one.
Watch out Insisting on matching your old level is how you end up current in title but obsolete in skill.
- 3
Stay long-term focused through the tunnel
Accept that the next couple of years are the transition tunnel. Optimize the near term for staying modern and building credibility with founders, trusting that skills and leadership re-assert once the industry settles.
Pro tip Frame it as boarding the boat leaving the station for the new world — near-term discomfort buys the skip.
In the wild
When Singhal started his heads-of-product community five years ago, it had one founder for the first few years (~60-70 members). In the last 12 months, growing to ~125, it now has 14 founders — people whose 'skip' move was not another product-exec role but founding a company.
→ Illustrates the skip lens in action: senior leaders choosing the move-after-next (founder/CEO/cross-functional C-level) over the obvious next lateral.
A very senior person in Singhal's group interviewed for a Chief HR Officer role because a forward-leaning company wanted a product-manager background — the obsolescence, judgment, and builder skills — in the HR function.
→ Shows how an egoless, skip-oriented view opens roles up and down the stack that a 'stay in my lane at my level' mindset would never surface.
Common mistakes
Optimizing the next move instead of the skip
Chasing the best immediately-available title or comp can lock you into a stale environment and close off the move-after-next. The heuristic is to protect the skip opportunity, even at near-term cost.
Letting ego set a level floor
Saying 'I was a leader, I only consider roles at that level' filters out exactly the hands-on, current-making moves that keep your skip open. Ego-driven level-matching optimizes status now and forfeits relevance later.
Is it for you?
Best for
Senior operators navigating the AI transition who must weigh a near-term move against long-term career positioning.
Not ideal for
Early-career people who need to build baseline competence first, or anyone in a stable field where the industry isn't being reinvented under them.
From the transcript
“the best career advice is always not thinking about the next move, but the move after”
“What's the skip job? What's the skip opportunity?”
“you have to swallow your ego”
“I want people This is an extension of our last conversation. It's not only is it in vogue to be hands-on”
“Once I get to the new world, the cream rises to the top”
From the episode
Why half of product managers are in trouble
Nikhyl Singhal (Meta, Google)