Table of Contents
Most successful professionals are caught in what Nikhyl Singhal calls "the greyhound trap"—chasing artificial goals until they catch them, then losing all motivation to run again. After mentoring hundreds of product managers and executives, he's identified why so many high achievers burn out and how to build a truly meaningful 60-year career.
The trap isn't failure—it's success without a plan for what comes next. Understanding this pattern could fundamentally change how you think about your career trajectory and long-term fulfillment.
Key Takeaways
- Most successful people fall into the "greyhound trap"—achieving their goals but having no plan for what comes next, leading to depression and purposelessness
- Career planning should work backwards from your end state, thinking about the job after next rather than just the next promotion
- "Ex-growth companies" (well-funded startups still seeking product-market fit) are career killers where employees often lose half their compensation in worthless equity
- The strongest executives often have massive blind spots created by their superpowers—what got you here won't get you there
- Four reasons you're not getting promoted: no advocate seeing your potential, no actual role available, impatience, or significant development areas you refuse to acknowledge
- The rise of senior IC tracks is one of the best developments in tech, offering legitimate alternatives to management for skilled builders
- Building authentic feedback systems requires creating safety, triangulating input from multiple sources, and learning to repeat back criticism better than it was given
- Community learning often provides more value than formal management training—finding the right peer groups accelerates professional development
- Act 3 career planning (30+ years in) should focus on scaled giving rather than scaled earning, requiring early preparation to avoid the greyhound trap
Timeline Overview
- 00:00–07:07 — The Mentoring Philosophy: How Nikhyl helps hundreds of PMs through "911 calls" during career transitions, the power of community learning, and why crisis moments offer the best coaching opportunities
- 07:07–14:50 — Long-term Career Strategy: The danger of short-term thinking, working backwards from your end state, why promotion-focused conversations miss the bigger picture, and the value of diverse experiences over logo collecting
- 14:50–25:25 — The Ex-Growth Company Warning: How zero interest rates created zombie startups, signs your company lacks product-market fit, why well-funded companies without traction become career traps, and when to leave versus stay
- 25:25–39:50 — The Promotion Problem: Four systematic reasons people don't get promoted, how to extract authentic feedback, why formal reviews miss the truth, and the epidemic of untrained managers in tech
- 39:50–51:27 — Management Evolution: Why the senior IC path is revolutionizing careers, how to become a better manager through shared steering wheels, the vampire invitation model, and building learning communities
- 51:27–59:45 — The Shadow of Superpowers: How strengths become weaknesses at senior levels, why contradictory feedback reveals development areas, and the process of rebuilding core competencies that made you successful
- 59:45–1:12:20 — Act 3 Career Planning: The greyhound metaphor for achieving goals without next steps, why successful people face unique mental health challenges, transitioning from scaled earning to scaled giving, and building 60-year career arcs
The Greyhound Track Metaphor: When Success Becomes a Trap
Nikhyl Singhal's most powerful insight comes from an unlikely source—childhood visits to Midwest dog tracks. "The way they motivated the dogs was they had these fake rabbits that would go around faster than the dogs, which would motivate the dogs to go around in circles. The moment that the dogs accidentally touched the rabbit, they would never run again because there was like, 'Well, what's next? I've achieved what I was looking for.'"
This metaphor perfectly captures a phenomenon Singhal observes repeatedly among successful professionals. They spend decades focused on specific goals—becoming VP, hitting certain compensation levels, building successful companies—but never consider what happens after achieving them.
"Your listeners are spending time focused on 'one day I will be X, I will be that vice president, I will have more money, I will have built something,' but they don't think about what happens next." When they succeed 30 years into what might be a 60-year career, they face an existential crisis with half their working life remaining.
The solution isn't avoiding ambitious goals—it's building what Singhal calls "Act 3" thinking early in your career. This requires considering not just your next role, but the role after that, and ultimately what will motivate you for the decades following traditional career milestones.
Working Backwards from Your End State: The Skip Framework
Traditional career advice focuses on immediate next steps, but Singhal advocates for working backwards from your ultimate professional destination. "Think of career as a product. If you're building a good product, you think about what a great product would look like and then you break it into version one, version two, version three."
This approach, which inspired his newsletter and community name "The Skip," fundamentally changes decision-making. Instead of asking "Should I leave this difficult job?" you ask "Does staying here serve my long-term vision of becoming a founder?" or "Will grinding through this ambiguity teach me skills I need for the role after next?"
The Logo Collection Trap: Many professionals focus on accumulating prestigious company names rather than building meaningful skills. While Singhal acknowledges that MAGMA companies (Meta, Apple, Google, Microsoft, Amazon) provide valuable scale experience, he warns against chasing logos purely for resume enhancement.
"If you're a product person, you probably got into the business because you like building stuff... The more diverse career you have, the better builder you are." The key is seeking experiences that teach different phases of company building—pre-product-market fit, scaling from smoke to fire, and optimizing mature products.
The Ex-Growth Company Epidemic: A Hidden Career Killer
One of Singhal's most urgent warnings concerns "ex-growth companies"—startups that raised substantial capital during the zero-interest-rate era but haven't found sustainable growth. These companies represent a massive but hidden threat to tech careers.
"There are these large number of growth companies who have raised substantive dollars, so they're not going to run out of capital... but many of their contemporary companies that went public are worth 10% or less than what they were worth back then."
Warning Signs of Ex-Growth Companies:
- Still seeking product-market fit despite hundreds of millions in valuation
- Reframing core products to find new markets
- Strong hiring but unclear growth metrics
- Privately held while public comparables have crashed 90%
The Employee Dilemma: Unlike founders who can recap companies and reset stock prices, employees have limited options. "A lot of times half or more of their compensation is in equity, and we just concluded that most of their equity may not be worth anything. Are you willing to take a half pay cut to work for 20% of what you can get in the market?"
Singhal's advice is stark: recognize these situations quickly and leave. The opportunity cost of staying is simply too high, especially for professionals whose compensation depends heavily on equity appreciation.
The Product-Market Fit Reality Check
Distinguishing between companies with genuine traction and those struggling requires understanding what product-market fit actually feels like. Singhal uses a simple framework: "How much work do you have to do to generate pull? When companies are putting very little in marketing and people are coming in the door, or there's such an easy sale, you've got it."
The "Sucking Sound" Test: True product-market fit creates what he calls a "sucking sound"—customers pulling your product into the market with minimal sales effort. Companies still working hard to convince customers, regardless of their valuation, likely haven't achieved this state.
The OpenAI Example: "Right now with OpenAI, we're seeing ridiculous pull, but we may not be seeing massive revenue or profitability. But that pull concept feels like the most appropriate way to define it."
This framework helps employees assess whether they're building something the market wants or pushing a product that requires constant effort to maintain growth.
The Four Reasons You're Not Getting Promoted
After promoting hundreds of people and analyzing countless stalled careers, Singhal has identified four systematic reasons people don't advance—most of which have nothing to do with performance.
1. No Advocacy: You need someone to see your potential and fight for your promotion. "You need someone to see the magic in you to be promoted." If your manager or promotion committee doesn't recognize your value, you're in the wrong environment, not necessarily underperforming.
2. No Available Role: In the current market, many companies have eliminated layers and stopped creating new positions. "This is not as present in hyper-growth because the next role always did exist... Now there's lots of examples of people who are qualified and working at the next level, but the job doesn't exist."
3. Impatience: Leadership transitions take longer than IC progressions. "The highest performers have succeeded because they have set their goals to be more aggressive than what was average achievable. They're like, 'great, I'll see you in a year,' and then they get frustrated when they can't do that."
4. Unacknowledged Development Areas: The most challenging situation occurs when you have real blind spots that you refuse to see or address. These often stem from overrelying on the very strengths that made you successful.
The Shadow of Superpowers: When Strengths Become Weaknesses
Singhal's most sophisticated insight concerns how professional strengths can create career-limiting shadows. "Everyone focuses on your superpowers, but no one ever thinks about what shadows they create."
Common Examples of Superpower Shadows:
- Great collaborators who can't present strong opinions when needed
- Amazing listeners who struggle with decisive action
- World-class storytellers who avoid getting into details
- Structured thinkers who can't handle blue-sky innovation
- Strong political operators whose decisions become unprincipled
The Executive Trap: "You're collaborating as long as people agreed with your point of view. Now as a leader, we're asking you to be opinionated, and because you think you're an amazing collaborator using the exact same toolset... when you're dealing with senior people that may not even be in your function, they recoil."
Recognition Process: The key to identifying these shadows is listening to contradictory feedback—especially criticism that seems to contradict your known strengths. "Do not dismiss that. Recognize most likely you're doing it correctly; you just have gotten to the next level."
Building Authentic Feedback Systems
Creating environments where people give honest feedback requires specific techniques that go beyond formal review processes. Singhal emphasizes that "the more scale the company is, the more they have these systems in place which provide formal feedback, but honestly... the signal that comes out is dramatically different than the formal feedback."
Tactical Feedback Techniques:
- Triangulate input from multiple sources who see you differently
- Create safety by never showing retaliation to difficult feedback
- Repeat criticism back better than it was originally presented
- Publicly recognize people who give you constructive feedback
- Ask specifically for feedback on your perceived strengths
The Jules Walter Model: Singhal cites fellow podcast guest Jules Walter as exemplary: "Jules will look for feedback, then he'll repeat it back to me better than even I presented it... Anyone who's explaining it to a place that they not only internalized it but they can articulate clearly understand the value."
The Community Learning Revolution
Traditional management training has failed spectacularly in tech, creating what Singhal calls an "epidemic" of untrained managers. The solution isn't better corporate L&D programs—it's authentic peer communities.
"In a hundred years, when archaeologists look back and see tech in the early years, they'll say that the biggest surprise was how much we thought it was okay to not train managers."
The Power of Community Learning: Singhal built The Skip CPO community by recognizing that senior product leaders faced similar challenges in isolation. "People were so empowered by the fact that the problem they were hitting was not just them... then they would say, 'I actually had this and now I figured out a way out.'"
Why Community Works Better Than Training:
- Creates authentic safety for vulnerable conversations
- Provides real-time problem-solving during crises
- Builds accountability through peer relationships
- Scales learning across multiple similar challenges
- Offers diverse perspectives on common problems
The Rise of the Senior IC Path
The recent pullback from growth-at-all-costs has created unexpected benefits, particularly the legitimization of senior individual contributor tracks. Singhal sees this as "one of the best things to happen to our industry."
Historical Problem: During hypergrowth, companies promoted strong ICs into management roles without training, creating mediocre managers who couldn't build effectively. Meanwhile, the best builders were pushed away from what they loved doing.
The New Reality: "If I'm looking to hire and someone walks in and says, 'I've been an IC for that whole time, and during that time I went from learning something to demonstrating it to really being able to take it forward, and I got one of these ambiguities mastered—I'm an expert in domain, I'm an expert in managing organizations—I don't need a team ambiguous expert. That's not my hard part.'"
This shift creates genuine career paths for people who prefer building to managing, similar to established tracks in engineering and design.
The Vampire Invitation Model of Management
For those who do pursue management, Singhal offers a counterintuitive approach that challenges traditional command-and-control thinking. "You're more like the vampire knocking on the door—you have to be invited in. You just can't walk through the threshold."
The Shared Steering Wheel: Effective management isn't about delegation or gradual handoffs. "It's more like the sidecar on the motorcycle where the person's driving the motorcycle and I'm on the sidecar, and whether I like it or not, I'm attached, but I have this relatively specific role of giving counsel."
Practical Application: When starting with a new report, Singhal asks, "What can I help you with?" Often the answer is, "I don't need you. I wasn't excited about you as a manager. I don't need another layer between you and the CEO—get out." Rather than forcing engagement, he waits until they invite him into specific areas where he can add value.
Act 3 Career Planning: From Earning to Giving
The most profound challenge facing successful professionals is planning for what Singhal calls "Act 3"—the potentially 30+ years of career after achieving traditional success metrics.
The Economic Transition: "All variations come into two categories: ways to drive more scaled economics—I've made millions, my North Star is to now make tens—or the other arc is around giving."
Why Act 3 Matters Now: With longer life expectancy and desk-based work extending careers to 60+ years, the traditional model of retiring at 65 no longer applies. "Even if you're 20 or 30 years in your career, you're only halfway through. This Act 3 could be a thing."
The Giving Path: "If you were able to do that for 30 years and be giving, not only is that going to be more fulfilling than your Act 1 and Act 2, but it's tremendous for society." Examples include content creation, teaching, mission-driven companies, or scaled coaching.
Starting Early: The key insight is beginning Act 3 planning during Act 2 success, not after achieving all career goals. This prevents the greyhound trap of success without purpose.
Common Questions
Q: How do I know if I'm at an ex-growth company?
A: Ask two questions: Are we scaling a product customers love, or still trying to find that customer sucking sound? If you're still searching and valued at hundreds of millions, you're likely in an ex-growth situation.
Q: What's the biggest mistake people make when asking for feedback?
A: They immediately justify or defend against criticism instead of listening and repeating it back. Create safety by thanking people and demonstrating you understand their perspective.
Q: Should I prioritize getting promoted or building skills?
A: Work backwards from your long-term goals. Promotion serves career advancement, not the reverse. Focus on the story you'll tell about this role in your next interview.
Q: How do I identify my superpower shadows?
A: Look for contradictory feedback that challenges your perceived strengths. If people say you're not collaborative despite seeing yourself as highly collaborative, investigate how your collaboration style might not work at your current level.
Q: Is the IC path really viable long-term?
A: Yes, especially now. Companies are recognizing that their hardest problems require deep expertise, not management layers. The key is mastering specific ambiguities (domain, market, organization) rather than becoming a generalist.
Conclusion
Nikhyl Singhal's career wisdom challenges conventional thinking about professional success. The greyhound trap—achieving goals without planning what comes next—affects even the most accomplished professionals, leading to burnout and purposelessness despite external success.
Building a 60-year career requires working backwards from your end state, avoiding the trap of ex-growth companies, understanding why promotions actually happen, and planning for an Act 3 focused on giving rather than earning. Most importantly, it requires recognizing that your greatest strengths may become your biggest obstacles as you advance, demanding continuous reinvention of the very skills that made you successful.
Practical Implications
• Evaluate your current company: Ask honestly whether you're scaling something customers love or still searching for product-market fit
• Build feedback systems: Create authentic ways to receive criticism, especially about your perceived strengths
• Plan your skip job: Think about the role after your next role when making current career decisions
• Join learning communities: Find peer groups where you can be vulnerable about challenges and learn from others' experiences
• Identify your shadows: Examine what weaknesses your superpowers might be creating at your current level
• Start Act 3 planning early: Consider what will motivate you after achieving traditional success metrics
• Focus on story-building: Ensure your current role creates compelling narratives for future opportunities
• Embrace the IC path: If you love building, consider senior IC tracks as legitimate alternatives to management
