The Advice Paradox

Sunday morning, October 5th. Reading another "how I made it" post from a successful founder who attributes their success to hustle and grit while casually mentioning they went to Stanford and their parents invested the first $500K, and realizing that the most successful people are often the least qualified to explain how to replicate their success.

The Survivor's Certainty

Here's the paradox: we ask successful people how they succeeded, and they tell us with great confidence. They write books, give talks, create frameworks. They're certain about what worked because they did it and it worked. But their certainty is precisely what makes their advice unreliable.

Successful people have compressed their entire experience—all the luck, timing, network effects, inherited advantages, and context-specific circumstances—into a simple narrative of universal principles. "Work hard." "Follow your passion." "Take risks." "Build relationships." These principles feel true because they were present in the person's journey. But so were a hundred other factors the person has forgotten or never recognized.

The programmer who built a successful startup says it's all about technical excellence and user focus. They're not lying—those things mattered. But they don't mention that they started building in 2009 when AWS made infrastructure cheap, or that their college roommate introduced them to an angel investor, or that they could afford to work for equity because their spouse had health insurance and a stable income.

Those contextual factors weren't part of the heroic narrative they constructed about their own success. So they teach principles that assume everyone has the same context they did—and then blame people who follow those principles and fail for not executing hard enough.

The Survivorship Filter

We systematically seek advice from people who survived. The startup founder whose company succeeded. The investor who made it big. The author who broke through. These are the people we listen to because their success proves they know something.

But success proves only that they succeeded, not that they know why. And crucially, we never hear from the people who did exactly the same things but failed due to timing, luck, or circumstances beyond their control. They're invisible—filtered out by survivorship bias before they can complicate the narrative.

The result is that successful people's advice over-weights replicable behaviors (hard work, focus, persistence) while under-weighting non-replicable circumstances (timing, network, initial resources). Not because they're dishonest, but because the replicable behaviors are what they can consciously remember doing, while the circumstances were just the water they swam in.

If ten people follow the same strategy and one succeeds, we listen to the one. They tell us their strategy works, and we believe them because they're living proof. We don't listen to the nine who followed the same strategy and failed—they must have lacked something, must not have executed properly, must not have really followed the strategy.

This creates advice that's systematically biased toward attributing success to controllable factors while ignoring uncontrollable ones. It's optimistic and empowering, which is why people like it. It's also usually wrong.

The Contextual Blindness

The more successful someone is, the harder it becomes for them to see the context that enabled their success. Success feels earned—you remember all the effort, all the decisions, all the work. You don't remember the things that were just there: the social capital, the economic safety net, the timing, the doors that opened easily because of factors you didn't cause.

This isn't malicious. It's cognitive. Humans are terrible at distinguishing between what we did and what happened to us. We construct narratives where we're the protagonist, making choices that drive outcomes. The context becomes scenery, not cause.

The author who succeeded gives advice about writing great content and building an audience. They don't see that they started writing when Twitter was young and audience-building was easier, or that their background in an interesting industry gave them novel insights, or that they had the financial runway to write for years before making money.

When someone follows their advice—write great content, build an audience—but doesn't have that context, the advice fails. And the successful person interprets this as the follower not executing properly, not working hard enough, not having what it takes. The idea that the advice itself might be incomplete—missing the contextual factors that were actually crucial—doesn't occur to them because those factors are invisible from their perspective.

The Replication Problem

The implicit promise of advice is replication: if you do what I did, you'll get what I got. But this only works if success is primarily caused by reproducible actions rather than contextual circumstances.

For some domains, advice works well. "Here's how to implement binary search" is reliable because the context (a sorted array, a comparison function) is standard and explicit. "Here's how to negotiate a raise" can work because the context (employee-employer dynamics) is relatively consistent.

But advice about major life outcomes—how to build a successful company, how to become a successful writer, how to make it in a competitive field—is trying to replicate outcomes that depend heavily on non-replicable context. Following the same actions in different circumstances produces dramatically different results.

The person who succeeded by "following their passion" might have had financial support that let them pursue low-paying passion work until it paid off. The person who succeeded by "taking big risks" might have had safety nets (family money, valuable credentials, strong networks) that made their risks less risky. The person who succeeded by "working 80-hour weeks" might have been young, healthy, and without caregiving responsibilities.

None of this makes their success less real. But it makes their advice less replicable. They're teaching you the visible part of their strategy while assuming you have the invisible infrastructure that made it work.

The Prescription Problem

Bad advice doesn't just fail to help—it actively harms by prescribing approaches that worked in one context as universal solutions.

"Just start a company"—great advice if you have savings, low expenses, strong networks, and a tolerance for risk. Potentially disastrous if you have debt, dependents, limited runway, and no safety net.

"Say no to opportunities that aren't aligned with your goals"—wise if you're established and opportunities come to you regularly. Self-sabotaging if you're early in your career and need to build skills, credibility, and relationships through whatever opportunities arise.

"Don't worry about money, follow your passion"—potentially freeing if you have financial security. Tone-deaf and dangerous if you need to pay rent and support a family.

The successful person isn't wrong that their approach worked. But they're wrong to assume it's universally applicable. They've mistaken "this worked for me in my context" for "this is how success works."

When people follow this context-free advice and fail, they blame themselves. They didn't work hard enough, weren't passionate enough, didn't take enough risks. The advice-giver blames them too—clearly they didn't really commit, didn't really follow the strategy. Nobody questions whether the strategy requires contextual preconditions that the follower didn't have.

The Alternative: Conditional Advice

The solution isn't to ignore successful people or dismiss their experience. It's to demand conditional advice that makes context explicit.

Instead of: "Here's how I succeeded" Try: "Here's what I did, and here are the circumstances that made it possible"

Instead of: "This is how you build a successful company" Try: "This is how I built a company in these circumstances, and here's how much of it depended on factors I couldn't control"

Instead of: "Follow these principles" Try: "These principles worked for me when I had these advantages—if your situation is different, you might need different principles"

This isn't false modesty. It's epistemological honesty. Success is multicausal, and most causes are circumstantial. Advice that pretends otherwise isn't inspirational—it's misleading.

The best advice acknowledges uncertainty: "This worked for me, but I'm not sure which parts were essential versus which were specific to my circumstances. Here's what I think mattered most, but take it as one data point, not a blueprint."

The Receiver's Responsibility

If you're seeking advice, your job isn't to find the most successful person and copy them. It's to find people whose context resembles yours and learn what worked in similar circumstances.

The programmer who succeeded by dropping out of college might be famous, but if you don't have their context (resources, network, specific skills), their advice isn't for you. The person who succeeded through slower, less dramatic means in circumstances closer to yours might have more relevant insights—but they're less visible precisely because their path was less exceptional.

Ask different questions:

• Not "What did you do to succeed?" but "What circumstances made it possible for that approach to work?"
• Not "What should I do?" but "What would you do differently if you had my constraints?"
• Not "What's the secret to success?" but "What advantages did you have that you didn't realize at the time?"

And recognize that even good advice might not apply to you. Success is path-dependent and context-sensitive. Someone else's winning strategy might be your losing one.

The October 5th Practice

Today, when you encounter advice—whether in person, in a book, in a post—pause and ask:

• What context is this person assuming I have?
• What advantages did they have that they're not mentioning?
• Would this advice work if I didn't have those same advantages?

And when you give advice, practice epistemic humility:

• Acknowledge the circumstances that enabled your approach
• Separate what you did from what happened to you
• Recognize that your success might not be fully replicable

The goal isn't to become cynical about all advice or to never learn from successful people. It's to stop treating context-dependent success stories as context-free universal principles.

The best advice doesn't promise replication. It offers perspective: here's what someone tried, in their specific circumstances, with their specific advantages and constraints, and here's what happened. You can learn from it without trying to copy it.

Success isn't a recipe—it's a story. And stories are specific to their tellers, their contexts, their moments in time. Anyone who tells you otherwise is selling you certainty they don't actually have.

The advice paradox resolves when we stop asking "How do I replicate your success?" and start asking "What can I learn from your experience that applies to my different circumstances?" The first question assumes success is reproducible if you just follow the right steps. The second recognizes that success is contextual, and the best you can do is adapt principles to fit your situation rather than trying to recreate someone else's path.

The most useful advice doesn't come from the most successful people—it comes from people whose context resembles yours. Before following advice, ask what circumstances the advice-giver is assuming you have. Before giving advice, acknowledge the advantages and timing that made your approach work. Success is contextual, not universal. The person who tells you exactly how to succeed is either lying or ignorant of their own luck. The person who tells you what they tried, why they think it worked, and what circumstances enabled it—that person might actually teach you something.