Monday morning, December 16th. Watching someone follow startup advice from a founder who succeeded in 2008 with a SaaS product, trying to apply it to a hardware company in 2025. The advice sounds wise. It's incredibly detailed. It's completely wrong for their situation. They'll probably fail and assume they executed poorly, never realizing they were following a map to a different destination.

The Advice Industrial Complex

What we believe about advice:

  • Successful people have figured something out
  • They can articulate what made them successful
  • Their strategies will work for others
  • Detailed advice is better than vague advice
  • More advice is better than less advice

The reality:

  • Most successful people got lucky and retrofitted a narrative
  • Post-hoc explanations rarely match what actually mattered
  • Context matters infinitely more than tactics
  • Specific advice is usually more harmful than generic advice
  • Most advice just adds noise

Thesis: Advice suffers from three fundamental problems that make it worse than useless. First, survivorship bias—we only hear from winners, who often won for reasons they don't understand. Second, context collapse—advice that worked in one situation gets applied to wildly different contexts. Third, attribution error—successful people mistake correlation for causation in their own stories. The result is an advice ecosystem where generic guidance is too vague to act on, specific guidance is too context-dependent to transfer, and most "wisdom" is just successful people's autobiographies cosplaying as universal principles. The most honest advice is usually: "here's what I did, your situation is probably different, good luck figuring it out."

The Three Problems with Advice

Problem 1: Survivorship Bias on Steroids

The mechanism:

Every successful person has a story about what made them successful. These stories are:

  1. Selected from winners only - We never hear from the 99 people who did the same thing and failed
  2. Retrospectively constructed - The narrative is built after knowing the outcome
  3. Causally confused - Success came from luck, timing, or hidden factors, but gets attributed to visible actions

Example: The startup advice trap

Famous founder's story: "I succeeded because I was relentlessly focused on product quality. I ignored marketing for the first two years and just built the best product possible. Our users found us organically and we grew through word of mouth."

What actually happened:

  • They launched during a gold rush period in their category
  • Their first 100 users came from a popular blog post that went viral (luck)
  • A competitor made a catastrophic PR mistake the same month (timing)
  • Their CTO knew the right people to get initial distribution (network effects)
  • The market was growing 300% year-over-year anyway (rising tide)

The advice they give: Focus on product quality, ignore marketing.

What happens when you follow it: You build a great product no one finds out about, burn through your runway, and fail. Then you assume you didn't focus enough on product quality.

The pattern repeats everywhere:

  • "I succeeded by working 80-hour weeks" (No, you succeeded despite working 80-hour weeks, or you survived the 80-hour weeks because you were already successful enough to have runway)
  • "I succeeded by being authentic on social media" (No, you were already successful and people wanted to hear from you)
  • "I succeeded by focusing on one thing" (No, you tried 15 things, this one worked, then you rationalized your focus)

Problem 2: Context Collapse

The pattern: Advice gets decontextualized as it spreads.

What happens:

  1. Someone succeeds in a specific context with specific advantages
  2. They extract "principles" from their experience
  3. These principles sound universal
  4. People in completely different contexts try to apply them
  5. The advice fails because the context was load-bearing

Example: The "just ship it" advice

Original context:

  • Engineer at Google with distribution built-in
  • Working on a product with an existing user base
  • Internal support systems for infrastructure
  • Multiple teams handling different concerns
  • Advice: "Don't overthink it, just ship and iterate"

Applied to:

  • Solo founder with no users
  • First product launch
  • No infrastructure, no team, no distribution
  • Has to do everything themselves

Result: They ship something broken, get no users, waste their launch moment, and learn nothing because there's no feedback loop.

Why it failed: The "just ship it" advice assumed you have:

  • Distribution (so shipping gets you feedback)
  • Infrastructure (so you can actually iterate quickly)
  • Users who will tolerate roughness (because they're already invested)
  • A team (so you're not doing everything yourself)

None of these applied. The advice was sound for its original context and actively harmful in the new context.

Problem 3: Attribution Error

The mechanism: Humans are terrible at identifying what caused their success.

Why:

  1. Outcome bias - Knowing we succeeded makes everything we did seem necessary
  2. Narrative coherence - We construct stories that make sense, not stories that are true
  3. Visibility bias - We can see our actions but not the invisible factors (timing, luck, network effects)
  4. Ego protection - Attributing success to skill feels better than attributing it to luck

Example: The morning routine myth

Successful person's story: "I wake up at 5 AM, meditate for 30 minutes, exercise for an hour, then do deep work until 9 AM. This routine is the foundation of my success."

What's actually happening:

  • They're financially secure enough to control their schedule
  • They don't have young children
  • They have help with household tasks
  • Their chronotype happens to align with early waking
  • Their success came from being in the right industry at the right time with the right network

The advice they give: Wake up at 5 AM and meditate.

What happens when you follow it:

  • You're exhausted because you're a natural night person
  • You miss late-night networking that's actually valuable in your industry
  • You develop sleep debt that hurts your performance
  • You feel like a failure because the "successful person routine" doesn't work

The reality: The routine is a symptom of their success, not the cause. They can afford to have a perfect morning routine because they're successful, and they attribute the correlation backwards.

Why Specific Advice is More Dangerous Than Generic Advice

Intuition says: More specific advice should be more helpful.

Reality: Specific advice is more dangerous because it feels actionable.

Generic advice:

  • "Work hard"
  • "Be persistent"
  • "Focus on what matters"

Problems: Too vague to act on, obviously incomplete, everyone knows to take it with a grain of salt.

Benefits: Hard to misapply catastrophically, forces you to figure out your own specifics, doesn't create false confidence.

Specific advice:

  • "Send 50 cold emails per day to potential customers"
  • "Spend 4 hours per week on content marketing"
  • "Use a Kanban board with these specific columns"

Problems:

  • Feels actionable so you actually do it
  • Might be completely wrong for your context
  • Creates false confidence that you're "doing the right things"
  • Prevents you from thinking about what actually matters in your situation

Benefits: None, really. If it happens to fit your context you'd probably figure it out anyway.

The dynamic: Specific advice is dangerous precisely because it's concrete enough to follow. You do the specific thing, it doesn't work, and you assume you executed poorly rather than questioning whether the advice applied to your situation.

Generic advice is useless, specific advice is dangerous, and the goldilocks zone barely exists.

What Actually Helps

If advice is broken, what works?

1. Situation-Specific Diagnosis

Not: "Here's what worked for me" But: "Tell me about your specific situation and I'll help you think through it"

Example:

  • "Should I do content marketing?" → Wrong question
  • "I have a B2B SaaS product selling to enterprise, 6-month sales cycles, selling to CFOs. Where should I focus distribution?" → Now we can actually think

Why it helps: Forces you to understand your actual constraints and opportunities rather than pattern-matching to someone else's situation.

2. Decision Frameworks Over Specific Tactics

Not: "Use OKRs for goal-setting" But: "Here's how to think about whether a goal-setting framework would help you, and what properties it should have for your context"

Example:

  • Bad advice: "Do daily standups"
  • Framework: "Figure out what information needs to flow between whom, how often, and pick a communication structure that minimizes overhead for your team size and distribution"

Why it helps: Teaches you to reason about your situation rather than cargo-culting someone else's tactics.

3. Anti-Advice: What Definitely Doesn't Matter

Sometimes the most valuable guidance is negative:

  • "You're obsessing over your logo, that won't matter for at least two years"
  • "You're spending 20 hours comparing project management tools, just pick one"
  • "You're worried about scale when you have 10 users, premature optimization"

Why it helps: Eliminates wasted motion without prescribing a specific path forward. Creates space for you to think about what actually matters.

4. Raw Data Over Interpreted Narrative

Not: "I succeeded by focusing on quality" But: "Here's my timeline: month 1 I did X and got Y result, month 2 I did Z and got W result, at month 6 this happened, and here's what I know about the market conditions at the time"

Why it helps: Lets you extract your own lessons based on similarity to your situation rather than accepting the narrator's causal story.

5. Multiple Contradictory Examples

The pattern: Show 5 people who succeeded with completely different strategies.

Why it helps:

  • Destroys the myth that there's one right way
  • Shows that context determines strategy
  • Forces you to think about what differentiates the contexts
  • Prevents cargo-culting any specific approach

Example:

  • Founder A: Focused on product for 2 years, ignored marketing, succeeded
  • Founder B: Focused on marketing, mediocre product, succeeded
  • Founder C: Did both simultaneously, succeeded
  • Founder D: Outsourced both, succeeded
  • Founder E: Gave up on both and pivoted, succeeded

The lesson: The strategy doesn't matter nearly as much as you think. Understanding your market, having a feedback loop, and being resourceful matter.

The Advice Paradox

Here's the contradiction in this essay:

I just spent 1,500 words explaining why advice doesn't work, which is itself advice about advice. The meta-advice is: "don't trust advice, including this advice."

So what should you actually do?

When receiving advice:

  1. Ask about context - What was your specific situation? What advantages did you have? What was the market like?
  2. Look for survivor bias - How many people did the same thing and failed?
  3. Check attribution - Is this what actually mattered or just what you remember doing?
  4. Extract principles, not tactics - What was the reasoning behind your specific actions?
  5. Get multiple contradictory examples - Who succeeded doing the opposite?

When giving advice:

  1. Describe your specific context - Market conditions, your advantages, timing, luck factors
  2. Admit uncertainty - "This worked for me but I don't actually know why"
  3. Give frameworks not tactics - Teach reasoning not actions
  4. Point out what didn't matter - "I obsessed over X but in retrospect it was irrelevant"
  5. Suggest diagnosis over prescription - "Tell me more about your situation"

When seeking guidance:

  1. Don't ask "what should I do?" - Ask "how should I think about this?"
  2. Don't pattern-match to success stories - Analyze your specific constraints
  3. Don't collect advice - Experiment and get feedback
  4. Don't optimize for confidence - Optimize for learning
  5. Don't trust anyone who's certain - Trust people who say "it depends"

Key Takeaways

The uncomfortable truths:

  1. Most success is luck, timing, and context—not repeatable tactics
  2. Successful people are usually the worst people to give advice because they have the most survivor bias
  3. Specific, actionable advice is usually more dangerous than vague platitudes
  4. The advice that would actually help you is probably "figure out your own situation"
  5. The best advisors ask questions rather than prescribe solutions

What to do instead:

  1. Build your own feedback loops instead of following advice
  2. Study multiple contradictory examples instead of one success story
  3. Learn frameworks for thinking instead of tactics for acting
  4. Treat all advice as one person's autobiography, not universal truth
  5. Get comfortable with "it depends" as the most honest answer to most questions

The hard part:

  • Following advice feels like taking action
  • Figuring it out yourself feels like flailing
  • But the person who learns to diagnose their own situation will always beat the person who's good at following other people's advice

The paradox:

  • The best advice is usually "this probably won't help you"
  • The worst advice is usually detailed, specific, and confidently delivered
  • The people most certain about what you should do are usually the least helpful
  • The people who say "it depends, tell me more" are usually onto something

Most advice fails because it treats your situation like a problem with a known solution, when it's actually a unique puzzle you need to solve yourself. The goal isn't to find the right advice. The goal is to get good at figuring out your own situation.

Today's Sketch

December 16, 2025