Saturday morning, February 7th. I'm scrolling through LinkedIn and every third post is someone packaging their success into "3 actionable steps." Step 1: Identify your strengths. Step 2: Leverage your network. Step 3: Execute consistently. It's not wrong exactly. But it's also completely useless. Anyone who's actually built something knows that the real insights—the ones that made the difference—can't be compressed into action items. They emerged from context, timing, and a hundred failures that can't be replicated. Yet we keep seeking and giving advice as if wisdom transfers like software updates. It doesn't. The advice paradox is this: what can be clearly articulated is usually what you already know, and what you actually need to learn can't be told to you.

The Thesis

The most valuable advice is fundamentally unactionable, and actionable advice is usually either obvious or wrong for your context. Real wisdom can't be transmitted through advice—it has to be earned through experience. The advice paradox exists because we want shortcuts to understanding that only comes from doing. We ask for recipes when what we need is taste, and taste can't be taught through instructions.

This shows up everywhere:

  • The entrepreneur who reads "find product-market fit" a thousand times but only understands what it means after building three failed products
  • The writer who's told "show don't tell" but can't implement it until they've written 100,000 bad words and suddenly feel the difference
  • The investor who learns "buy low, sell high" but loses money for years before developing the pattern recognition that makes good calls
  • The manager who receives "hire A players" advice but can't recognize one until they've been burned by B and C players enough times
  • You, reading self-improvement content that makes perfect sense intellectually but somehow doesn't change your behavior at all

The pattern is always the same: advice that's clear enough to act on is either too obvious to be useful or too context-free to apply. The insights that actually matter are illegible until you've already done the work to understand them.

Why Advice Fails

Useful advice is illegible until you already understand it:

"Write every day" sounds simple. But what does it actually mean? Write morning or evening? Fiction or journal? Through resistance or only when inspired? When do you stop? How do you know if it's working?

The person who's successfully built a writing practice knows these answers for themselves. But they can't transfer that knowledge to you because their answers emerged from their specific constraints, psychology, and goals. Your version will be different.

The advice "write every day" only becomes actionable once you've already figured out how to make it work for you. At which point, you didn't need the advice.

Context gets stripped in transmission:

When someone successful says "I worked 80-hour weeks for three years," that's not advice—it's a data point from a specific person in a specific situation. Their risk tolerance, financial runway, domain expertise, network, and market timing made that strategy work.

But it gets compressed into "work hard" and passed on as universal advice. Some people follow it and burn out. Others apply it at the wrong stage. A few get lucky and it works, then credit the advice instead of the context.

The advice that reaches you has all the context filtered out. What's left is a fortune cookie that might be right or might be catastrophically wrong, and you won't know which until you've already bet years of your life on it.

We want recipes but need taste:

"How should I price my product?" The real answer: it depends on your market, positioning, costs, customer segments, competitive landscape, and growth strategy. Also, you'll probably get it wrong initially and need to adjust based on data.

But that's not satisfying. People want: "Charge 3x your costs" or "Start high and discount later." These are actionable! And also useless without the judgment to know when they apply.

The actual skill is developing taste—the ability to feel what's right in your specific context. But taste can't be transmitted through advice. It's built through repeated exposure, feedback, and reflection. The advice seeker wants to skip that process. The advice paradox is that you can't.

Why We Keep Seeking It Anyway

Advice is cheaper than experience:

Experience takes time and risk. Advice is free and immediate. Of course we prefer advice. It promises the insight without the pain.

But that's not how wisdom works. Understanding doesn't transfer through words—it emerges from grappling with problems directly. The advice feels like a substitute for experience, but it's not. At best, it's a map. And the map is never the territory.

It provides the illusion of progress:

Reading advice feels productive. You're learning! Taking notes! Building frameworks! But you're not actually getting better at the thing—you're getting better at consuming content about the thing.

Real progress requires doing, failing, adjusting, and repeating until you develop your own understanding. That's slow and uncomfortable. Advice consumption is fast and comfortable. So we substitute input for output and wonder why nothing changes.

Someone did transfer wisdom... once:

Sometimes advice does click. Someone says something at exactly the right moment when you're ready to hear it, and it genuinely shifts your perspective. This happened once, so you keep seeking it, hoping for another hit.

But that moment worked because of your accumulated context, not because the advice was better. You'd heard similar things before and ignored them. This time you were ready. The advice didn't create understanding—it unlocked understanding you'd already built but hadn't articulated.

What Actually Works

Seek principles, not instructions:

Bad advice: "Post on Twitter every day at 8 AM." Better: "Consistent presence in the right channels matters more than sporadic brilliance."

The first is actionable but probably wrong for you. The second is illegible but gives you room to find your version. Principles point you in a direction. Instructions pretend to be the path.

Use advice as hypotheses, not truth:

When someone says "cold email works," don't treat that as gospel. Treat it as: "This person found cold email effective in their context. Let me test if it applies to mine."

Frame advice as experiments to run, not facts to implement. Most advice is wrong for you specifically. The goal is to quickly test and discard what doesn't fit while keeping what does.

Build taste through volume:

You can't shortcut developing judgment. The only way through is volume.

Want to know what good writing looks like? Read 100 books. Want to understand product-market fit? Build 5 products. Want to hire well? Interview 100 candidates.

There's no advice that replaces this. The pattern recognition that lets you make good calls only comes from repeated exposure and feedback. Stop looking for the shortcut. There isn't one.

Give process, not conclusions:

When you're asked for advice, don't share what worked—share how you figured out what worked.

Instead of "I price at $99/month," try: "I tested three price points with small customer sets, tracked conversion and retention, then increased to the highest price point that didn't hurt retention. Here's how I structured the tests."

The process transfers. The conclusion doesn't. Give people the tools to figure it out themselves, not the answer that worked for you.

The Uncomfortable Truth

Most advice is just someone's hindsight narrative. They did things, some worked, they construct a story about why, and package it as transferable wisdom. But the story is probably wrong—they're giving too much credit to actions and not enough to context, luck, and timing.

This doesn't mean advice is worthless. It means advice is limited. Use it to generate ideas and spot blindspots, but don't expect it to substitute for doing the work yourself.

Here's what you should actually do:

  • Stop collecting advice - You already know enough to start
  • Start doing things - Action generates specific questions that lead to useful learning
  • Build your own taste - Do enough volume that patterns emerge naturally
  • Share process, not conclusions - When helping others, give them your method, not your answer
  • Recognize illegible knowledge - The best stuff you've learned probably can't be explained, only practiced

The advice you're seeking won't save you. The experience you're avoiding is what teaches you. The sooner you accept this, the sooner you can stop waiting for permission or perfect information and start building the understanding that only comes from doing.

Stop reading. Start doing. The advice you need will emerge from the work itself.

Today's Sketch

February 07, 2026