The pattern looks like this. Someone solves a hard thing. They look back at what they did. They compress it into a clean lesson, often a list, and they ship it. Other people read the lesson and try to apply it, and it mostly doesn’t work for them, and they don’t know why.
The mistake isn’t the original person being dishonest about what they did. The mistake is the compression happening before anyone saw enough of the original situation to know which parts were transferable. I spent a long time being on the wrong side of this, both as the giver and the taker of advice. Eventually I started to notice the shape of it.
Compression hides the situation.
When you describe what worked, you reach for the cleanest version of the story. You compress out the specifics. The team you had, the timing of the market, the personal advantages you didn’t notice you had, the things you tried first that didn’t work, the cushion of capital or relationships or experience that let you take the risk in the first place. What’s left in the compressed version is the move. Not the situation that allowed the move.
The reader gets the move and not the situation. They try to make the move from their own situation, which is not the situation the move was made in. The move doesn’t land. They blame themselves, or they decide the original advice was wrong, but the actual story is that the advice was a function call that needed the original situation to be supplied as an argument, and the situation got compressed away. This is why “ten rules for X” articles age so badly. The rules are the function. The situation that made them work is not in the article.
Sequence matters.
There’s a principle from systems work that I’ve come to apply to almost everything. First make visible, then observe, then compress. Reversing this sequence is how you get advice that fails for everyone but its author. The honest version of giving advice would go: “Here’s what I did, here’s the situation I did it in, here’s what I tried first that didn’t work, here’s the part I think transfers and the part I think doesn’t.” That’s not a tweet, not a listicle, not a viral LinkedIn post. It’s almost never what gets shared. The viral version is “Three things I wish I’d known earlier,” which is a compressed function with the situation stripped out. Easy to share, satisfying to read, almost impossible to apply.
I am not trying to be sanctimonious here. I have done this. I’ll do it again. It’s hard to talk usefully about your own experience without compressing the parts that turn out to have been load-bearing. But knowing this is happening changes how I read other people’s advice now.
How I read advice now.
When I hit a piece of advice that looks compelling, I try to do one thing before I take it. I try to ask, what was the situation. What did this person have that I might not have. What had they already tried before this thing worked. What is the cost of being wrong about whether this advice transfers. If I can’t answer those, I treat the advice as interesting but unverified.
Most of the advice on the internet about how to live a life, run a company, raise a kid, build a habit, manage a team, save for retirement, or be a better partner is a compression with no situation. It’s not bad. It’s just unfinished. Half the function got delivered.
The exception, the place where advice is sometimes load-bearing, is when the person giving it has watched many situations, not just their own. A doctor who’s seen thousands of patients. A coach who’s run hundreds of teams. An investor who’s backed many founders. They can compress more honestly because they’ve been able to triangulate which parts of “what worked” actually carried across situations and which were specific to one person’s setup. That kind of advice is rarer than it looks, because most public advice comes from one person describing one situation.
What to do instead.
The move that has served me better than any advice is to make the situation visible first, before I look for advice. Sit with the actual thing. Watch it for a while. Write down what’s actually happening. Notice patterns. Name what doesn’t match anything I’ve seen elsewhere. Notice what feels weird. Get specific.
Then, once the situation is clear, advice becomes useful, because I can finally tell which advice fits the situation and which doesn’t. The advice was never the limiting factor. The visibility was. If you find yourself reaching for advice constantly, the constraint isn’t the supply of advice. The supply is unlimited. The constraint is that you haven’t yet made your own situation visible to yourself, so anything you read is equally appealing, and you can’t tell the difference between what would help you and what worked for someone else.
The compression comes after the seeing. If you skip the seeing, the compression breaks under you.