Advice is for losers

No successful path in life is replicable. What worked for someone else won’t work for you.

So asking exactly how they did it is a bad question.

But asking for advice is beaten into us from a young age. We’re told to follow the rules, walk the trusted path, and listen to those ahead of us.

Preconditioned to outsource our thinking to others.

My friend Andrew Wilkinson’s take on advice frames it perfectly: “Here’s the number I used to win the lottery.”

Advice is survivorship bias wearing a suit.

When someone tells you what worked for them, they’re only telling you one side of the story. They don’t know about the thousand other people who did the exact same thing and got nothing.

The person who tells you to “just cold email CEOs” did that and it worked. But they can’t see the graveyard of people who sent those same emails and never heard back. The dead don’t write blog posts.

Even worse, the person giving the advice often doesn’t fully understand why it worked. They think it was the cold email. It might have been their timing, their network, their last name, or dumb luck.

They’re not lying. They just don’t have the full picture. Nobody does.

Advice creates debt.

This one’s sneaky. I first heard it from my friend Chris Sparling.

The moment someone gives you advice, an invisible contract is signed. They’re now invested. Not financially, but emotionally. They’ve put a piece of themselves into your decision, and now they want to see it play out.

If you follow their advice and it works, great. They feel validated. The relationship strengthens.

But if you don’t follow it? The dynamic shifts. There’s a quiet friction. A subtle feeling that you wasted their time. Or worse, that you think you know better.

And here’s the real trap: knowing this, you become less likely to trust your own instincts. You override your gut because you don’t want to disrespect someone you admire. You follow advice you don’t fully believe in because the social cost of ignoring it feels too high.

That’s not mentorship. That’s obligation.

Advice strips out all the context that matters.

“Hire slow, fire fast.”

“Don’t take outside capital.”

“Always raise more than you think you need.”

These sound like wisdom. They’re bumper stickers.

The person who says “don’t take outside capital” might have had a spouse earning six figures, a paid-off house, and a business that was profitable from day one. Their context made that possible. Yours might not.

Advice arrives clean. Confident. Final. But the mess that produced it, the doubt, the reversals, the luck, the near-misses, all of that gets stripped away. You’re left with a conclusion that’s been divorced from the conditions that created it.

And conclusions without context are dangerous. Because they feel true. They sound authoritative. And you’ll follow them into a situation they were never meant for.

I’ve lived this.

For ten years, the most common advice I’ve received running a sock company is: “You should do underwear.”

Every time, the person delivers it like they’ve just cracked the code. Like this thought hasn’t crossed my mind a thousand times. Like I haven’t already tried it.

Then they run the full playbook. They reference some brand that started with one product, expanded into adjacent categories, and became a billion-dollar company. They say “trust me, just do it.” They tell me to loop back and send them a pair, they’d love to test them.

They mean well. They genuinely want to help.

But watch the three problems stack up in real time:

The survivorship bias: they’re pointing to the brand that made it. Not the dozens that expanded too early and diluted themselves into irrelevance.

The debt: now they’re waiting for me to act on their insight. They’ll check in. They’ll ask how the underwear line is coming. And if I don’t pursue it, there’s that quiet implication that I’m leaving money on the table. That I’m not thinking big enough.

And the missing context: because here’s what “just do underwear” ignores:

We sell socks. A unisex product. Introducing underwear means repositioning our entire company as gendered. That changes everything. The website, the marketing, the brand identity we’ve spent nearly a decade building.

Then there’s buyer psychology. Socks and underwear live in the same drawer, but that doesn’t mean the purchase behaviour is the same.

Then competition, is this a saturated category, and do we honestly believe we can win?

And the focus question underneath all of it, are our resources better spent maximizing the opportunity we already have, or splitting our attention to chase a new one?

Maybe selling underwear is a good idea. Maybe we’ll do it one day.

But “you should do underwear” doesn’t help me get there.

You know what would?

Hearing the story of how that billion-dollar company actually expanded. When they did it. What resources they had. How long the new category bled money before it worked. What almost went wrong.

That’s the difference. Advice gives me a conclusion. The story gives me something I can actually use.

Ask for stories instead.

Ask people what happened. Not what you should do.

“What happened when you raised your first round?”

“What did the first six months look like after you launched?”

“What almost killed the business?”

When someone tells you a story, you get the raw material without the prescription. You hear the nuance. The contradictions. The moment they almost did the opposite of what they’re now known for.

Stories let you pattern-match against your own situation. You pull out what’s relevant and leave the rest. You do the thinking yourself.

Advice gives you someone else’s recipe. Stories give you ingredients.

The deeper point is this.

If you want to be great, and I mean actually great, not just successful by someone else’s definition, you cannot follow. Following is how you become average with extra steps.

Every meaningful thing I’ve built came from ignoring the playbook.

The best conversations I’ve had with people I admire were never the ones where I asked “what should I do?”

They were the ones where I asked “what happened?” And then sat in the discomfort of figuring out my own path.

That discomfort is the point. It’s where the real thinking happens.

Stop asking for directions. Start collecting stories.

Then build your own map.