Wisdom, A Lossy Compression

Over the past two to three years, I’ve found myself transitioning from being the one who sought advice and wisdom to someone who is also being asked for it. Every time I find myself giving advice—or what people like to call wisdom—something weird happens. Time slows down. I start replaying memories, extracting lessons, and trying to phrase them in a way that offers some semblance of structure, hoping the other person can follow along and find it useful. But just before I open my mouth or start to type, a question pops up: “What the hell do I know about this?” Do a couple of experiences, or struggles with a similar problem, really qualify me to give advice?

I haven’t managed to stop that question from playing in my head like a broken record, so I decided to sit with it.

Our addiction to lossy compression

Probably a side effect of being in tech, but my YouTube, Twitter, and Instagram feeds (which I open about once a quarter) are filled with content titled things like “Naval Ravikant shares the best advice ever” or “Steve Jobs reveals the secret to being successful.” Each one claims to deliver wisdom in thirty seconds—enough to turn around not just my life, but maybe even a company of a hundred thousand people.

I scroll. Fifteen minutes later, when my screen-time timer blocks access, I find myself staring at my reflection in the dark screen, wondering: how do I get sucked into this, every, single, time? Is this how I sound? Is this the effect I have? Is this the effect others have on me when the same words are spoken in real life?

If you work in tech, you’ve been in one of those hour-long meetings with way more people than two pizzas can feed. Right toward the end—after a round-robin debate that leads to no decisions—the person with the highest title chimes in: “Make something people want.” And the eye roll is so hard it actually hurts.

What is it about us, as humans, and sounding witty? What fear are we compensating for? I get why we’re addicted to quirky dance videos, cats playing pianos, and food content on the internet. But wisdom videos? Half of them are clips from literal college lecture halls—the same lecture halls where half the audience is mainlining caffeine just to stay awake.

Even long-form content isn’t much better. A lot of it falls under what Andrej Karpathy has rightly called edutainment.

We’re looking for shortcuts or procrastinating—even when we know better.

What advice and wisdom are missing (stories & time)

When I was a kid and my dad gave me advice, it usually came in the form of an hour-long story. Excruciatingly detailed. Vivid. And somehow, I found myself hanging onto every word. Those lessons are now muscle memory.

Nowadays, we skip the stories. We want the lesson. The takeaway. The wisdom. I often catch myself nudging one of my mentors, David, to skip the story and just tell me what I should do—probably because I think I can instantly apply it to my situation. As if understanding fluid dynamics would let you bend the ball like Beckham. It might help, but it won’t get you even close.

Stories tell us why it will be hard. Why it will take longer than we expect. Why will we stumble the first few times—or the first hundred. Without that context, there’s a mismatch between what the wisdom suggests and what it actually takes to get that outcome.

At an MIT lecture, Steve Jobs was once asked about the greatest lesson he learned at Apple. He said:

“When I see something not being done right, my first reaction isn’t to go fix it. It’s to say: ‘We’re building a team here, and we’re going to do great stuff for the next decade, not just the next year. What do I need to do to help the person who’s screwing up learn, versus how do I fix the problem?’”

I can recite this from memory now—partly because it’s good advice, and partly because YouTube shows me this clip once a day.

But the algorithm skips "before" footage. How long did it take Steve Jobs to learn this? How many people did he lose because he got in their way before he reached this realization? What does it actually mean to do that in practice? Without the stories, it is really hard to replicate.

Everyone’s trying to find mentors, setting up thirty-minute monthly syncs. The first five minutes go to small talk. The next five to explain the problem. Then, in fifteen minutes, the mentor fast-forwards through a lifetime of experiences, extracts a sharp takeaway, and ends with something like “Ship, ship, ship” or “Know your stakeholders.”

There’s rarely a story. And if there is one, it’s glossed over in the rush to get to something quotable. Everyone leaves feeling good—but nothing actually changes.

The biggest problem with skipping the story is that it distorts time. Smart, experienced people can compress decades of lessons into a few sentences. I didn’t realize this for a long time, but that compression is lossy. Without knowing how long it took—or how much trial and error was involved—we aren’t set up to succeed. We think that now that we have the knowledge, we can skip the work.

It doesn’t work that way. You might start more prepared. You might avoid a few mistakes. But you’ll make new ones. There’s no skipping the grueling workouts.

Fear as the real substrate of advice

So is listening to the full story the answer? It’s part of it. I think we miss ‘why’ we are looking for wisdom.

I’ve noticed that I end most of my advice with, “Go try it.” And I’ve realised that we usually seek advice when we’re afraid—when fear is stopping us from acting—not because we don’t know what to do.

Fear of losing a job makes us avoid risks. Fear of rejection makes us hesitate to ask for a raise. Fear of losing a friend keeps us from being candid. Fear of inexperience keeps us from trying something new.

Acknowledging fear is hard, so we turn to others.

We’re loss-averse by default. Despite what economists might hope, we don’t behave like rational beings.

It took me six years to learn how to focus. I still struggle with it, but I now understand it. What helped was realizing that my fear—of not being seen as someone who could juggle everything, of being the person who doesn’t always say yes—was what kept me unfocused.

Counterintuitively, focusing helped me get more done, and more importantly, helped me do harder things. I remember the day clearly. It was sunny in Geneva, Switzerland, in a room about six hundred meters from the Rolex factory. That was the day I wrote five priorities for my team on a whiteboard.

We stuck to those five things for almost sixteen months, despite weekly debates about squeezing something new in every Friday. Eventually, we launched the product. That approach helped me scale myself across six products. It sounds counterintuitive, but by focusing, I got more done.

It wasn’t wisdom that helped me. It was acknowledging the fear.

My revised approach is to first ask people what they’re afraid of. I’ve come to believe that advice should start there. From there, we can share our story—not as a prescription, but as proof that the fear can be worked through. It will be hard. It will take time. There will be stumbles. But it’s possible.

Instead of offering neat, rhythmic sentences that pretend to be answers, we should nudge people toward the courage to act despite fear.

Courage is a muscle. It needs to be built. We can’t give people answers, and pretending that’s what advice does is a disservice. And if you are on the other side of the table, do not accept answers. Ask for stories. Ask for where they stumbled along the way, and why did they keep going.

Most advice is usually spot, fucking, on. It just skips over fear and makes action sound like a knowledge problem.

So I plan to ask: ‘What do you want to do? Why aren’t you doing it? What are you looking for from me?’ Most of the time, people already know the answer. My job is to help them get past the fear—by sharing my own stumbles, not pretending I have all the answers. Then tell them: ‘I’ve got your back.’