The Path To Wisdom - Don't Learn From Your Mistakes

It's smarter to learn from other people's mistakes. Here's how.

I used to think that the folks with the most successful careers collected the most scars. These scars are proof of learning, but that doesn’t mean it’s the best way to learn, far from it.

Nearly 10 years ago, I thought I was ready to be promoted to Principal Engineer at Amazon. It’s the most difficult promotion at the company, and I knew navigating the process was just as important as technical skill.

I also knew the deck was stacked against me. Due to attrition, I was reporting to a manager who was too low-level to effectively support a promotion at that scope. There were no other Principal Engineers near my team, which meant getting the necessary feedback and support would be almost impossible.

But I thought I was different. I saw the significant headwinds and believed I would be the exception.

I wasn't.

That promotion cycle was a painful, drawn-out failure. It took another 4 years and 5 attempts before I finally succeeded. I learned a hard-earned lesson about the importance of organizational and managerial support, but it came at a huge personal cost in stress, frustration, and lost time. It was what I call a 4-D lesson—wisdom gained by walking through fire.

This experience forced me to develop a mental model for how we learn. I call it the 4D Learning Framework. I wish I knew about it when I was younger, it would have saved me so much grief.

1. The 4D Learning Framework

Not all lessons are created equal. They exist in four distinct dimensions, each with a different level of cost and impact. To understand them, let's trace a single raw lesson, "don't drink to excess," through the framework.

• 1-D: The Proverb. This is wisdom as a soundbite. It’s hearing a parent say, "Everything in moderation." It’s a contextless echo that’s easy to hear and even easier to dismiss.

• 2-D: The Textbook. This is structured knowledge. It’s the health class in high school where you learn about the long-term effects of alcohol on the liver. It's a blueprint of consequences. You understand the theory, but you haven't felt it.

• 3-D: The Ringside Seat. This is vicarious experience. It’s growing up with an alcoholic family member and witnessing the destructive impact on their life and the lives of those around them. You witness their pain and learn the lesson on a gut level, without paying the price yourself.

• 4-D: The Scar. This is direct, personal experience. It's your own battle with alcoholism. The lesson is branded into your memory forever through immense personal suffering. It’s the most powerful way to learn, and the most painful.

Actionable Advice: Take 10 minutes to do a "Wisdom Audit" of your own life. Look at the following domains and honestly assess what dimension of learning you're operating from. Are you running on 1-D proverbs or 4-D scars?

• Career Path

• Financial Health

• Romantic Relationships

• Key Friendships

• Physical Health

• Mental Well-being

• A Core Hobby or Skill

• Communication Style

• Time Management

• Personal Integrity

• Spirituality & Purpose

For example, if a 30-year-old Steve had done this exercise, it might have looked like this:

• Career Path: 2-D. I understood the promotion process at Amazon intellectually, but I hadn't yet experienced the painful 4-D failure that taught me how critical organizational support really is.

• Financial Health: 2-D. I was just starting to read blogs about the FIRE movement. I had the "textbook" knowledge but hadn't yet put it into a real, long-term practice.

• Romantic Relationships: 2-D. I had just met the woman who would become my wife. All the lessons about building a life together were still theoretical knowledge, not yet the earned wisdom of shared experience.

• Physical Health: 4-D. I was doing CrossFit five times a week and getting injured a lot. This was a direct, painful lesson—a scar—that taught me about the importance of moderation and listening to my body.

• Spirituality & Purpose: 1-D. I hadn't done the deep work to understand what that actually meant for my life.

2. The Strategy: How to Collect Wisdom, Not Scars

The most powerful strategy for accelerated growth is to intentionally seek out 3-D lessons. You want a ringside seat to other people's experiences.

Early in my career at Amazon, I had a ringside seat to a painful 3-D lesson. A senior colleague, someone I respected, was giving a presentation to a large group, including several vice presidents. He knew his material cold, but he hadn't practiced the delivery. He was stilted. He resorted to reading his slides, which were walls of text, out loud. He got a tough question about his data, and he completely fell apart. He became defensive, flustered, and lost all credibility in the room.

Watching it was excruciating. I felt the second-hand embarrassment and anxiety for him. In that moment, I learned a lesson that would have taken me years of my own failures to understand: for a high-stakes presentation, knowing your material isn't enough. You have to practice performing under pressure.

He got the 4-D scar, a painful public failure. I got the 3-D lesson. That single experience has shaped how I prepare for presentations ever since.

It’s the same reason I shared the story last week about my "quick fix" retry mechanism that brought down a critical service. That was a 4-D scar for me, but by sharing it, I hope it can be a 3-D lesson for you. You get the ringside seat to the failure without the 2 AM pager alert.

This is the entire reason I'm starting my new podcast. My goal is to sit down with people who have already run the experiment and collect their 3-D and 4-D lessons. I want to ask them about the scars they got so you don't have to get them yourself. It’s about making previously high-cost wisdom accessible to people.

Actionable Advice Look at the results of your Wisdom Audit. Pick one area where you are currently at a 1-D or 2-D level. Now, find someone who is clearly operating at a 4-D level in that same area. Instead of asking them for generic knowledge ("How do I get better at X?"), ask for a story that builds understanding: "What was the hardest lesson you had to learn about X?" This approach is the fastest way to level up your understanding. Ask them for the story of how they learned it, not just their takeaway. The story is much more signal-rich than the conclusion.

3. The Stubbornness Problem: Why We Insist on Getting Scars

Even when we have a clear blueprint or a ringside seat to someone else's failure, a part of us still believes, "That won't happen to me." This is our own stubbornness, the ego that insists we are the exception to the rule. It's the final barrier that pushes us from an easy 3-D lesson into a painful 4-D scar.

I saw this happen in real-time last month. Every year, on America’s Independence Day, my wife's family has a huge reunion by a lake, with close to 200 people. As it got dark on the Fourth of July, some people started lighting off big, professional-grade fireworks. I took my young kids to watch, and as they ran around excitedly, I gave them the classic 1-D parent lesson: "Be careful!" They nodded, but the words were just theory to them.

Then, a man walked over. He knelt down, looked them in the eye, and said, "Hey kids, be careful." And he held up his right hand. He only had two fingers. He told them he'd had a fireworks accident a couple of years ago when he wasn’t being careful.

The message landed instantly. They stopped running. They understood. My words were a textbook. His hand was a scar. They got a ringside seat to his 4-D lesson, and it taught them more in five seconds than I could have in a lifetime of lectures.

Heck, it scared me straight.

Actionable Advice Practice the "It Could Be Me" exercise. The next time you witness a 3-D lesson—a car grisly car accident on the road, a colleague getting laid off, a project failing, a friend's bad investment—your first instinct might be to find reasons why you're different or smarter. Resist that urge. Instead, force yourself to ask: "What are the specific, plausible circumstances that could lead to this exact same thing happening to me?" This exercise replaces your defensiveness with humility, allowing you to absorb the lesson without needing the scar.

The Podcast is Live

The goal is to climb the ladder of learning to wisdom as efficiently as possible. You want to move past the empty proverbs to get a ringside seat to a 3-D lesson.

But seeing things with your own eyes is rare. This is where I believe content like this newsletter, YouTube channel and my new podcast can play a unique role. It can’t be truly 3-D. But it can be 2.5-D—online content enriched with a high-fidelity, real-world story. It’s the next best thing to being there.

My goal is to bring you as close to the fire as possible, without you having to get burned.

Stop collecting scars. Start collecting wisdom.

And on that note, the podcast is officially live.

The first episode is a conversation with Gergely Orosz, author of The Pragmatic Engineer, the #1 technology newsletter in the world. We go deep on the future of engineering and the lessons he's learned.

You can listen to the ad-supported version of our conversation on YouTube here:

I’ve already shot 5 more episodes with some amazing guests. Let me know in the comments who I should speak to next.

As a subscriber to this newsletter, you can also become a paid member to get access to the full, ad-free conversation, plus the entire archive of A Life Engineered.

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