What's the biggest lesson you've learned? | Q+A

A speaker recounts a Chinese proverb to argue that events aren't inherently good or bad but depend on perspective. He reflects that strengths can become liabilities and weaknesses can hide opportunities, shares personal examples (disorganization, lost business cards), and emphasizes the career-changing lesson of admitting "I don't know" and asking for help in professional settings.
Chapters
There's a great Chinese story. It's a Chinese proverb. It's told many ways, but here's the way I heard it. A young man is born with an unbelievable gift for horse riding. And everyone in the village says, you're so lucky. And the monk says, we'll see. And he falls off his horse and breaks his leg, ends his career. And everyone in the village says, you're so unlucky. And the monk says, we'll see. And then war breaks out and all the young men are sent off to battle, but he can't go because of his busted leg. And everyone in the village says, you're so lucky. And the monk says, we'll see. And the point is, good, bad, I don't know what those things are. We perceive things as good or bad because of the lens we're looking through. And what I have learned about my own life and my own career is that every strength that I have has liability. And every weakness that I have, there is hidden opportunity, right? So, for example, self confidence. Really important. Gotta have self confidence, right? The liability of self confidence is sometimes you come across a little cocky. Liability. You have to manage that. It's called humility. We like humility. Because what it means is, I don't believe my own press, right? That's what humility is. I have these strengths, and I acknowledge those strengths. I understand I have to manage them for fear that they will actually become liabilities. But the opposite is also true. So I'm disorganized, right? I'm not organized, which huge liability. You know, somebody says, we got to do business with you. They give me their business card, I'll lose it.
You know, and it's bad. And it. And I beat myself up of it. And I'm like, I'm leaving money on the table. Like, I'm literally cause myself so much stress because I'm disorganized. I've tried all kinds of systems, and they're good for like a week. And then I go back to my old ways. Here's what happened. Early on in my career, I'd meet somebody, they'd say, we have to do business with you. They give me their business card. A week and a half later, two weeks later, I find their business card underneath something with a bunch of dust bunnies. I'm like, oh, shit, right? Everybody else who's organized already called them the next day, already sent them an email. They're all over it.
I call them up a week and a half later and be like, hey.
Turns out they Wanted to do business with me even more because they thought I was busy.
Good, bad, I don't know. Now, I'm not taking pride in my disorganization. I'm simply saying in all of my weaknesses, there are hidden opportunities. And what I'm trying to do. Again, I don't believe in good, bad, right, wrong. I believe in balance. And what I'm trying to do is recognize that when I beat myself up, where's the lesson? I've stopped trying to think of things as right decisions and wrong decisions, and now I try to think of them as right decisions and lessons learned. And I will beat myself off if I didn't learn the lesson. I repeat the mistake that I take that hurts me. But the biggest mistake I've made in my life that caused me more pain that I had to overcome, was the false belief that I have to know all the answers. And when I don't, I have to pretend that I do. For some reason. When we're in a position of authority or rank, or when you're the frontman, you're the sales guy, having all the answers is what we think we have to have. And it turns out when we have an answer for everything, people actually don't believe we have an answer for anything, because nobody has the answers to everything. And the biggest lesson I learned is in a professional context, in a meeting, in a sales opportunity, when somebody asks me a question, for me to say, I don't know.
Or let's find out together, or there are other people who are better qualified to do that than me. I remember in early sales meetings when I learned this lesson, I used to be able to great. I used to be great at everything because I had to be right. I got to portray confidence. It is a new business. And it got to the point where it was so hard to win business that at some point, I think I probably, in a moment of weakness, quite frankly, I was probably exhausted. That's usually how one learns these lessons, because you let your guard down in a meeting. Somebody said, we want you to do this, this, and that. I'm looking at tons of money on the table. And I said, I'm really good at that. I'll do that. I'm okay at that. That I really strongly recommend you hire somebody else because I suck at that. I'll work with them, but I won't do it. The fact that I said that they wanted to hire me to do everything even more because they've never had anybody that honest. All the other sales guys who were pitching their business for the same thing. Told them they were great at anything, everything. I was the only one who said so. So?
So the whole idea of saying, I don't know, even to my own colleagues, I need help profoundly, profoundly changed the course of my life. Turns out we're constantly surrounded by people who want to help us, including our own clients. But they didn't offer their help because they didn't think we needed it, because we said we knew everything. So for me, that lesson was one of the biggest mistakes that I've made in my whole career. And I think when you say something that went right.
Was having the courage to ask for help when I was in really, really bad shape, when I was really down to simply call a friend and say, I'm struggling.
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