What I Wish I'd Known at 20 (That Nobody Bothered to Tell Me)
Manage episode 509014510 series 3682265
"At the time I'm recording this, I'm 45 years old. And if I could go back in time and talk to the 20-year-old version of me, this is what I'd say. I'd say I know you're an idiot. You are still an idiot, 25 years later."
If I could have a conversation with my 20-year-old self, it would be short - not because there isn't much to say, but because he wouldn't listen to most of it. At 20, I thought success came from following rules, working hard, and waiting for opportunities to find me. I was wrong about everything.
The three life-changing lessons from 25 years of entrepreneurship:
Lesson 1: Your biggest strengths will become your biggest weaknesses At 20, I was proud of my ability to analyze situations thoroughly. This helped me excel in school and early jobs. By 30, this same strength had become my greatest weakness - I was so good at finding potential problems that I talked myself out of risks that could have changed my life. Every strength taken too far becomes a liability.
Lesson 2: Most opportunities disguise themselves as work "The fun you have, the fact that you look at every idea as a possible new experience or as something that can be solved means you're going to be the type of person that takes risks, that sees opportunities when they come your way, or that is willing to invent new things. Inventing new things, trying new things, going against what everybody else is doing, is how you're going to make your name, your fortune, your future and find fulfillment in life."
Lesson 3: Keep having fun (this is the most important one) "So many people get into their 30s and their 40s and they don't have fun anymore. They know what fun used to be and try to rekindle that every now and then. But they stop having fun with just ideas and the people around them. They don't have fun at work. They're not creative thinkers anymore."
The brutal truth about following advice: The most expensive mistake I made wasn't choosing the wrong business model - it was following advice from people who had never actually built what I was trying to build. I spent years implementing strategies from business books written by consultants who had studied successful companies but never run one themselves.
What I wish someone had told me: Your biggest regrets won't be the risks you took that didn't work out - they'll be the opportunities you didn't pursue because you were waiting to feel ready. The perfect time to start was 20 years ago. The second-best time is now.
Original YouTube video: https://youtu.be/NSAHZjNQUc0
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This podcast is the audio version of the First Step Entrepreneur YouTube channel.
25 episodes