What I Wish I'd Known at 20 (That Nobody Bothered to Tell Me)

By Art Harrison • June 21, 2025

At 20, I thought I knew how life worked. I was wrong about everything. Here are the uncomfortable truths that would have saved me years of mistakes.

If I could go back and 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 the rules, working hard, and waiting for opportunities to find me. I thought the smartest people made the fewest mistakes. I was wrong about everything.

Twenty-five years later, here's what I wish someone had told me. Not the motivational fluff—the practical, uncomfortable truths that would have saved me years of trial and error.

1. Your Biggest Strengths Will Become Your Biggest Weaknesses. At 20, I was proud of my ability to analyze situations thoroughly. It made me feel smart. By 30, this same strength had become my greatest weakness. I was so good at finding potential problems that I talked myself out of taking risks that could have changed my life. My thoroughness became paralysis. It's a lesson I had to learn the hard way about Overcoming Analysis Paralysis. Your attention to detail can become perfectionism. Your caution can become cowardice.

2. Nobody Knows What They're Doing (Including Successful People). I spent my twenties waiting to feel ready. I assumed successful people had figured something out that I hadn't. Then I started working with executives and discovered they're all making it up as they go along. The difference isn't that they know more—it's that they're comfortable acting despite not knowing everything. Competence comes from acting while feeling incompetent.

3. Your Timeline Is Completely Wrong. At 20, I had my life mapped out in five-year increments. I thought success was a linear progression. Real life doesn't work that way. The most important opportunities come at unexpected times. Success comes in waves, not steady increments. Stop holding yourself to arbitrary timelines and focus on consistent action.

4. Failure Is the Best Education Money Can't Buy. I was terrified of making mistakes because I thought they reflected poorly on my intelligence. This was incredibly expensive. While I was protecting my reputation, others were gaining experience. The breakthroughs I eventually had didn't come from avoiding failure—they came from failing faster and learning more systematically than my competitors. It is the most direct path to Building Confidence to Act Despite Uncertainty.

5. Action Beats Intelligence Every Time. In school, being smart meant having the right answers. In business, being smart means taking action with incomplete information and adapting. I watched "less intelligent" people build successful careers while "smarter" people got stuck in planning phases that never ended. The difference wasn't IQ—it was a willingness to act before feeling ready.

Your worth isn't determined by your achievements. You're valuable whether your first project succeeds or fails. Start before you feel ready. The lessons that matter most can't be taught—they have to be experienced.

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Video Transcript

At the time I'm recording this, I'm 45 years old. And if I get 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. So this video is for you because, despite the fact that there are probably hundreds of people out there sharing advice on things you should do, how you should take care of your body and your money, you're not going to watch them. And even if you do, you don't have the type of attention span that's going to remember 50 different things. So I'm going to tell you the three things I want you to know or remember to make sure you're living the best possible life; that you have opportunities that most people would only dream of. And the first one's probably the most important. Keep having fun. So many people get into their 30s and their 40s and they don't have to have fun anymore. They know what fun used to be and they try to recindle 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. And if you can keep that creativity and that fun, you will differentiate yourself from everybody else that you experience in life and in business. 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 as opportunities when they come your way or that is willing to invent new things - and 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. So stop trying to be so serious. You don't have to be the grown up in the room to succeed. As long as you're adding value, you can have fun every single day. It's not that difficult, but most people don't do it. So just be that guy that has fun and continues to deliver on value and you will succeed more than you even can imagine right now. And I'm being serious. I'm the older you, remember. I am in my house right now in pajamas. I have been in pajamas for about 80% of my career and I've made more money than most people will make in their career. That's the type of fun that I have. And it's not just that pajamas are fun. It's that I've never done things the way that I was expected to do them. I just decided what I enjoyed doing. I had clarity on that and I just pursued it. And that's given me the freedom to be a pajamas guy for a good 20 years now. And, I'm not looking back. The next thing I'd tell you is remember that it's okay to learn from other people, but you shouldn't judge them and you should do the things they're not willing to do. Part of having fun, taking risks, being a pajamas-guy means that you're going to see a lot of people that want to do things a traditional way. But if you want to grow real wealth, if you want to have freedom and autonomy, if you want to be creative, if you want to live a life that's differentiated from everybody else, the easiest way to do that is to look at the things that they don't like doing, the things that are annoying them, the things they complain about and figure out a way to do it better, or just to do the job, because they will pay you money to do something that they don't want to do. And it may sound like grunt-work initially, but you can turn that into a business. You can turn that into a side hustle. You can turn that into the springboard for your career. People are inherently lazy. And I don't mean that as a judgment on them. It's just human nature. You're lazy in so many ways. By the way, side tip is when you get older, clean the GD stairs because this is gross. I'm making videos on your stairs right now and you have not done a good job of taking care of that. But anyway, back to the point, people are lazy. People are scared of taking risks. People don't want to do things that they haven't tried before that they don't know they're going to be successful at. So if you're willing to do that, you will succeed. The third thing that I would tell you, probably one of the more important things is that money isn't everything. And it's actually relatively easy to come by. It's not easy for everybody. But if you're willing to think differently, if you're willing to have fun and do the things that people don't want to do, there are so many different ways to make money. Don't think that a salary, a promotion, a few stock options here or there are going to create the type of wealth you want. You can create assets for yourself. You can make videos. You can write a book. You can become a consultant or a coach or a freelancer. There are so many different ways you can make money. Figure out what it is you love to do and then get creative on how you do it. You can look up a guy later on and he'll explain to you how numbers can be moved in any way you want. A lot of people think about how many things they'd have to sell at $20 a pop to make a million dollars. But you're smarter than that. Know you can move the numbers. Instead of selling 50,000 units of something for $20. Maybe sell 5,000 units for $200, or 500 units for $2,000. There's so many different ways you just have to think about money differently. Money isn't tied to time. If you're only thinking of it that way. If you're working for an hourly rate, if you're thinking about your promotion or salary, it's fixed. You're only going to have so much time in life. You're only going to have so much time to work and have fun and be different. So look at money the same way and say, I want to make money when I'm sleeping. I want to make money in all kinds of different ways and be creative with that. If you can do those three things. If you can just remember to have fun, if you can learn from other people but also do the things that are not willing to do and think about money differently. My God, you will do so many amazing things. There's a ton of other advice that I should probably give you. I should probably tell you to make exercise a regular part of your life, to take care of yourself, to find a partner who you love and you will do all of those things. As long as you're having fun, you will be a magnet for those people. If you're having fun, exercise, activity will just become part of life because you'll be excited to be out in the world. Eating, I don't know. You sometimes need to work on that. But that advice is easy to come by. The advice that matters most is simply to be different, to enjoy your life, and go out and do it. That's what I've done and if you get to do the same things that I've done, the same experiences, you will be incredibly happy. And the last things I'd tell me, since I'm here, I know I said only three is subscribe to this channel. This is what I do now because of the freedom, because of the risks, because of the opportunities I've had, I get to be a pajama guy again in my house making videos. So subscribe to this channel right now because the videos that I'm making are for you. There to make sure that you go down the same path I went down or maybe even a better one that I went down. So you could live a life that is full of fun and joy and money and freedom. Because that's what you want. You're 20 years old. You're already thinking about the life you want. The house you want. The type of stairs that you want to have behind you. And you can have all of those things. It's not that hard. The hardest part is just changing the way you think about the world and recognizing that you don't have to be anybody but yourself to succeed. So if you're ready for that, as I said, subscribe and check out this video. This is one of the videos that I made about who I am and how I managed to be myself and succeed all of the time.