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6 mistakes you need to make at least once.

Maybe the road to success is paved with mistakes.

6 mistakes you need to make at least once.

You can’t achieve perfection. You can’t even fool the rest of the world into thinking you have.

Instead, getting somewhere — getting anywhere — in life is about going through a process of experimenting, making mistakes, learning, and improving.

If you try to get around that process, the only thing that happens is you become completely wound up in yourself and you fail to improve your work, your product, or your creative skills.


I’ve learned over the last 15 years that success in life isn’t best measured by what you achieve. It’s measured by what you overcome. For me, that has meant overcoming the sheer weight of my own mistakes.

If you pretend that you don’t make mistakes, you lose the chance to do remarkable things.

Instead, you’ll spend your time doing safe things. So celebrate your mistakes. Don’t glorify them — but look at them as chips that can be cashed in for future success.

All photos via Redd Angelo, used with permission.

Here are six mistakes I think you almost have to make to be successful and fulfilled in life:

1. Trust the wrong people.

When you’re starting out, you want to be a trusting person. Start out optimistic, open-minded, and free. Don’t be too quick to judge because you’ll be basing that judgment on zero data.

By trusting everyone, you’re going to end up trusting the wrong people. This just happens, because the world is full of crappy types who want to screw you over and take everything you’ve got.

This is going to teach you who is actually worth trusting in the future. It will give you the information you need to make informed and valuable choices around who is worth trusting and who is not worth your time. Trust the wrong people because it’s one of the only ways to end up trusting the right ones.

2. Screw up your finances.

Everyone should make at least one bad financial decision. This is something I truly believe. There’s just something about that moment of realization, when it hits you that you’ve made a truly terrible mistake with your money, that can sober you up for life.

My mistake? Debt. $10,000 worth of credit card debt, racked up funding software development. That’s something you can’t just shrug off or think away with positive thoughts. That’s something that wakes you up sweating and panicking.

I’m on my way out of that. Well on my way. It’s a mistake I can’t see myself making again, and it’s a mistake I know I’ve learned from.

3. Choose a bad career path.

I love it when people tell me they started out on a career, founded a company, designed something, and then quit when they realized it wasn’t for them. How brave is that? To be able to admit that you walked the wrong path and take the time to switch?

I think one of the only ways to know what you really want to do is to try a whole bunch of things and learn what it feels like when you’re doing the right one. That gives you the knowledge you need to make a better choice.

Choosing a bad career path sucks, and it can feel like a huge setback. I’ve done it enough times to know that when you’re right in the middle of it, you will feel like a failure. Don’t look on it as a waste of time. Trust me, it’s not.

4. Make selfish decisions.

When you’re young, you’re selfish. This isn’t an indictment of millennials — I am one. The fact is, we are taught empathy throughout our formative years, but it’s not a skill that can be learned in the abstract. Empathy is something that can only be picked up with hands-on experience.

And that means you’re going to make selfish decisions. Maybe you’ll screw over the co-founder of your start-up. Choose money over your family. Break up with a person who trusted you, in the worst possible way. I’ve done all of that.

Seeing the impact of those selfish choices breaks you. In little ways, in big ways. It changes the way you see other people. If you’re lucky, it stops you from being able to pretend that everyone else in the world is a non-player-character in a game.

5. Take the easy way out.

It’s so hard not to do this. It’s so hard not to take the easy way out when you know how much simpler it will make your life. And when you haven’t been burned, it’s hard to see a reason why you shouldn’t try to shift the blame or do a half-assed job.

But do it once, and you should learn something: Taking the easy way out will often come back to bite you. You will likely regret it. Quality will suffer, your reputation will suffer, and your own experience of it may even be terrible.

“Don’t do anything by half. If you love someone, love them with all your soul. When you go to work, work your ass off. When you hate someone, hate them until it hurts.” — Henry Rollins

6. Work too hard.

I see this from would-be start-up founders and artists and writers every day. They talk about hustling 18 hours a day. They tell you they’ve worked every weekend, every night. They buy into the fallacy that letting your work rule every waking moment is the only way to be successful.

“I’ll sleep when I’m dead.”

“It’s all part of the hustle.”

“You can start up or rest. You can’t do both.”

This is all a complete fabrication. It’s been propagated by the insane work schedules of a small percentage of billionaire founders and visionary creatives who were able to function on a fraction of sleep every night.

They are the exception. You are the rule. If you choose to work too hard once and you burn out, that’s an awesome opportunity to learn. But you have to learn from it. You have to learn that trying to maintain that level of skewed work-life balance is rarely going to work for you.

One of the guiding forces in my life has been my ability to screw up completely, get back on my feet, and keep on swinging.

Did I shut down a creative services agency because I had zero idea of how to run a business? Absolutely. Did I get completely ripped off by a former business partner and end up massively in debt? I won’t deny it.

Did I drop out of law school and fail to accomplish anything more meaningful than binge-watching TV for seven months? That checks out.

But the unifying theme behind every mistake I’ve made is that no matter how long it took, I learned something. I took something home. I gained valuable information about myself, my challenges, and my path.

So screw up once in a while. Hell, screw up every day! And take something from those mistakes, because in my book, messing up is a quicker road to success and satisfaction than being perfect every day of the week.

Photo by Anna Shvets from Pexels
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