The Success Paradox: Why Your 'Character Flaws' Might Be Your Superpowers

After 20+ years of building online businesses, I’ve learned something that would’ve saved me a lot of headaches if I’d figured it out sooner.

Being humble is overrated.

I know, I know. That statement probably made some of you uncomfortable. Good. We’ll come back to why in a minute.

See, I’ve been thinking about this study on hyper-successful people. Not your average “finally got my first 1,000 subscribers” successful. We’re talking about the ones who make most entrepreneurs uncomfortable. The ones who don’t just hit their goals but blow past them like they’re standing still.

You know what they found? Three traits these people shared. And buddy, the first two are going to make a lot of people squirm.

The Traits Nobody Wants to Talk About

First up? A superiority complex.

I can feel you cringing. Nobody likes that phrase. It sounds like that guy who mansplains crypto at parties or the “thought leader” who starts every post with “here’s why everyone else is doing it wrong.”

But what if we’ve got it backwards? What if that discomfort you’re feeling isn’t about them – it’s about you?

Here’s what got me thinking. The other day I posted about aiming for $2.5M in the next 12 months. The responses were fascinating. Not the supportive ones or even the skeptical ones. The ones that stuck with me were from people who felt the need to explain why they were aiming lower.

“Well, I just want to make $60,000 because that will be enough for me.”

Cool. Genuinely. No shade. But why do you feel the need to justify your goals to me? And more importantly, why do I feel this weird pressure to downplay mine?

When Success Makes People Uncomfortable

That’s when it hit me. We’re not just talking about success traits here. We’re talking about permission. Permission to want more. Permission to believe you’re one of the few who can actually pull it off.

The second trait? Massive insecurity.

Now it gets interesting.

Because these hyper-successful people aren’t just walking around thinking they’re hot stuff. They’re driven by this constant, gnawing feeling that they’re not enough. That there’s more to do, more to achieve, more to become.

And if you’re thinking “wait, isn’t that unhealthy?” you might be asking the wrong question.

Maybe the real question is why we’re so quick to pathologize ambition. Why we’re so comfortable telling people to “be realistic” when all that really means is “stay safe.”

I’ve been guilty of it too. Spent years trying to file down my edges. Make myself more palatable. More humble. More “realistic.”

You know what that got me? Three successful-on-paper businesses that made me want to stab myself in the eye with a fork.

I’m done writing down goals that make other people comfortable. Done pretending I don’t think I’m one of the few who can pull this off.

And if that makes you uncomfortable?

Good. Let’s talk about why.

What No One Gets About Superiority

My generation might be the last one that got completely screwed by humility culture.

Growing up, having big dreams wasn’t just discouraged – it was seen as a character flaw. Like you were telling everyone else they weren’t good enough just by wanting more for yourself.

Want to build a million-dollar business? Better whisper it. Want to impact millions of lives? Keep that to yourself, buddy. Someone might feel bad about their own goals.

Here’s the thing about a superiority complex that nobody talks about. It’s not about thinking you’re better than everyone else. It’s about believing you can do things that most people won’t even try.

The Soccer Story

When I played soccer, I was brash and confident. I wanted to win and worked towards that goal every chance I got. Nobody ever told me to try not to win as hard.

But with business? The whole discussion changes.

“Be humble.”
“People don’t like people who show out.”
“Stay level-headed.”

It would be easier if people just said what they really mean “Stop doing the things I’m too scared to do.”

The New Generation Gets It

Now I’m watching videos by people 20 years younger than me where they make it seem silly not to aim big. What’s the worst that could happen?

And you know what? They’re right.

These kids aren’t walking around being jerks to everyone. They’re not putting others down. They’re just refusing to make themselves smaller to make others comfortable.

That’s the superiority complex we actually need. Not the “I’m better than you” kind. The “I believe I can do this, and I don’t need to apologize for it” kind.

The $2.5M Mindset

When I say I’m going for $2.5M in 12 months, do I think anyone can pull it off?

Nope.

But I think I’m one of those that can. I believe I’m one of those that can.

That’s my superiority complex, and when it’s framed that way, I can live with that. Because it’s not about putting others down. It’s about lifting myself up to where I believe I can be.

The people I’m blessed to be working with? I hype them up every chance I get and I don’t want them to downplay anything. Because I’ve seen what happens when someone finally gives themselves permission to believe they’re capable of exceptional things.

The Real Problem with Success

Here’s what I’ve learned after two decades in this game. People don’t actually have a problem with success. They have a problem with people who refuse to pretend they’re not capable of it.

You can succeed – as long as you act surprised when it happens.
You can win – as long as you pretend you got lucky.
You can do big things – as long as you make them seem small.

But what if we just… didn’t?

What if instead of pretending we’re not capable of exceptional things, we owned it? What if instead of downplaying our goals, we amplified them?

What if instead of asking “who am I to think I can do this?” we started asking “who am I not to?”

The Permission Slip You Never Got

So here it is. Your permission slip to believe you’re capable of exceptional things.

To have a healthy superiority complex.
To believe you can do what others won’t even try.
To stop making yourself small.

Just remember – this isn’t about being a jerk. It’s about being honest. About what you want. About what you believe you can achieve. About who you know you can become.

I think people really only care about you being kind. Don’t be a jerk.

But stick your damn chest out.

And if someone tells you to be more humble? Remember this isn’t about them. It’s about you refusing to play small anymore.

That kind of superiority complex? Yeah, I can live with that.

The Thing Nobody Admits About Success

Want to know the weirdest part about those hyper-successful people? Right next to that superiority complex sits a massive insecurity.

Yeah. Plot twist.

These same people who believe they can achieve exceptional things? They never feel like they’ve achieved enough. There’s this constant gnawing feeling that they need to do more, be more, achieve more.

Most people would call that unhealthy. But I’m starting to think we’ve got that backwards too.

The Never Enough Game

We’re encouraged to believe we are enough, and technically, we are all enough but that also assumes we are built the same.

I can appreciate what I’ve done in my life but also feel like I haven’t accomplished anything because it doesn’t feel like I have.

And you know what? I don’t know if it will ever feel like it but it’s more fun for me to chase the feeling than just shrug and call it that.

That’s the part most people miss about insecurity at this level. It’s not about self-hatred. It’s not about thinking you’re worthless. It’s about knowing there’s more in you and being uncomfortable until you get it out.

The Grace Trap

There’s this popular idea right now about giving yourself grace. And look, I get it. Sometimes we all need to ease up on ourselves.

But there’s this fine balance between giving yourself too much grace versus being way too hard on yourself.

If you don’t have big goals or aspirations none of this matters so don’t sweat it. But if you’re the type who feels that constant pull toward something bigger? That insecurity might be the very thing pushing you forward.

The Comfortable Lie

Here’s the comfortable lie we tell ourselves “If I just achieve X, then I’ll feel secure.”

But talk to anyone who’s achieved something significant and they’ll tell you – the goalposts always move. The target always shifts. The horizon keeps expanding.

And maybe that’s not a bug. Maybe that’s the feature.

Why Your Therapist Might Be Wrong

Now, I can hear the wellness crowd getting ready to come at me with their journals and their “you are enough” mantras.

And look, if you’re dealing with clinical anxiety or depression, none of this applies. Go talk to a professional.

But for the rest of us? Maybe it’s time to stop pathologizing the very thing that drives us forward.

Maybe that voice saying “you could do more” isn’t your enemy.
Maybe that feeling of not being satisfied isn’t something to fix.
Maybe that insecurity is actually ambition in work clothes.

The Truth About Drive

I spent years trying to make peace with where I was. Trying to feel “satisfied” with my achievements. Trying to quiet that voice that kept saying “more.”

You know what happened?

Nothing.

Because here’s what I’ve learned. That insecurity? That feeling of not being enough? It’s not about self-worth. It’s about potential.

It’s not saying “you’re not enough as a person.”
It’s saying “you’re not done yet.”
It’s not saying “you’re worthless.”
It’s saying “you’re capable of more.”

The Sweet Spot

The magic happens when you can hold both truths at once.

You can believe you’re one of the few who can achieve exceptional things AND still feel like you haven’t scratched the surface of what you’re capable of.

You can know you’re enough as a person AND still want to push yourself further.
You can appreciate how far you’ve come AND be hungry for more.

That’s not a contradiction. That’s rocket fuel.

The Permission You Really Need

So here’s your next permission slip.

It’s okay to never feel satisfied with your achievements.
It’s okay to always want more.
It’s okay to let that insecurity drive you forward.

Just remember – this isn’t about beating yourself up. It’s about being honest about what drives you.

And if someone tells you that’s not healthy? That you should learn to be content?

Remember this isn’t about them. It’s about you refusing to settle for less than what you know you’re capable of.

That kind of insecurity? Yeah, I can work with that.

Where Most People Stop Reading

Most people will read this far and do exactly nothing with it.

They’ll nod along, maybe share it, possibly even drop a “this resonated” comment. Then they’ll go right back to playing small because that’s what feels safe.

But you’re still reading. Which means you might be ready for what comes next.

The Third Trait That Everyone Gets Wrong

Remember that study I mentioned at the start? The one about hyper-successful people?

There was a third trait they found. Impulse control.

And this is where I go off script because with ADHD this hits different.

See, most people read “impulse control” and think it means always making the rational choice. Being careful. Playing it safe.

But what if we’ve got that backwards too?

What if real impulse control isn’t about controlling your impulses to dream big or believe in yourself? What if it’s about controlling the impulse to shrink? To play it safe? To make yourself smaller so others feel comfortable?

The Only Thing That Actually Matters

Here’s what I know after two decades of building businesses.

Success isn’t about controlling your impulses to be great. It’s about controlling your impulses to be average.

It’s about catching yourself when you start to downplay your goals.
It’s about stopping yourself when you’re about to apologize for your ambition.
It’s about redirecting yourself when you start to shrink.

Your Real Problem

Your problem isn’t that you have a superiority complex. Your problem is that you’ve been taught to see it as a problem.

Your issue isn’t your insecurity. Your issue is that you’ve been told to get rid of it instead of using it.

And your impulse control? Maybe it’s been focused on the wrong impulses.

What Happens Next

This is usually where I’m supposed to wrap everything up in a nice bow. Give you three action steps. Make you feel good about reading this far.

But I’m not going to do that.

Instead, I’m going to tell you what’s actually going to happen next.

Some of you will close this and immediately go back to playing small. That’s fine. This message wasn’t for you.

Some of you will feel uncomfortable with how much this resonated. Good. Sit with that discomfort. It’s telling you something important.

And a few of you? You’ll recognize this as permission to finally go all in. To stop apologizing for your ambition. To use your superiority complex and your insecurity as the rocket fuel they are.