I spent my twenties watching talented people stay stuck.
Working in team building, I’d see the same pattern: brilliant individuals who had everything they needed to succeed, except the ability to get out of their own way.
One guy stands out. Sharp as hell, could solve problems nobody else could touch.
But he’d rather quit than have one awkward conversation with his boss about a project deadline. Last I heard, he was on his fourth job in five years, still avoiding the same conversations.
That’s when I realized something: the difference between those who achieve extraordinary things and those who don’t isn’t talent, connections, or even luck. It’s whether they face the obstacles that everyone else runs from.
After years of training high performers and studying what makes people tick, I’ve identified eight major obstacles that separate those who break through from those who stay stuck.
These aren’t the obvious ones like “lack of money” or “no connections.” These are the internal barriers that most people never even recognize, let alone overcome.
1. The fear of being seen trying and failing
This one’s brutal because it disguises itself as “being strategic” or “waiting for the right moment.” But really, it’s the terror of looking incompetent in front of others.
I watched this destroy a colleague’s consulting business before it started. She spent two years “perfecting” her website instead of calling potential clients.
The website was never the problem. The problem was that calling clients meant risking rejection where people could see it happen.
Here’s what people who achieve extraordinary things understand: everyone looks stupid when they’re learning something new. The CEO who now runs a billion-dollar company once stumbled through their first investor pitch. The expert surgeon once had shaky hands on their first incision.
The obstacle isn’t the possibility of failure. It’s the fear of being witnessed in the attempt.
Once you accept that looking foolish is the entry fee for anything worthwhile, you stop waiting for perfect conditions that never come.
2. The comfort of incomplete action
You know that person who’s been “working on their book” for six years? Or “launching their business” since 2019? They’re not procrastinating. They’re addicted to the safety of incomplete action.
As long as the project isn’t finished, it can’t fail. As long as the business isn’t launched, it can’t go under. There’s comfort in the eternal “almost.”
I did this with a training program I developed. Spent months tweaking the curriculum, adjusting the slides, refining the exercises.
The truth? It was ready after month two. I just couldn’t handle the vulnerability of putting it out there and having it judged.
People who break through understand that done is better than perfect, because done can be improved, but perfect never ships.
3. The weight of other people’s expectations
Growing up in a “don’t complain, handle it” household, I learned early that disappointing others was worse than being miserable yourself.
One parent would say “get on with it,” the other would try to empathize, and I became the translator between both worlds, never quite sure which voice was mine.
This creates a special kind of paralysis: you can’t move forward without letting someone down, so you don’t move at all.
I’ve seen this trap destroy careers. People staying in jobs they hate because their parents are proud.
Entrepreneurs abandoning profitable businesses because their spouse thinks it’s “too risky.” Talented individuals choosing safe mediocrity over risky excellence because someone, somewhere, might disapprove.
The breakthrough comes when you realize what Rudá Iandê captures perfectly in his book Laughing in the Face of Chaos: “Their happiness is their responsibility, not yours.”
4. The tyranny of perfectionism masquerading as “high standards”
This was my personal favorite hiding place for years. I wasn’t afraid or procrastinating – I just had “high standards.” Every email needed another edit. Every proposal required more research. Every decision demanded more data.
But here’s what I discovered: perfectionism isn’t about excellence. It’s about control. It’s the belief that if you just work hard enough, prepare thoroughly enough, you can eliminate all risk and guarantee success.
The people who achieve extraordinary things have high standards too.
The difference? They apply those standards to outcomes, not to every minor step along the way. They know that a good decision made today beats a perfect decision made never.
5. The inability to tolerate temporary discomfort
Most people think discipline is about willpower. It’s not. After years of studying high performers, I’ve learned that discipline is often a consequence of environment, identity, and feedback systems, not personality.
But before any of that matters, you need to handle temporary discomfort without immediately seeking escape.
Can’t handle an awkward pause in conversation? You’ll never negotiate effectively. Can’t tolerate being bad at something? You’ll never develop new skills. Can’t sit with uncertainty? You’ll make impulsive decisions just to end the discomfort.
I see this constantly in the gym. Not the physical discomfort – most people can push through burning muscles. It’s the mental discomfort of being the weakest person there, of not knowing if your form is right, of possibly looking foolish.
So they quit after two weeks, not because their body gave out, but because their tolerance for discomfort did.
6. The stories we tell ourselves about who we are
“I’m not a morning person.” “I’m bad with money.” “I don’t do conflict.” These aren’t facts. They’re decisions we made about ourselves, usually based on a handful of experiences, that we now treat as unchangeable truth.
I told myself for years that I wasn’t a writer. Why? Because one high school teacher said my writing was “mechanical.” One comment, decades ago, became a core belief that almost stopped me from the career I have now.
People who break through challenge these stories constantly. They experiment with new identities. They test assumptions about their capabilities. They understand that “who you are” is largely a choice, not a fixed characteristic.
7. The addiction to being busy instead of effective
Here’s a truth that hurts: most “time management problems” are actually fear management problems.
We stay busy with email, meetings, and minor tasks because they feel productive without requiring us to face the scary stuff that actually moves the needle.
I had a client who worked 70-hour weeks but never seemed to make progress. When we tracked his time, 80% went to activities that didn’t matter. He wasn’t bad at time management. He was terrified of the high-stakes work that would actually determine his success.
Extraordinary achievers develop a different relationship with fear. They recognize it, acknowledge it, then do the scary thing anyway. As Iandê notes in his book, “Fear is not something to be overcome, but an essential part of the human experience.”
8. The refusal to accept reality as it is
This might be the biggest obstacle of all: the energy we waste fighting reality instead of working with it.
You didn’t get the promotion. Your business failed. Your relationship ended. The market crashed. These things happened. They’re facts.
But instead of accepting them and moving forward, most people get stuck in an endless loop of “this shouldn’t have happened” or “it’s not fair.”
I’ve done this. Spent months angry about a contract that fell through, as if my anger could somehow change the past. That energy could have gone toward finding three new contracts.
People who achieve extraordinary things have a different response to setbacks. They feel the disappointment, sure.
But then they ask: “Given that this is where I am, what’s my best move?” They don’t waste energy on what should have been.
Bottom line
These eight obstacles aren’t personality flaws or character defects. They’re human responses to uncertainty, vulnerability, and risk.
We all face them. The difference is that some people recognize them for what they are: not stop signs, but toll booths on the road to extraordinary achievement.
The path forward isn’t about becoming fearless or perfect. It’s about developing a different relationship with these obstacles. See them coming. Name them when they show up. Then make a conscious choice about whether you’ll let them stop you or not.
Start with one. Pick the obstacle that resonates most, the one that made you uncomfortable because you recognized yourself. Then do one small thing this week that directly challenges it. Make the awkward phone call. Ship the imperfect project. Disappoint someone’s expectations. Sit with discomfort for five more minutes.
Extraordinary achievement isn’t reserved for extraordinary people. It’s available to anyone willing to face what everyone else avoids.
