Why some leaders pull ahead while others stall
Hint: The reasons are simple, but they aren't what you think.
The narrative we’ve been sold is false.
The hockey stick up and to the right isn’t how most businesses are built, nor is it how most careers develop. Yet this is somehow the yardstick that we’ve all come to use to measure our progress against.
It’s no surprise that we believe it. Our brains gravitate toward simple ideas, even if they're filled with lies.
The actual tumult, twists, and turns of a real career (not a manufactured fairy tale) are hard to capture. They don’t make for the easiest social media posts. They’re complicated and take time to understand the context, the nuance. In short, it’s too much work to delve into, so we don’t.
Instead, we believe the false narrative that success comes from successive progress without any speed bumps or roundabouts.
And yet, examples abound to prove otherwise:
Steve Jobs was fired at the height of his first stint at Apple.
J.K. Rowling was on welfare, navigating depression and single-motherhood, and was rejected 12 times before the first installment of Harry Potter was published
Babe Ruth held the record for strikeouts for decades before he became a baseball superstar.
Thomas Edison was told he was “too stupid to learn anything” and was fired from his first 2 jobs for not being productive enough. He made 1,000 unsuccessful attempts before inventing the lightbulb.
We don’t hear these stories because we don’t seek them out, and they aren’t the sexiest headlines, especially in a culture that worships success.
They also aren’t widely available because the people featured also likely didn’t talk as much about their struggles as their successes.
Think about your friends who’ve achieved great heights. How often do you hear about their fears and setbacks?
Not often, is my guess. It’s easy to understand why not.
We are wired to peacock our wins and to hide our misses.
It’s safer to present a facade that communicates strength, power, and consistent success.
When I was feeling lost and depleted in my last job, I felt shame, guilt, and tremendous fear. It was all compounded by my intense desire to hide these feelings. It felt tantamount to surrending and admitting defeat if I acknowledged I didn’t feel steady or confident.
In fact, I remember talking to a former colleague in a catch-up call when I was particularly down, and I could see the empathy, but also the judgment in his eyes when I shared my challenges. I never heard from him again. I’m not saying he didn’t care, but our relationship wasn’t the kind that was strong enough for him to see me as anything but broken.
It’s not surprising I didn’t reveal how I was feeling to anyone else after that.
Why would I weaken my reputation?
Perception is reality, but it’s not what you think.
The people who succeed didn’t do it because they didn’t face snags. They didn’t possess magical powers, and they weren’t “the chosen ones.”
But they did find a way back to their confidence and purpose. They didn’t get there immediately (unless they were a bit delusional). There were likely many days and nights spent suffering, asking themselves existential questions.
But they eventually found their way through the darkness. Through trusted friends and family members, and through their own wisdom or faith in a higher power, they gave themselves:
Permission to Stumble
They either knew or simply accepted that issues would arise. They weren’t going to achieve their vision in a linear path. And just because they faced hurdles, those weren’t a reason to give up.
Obstacles were simply part of the journey.
This view sounds simple in theory, but for people who are used to winning or who have adopted the mindset that the only way forward is up, it’s actually a rather significant shift.
It means that you understand that negative signals are necessarily indicators of long-term failure. This one is worth pausing on for a moment because cognitively, it doesn’t make sense.
How can these two statements both be true at the same time?
You receive data that something on your critical path isn’t working
Your success isn’t doomed
The people who can reconcile those two concepts intellectually and emotionally are the ones who can continue to persist and don’t give up.
And while persistence isn’t a guarantee for success, quitting is a guarantee that you will fail.
So the learning isn’t just to keep going, it’s how you perceive the path and your progress on it.
Because if you are to convey to anyone else that you will win, first, you have to convince yourself.
That’s the perception that matters most.
Your own.
You don’t have to do it alone.
I don’t want you to misinterpret my story above as a guide to navigate the hard times alone. In fact, I feel the opposite.
It’s not that you should isolate yourself. It’s more about being selective about who you reach out to and when.
Every leader should cultivate their network at all times.
In the good times, it’ll feel easier because you’ll be bolstered by your success and positive vibes.
In hard times, lean on your closer ties, confidants who can support you and help you sustain the work and effort it takes to move through the inevitable obstacles without judgment.
Who you choose to reveal your vulnerabilities to matters. Don’t make the mistake I made and show all your cards to a weak link. Only do this with your trusted circle or hired help.
You might be surprised that when you ask for help from someone who you’ve established a relationship, you’re not actually draining the relationship.
As David Brooks noted in “How to Know a Person,” sometimes asking for help is one of the most meaningful ways to build trust. It’s a meaningful way to signal that you value the other person so much so that you are willing to be vulnerable and that you trust their input.
Relationships built through hardship are often the ones that have a more lasting and positive impact on both parties. Don’t resist reaching out, just be thoughtful about who and when.
And the power of revealing your stumbles isn’t just in helping you navigate through them. It’ll give the people in your trusted circle room to do the same.
Imagine a world where this is repeated over and over again?
That’s how we change the narrative of success from smooth and linear to bumpy and unpredictable, and help more leaders give themselves “permission to stumble” and persist on their path to success.
If you found this post helpful, please consider liking or sharing it with other leaders you think might benefit.
And if you’re one of the leaders who have given yourself permission to stumble and are ready to push ahead — bravo! I’d love to hear how it’s going.
May you lead without limits,
P.S. If you’re looking for someone to help you navigate meaningful challenges (or opportunities) at work or in your career, I have one opening for an individual client and one opening for a team engagement this summer.




This article is terrific. The narrative that success is linear makes everyone else feel like something is wrong when it is not. It’s a perception that only makes us feel alone in our most challenging moments.