When Winning Feels Like Losing: The Hidden Psychology of Performance Blocks

When Mikaela Shiffrin crossed the finish line in Milano Cortina last week and dropped to her knees in the snow, most people saw a champion reclaiming her place at the top. What she said in the press conference afterward was something far more important — and far less comfortable — than a triumph story.

Her father Jeff died unexpectedly in 2020. And the block that had been quietly dismantling her Olympic performances ever since wasn’t technical. It wasn’t physical. It wasn’t even grief in the conventional sense.

“Winning an Olympic medal without him here was terrifying to me before I knew that it was,” she admitted. After Beijing 2022, she recognized something even more unsettling — that she had felt relief at not winning. Relief that she didn’t have to experience standing on a podium while her father wasn’t alive to see it.

That is not a focus problem. That is not nerves. That is an unconscious psychological bind, elegantly constructed by a psyche trying to protect itself from an unbearable contradiction: I want this moment, and this moment will make his absence undeniable.

Clinicians sometimes call this an approach-avoidance conflict — but that term undersells what is actually happening. This is not ambivalence. What psychologists more precisely recognize here is what might be called a grief-success bind: the state in which achieving a desired outcome would make an unbearable loss undeniable, causing the psyche to unconsciously prevent the achievement. Distinct from fear of failure — this is fear of winning.

The unconscious solution? Don’t have the moment.

Shiffrin started working with her sport psychologist on this in July — months before the Games. Not on visualization. Not on arousal control. On something harder: whether she could let herself want to win, and grieve her father, at the same time. Whether joy and loss could coexist without one canceling the other out.

“Maybe today was the first time that I could actually accept this reality,” she said through tears after the race. “Instead of thinking I would be going in this moment without him, to take the moment to be silent with him.”

She didn’t resolve the grief. She integrated it. And that distinction is everything.

What the Standard Toolkit Misses

Performance psychology has given us an extraordinary set of tools. Visualization. Breath regulation. Attentional focus. Pre-performance routines. Cognitive reframing. These techniques are real, and they work — when the performer’s desire is clean.

But human desire is rarely clean.

The founders and executives I work with are among the most driven, capable people I’ve ever encountered. They’ve built companies from nothing, led teams through impossible circumstances, delivered results that should have made their careers. And yet — they stall. They almost close the round, then don’t. They get to the edge of the CEO role and find a reason to pull back. They build something significant and then, quietly, begin to undermine it.

When we look beneath the surface, what we find is not a skills gap. It is almost never a skills gap. What we find is a conflict — between what they consciously want and what success would actually mean.

In his book Blindspotting, Martin Dubin describes a pattern that is striking in its familiarity: the woman who is always passed over for promotion, who everyone recognizes as the glue holding the organization together, but who never quite makes the leap. From the outside, it looks like she’s been overlooked. But the deeper question is what Dubin invites us to consider: what would she have to give up if she were promoted? The answer, in many cases, is her identity.

Three Patterns I See Again and Again

The Indispensable One

Maria is a senior director at a mid-size biotech. By every external measure, she should have been a VP two years ago. She is brilliant, relentless, and genuinely beloved — the person everyone calls when something is falling apart. She has been told she is “being developed” for leadership. She has been passed over twice.

In our work together, something interesting emerges. When she imagines being promoted, the image that comes is not pride or satisfaction. It is aloneness. As a VP, she would have her own domain. She would delegate. She would stop being the person everyone needs in the moment.

Maria’s deepest identity is organized around being essential through proximity — the glue, the hub, the one who holds it together. Promotion wouldn’t reward that identity. It would end it. The org chart would change, but more than that: she would change. The version of herself that knows how to be needed in this particular way would have to be grieved.

She doesn’t know she’s protecting this. She experiences it as frustration, as being overlooked, as wondering what she’s doing wrong. The work isn’t about leaning in harder. It’s about examining who she would be if she stepped into a role where her value is less visible, less immediate, less felt.

The Underdog Who Can’t Close

David founded his company on the story he tells about himself: scrappy, resourceful, the guy who built something out of nothing without the pedigree, without the network, without anyone handing him anything. That story has been fuel. It has been identity. It is, in many ways, the whole point.

Now he is raising his Series B. The lead investor is committed. The round is essentially done. And David keeps finding problems — the terms aren’t right, the timing is off, he needs one more data point. His team watches, bewildered. His co-founder is quietly alarmed.

What David cannot yet see is that closing this round would mean becoming something he has never been: a founder with institutional backing, with real infrastructure, with a company that no longer fits the underdog narrative. Success would require grieving the identity that got him here.

The scrappiness was never just strategy. It was him. And the version of David who runs a scaled, well-capitalized company is someone he has not yet met — and is not sure he can trust. The work is not about closing the round. It’s about expanding his sense of self large enough to contain a new chapter.

The One Who Won’t Outlive the Mentor

Elena’s most formative professional relationship was with the woman who hired her at 26, saw something in her nobody else had, and spent a decade teaching her how to lead. When that mentor retired — and then, two years later, died — something in Elena’s ambition went quiet.

She continued to perform. Her reviews remained strong. But she stopped raising her hand for the big opportunities. She stopped angling for the CEO track she had been on.

In our sessions, she circles something she has never said aloud: that surpassing her mentor feels like a betrayal. That to become the kind of leader her mentor believed she could be — without her mentor there to witness it — feels unbearable in a way she cannot fully articulate.

Like Shiffrin, she doesn’t know she’s afraid to win. She experiences it as lost motivation, as uncertainty about what she really wants, as wondering if the ambition she used to feel was ever really hers. The work is about learning to carry the mentor forward rather than hold herself back. To let the achievement be a continuation of the relationship rather than evidence that she has moved past it.

What Integration Actually Looks Like

None of these people needed to be pushed harder. They needed to be seen more clearly — including by themselves.

The psychological work that Shiffrin describes is not exotic. It is not reserved for Olympic athletes with access to elite support teams. But it is deeper than most performance coaching goes, and it requires a specific kind of willingness: to look at what success actually means, what it would cost, and what version of yourself you would have to say goodbye to in order to step into it.

Dubin’s framework in Blindspotting is useful here because it names what so often goes unnamed: we have blind spots not because we lack intelligence, but because the blind spot is doing something for us. It is protecting us from a loss we haven’t consciously agreed to. Seeing it clearly means we have to grieve it.

Shiffrin said she started working with her psychologist on this in July. By the time she stood at the start gate in Cortina, she had done months of exactly this kind of work — not sharpening her focus, but expanding her emotional capacity to hold two true things at once. To want the moment and to ache for the person who isn’t there to share it.

“I do want this moment,” she said. “And I want him here too.”

Both things. At the same time. Without either one canceling the other out. That is not a mental skill. That is psychological integration. And it is, in my experience, the actual work that separates people who perform at the level they’re capable of from those who keep arriving at the threshold and turning back.

The Question Worth Sitting With

If you find yourself stalling at a threshold — a promotion, a funding round, a company milestone, a relationship — it’s worth asking not just what is in the way but what is the block protecting you from?

What would you have to feel if you got there?

What version of yourself would you have to leave behind?

What loss are you not yet ready to grieve?

These are not comfortable questions. But they are the ones that matter.

The Quiet Tension Journal Prompt

This is where it becomes yours.

Find a quiet moment, open your notebook, and write what comes.

When you read about the deeper conflict within Mikaela’s competing for gold, what did you find yourself thinking about in your own life? A goal you missed for a reason you couldn’t put your finger on?

Sharon Chirban, PhD is a clinical psychologist and executive coach with thirty years of experience, including former roles at Harvard Medical School and Boston Children’s Hospital. She works with high performers of every kind — founders, executives, athletes, and individuals navigating eating disorders — helping them understand not just how to perform, but what their performance is costing them, protecting them from, and trying to say. She sees clients at Amplify Wellness + Performance.