Navigating the Paradox of Success: When Achievements Lead to Self-Doubt

In the upper echelons of society—where C-suite executives negotiate billion-dollar deals, elite athletes medal on global stages, and high-performing professionals outpace their peers—a peculiar and often unspoken reality lurks: the more successful someone becomes, the more susceptible they are to self-doubt.

This phenomenon, known colloquially as the 'paradox of success,' undermines the conventional wisdom that confidence is the natural byproduct of accomplishment.

Instead, a growing body of psychological and behavioural research suggests that those who achieve the most often secretly question whether they've earned any of it. In recent years, life coaches, therapists, and mental health professionals have documented a surge in cases of imposter syndrome among highly successful individuals. This psychological contradiction has found resonance across industries—from Silicon Valley boardrooms to Olympic training centres.

One who understands this paradox intimately is Kasia Siwosz, a life coach whose clientele includes some of the world's top 1% performers. Based in London and operating globally, Siwosz has built her reputation not only on elite credentials—she's a former WTA tennis pro, a UC Berkeley graduate, a former investment banker, and a venture capitalist—but also on her ability to identify and disrupt the internal narratives that diminish self-worth at the summit of success.

When the Summit Breeds Uncertainty

Historically, psychologists Pauline Clance and Suzanne Imes introduced the concept of imposter syndrome in 1978 when they observed that high-achieving women often dismissed their accomplishments as luck. Over time, the diagnosis evolved to include men and non-binary individuals and has since become a pervasive psychological pattern among top-tier professionals.

A 2023 report by the International Coaching Federation revealed that nearly 62% of executives and high-level professionals experience persistent imposter-like feelings. Despite their track records, many fear being 'discovered' as frauds. This tension becomes especially pronounced in sectors emphasising performance over process—finance, tech, professional sports, and law.

Siwosz's work sits squarely in this space. Her clients are, on paper, wildly successful. Yet behind closed doors, she says, many feel inadequate or hollow. 'They'll say to me: 'I've built the company, I have the title, I even sold it for nine figures—but I still feel like I haven't arrived,'' she recounts.

The Achievement Trap

This internal erosion of self-belief often originates from the very systems that elevate high performers in the first place. In corporate cultures where long hours and relentless competition are valued, individuals are rewarded not for being but for doing—relentlessly. This creates what psychologists term 'conditional self-worth,' where identity is yoked to output.

'When your worth depends on performance, even your wins can feel like temporary reprieves instead of evidence of capability,' Siwosz explains. 'It's not that these people lack confidence. It's that their confidence isn't anchored internally.'

Her perspective is informed not only by her coaching practice but also by lived experience. Raised in post-communist Poland, Siwosz pursued professional tennis as a ticket to a better life, eventually earning a full athletic scholarship to study in the United States. She graduated from UC Berkeley and built a career in high-stakes finance and venture capital before founding her coaching business. The pivot came after a string of personal and professional reinventions, including the closure of her restaurant venture and a pandemic-induced pause in her VC career.

During that liminal moment, she says, she found clarity: 'Everything I'd ever done had prepared me to help others untangle the same patterns I'd lived through—pushing, proving, performing.'

The Quiet Epidemic at the Top

Experts in psychology and executive coaching increasingly point to a silent epidemic of emotional distress among elite professionals. Harvard Business Review has written extensively on executive loneliness. A 2022 McKinsey report linked overwork and performance pressure to rising mental health concerns among senior leaders.

Failure isn't just a professional risk for high achievers—it feels existential. Success, ironically, doesn't insulate them from self-doubt; it amplifies it. There's always more to lose, a higher bar to clear, and a greater fear of regression.

The problem, according to Siwosz, isn't simply external pressure. It's internal misalignment. 'So many of my clients have built incredible lives—but not necessarily their lives,' she says. 'They've been chasing expectations instead of fulfilment.'

Reclaiming the Self Behind the Success

Siwosz's coaching methodology emphasises introspection and emotional rewiring. Her proprietary program goes beyond traditional coaching advice or surface-level motivation. Instead, she helps clients dismantle subconscious patterns, challenge inherited belief systems, and re-establish a core sense of worth independent of achievement.

Key to her method is the cultivation of self-awareness. Clients are prompted to reflect on whose definitions of success they're living by and whether their pursuits still align with their values. In some cases, the answer is yes. In many, it's not.

She also guides clients in shifting from control to curiosity—from constantly anticipating failure to calmly exploring what comes next. It's a subtle but powerful repositioning. 'The goal is to move from proving to presence,' she says. 'To feel whole without needing to achieve something new just to justify your existence.'

Redefining Success from the Inside Out

As the conversation around mental health gains traction at all levels of leadership, coaches like Siwosz are playing an increasingly vital role. They offer tactical support and existential scaffolding for people who have scaled heights and found the view unexpectedly disorienting.

The paradox of success remains deeply misunderstood in a world that often conflates busyness with value and external achievement with internal peace. But through her work, Siwosz is illuminating a different path—where the inner life is no longer sacrificed on the altar of performance.

In doing so, she helps those at the top finally come home to themselves.