When Amy Madigan stepped on stage at the Academy Awards to accept the Oscar for Best Supporting Actress for Weapons, it marked more than a career milestone. It also challenged one of the most persistent myths surrounding women and success: the idea that if you haven’t “made it” by a certain age, your opportunity has passed.
Madigan’s win came more than 40 years after her first Oscar nomination in 1985, a moment that resonated deeply with many viewers, particularly women who have spent years navigating the cultural pressure of timelines around career, family, and achievement.
According to leadership expert, serial entrepreneur, and investor Chantell Preston, those timelines are largely manufactured, and often damaging.
In her upcoming book, The Success Lie, Preston argues that many women have been conditioned to believe their professional and personal potential comes with an expiration date.
“One of the most damaging lies women have been sold is that success has a deadline,” Preston says. “We’re taught that if certain milestones don’t happen by a certain age, we somehow missed our chance. But the truth is that leadership, confidence, and clarity often come later in life.”
Preston, the founder and CEO of Preston Partners and co-founder and co-owner of League One Volleyball (LOVB), has spent decades advising founders, executives, and high-performing leaders on how to rethink the assumptions that shape their careers. Through that work, she says she’s repeatedly seen women internalize a belief that success must happen early or not at all.
“From a young age, women often absorb messages that key life milestones must occur within a specific window. Our education must be completed by a certain age. Our career advancement has to be achieved quickly. And family decisions need to be made on schedule.
She says these narratives can create a constant sense of urgency, as though every decision carries the weight of a closing door; and, argues that the reality of leadership and career growth looks very different from the timelines many people have been taught to follow. As she outlines in her book, some of the most powerful leadership roles happen later in life, when we have accumulated experience, resilience, and perspective.
“By the time professionals reach their 40s, 50s, or beyond, they have often developed the skills that matter most in leadership: emotional intelligence, clarity of values, and the ability to navigate complex decisions,” she says. “Rather than starting from scratch, they are building from decades of lived experience.”
Another challenge women face, Preston notes, is the tendency to compare their progress with others. Social media, professional networks, and cultural narratives often highlight early success stories, reinforcing the idea that achievement must happen quickly.
But Preston encourages people to rethink the entire concept of a “correct” timeline.
“Some of the most powerful chapters of our lives are written after we’ve lived enough to know who we are and what truly matters.”
Madigan’s Oscar win offers a visible counterexample to that pressure. The moment illustrates that our careers, and our lives, are rarely linear.
“Breakthroughs can happen long after the moments the world assumes are most important,” Preston says. “For many watching the ceremony, the message was clear. Recognition, reinvention, and impact don’t have an expiration date.”
Preston believes moments like this are powerful reminders that success is not defined by speed, but by persistence and evolution.
“Madigan’s win is a win for all women who have wondered whether their best opportunities are behind them. I think this moment offers all of us a reminder that sometimes, the most meaningful success arrives exactly when experience has made it possible.”
