"I'm not Josie Grossie anymore!": How Imposter Syndrome Follows You Up the Ladder

We often think of imposter syndrome as something that plagues junior professionals—the law student worried about cold calls, the first-year associate convinced they don’t belong. But it doesn’t vanish with seniority. In fact, for many, it resurfaces in subtler, more surprising ways.

One of the most common is what I think of as time travel. You meet someone who knew you early in your career, and suddenly you feel like you’re right back there again. Maybe you’re now a partner leading a client pitch, but when you bump into the senior associate who trained you as a first-year, you instantly feel like that junior again—unsure, eager to please, worried about making a mistake.

It’s the same dynamic captured in the late-90s movie Never Been Kissed, where Drew Barrymore’s character—nicknamed “Josie Grossie” in high school—finds herself reliving old insecurities until she finally blurts out: I’m not Josie Grossie anymore! Sometimes senior professionals need the same reminder.

Why this happens

• Identity lag. People carry outdated versions of us in their minds, and encountering them can make us momentarily adopt that identity.

• Fear of being “seen.” At senior levels, the insecurity isn’t about raw competence—it’s about whether others fully recognize the professional you’ve become.

• The mirror effect. Someone else’s memory can trigger your own insecurities, even if they no longer define you.
  

How to move forward

• Notice it. Recognize the “time travel” when it happens. Naming it loosens its hold.

• Update your story. Remind yourself of the growth, skills, and credibility you’ve built since those earlier days.

• Stay present. Instead of worrying how they see you, focus on showing up as the professional you are now.
  

These moments of “time travel” are a reminder that growth is both external and internal. Titles, promotions, and achievements mark progress on paper, but sometimes our self-perception takes longer to catch up. Recognizing this gap is powerful—it helps us show compassion to ourselves and to others navigating the same experience. After all, part of leadership is remembering where you started, while also claiming with confidence who you’ve become.

By: Kandice Thorn, Founder, WorkBetter for Lawyers