The relationship that shapes your career (and nobody prepares you for)

Are you a 'sensitive striver' (an ambitious, emotionally attuned overthinker)? Then this piece is for you.

For this month’s Reflections – a series of conversations aimed at developing our toolbox beyond creativity – we’re exploring the art of managing up: how to navigate work relationships with intention, self-awareness and empathy, especially in systems where hierarchy, subjectivity and ambiguity run deep.

In the fashion industry, many of us are thrown into leadership or stakeholder-facing roles without any formal guidance on how to communicate boundaries, navigate feedback, or ask for what we need. We’re expected to intuit power dynamics, decode shifting priorities, and remain creatively productive. But what if these challenges weren’t just personal struggles to push through – what if they were signals pointing to skills that can be learned?

Melody Wilding’s new book, Managing Up: How to Move Up, Win at Work, and Succeed with Any Type of Boss, released last month, offers exactly that: a practical, compassionate framework for navigating professional relationships from any position. A licensed social worker and executive coach, Wilding teaches at Columbia University and has worked with executives at Google, Chanel, and JPMorgan. Her work centres on what she calls “sensitive strivers” – ambitious, emotionally attuned people who often struggle with overthinking, perfectionism, and burnout in high-pressure environments.

In this conversation, we unpack the core ideas behind Managing Up – from decoding your boss’s behaviour to asserting boundaries, gaining visibility, and shaping your career trajectory with intention. For fashion creatives navigating fast-changing teams, shifting leadership, and unclear expectations, these are the conversations we were never taught to have – but urgently need to learn.