In CONVERSATION WITH: Amy Rollings

Key Takeaways

• Squiggly careers are skill-building journeys that create invaluable expertise, not setbacks

• Tenacity means knowing when to push forward and when to strategically pause

• Authentic networking happens through genuine 1:1 connections instead of formal events

• The 40s can bring a confidence revolution where you finally do things for yourself

What happens when a fashion industry veteran finally stops apologising for her "squiggly" career and starts celebrating it instead? Amy Rollings' 20-year journey from Burberry's corporate corridors to Managing Director roles at fashion startups offers a masterclass in career adaptability, and the crucial art of knowing when to pause and breathe. Her latest chapter sees Amy embracing consulting work across multiple businesses while co-founding her own venture, proving her philosophy in action.

Amy's story resonated with me immediately and her path from fashion assistant intern to head of buying to general manager of digital teams mirrors the reality many of us face. Instead of a straight climb upwards, we often zigzag. What I love about Amy's perspective is how she's learned to embrace what she calls her "squiggly career" and her decision to take a step back, consult, and figure out what comes next, rather than defend it.

Learning to Be a Workhorse (and Unlearning It)

Amy's fashion journey began as a fashion assistant internship at Marie Claire in New York. "It really was a kind of Devil Wears Prada moment," she laughs, describing an intense introduction to the industry that for many is a rite of passage.

But it was her seven-year tenure at Burberry that provided the foundation for everything that followed. Starting in retail buying and working her way up, Amy gained comprehensive business training through their exceptional learning and development program where employees could access any course they wanted.

This early investment proved crucial although Amy admits she initially took the corporate mentality too far. She shares wearing being the first person into the office and the last one out as a badge of honour but looks back on this approach with a new perspective.

"I used to be a workhorse... I look back, and I was like, Amy, what were you doing? You're getting up so early and being in the office at 7:30 and then leaving at seven. You're only designing or selling things or buying shoes at the time, you really didn't need to be in the office!"

Amy's pivotal moment came at Kurt Geiger, where she made a career-defining leap from buying into completely uncharted territory: digital and general management. When offered the general manager role, despite never having managed a digital team or owned a P&L before, her response was simple. If they believed she could do it, she would. She jumped in and exponentially grew the business, describing it as "probably a pivotal moment in terms of my skill set and really broadening."

This willingness to embrace the unknown would become a defining characteristic of Amy's approach to her career - one that was shaped by a deeply personal experience early in her journey.

Knowing When to Push and When to Pause

Amy's combination of unwavering tenacity with self-awareness about when to strategically pause is refreshing and quite unusual. After her father passed away suddenly the night before she was due to start at Michael Kors - a significant career move after seven years at Burberry - everything she's done since has been driven by deeper purpose. This has given her career moves an emotional anchor beyond just professional advancement.

Amy has also learned the crucial importance of stepping back when needed, and she is refreshingly honest about the times in recent months she has needed space to think.

"I needed a freaking break. I was exhausted... I just needed time to breathe. When you're in a full-time job, you don't have the brain capacity to be able to think about what on earth you're doing."

Having said that, Amy describes herself as "definitely tenacious. I fall off and I get back on, and I don't get back on in the same company or with the same people or within the same vertical sometimes."

This approach continues to serve her well. She's currently saying yes to opportunities well outside her comfort zone and jumping straight in the deep end, which is something described by a connection on LinkedIn recently as 'very Amy'!

This resilience has taken her from fashion into interiors startups and back, always with openness to trying new directions. She's now working across three to four businesses doing everything from strategy and brand work to business development, even serving as MD of a talent agency, alongside helping her partner's design studio and interior architecture practice. Diversifying the people she works with and the industries she explores has considerably grown her network and skillset.

From her earliest days, Amy never limited herself to her designated role, always making connections across departments and building relationships throughout the company. Her rather inspiring and down-to-earth philosophy is that it's your life, so you have to make it your own. Nobody else is going to create it for you.

Building Your Personal Board of Directors

Amy's approach to networking completely rejects the traditional image of forced conversations at industry events, which is again utterly refreshing. She's never been interested in formal networking events, preferring instead to keep in touch with former colleagues and engage authentically on platforms like LinkedIn.

Instead, she's built what a friend introduced her to as a "personal board of directors" - a brilliant concept! These five or six people serve as her go-to for professional advice, showing up for each other as a sounding board and support network.

Amy's board champions diversity and authenticity. One member is someone she's never met face-to-face, but met through LinkedIn and developed a friendship over the past five years. Another is a former Michael Kors colleague she'd lost touch with for seven years before reconnecting two years ago.

"None of them are my closest friends, but they're close in other ways, and I couldn't navigate my career without them."

Her networking success comes from genuine openness to new connections - at the gym, walking her dog, even reconnecting with an old colleague she hadn't seen in 16 years, leading to a potential new collaboration. The power of these relationships is perfectly illustrated by her latest venture, which is co-founding a business with an old colleague she reconnected with after eight years apart. As Amy puts it, "there's a moral to the story there - always keep your network close." The key principle isn't to focus on what you can get out of someone but how you can forge a relationship which offers mutual support.

I'm a huge fan of women who lift up other women, and Amy is exactly that person. She's built a rock solid network which has led to countless opportunities for herself, but she's always consistently showing up for others too.

The 40s Confidence Revolution

At 41, Amy has reached a place many of us aspire to: complete confidence in her path and genuine excitement about what's ahead. But getting there wasn't smooth and she admits to significant anxiety about turning 40.

"I was actually quite anxious about it. And now I'm just like, my God, this is exactly where I'm meant to be, and this is going to be an amazing era and decade for me."

The transformation in perspective is profound. She's moved completely beyond seeking external validation:

"I definitely feel more confident than I've ever felt before. In your 20s or 30s, you're doing things for other people and now I'm doing it for me."

This confidence revolution reached its peak during a conversation that caught her completely off guard. At Milan Design Week, she was introduced to a friend's husband and found herself naturally explaining her career journey without the usual defensive tone. For years, Amy had struggled to articulate her non-linear path without feeling like she needed to justify every pivot. But this time was different.

"I had a conversation with him around this whole squiggly career, and after 10 minutes, I thought, 'Oh my God, I've actually confidently spoke about it for the last 10-15 minutes for the first time!'"

This conversation led to a viral LinkedIn post, showing just how many professionals struggle with the same feelings about career zigzagging and who welcome opening a dialogue about it.

My Take

Amy's story is ultimately about giving yourself permission to build a career that fits who you actually are, rather than who you think you should be. Her decision to step back and consult while figuring out her next move shows that sometimes the bravest career decision is allowing yourself to pause and breathe.

Needing space to think really resonated with me. It's a common theme I see in my coaching work and Amy's 'workhorse' mindset is something I can identify with from my own corporate days, feeling like I had to prove why I deserve to be there. Through my own coaching journey, I'm feeling much more energised approaching my 40s because I'm crystal clear on what I value and my purpose. It's so rewarding to me when my coaching clients find this clarity too and give themselves permission to go after what they really want from their careers and life.

My conversation with Amy also made me reflect on how grateful I am to have obtained an ILM Leadership qualification during my time at NET-A-PORTER, for giving me my first taste for coaching and skills I've used in other areas. Amy's strong foundation at Burberry shows how crucial early development investment can be. With L&D budgets often being cut first, those who can't fund their own development sadly just don't have the same opportunities.

What I find most inspiring is Amy's recognition that her perceived career setbacks - the company moves, industry pivots, non-linear progression - are actually her greatest professional assets. Her honesty about still figuring out work-life balance after 20 years and rejecting 5am club culture shows someone who's defined success on her own terms.

Amy's story ultimately proves that the most fulfilling careers aren't built by following someone else's blueprint, but by having the courage to write your own - squiggles and all.

Follow Amy’s journey on LinkedIn for inspiring posts and to be the first to hear about her new venture, launching very soon.

About the author: Drawing from her experience leading global Personal Shopping teams at NET-A-PORTER and MATCHES and ILM L7 Executive Coaching training, Pippa Mellor 1:1 fashion career coaching and personal shopping consulting services for premium and luxury fashion brands.