Written by Hayley Harrison

When I watched The September Issue in 2009, a documentary that follows editor-in-chief Anna Wintour and her staff during the production of the September 2007 issue of American Vogue, I decided I wanted to work in fashion. Fifth Foundations

Determined to pursue this passion, I studied Fashion Journalism at UCA Epsom, where I graduated with First-Class Honours much to my surprise. Academically, my GCSE and A-Level results had been fairly average as traditional exams were never my strong suit, but intelligence isn’t solely measured by exam performance; success often lies in how one applies their strengths. 

Following university, I secured internships and freelance opportunities at Cosmopolitan, Tatler, GQ, World of Interiors, and several smaller publications – experience I believed would pave the way for a permanent position at a magazine. However, I quickly realised that in this industry, the old adage “it’s not what you know, but who you know” holds significant weight.

After countless rejected applications and a four-month period of unemployment, I took a part-time role in visual merchandising at M&S while reassessing my next steps. 

I began to feel as though I had lost some of the enthusiasm I once had for fashion. If I’m being completely honest, there was also a lingering sense of bitterness – mostly due to a certain lecturer (no one that I’m still in touch with) who insisted that liking certain designers, magazines, brands, or photographers meant you weren’t ‘cool.’ I discarded years’ worth of ELLE magazines I had lovingly collected and altered my tastes in an attempt to fit in only to realise it made no difference. Annoyingly, my naive, university-age self listened. However, as I near my 30th birthday, my more seasoned self would have a few choice words for said lecturer. I suppose they did me a favour in one sense…I have no idea where I would store all those ELLE magazines now! 

I had walked past the News Building a couple of times over the years thinking I’d love to work there one day. If you believe in manifestation you could say the universe was already steering me in the right direction because I eventually found myself walking through its doors as an employee. 

I joined the events team at News UK, where I spent 11 months assisting with a range of internal and external events. During that time, Olly presented his vision for what is now The Fifth at a company huddle, and my interest was immediately piqued. Having grown up during the rise of The Brit Crew – think Tanya Burr, Zoe Sugg, Alfie Deyes, and co. – I had spent countless hours on YouTube and, later, Instagram so social media was ingrained into my everyday life. It felt like the perfect next step and Olly’s ideas felt particularly exciting during a time when the space was still relatively new. 

I emailed him and asked if he had any vacancies and he said he was looking for an assistant. 6 years later I’m still here getting exasperated with him for touching his diary and messing it up, and feeling grateful that I work for the best there is. 

Personally I think the dynamic between a boss and their assistant is only successful when the assistant is seen as a collaborator rather than a subordinate. Olly’s always encouraged me to have a voice, which he probably regrets sometimes. 

Over the past six years at The Fifth, my role has taken on many forms. While I have always been Olly’s assistant first and foremost, I have also taken on various other responsibilities along the way. One of the most fun aspects of working at a startup is the collaborative spirit. Everyone comes together, picking up tasks where needed. 

With the support of our now Senior Account Director, Jules, and the ‘Campaign Cogs,’ as we affectionately called ourselves, I contributed to campaign delivery for brands such as Disney+, Rimmel, and Fenty. Being involved in the entire campaign process gave me a deeper appreciation for the immense effort behind each one, along with a sense of pride in seeing the final product come to life. 

In my current role as Executive Assistant I work closely with Olly and other senior leaders across the agency, as well as the organisation’s internal and external stakeholders, to implement Olly’s vision through strategic executive support and the usual operational and administrative functions. But most importantly, I get Olly his skinny lattes. 

My advice to anyone starting out is to remain open to new opportunities and career paths. Not ending up in the field you studied at university doesn’t mean you’ve failed. You may discover a path that aligns even better with your skills and strengths, leading to a more fulfilling and rewarding career. 

Send the email. Make yourself indispensable but that doesn’t mean running yourself into the ground – become an expert in things your other team members aren’t. And please don’t listen when someone tells you it’s not cool to like something. IT IS!