As summer winds down and routines return to normal, it is a natural time to pause and reflect on your career. Are you on the path you want to be on? Do you feel fulfilled in your current role, or are you ready to take the next step?
One of the most powerful ways to answer these questions is to listen to advice from people who have walked a similar path. Executive Assistants often have extraordinary career journeys, full of zig zags, opportunities taken, and lessons learned from risks that paid off.
Here are five career insights to inspire you as you think about your next chapter, with space to hear directly from other EAs who have lived it.
Be Open to Career Detours
Sometimes, the fastest way forward is sideways. Many assistants feel “stuck” after years in the same role, despite having a wealth of skills to offer. Taking a detour, whether into a different industry, supporting a new type of leader, or even shifting temporarily into project or operations work—can unlock energy, growth, and opportunities you never imagined.
“While working closely with my previous CEO, we developed a way of managing executive and crisis communications across the business in the absence of any dedicated comms support. I discovered a passion for communicating key messages in a way that resonates with our 12,000+ colleagues. I realised I had a talent for simplifying complex information and tailoring it to different audiences, making it easy to digest and relevant regardless of role.
I also found a love of writing – creating narratives that bring leadership decisions to life. When a change in leadership occurred, I pitched my dream role: blending my communications skills with the day-to-day management of the CEO office.
Today, as Head of Internal Comms in the CEO Office, I maintain my close relationship with the CEO and executive team, giving me both a seat at the table and a hand in shaping our strategic narrative. Designing and delivering my own internal comms strategy has set my career on an entirely new trajectory.”
– Gabrielle Baldwin, Head of Internal Communications and CEO Office, HALFORDS GROUP PLC LinkedIn
Every Decision is Not Forever
It is easy to put enormous pressure on yourself to make the “perfect” career decision. But in reality, very few choices are permanent. Careers are rarely straight lines – they are more like winding paths that only make sense when you look back.
“When I left the legal field to take an executive assistant role at an ed-tech start-up, I worried I was making a mistake. I had spent years preparing for a legal career, and stepping away from that path felt like abandoning a plan I had worked so hard to build. I wondered if I was trading stability for chaos, and if I would one day regret leaving the “safe” route I thought I was meant to follow.
But that choice turned out to be one of the best opportunities of my career. Working at a start-up pushed me out of my comfort zone, taught me to adapt quickly, and allowed me to grow alongside a mission-driven team. I learned that my skills weren’t tied to one industry, and that resilience and adaptability are qualities I can carry anywhere.
What once felt risky became the pivot that reshaped the way I approach every opportunity. Sometimes the choices that scare you most are the ones that open the doors you’re meant to walk through.”
– Sandra Loyola, EA at End Poverty in California LinkedIn
Explore Different Sectors
Executive Assistants are needed everywhere, from corporate boards to charities, from start-ups to government offices. Each sector teaches you something new and adds depth to your skills. Moving between environments also keeps your career fresh and expands your influence.
“I have always worked in retail, but my career has taken me from high-end to high street, and from customer-facing and office-based roles to head office. The experience of serving demanding clientele in high-end retail prepared me for handling the trickiest situations as I moved sectors. It also gave me invaluable ‘shopfloor’ insight, which has set me up well to thrive in a large retailer’s head office.”
– Jennifer Thomas, EA to CFO at John Lewis
Do Not Stay Too Comfortable
Growth comes from stretching yourself, not from staying in your comfort zone. Whether it is volunteering for a big project you are only partly ready for, taking on a stretch assignment, or applying for a role that feels just beyond your reach, these are the experiences that fuel growth.
“In every job I’ve taken, I’ve never met 100% of the criteria – probably not even 90%. But I’ve always trusted that I could learn on the job and do it well, and that was enough for me to feel ready.
I’ve put myself in the line of fire many times: leading panel discussions, hosting large events, and managing sensitive initiatives. Each time, I learned that passing up the opportunity would have been a disservice to myself. Taking the risk has always paid off, and I’ve never regretted it.”– Kimberley Mensah, People Lead at Cambridge Enterprise LinkedIn
Look for the Gaps You Can Fill
Sometimes the best opportunities come from seeing a need that no one else has stepped up to meet. That could be introducing a new process, taking on responsibility for a project, or creating a role for yourself by showing where you can add value.
“Be yourself and follow your intuition. It sounds simple, but it’s easy to get caught up in trying to model yourself after another ‘superstar EA’ and lose what makes you unique. They became successful because they found their own groove and style – something that can’t be replicated. Trying to become like someone else means you’ll always be following instead of leading.
If something works for another EA but not for you, that’s okay. Once I let go of what I thought the ‘best EA’ should look like and focused on being myself, I became the best version of me. That shift trailblazed my career growth – from being an EA to now managing Operations at the world’s leading SpaceTech VC.”
– Manisha Koolman, Operations Manager at Seraphim Space LinkedIn
So…as you move into the next season of your career, ask yourself:
- What detour might spark new passion?
- What risks could you take to push yourself forward?
- Where are the gaps you could step up to fill?
Your career as an EA does not have to be a straight line. The zig zags, risks, and experiments often become the most defining and rewarding chapters.