Love what you do but not the way you’re doing it? Caroline Marshall looks beyond the traditional career ladder at new ways experienced Assistants can make work work for them.
“I fell into this role.” I think I’d be very rich if I received a pound every time an Assistant or business professional said this to me. I’m very much included in this demographic. I fell into my first role working for a managing director at a major global newspaper. That turned into a steady stream of maternity covers, until my boyfriend (now husband) went back to study for a master’s degree, and that was the push I needed to settle into a role. I then spent four years building my skills in administration at the National Health Service (NHS) but I was always looking for more. I needed a goal, a path, and I couldn’t see where mine was going. I sidestepped into communications for a bit, mostly to be somewhere else while I worked out my next move. And somehow, I knew, instinctively, that it would be into a small business or startup.
Years on, I can see I’m far from alone in this. So many of us can see we are excellent Assistants, but we don’t get handed the same career ladder to potentially follow, as our colleagues in legal, communications, HR, finance, or operations do. They all seem to have a clear route up to the C-suite. (To be clear, the ladder should be there if we want it, not because we have to climb it.)
Maybe for you it hasn’t been ladder frustration, exactly. Maybe it’s limited promotion opportunities, flat structures, role ambiguity, or organisations that just can’t seem to build a progression path – usually because of that old idea that advancement only comes from managing people.
One way to take back control is by designing your own career. Build the path you need, at the life stage you need it.
The Different Career Models Available
Different ways of working are on the rise, for good reason. Since Covid, remote working has shown all of us, in a way we can’t now unsee, that we can work smarter around families, caring, and travel. Technology enables us to work remotely from or homes, offices or anywhere that has a decent Wi-Fi connection. We have also seen many redundancies happen. We can’t control that, but we can control our own approach to our careers.
If you’ve only ever worked employed roles, you already have the skills to branch out. What felt like a huge “risk” is really applying skills that used to be seen as only for entrepreneurs: networking, personal brand, communication, growth mindset, commercial awareness. Everyone needs these skills now, in this uncertain, AI-shaped world we’re in. If you’re seeing a gap, work on that skill first, before you worry about changing your whole model.
Career Models: Which One is Right for You?
Traditional employed career
One paid role with a clear title and job description. Advantages usually include paid leave, funded development, and a ready-made working environment. Challenges tend to be a lack of opportunities (in our field specifically), less control over your career, and the risk of landing somewhere toxic, or somewhere that just doesn’t suit you.
Independent business owner
I’m biased, obviously, since this is where I am. The perks are building things your way, creating a culture that’s actually yours. What doesn’t get said enough is that it isn’t for everyone. It’s uncertain, it’s stressful, everything falls on you, and you have to really want that.
The fractional Assistant
This can also be known as a Virtual Assistant (VA), or a freelance Assistant. The same skillset, but as a service to several clients instead of one employer. What I loved when I went client-facing was that clients are seeking out your expertise specifically, so you get more autonomy and more flexible hours. You can work from home, because you only take clients who actually fit you. But you also take on the whole self-employed life: no sick pay, no holiday pay, no benefits, and a completely new skill of managing clients while trying to balance income against the risk of overbooking. A nice problem to have, but still a problem.
The portfolio career
A few roles at once. A fractional chief of staff position, a non-executive post, some mentoring on the side. Great if you love variety over one focus, but your time gets stretched thin fast without proper boundaries.
The hybrid career
Combining a few income streams, usually more varied than a portfolio career. Employment mixed with freelance work, maybe some investing too. Good if you want to keep the security of employment while testing other things or building other pots of income.
From Career Ladder to Career Design
All of this can sound terrifying. We’ve been told for years that employment is the “safe” option. However, if your current setup isn’t the right fit, but your Assistant career very much still is, my hope is that you look at changing the setup, not the career. That sounds like a lot, but really you just need the first step.
Career design is not just for the new parent, or the person now caring for elderly parents, realising full-time office life doesn’t fit anymore. It’s for the experienced Assistant who keeps job-hopping just to feel excited again, when really it was never the directors or the organisations. It’s also for the freelance Assistants who are ready to bring their expertise back into an employed role for the pay and the benefits they went without whilst they were focused on family. What they all have in common is a reason, and a chance to look at their career differently, without throwing away years of good experience. What each of them need is a different way of bringing their skills to the market.
Designing Your Own Career Roadmap
If you’re stuck on where to even start, don’t overhaul everything at once.
Pick one small step:
- Have one honest conversation about what you actually want
- Ask for a change in scope, flexibility, or responsibility
- Start something small on the side, even an hour or two a week
- Reach out to someone already working in a model you’re curious about
- Say no to something that no longer aligns
- Review your current role; what would you change if you could?
Then sit with the bigger questions:
- What do I want my life to look like right now?
- What are my non-negotiables?
- What am I known for?
- Does my current setup support that, and is it in my control to change if it doesn’t?
- If not, what would support it?
Nothing has to be forever. You might need to change something now. You might not. Just consider where you are today, and where you actually want to be longer term.
Closing Thought
There isn’t one way to build a successful career in executive support. You might move between employed roles, freelance work, fractional positions, portfolio careers, and hybrid combinations. Sometimes you step sideways. Sometimes you step back, entirely.
I’ve done all of it: freelance, employed, part-time, hybrid, and now business owner. Every one of those paths got me to where I actually fit now, running a business that works around my children, that’s got me through maternity leave, and that meets my income goals. I fell into this industry, but it turns out this industry is where I needed to stay – I just needed to change the setup.
