There’s a curious tendency to treat virtual assistants as something entirely separate from the rest of the management support world. As if working remotely and running your own business suddenly means you’re no longer an Executive Assistant, no longer part of the profession, no longer wrestling with the same pressures.

The truth is virtual assistants are right in the thick of it. They are Executive Assistants, just without the safety net of an employer. They face all the same challenges – supporting demanding executives, juggling constantly shifting priorities, keeping pace with evolving technology – but with the additional weight of running a business balanced precariously on their shoulders.

Some make the leap to virtual assistance because they crave freedom and flexibility. Others find themselves pushed from traditional roles, often after years of loyal service, and discover they’re stitching together a business out of sheer necessity rather than choice.

When entrepreneurship isn’t a choice

This reality is partly why I’ve moved away from the concept of ‘secretarial entrepreneurship’ that I championed in keynotes and training sessions since 1997. The concept has matured into what I now call The Future-Proof EA.

You’ll notice other speakers and trainers advocating for entrepreneurial skills for Executive Assistants and management support professionals. It’s a valid perspective. Being brilliant at your job isn’t enough anymore; EAs must also learn to market their value to executives and stakeholders across their organisation.

But there’s a shadow side to this conversation. Too frequently, entrepreneurial skills are linked to women being edged out of corporate spaces with few alternatives but to strike out alone. The news portrays this as positive: look at all these brilliant female entrepreneurs launching businesses! The lived experience, however, is too often steeped in financial anxiety and professional uncertainty.

As someone who approaches this work as a trained trauma-aware writer, I recognise the negative associations that entrepreneurial language can trigger for secretaries, assistants and administrative professionals who didn’t choose this path but had it thrust upon them.

The invisible battle

Succeeding as a Virtual Assistant demands a razor-sharp mind, an unwavering backbone and an unshakable sense of self-worth. It’s not just about delivering exceptional work. It’s about proving, repeatedly, that you’re worth hiring in the first place.

For an in-house EA, the parameters are clearer. You support your executive, you navigate the labyrinth of office politics, you handle sensitive information with discretion, and if you perform well, your position remains secure.

Virtual assistants manage all of this while also finding their own clients, negotiating their rates, pursuing late payments, marketing their services and weathering the emotional turbulence of self-employment. When work slows, there’s no salary to fall back on. When clients go quiet, there’s no HR department to chase unpaid invoices.

Let’s be frank: the online Virtual Assistants landscape is saturated beyond measure. It’s not only experienced professionals transitioning from corporate roles. It’s new entrants offering rock-bottom rates, automation tools threatening to replace administrative services and a growing number of businesses convincing themselves they can function without dedicated support.

The most significant challenge isn’t competence; it’s visibility. You could be the most exceptional Virtual Assistant in existence, but if nobody knows you’re there, your skills remain in the shadows.

When experience meets market reality

One of the most difficult truths many virtual assistants confront is that experience isn’t always the golden ticket they believed it would be. Having decades of high-level support experience is undoubtedly valuable, but not all clients recognise this value. Some gravitate toward the cheapest option regardless of quality. Others lack clarity about their actual needs and end up hiring the wrong support altogether.

For experienced Executive Secretaries and Personal Assistants transitioning to virtual work later in their careers, there’s also the unspoken reality of age discrimination.

You can position yourself as a seasoned professional with unmatched expertise, but if a potential client is seeking someone younger, cheaper and supposedly more ‘tech-savvy’ (which often simply means willing to accept lower compensation), you’re facing an uphill struggle. It’s not insurmountable, but it requires Virtual Assistants to be as strategic about their positioning as they are about developing their skills.

Neither employee nor outsider

Another crucial distinction between in-house and virtual assistance is the nature of the client relationship. In traditional settings, an Executive Assistant has employee status. Expectations are defined. Performance has metrics. Boundaries exist (even when unspoken).

Virtual assistants, however, exist in an ambiguous territory. They aren’t employees, but they aren’t entirely separate from their clients’ operations either. They often occupy a blend of partner, consultant and service provider roles. This ambiguity can be freeing but also challenging to navigate.

Clear boundaries become essential. Some clients expect a Virtual Assistant to remain perpetually available without recognising they’re engaging a service provider, not acquiring a staff member. Others view VAs as extensions of their team without offering the corresponding loyalty or security they’d provide an in-house employee. Virtual assistants must establish terms from the beginning. If they don’t, clients will define those terms for them, often to the VA’s detriment.

The growth question

Then comes the question of scaling. When a Virtual Assistant achieves success, demand inevitably exceeds capacity. Do you increase your rates and maintain a solo practice, or do you begin bringing in associates? Do you stay directly involved with clients, or do you shift toward team management?

Some Virtual Assistants transition to running boutique agencies, delegating client work while concentrating on business development. Others prefer maintaining solo practices and direct client relationships.

Neither approach is inherently superior, but it’s a decision requiring deliberate consideration. Growth isn’t merely about increasing revenue. It’s about fundamentally changing your role. If you’re spending all your working hours managing other Virtual Assistants instead of doing the work that brings you satisfaction, is this still the right business model for you?

The authentic narrative of Virtual Assistance

Virtual Assistants aren’t some separate category of administrative professionals. They are executive assistants, office managers and skilled administrators who happen to be running their own businesses.

Some have chosen this path deliberately. Others have found themselves on it through circumstance or necessity. Either way, they remain as integral to the management support profession as any in-house EA, confronting the same workplace transformations, the same challenges and the same constant need to demonstrate their value every single day.

The difference is they do this without organisational backing. And that requires a level of resilience, skill and determination that should never go unacknowledged.

It reminds me of the observation about Ginger Rogers that she “did everything Fred Astaire did, but backwards and in high heels.” Virtual Assistants are delivering exceptional support while simultaneously running a business. They’re dancing backwards in high heels while also choreographing the entire show.