Virtual Assistant: An Alternative Pathway?

Gina Theofilidou details her journey to Virtual Assistant and offers advice for those considering making the switch

For 24 years, I built my career inside boardrooms, leadership teams, and complex organizations as an Executive Assistant in multinational and Greek companies. I used to believe that experience would eventually be rewarded. Not dramatically, but in a way that would let me feel secure.

In 2014, in the middle of the Greek financial crisis, I found myself back on the job market. I remember reading one job description late at night, after another long day of applications, and closing my laptop with a strange feeling in my heart. The role expected a strategist but paid like an entry-level position. It felt disappointing and irrational. The emotional and operational weight of the role was heavier than ever, yet compensation had moved in the opposite direction. There was no longer a logical connection between value and reward.

At 42, I realised that I would have to either accept a system that no longer reflected my worth or design a different professional reality. That is how my transition began, not away from the profession, but into a new way of practising it.

A Market That Changed Before We Did

Leadership today rarely operates in one place. Teams work across countries and time zones. Decisions are faster, expectations are higher, and complexity is part of our daily reality. What has not changed is the need for trusted, high-level support. In countries such as the United States and the United Kingdom, the Virtual Assistant (VA) model has existed for more than two decades. Experienced Assistants were operating independently long before remote work became mainstream. In many parts of Europe, however, this shift became visible more recently, especially after the pandemic accelerated remote and hybrid working models. The Virtual Assistant role is not a trend; it has evolved as a response to how work itself changed.

The Identity Shift No One Warns You About

As employees, our value is reflected through titles, reporting lines, and performance frameworks. As business owners, that validation must be generated. I remember reviewing one of my first proposals as a VA and pausing at the fee. It was the first time I had to calculate my work as a business owner.

As an employee, your salary is a number. As an entrepreneur, your fee must include much more than your time. It must cover health insurance contributions, professional taxes, accounting support, software subscriptions, equipment, training, business development, and the months when income is not predictable. I realised I was no longer pricing hours. I was pricing sustainability.

That was the moment I understood something deeper: financial clarity is not administration – it is leadership.

I had to understand cash flow, obligations, and long-term planning. When you run your own professional practice, structure is what protects your freedom. Freedom without structure creates anxiety. Freedom supported by structure creates stability. When the proposal was accepted, what I felt was responsibility instead of relief – the responsibility to deliver consistently at that level and to build a professional ecosystem that could support both my clients and my own long-term stability. That was the real shift, from role-holder to business owner.

Designing Your Own Value

In my first year, I accepted a wide range of assignments – board preparation, event coordination, and operational troubleshooting across time zones. I could do all of it. I had done it for years inside organizations. But running a business requires something different. It requires clarity. I had to ask myself tough questions: What do I want to be known for? Where do I create the most value? What kind of partnerships do I want to build?

Gradually, I stopped presenting myself as “available for everything” and started defining clear service areas based on my strengths: strategic operations, executive-level coordination, leadership support structures. That clarity changed the quality of my conversations. Clients no longer saw me as an extra pair of hands. They began to see me as a thinking partner. And that shift made my business stronger – but more importantly, it made my contribution clearer.

Building Your Own Community

There were days when I missed being physically part of a team. The quick exchange before a meeting. The shared look across the room when something unexpected happened. The informal debrief after a long board session. Working virtually can feel too quiet if you are not intentional. I realised that if I wanted to remain strong professionally, I had to build connections on purpose. I joined peer groups. Ι participate in weekly co-working sessions with other VAs across Europe. I scheduled regular conversations with other Senior Assistants and business owners. I also invested in mentoring and professional communities. When you work independently, no one creates that environment for you; you must design it yourself.

A Shift vs an Escape

The Virtual Assistant role is not an exit from the profession. For many of us, it becomes a deeper expression of it, one that honors experience and expands influence. For me, this pathway brought four clear benefits.

First, broader perspective. Working with different leaders and organizations sharpened my thinking. I see patterns faster. I design solutions more clearly.

Second, alignment. I focus on what I do best and build services around that strength. Clarity improves both the quality of my work and the quality of my partnerships.

Third, ownership. I manage my time, my standards, and my financial structure. I no longer wait for recognition inside a hierarchy. I build credibility through results.

Fourth, resilience. Running a professional practice strengthens decision-making, boundaries, and long-term thinking. You grow personally as well as operationally.

This is an evolution of the support profession. Virtual Assistants are business partners and strategic operators. We lead our own professional ecosystem. This path requires courage and responsibility. It is not for everyone. But for Senior Assistants who feel that their expertise deserves a wider horizon, it offers choice, clarity, and the opportunity to move from role to ownership.