After speaking at a two-day executive assistant event in London, a woman approached me with a confession. She held one of the most prestigious EA positions imaginable – supporting a senior official at a major international organisation – yet her dream was to work for a travel company specialising in Spanish holidays.

The disconnect between her current status and desired career move stopped me in my tracks. It wasn’t the typical “How do I climb higher?” question I usually field. This was someone at the pinnacle of our profession wanting to make what conventional wisdom would call a step down.

But was it really?

The career ladder is actually a web

We’ve been fed a persistent lie about professional growth. The narrative goes: start at the bottom, climb upward, achieve success by reaching the highest possible rung. Each career move should bring more status, authority and compensation. Anything else is failure or, at best, stagnation.

What utter nonsense.

When I left my role as editor-in-chief at DeskDemon to move into content design for government services, many colleagues viewed it as a puzzling sideways move. Why leave a position where I had built significant authority and recognition? The question revealed more about their limited perspective than about my career choices.

Careers aren’t ladders; they’re webs of interconnected experiences, skills and relationships. Movement in any direction can create value if it aligns with what actually matters to you.

When I wrote the Universal Credit website, for example, I worked with a colleague who previously worked in banking. His career move was motivated by his genuine desire to give something back to society by helping to improve the UK’s welfare system. 

The EA who dreamed of working in Spanish travel wasn’t describing failure. She was articulating a profound understanding of her authentic interests, something many professionals never achieve, no matter how high they climb.

How we end up where we never meant to be

Her situation raised an equally fascinating question: how had she ended up in such a high-profile position if it wasn’t aligned with her true interests? It can hardly have been happenstance.

In my experience, this disconnect happens through a series of incremental decisions that seem perfectly logical in isolation:

• You excel at something, which creates opportunities for advancement.
• Each advancement brings increased status and compensation, which provide external validation.
• External validation becomes addictive, drowning out the quieter voice of internal satisfaction.
• Before you know it, you’re several promotions into a trajectory you never consciously chose.

I’ve witnessed this pattern repeatedly throughout my career. A brilliant EA I worked with at a financial services firm kept being promoted into increasingly senior support roles. She was exceptional at navigating complex stakeholder dynamics and managing impossible executives. But what she actually loved was event planning, the part of her job that diminished with each promotion as she moved further from practical execution into pure strategic support.

When she finally left to start her own events business, colleagues were shocked at her career move. They saw only what she was giving up, not what she was moving toward.

The transferable skills reality

For the EA dreaming of Spanish travel, the path forward isn’t about starting over, but about translation.

My career transitions across executive assistance, office management, publishing and content strategy weren’t random shifts. They were strategic applications of foundational capabilities to new contexts. The skills that make someone exceptional in management support (systems thinking, stakeholder navigation, communication architecture or problem anticipation, for example) are precisely the capabilities that create value across countless other fields.

The challenge isn’t developing new skills; it’s articulating how existing capabilities apply in different contexts:

• A senior EA’s experience managing complex international scheduling translates directly to travel logistics coordination
• The diplomatic skills required to navigate senior leadership politics are exactly what’s needed to handle challenging client situations
• The ability to anticipate needs before they’re articulated is invaluable in customer experience design

When I transitioned from managing international offices to editing business publications, I didn’t suddenly develop an entirely new skill set. I applied my existing understanding of organisational dynamics and information flow to a different context. The core capabilities remained the same; only the application changed.

The evolution vs. revolution question

Not everyone wants to make a dramatic career move. Many management support professionals simply want to evolve within their existing roles, perhaps toward positions like Chief of Staff that represent a natural progression rather than a fundamental reinvention.

This evolution requires its own strategic approach:

1. Identify the gap between current and desired roles
   What specific responsibilities differentiate a senior EA position from a Chief of Staff role? In most organisations, the distinction involves greater involvement in operational decision-making, team leadership and strategic planning.
2. Create opportunities to demonstrate capabilities in these areas
   Rather than waiting to be given new responsibilities, find ways to showcase relevant skills within your current role. When I was advising an EA who wanted to move into a Chief of Staff position, we identified opportunities for her to lead cross-functional projects that demonstrated her strategic capabilities long before the formal promotion was available.
3. Build the right relationships
   Evolution within an organisation depends as much on relationship architecture as on skill development. Identify whose support will be critical for your desired transition and invest in those professional connections.
4. Adjust your professional narrative
   How you describe your current role shapes how others perceive your potential. Start incorporating language that bridges your current position and desired evolution.

The preparation imperative

Whether contemplating revolution or evolution, career move requires systematic preparation. When I’ve successfully navigated industry shifts, it wasn’t through impulsive leaps but through deliberate groundwork:

1. Deep research into the target field or role
   For the EA interested in Spanish travel, this means understanding the business models, key players, industry challenges and required capabilities in that specific sector. General interest isn’t enough; specific knowledge is essential.
2. Reality testing through conversations with insiders
   Before changing industries, I always sought candid conversations with people already doing the work I was considering. Their unvarnished perspectives prevented me from romanticising new roles and helped me understand the genuine challenges I would face.
3. Building a transitional narrative
   A successful career move requires a compelling story that makes your move appear logical rather than random. This isn’t about misrepresenting your experience but highlighting the throughline connecting your past achievements with your future direction.
4. Financial planning
   A career move often involves temporary steps backward in compensation or stability. Without practical financial preparation, many promising career evolutions die before they truly begin.
5. Skills gap analysis and development
   While many capabilities transfer across contexts, sometimes a career move requires specific technical knowledge or credentials. Identifying and addressing these gaps before they become barriers is essential.

The philosophical underpinning

Beyond the practical considerations, the EA’s question raises deeper philosophical issues about career satisfaction. What makes someone at the pinnacle of one field dream of starting fresh in another?

In my experience, it often comes down to the distinction between extrinsic and intrinsic motivation:

Extrinsic motivation comes from external rewards: status, recognition, compensation, advancement. These are powerful drivers but ultimately limited in their ability to create lasting satisfaction.

Intrinsic motivation emerges from the work itself: the activities that engage you so completely that time seems to disappear, the challenges that energise rather than deplete you, the sense of purpose that makes effort feel worthwhile.

The EA with the prestigious position had achieved remarkable extrinsic success. Yet something about Spanish travel – perhaps the cultural connection, the focus on creating positive experiences or simply the subject matter itself – sparked intrinsic interest that her current role couldn’t match.

This distinction explains many seemingly puzzling career choices: the banker who becomes a teacher, the lawyer who opens a restaurant, the corporate executive who starts a non-profit. These aren’t failures of ambition but triumphs of self-awareness, recognitions that extrinsic success without intrinsic engagement creates a peculiar form of high-status dissatisfaction.

The advice I actually gave

So what did I tell the EA who approached me after my talk?

First, I congratulated her on her self-awareness. Knowing what you actually want rather than what you’re supposed to want is rarer and more valuable than people realise.

Second, I suggested she start by articulating exactly what aspects of Spanish travel engaged her. Was it Spain itself? The logistics of travel planning? The customer service element? The more precisely she could identify her interest, the more effectively she could target her transition.

Third, I encouraged her to view her current position as an asset rather than an obstacle. Her high-level EA role had equipped her with exceptional capabilities and connections that would distinguish her in the travel industry, if she could effectively translate their relevance.

Fourth, I recommended creating bridging experiences before making a complete leap. This might mean volunteering to organise team trips to Spain, planning employee travel for her organisation or developing side projects related to Spanish culture and tourism.

Finally, I challenged her to consider whether she needed a complete career reinvention or simply more space for her Spanish travel interest. Sometimes what appears to be career dissatisfaction is actually a need for more balanced self-expression across professional and personal domains.

The courage to redefine success

What struck me most about the EA’s question wasn’t the practical challenges of her desired transition but the courage it reflected. In a profession often defined by service to others’ ambitions, she was articulating her own vision of meaningful work.

That’s not stepping down. That’s standing up.

Whether you’re contemplating a dramatic career move or a subtle evolution in your current role, the fundamental questions remain the same: What work genuinely engages you? What contribution do you want to make? What skills do you most enjoy using?

The answers rarely align perfectly with conventional career ladders or external expectations. But they’re the only foundation for professional choices that lead to genuine satisfaction rather than impressive dissatisfaction.

The most successful career move isn’t always up. Sometimes it’s sideways, diagonal or into territories that don’t appear on standard organisational charts at all. The direction matters less than the alignment between your authentic interests and your daily work.

That’s not just career advice. That’s life advice.

Interested in exploring these ideas further? I’m developing workshops and speaking engagements on navigating career transitions and evolution for management support professionals. Connect with me to discuss how these concepts could benefit your organisation or event.