In an era defined by accelerated technological disruption and shifting global markets, the traditional linear executive career path – climbing the corporate ladder – is increasingly being challenged, no longer guaranteeing long-term relevance, fulfilment, or financial security.
For many senior leaders, the time is ripe to consider a more agile, resilient approach: the portfolio career.
Once seen as the preserve of semi-retirees or creatives, portfolio careers are now a strategic choice for executives at all stages of their professional life. A portfolio career can combine multiple concurrent roles—such as board appointments, consulting assignments, advisory positions, teaching, entrepreneurial ventures, and speaking engagements—into a cohesive professional narrative.
According to a recent report by Korn Ferry, over 65% of senior executives are actively exploring alternative career models beyond traditional full-time employment. Meanwhile, Harvard Business Review highlights that portfolio careers are increasingly being adopted by experienced leaders seeking greater autonomy, intellectual variety, and purpose-driven work. PwC’s Future of Work report also highlights a major pivot towards project-based, flexible working structures—especially among senior professionals seeking impact across a variety of domains.
Artificial intelligence (AI) is a key driver in this evolution. As AI automates many transactional and analytical tasks —particularly in finance, operations, and strategic planning—the emphasis has shifted towards uniquely human strengths such as critical judgement, ethical decision-making, relationship building, and creative problem-solving. These are precisely the capabilities that define successful portfolio executives.
For executives in transition, the portfolio model offers the opportunity to test new sectors, refine strategic skills, and expand one’s global network—all while maintaining income diversification and optionality in a volatile job market.
There is no such thing as a typical portfolio career but executives might generally maintain three to seven different professional engagements simultaneously. This might include:
A Spencer Stuart study shows that FTSE 100 boards are increasingly welcoming executives with multi-sector and international exposure—traits often cultivated through portfolio careers.
However, the key is coherence, not volume—ensuring all components align with a central narrative and reinforce each other in knowledge, network, and strategic positioning.
As portfolio careers gain momentum, geographic context plays an increasingly important role in shaping opportunities. Cultural norms, regulatory environments, and market maturity can all influence how portfolio models are adopted and where demand is strongest for executive talent on a flexible or advisory basis.
Understanding the regional landscape allows executives to position themselves more effectively—whether by tapping into global networks, aligning with governance trends, or pursuing cross-border engagements that enhance strategic visibility and impact.
United Kingdom: The UK is particularly fertile ground, with a long-standing tradition of non-executive directorships, a strong consulting culture, and increasing acceptance of part-time executive roles. The Institute of Directors and Financial Reporting Council have both highlighted the growing role of experienced portfolio professionals in enhancing board diversity and governance.
United States: While portfolio structures are more common in tech, finance, and healthcare, adoption is growing across sectors as flexible models gain traction. US executives often tap into the scale of the market and the abundance of venture and PE-backed firms seeking seasoned advisors.
Europe: Nordic countries lead in flexible executive models, while Southern Europe remains more conservative, favouring full-time engagement. The EU’s labour laws can complicate portfolio arrangements, but this is often offset by a thriving independent consulting scene.
Asia-Pacific: Singapore stands out as a hub for senior advisors and portfolio executives, particularly those with Western experience and local cultural fluency. Japan and South Korea, traditionally hierarchical, are increasingly open to flexible models as governance reforms take hold.
Making the transition to a portfolio career requires more than intention—it demands strategic foresight, personal clarity, and operational readiness. This shift isn’t simply about doing more things; it’s about doing the right things in a coordinated, purpose-driven way.
Executives considering this path must approach it with the same rigour they would apply to any major business transformation: assessing their market positioning, identifying their core value proposition, and building the infrastructure to operate across multiple domains with consistency and credibility.
Whether you’re planning a full transition or exploring a phased approach, the steps below will help lay a solid foundation for a sustainable and high-impact portfolio career.
Conduct a strategic skills audit: Assess your most marketable capabilities. Engage a coach or mentor to benchmark your value against current market needs, especially in AI, digital transformation, and ESG.
Clarify your proposition: Define your unique offer. Align your LinkedIn profile, website, and public presence with a consistent and compelling message.
Build credibility: Engage in thought leadership, publish insights, speak at events, and serve on expert panels.
Expand your network: Tap into personal and professional contacts. Many roles are secured through trusted introductions rather than public postings.
Start incrementally: Begin with a board role or consultancy alongside traditional employment to test the model before fully transitioning.
Invest in your infrastructure: Build systems for client management, financial planning, digital communication, and time management from the outset.
A portfolio career offers senior executives an attractive alternative to traditional employment—blending autonomy, intellectual variety, and influence across multiple sectors. However, it is not a model suited to every executive.
The flexibility to design one’s professional life around personal values, interests and lifestyle is a key draw. It also allows for diversified income streams, expanded networks, and exposure to varied business models—all of which can extend an executive’s relevance and influence in a fast-changing world.
However, this freedom comes with structural and operational demands that should not be underestimated. Key challenges include:
Maintaining a Clear Professional Identity
Without the anchor of a single title or organisation, it can be challenging to articulate a cohesive professional narrative. Executives must develop a compelling value proposition that unites their various roles and communicates their unique offering clearly and consistently.
Managing Income and Financial Planning
Income can be variable and irregular. Some roles may pay quarterly, others upon delivery or via equity. Executives must be financially prepared for income variability and the need to self-fund traditional employment benefits. Building a financial buffer of 6–12 months of essential expenses is strongly advised.
Avoiding Overextension
The temptation to accept multiple opportunities can lead to overcommitment. Many portfolio executives report longer hours, particularly in the early stages. Success relies on setting clear boundaries, defining scope in each engagement, and prioritising roles that align with long-term strategic goals.
Handling Operational Complexity
Juggling multiple roles comes with increased administrative burden—contracts, scheduling, compliance, invoicing, and taxes, often across jurisdictions. Leveraging digital tools such as CRMs, calendar managers, accounting software, and workflow automations is crucial to avoid distraction from core value-adding activities.
Sustaining Strategic Direction
Without a clearly defined strategic direction, a portfolio can risk fragmentation. Executives should regularly review and realign their roles to ensure coherence, value contribution, and progress toward long-term career and lifestyle goals. A trusted mentor, coach, or peer board can support this process.
Crucially, this is not an all-or-nothing decision. Many senior professionals begin their transition gradually—taking on a board seat, advisory engagement or consulting project alongside a primary role—to test the model, refine their proposition, and build momentum.
For some, a portfolio career is a launchpad into new sectors and innovation. For others, it offers a fulfilling path into the later stages of their professional journey—balancing commercial impact with flexibility and personal fulfilment.
In an era of accelerating change, a well-structured portfolio career is not a compromise. It’s a strategic response—designed for those ready to lead on their own terms.
The Rialto team are experienced in guiding senior professionals through executive transitions—whether building a full portfolio, exploring strategic exits, or shaping a second-act career. With deep market insight and an international network, we support our clients in navigating the complex, evolving landscape of executive work.
Contact us today to explore how we can support your transition.
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