Key Themes

• 47% of the global workforce identifies as self-employed
• The gig economy accounts for 12% of the international labour market
• 52% of professionals seek careers beyond a single employer
• Portfolio careers require strategic planning, adaptability, and strong personal branding
• Sustainability depends on financial stability, pipeline management, and self-agency

Verbal Introduction

In this episode, we explore how to turn a portfolio career into a stable, profitable long-term model. From balancing multiple roles to managing your personal brand and business operations, we’ll share strategies to help you design a career that aligns with your goals and risk profile.Portfolio careers offer freedom and variety—but they also demand discipline. We’ll cover how to stay current, fill your pipeline, and maintain momentum across diverse roles.Let’s dive into the essentials of building a successful portfolio career.

About Lee de Winton

Lee de Winton is a seasoned leader across military, commercial, and corporate sectors. She began her career in the UK Royal Navy as an Air Traffic Control Officer, later serving in the Royal Australian Air Force (RAAF) in roles including National Airspace Manager – Defence, Commanding Officer 381 Squadron, and Base Commander in Afghanistan.Her commercial leadership includes CEO of Sydney Metro Airports and Head of Freight Operations at Qantas. She’s held interim executive roles at Georges River Grammar and Pacific Aerospace, and was awarded the 2012 Telstra Business Woman’s Award for Community and Government.Lee currently serves as Chairperson of the Forum on Western Sydney Airport and Non-Executive Director at Newcastle Airport, and remains active in community development through the Canterbury Bankstown Chamber of Commerce.

Interview Questions

1. What are the most common questions or surprises professionals face when shifting to a portfolio career?
2. Can you share insights from your interim and NED roles, and how they differ from your military and corporate experience?
3. What can professionals do now to prepare for longer, more flexible careers?
4. How has your military background shaped your leadership style in commercial settings?
5. How do you manage multiple roles while keeping your future work pipeline active?
6. What’s your approach to building a personal brand?
7. How do you stay current in your field?
8. How do you manage the “back office” of your portfolio career?
9. Final question: What’s one piece of advice you’d like to leave our Portfolio Pod audience with?

Reference Material

• DemandSage (2025). Freelance Statistics: Global Workforce Trends
• Pebl (2025). Gig Economy Statistics: The Rise of Independent Work
• Jobstik (2025). Future of Work Report: Career Autonomy and Diversification

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Key Themes

• Portfolio careers are growing 3x faster than traditional employment
• 68% of professionals want more flexibility, yet only 32% feel they have it
• By 2030, 50% of high-skilled professionals will work independently
• Adaptive intelligence is the new currency for career longevity
• Failure is a feature, not a flaw—especially in non-linear careers

Verbal Introduction

The world of work is changing fast. Traditional career paths are giving way to portfolio careers—where professionals combine multiple roles, income streams, and areas of expertise. But is this shift sustainable?In this episode, we explore why portfolio careers are becoming mainstream, what’s driving the change, and what it means for professionals navigating today’s evolving landscape. About Andrea ClarkeAndrea Clarke is a work futurist, leadership expert, and founder of CareerCEO. She helps leaders and learners anticipate change and design intentional futures through writing, speaking, and masterclasses.Her first book, Future Fit, won the Australian Business Book of the Year in 2019 and was a finalist in the UK Business Book Awards. Her latest release, Adapt (March 2025), introduces a four-step framework—Engage, Accept, Activate, Release—for transforming life and career in the face of change.In this conversation, Andrea shares insights on adaptive intelligence, career reinvention, and the rise of portfolio careers.

Interview Questions

• In Adapt, you talk about shifting from reacting to shaping change. How does this mindset apply to portfolio careers?
• You emphasise adaptive intelligence as key to future success. What does that look like in practice?
• Are portfolio careers a sustainable future or just a trend? What signals support their long-term viability?
• How can professionals overcome fear of failure when transitioning from traditional employment?
• You frame failure as a feature, not a flaw. How can professionals reframe setbacks as growth?
• How has the post-2020 shift in mindset influenced the rise of portfolio careers?
• What tools or habits help professionals build adaptability while juggling multiple roles?
• How do self-agency and ownership support the design of meaningful, adaptive careers?
• Final question: What’s one piece of advice you’d like to leave our Portfolio Pod audience with?

Reference Material

• Clarke, A. (2025). Adapt: Move from reacting and responding, to anticipating and shaping change. Sydney: Simon & Schuster
• TalentVine (2025). The Rise of Portfolio Careers & Fractional Roles
• White, L. (2023). Global survey confirms it: Flexibility is key, HRD Australia
• Green, D. (2025). The Key Role of HR in Successfully Integrating a Blended Workforce, Digital HR Leaders Podcast, Episode 201

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Guest: Alison Hernandez, Longevity specialist, Future of Work Advisor, founder of Recreate 100, HSM Advisory.

• Longevity isn’t just about living longer—it’s about maintaining health, mobility, and cognitive function for a fulfilling life
• As we all live healthier longer work will play an important part in healthy aging
• People with more autonomy in their work are 55% happier and 30% more productive

Our Verbal introduction

In today’s episode we explore how portfolio work can create a healthier work-life balance and rediscover purpose. Who doesn’t want to build a career that truly aligns with your values?

Portfolio careers offer a new chapter to those transitioning from traditional executive roles. They allow a way forward where you define your own schedule, choose projects that excite you and create a career that supports your well-being over a longer period. It’s about creating a career that works for you and not the other way around.

Importantly a portfolio career is NOT a replacement for a permanent role, it is a shifting to a whole new way of working. The shift is profound and the coaching needed for individuals to decide if it is right for them cannot be underestimated or undervalued. You need to be clear that you are running towards a portfolio career rather than running away from something be that politics, burnout, disappointment a redundancy or not getting a promotion. A portfolio career isn’t for everyone, we often say, “it’s a stage, not an age” and so today we thought we would talk to one of the best in the business for coaching people through transition.

Our intro to Alison

This podcast is where you come to hear about the future of work and we can’t talk about future of work without overlaying the themes of longevity, transition and career mobility. Today, we’re thrilled to welcome Alison Hernandez, a Longevity Specialist, Future of Work Advisor, and Career Mobility & Transition Expert.

Alison has spent over 25 years helping individuals and organisations navigate career transitions, workforce transformations, and the evolving landscape of work. As an advocate for family-friendly workplaces, she’s passionate about designing environments that support employees at every stage of life. Alison is the APAC leader for HSM Advisory which is Professor Lynda Gratton’s consulting business and also has her own podcast: Longevity Listen. She has her very own portfolio career so we are looking forward to this discussion.

In this episode, we’ll dive into Alison’s insights on the longevity economy, the 100-year life, and discuss sustainable productivity. We’ll also discuss her work with ReCreate100, a movement focused on reshaping how we think about ageing and career transitions. Let’s get started!

Questions:

• Alison as a coach of many years can you share with our audience the most common questions, concerns and surprises people have who are transitioning from an executive career to a portfolio way of working?
• Can you tell us about ReCreate 100?
• What can people do to prepare themselves for engaging with work longer?
• What does work have to do with longevity?
• How is working longer good for us?
• Can you explain the concept of sustainable productivity & how it is the antidote to burnout?
• What advice would you give to someone trying to structure a portfolio career that truly reflects their values and strengths?
• How do you balance variety, income, and personal fulfillment?

Episode 2 - Reference and Source Material

• A study published in the Journal of Applied Psychology found that employees with high levels of workplace autonomy had a 47% higher job satisfaction compared to those with less autonomy.
• Research indicates that increased perceived autonomy can significantly improve individual and group productivity, positively impacting mood and performance

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In this episode of The Portfolio Pod, co-hosts Caroline McAuliffe and Jacinta Whelan, explore the seismic shifts redefining the world of work. With traditional career paths giving way to portfolio careers, project-based roles, and flexible work models, we ask: Is one job still enough?

Our guest, Steve Vamos—former CEO of Xero and veteran of Microsoft, Apple, and IBM—shares insights from his book Through Shifts and Shocks, offering a front-line perspective on navigating disruption and building a resilient, purpose-driven career.

We unpack the evolving nature of leadership and career design in a world where one job may no longer be enough. Steve Vamos shares how the shift from traditional employment to portfolio careers is reshaping how we define success, lead others, and navigate change. We explore the balance between the “being” and “doing” of leadership, and how identity evolves when stepping outside corporate structures.

Steve offers practical insights for managing transitions and uncertainty, especially in careers marked by flexibility and frequent reinvention. Drawing on decades of experience in tech—from mainframes to AI—he reflects on the timeless skills that remain essential and how to prepare for the next wave of disruption.

We also dive into the mindset needed to thrive in a non-linear, multi-career world, including how to lead without a formal title and influence without authority. Finally, we explore how CEOs and corporates are rethinking talent strategies in response to the rise of fractional roles and AI-driven transformation. Steve leaves listeners with one powerful piece of advice for navigating the future of work—tune in to hear it!

Source References for Episode Quotes & Data Points

Featured Book

Through Shifts and Shocks: Lessons from the Front Line of Technology and Change by Steve Vamos

Key Data Points

• 65% of today’s children will work in jobs that don’t yet exist (WEF)
• 30% of tasks in most jobs could be automated by 2027
• 40%+ of organisations are shifting to on-demand, flexible talent models

Book Reference

• The Rise of the Interim Executive
  Official Website: The Rise of the Interim Executive
• Also available on Amazon Australia

Host LinkedIn Profiles

• Caroline McAuliffe – LinkedIn Profile
• Jacinta Whelan – Linkedin Profile

See omnystudio.com/listener for privacy information.

In this inaugural episode of The Portfolio Pod, co-hosts Caroline McAuliffe and Jacinta Whelan lay the foundation for a series of conversations that explore the evolving nature of executive careers and the future of work.

Born from the insights and momentum of their co-authored book, The Rise of the Interim Executive, this episode introduces the why behind the podcast: to create a forum where experts, practitioners, and forward-thinking leaders come together to discuss, challenge, and debate how we engage with work in a rapidly changing world.

As organisations evolve to become more future-ready and sustainable, and individuals increasingly choose portfolio careers over traditional executive roles, this episode sets the tone for what’s to come — a space for education, inspiration, and agency.

Caroline and Jacinta share their vision for empowering professionals to take ownership of their career transitions, offering hope and practical insight into how to be prepared, empowered, and excited about this next phase.

Source References for Episode Quotes & Data Points

'65% of Senior Executives Are Exploring Portfolio Careers'

Rethinking the Executive Path: Rise of the Portfolio Career – Rialto Consultancy

Read the report

'53% of Executives Seek External Roles for Innovation and Learning'

How Portfolio Careers Are Redefining Executive Success – Forbes

Forbes article

'AI and Flexibility Are Driving the Shift'

PwC Future of Work Report

PwC Future of Work

'Human-centric skills and flexible work structures'

Mercer Global Talent Trends Report 2024–2025

Mercer Talent Trends

Book Reference

• The Rise of the Interim Executive
  Official Website: The Rise of the Interim Executive
• Also available on Amazon Australia

Host LinkedIn Profiles

• Caroline McAuliffe – LinkedIn Profile
• Jacinta Whelan – Linkedin Profile

Disclaimer
The views, opinions, and advice expressed by hosts and guests on this podcast are solely their own and do not necessarily reflect those of the producers or affiliated organisations. This content is intended for entertainment and educational purposes only and should not be considered a substitute for professional advice.

If any topic discussed raises personal concerns or emotional distress, we strongly encourage listeners to seek support from qualified medical, psychological, or mental health professionals.

See omnystudio.com/listener for privacy information.