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
What are the most common questions or surprises professionals face when shifting to a portfolio career?
Can you share insights from your interim and NED roles, and how they differ from your military and corporate experience?
What can professionals do now to prepare for longer, more flexible careers?
How has your military background shaped your leadership style in commercial settings?
How do you manage multiple roles while keeping your future work pipeline active?
What’s your approach to building a personal brand?
How do you stay current in your field?
How do you manage the “back office” of your portfolio career?
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

Key Themes
<ul>
<li>47% of the global workforce identifies as self-employed</li>
<li>The gig economy accounts for 12% of the international labour market</li>
<li>52% of professionals seek careers beyond a single employer</li>
<li>Portfolio careers require strategic planning, adaptability, and strong personal branding</li>
<li>Sustainability depends on financial stability, pipeline management, and self-agency</li>
</ul>
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&rsquo;ll share strategies to help you design a career that aligns with your goals and risk profile.Portfolio careers offer freedom and variety&mdash;but they also demand discipline. We&rsquo;ll cover how to stay current, fill your pipeline, and maintain momentum across diverse roles.Let&rsquo;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 &ndash; 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&rsquo;s held interim executive roles at Georges River Grammar and Pacific Aerospace, and was awarded the 2012 Telstra Business Woman&rsquo;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
<ol>
<li>What are the most common questions or surprises professionals face when shifting to a portfolio career?</li>
<li>Can you share insights from your interim and NED roles, and how they differ from your military and corporate experience?</li>
<li>What can professionals do now to prepare for longer, more flexible careers?</li>
<li>How has your military background shaped your leadership style in commercial settings?</li>
<li>How do you manage multiple roles while keeping your future work pipeline active?</li>
<li>What&rsquo;s your approach to building a personal brand?</li>
<li>How do you stay current in your field?</li>
<li>How do you manage the &ldquo;back office&rdquo; of your portfolio career?</li>
<li>Final question: What&rsquo;s one piece of advice you&rsquo;d like to leave our Portfolio Pod audience with?</li>
</ol>
Reference Material
<ul>
<li>DemandSage (2025).&nbsp;<a href="https://www.demandsage.com/freelance-statistics" data-saferedirecturl="https://www.google.com/url?q=https://www.demandsage.com/freelance-statistics&amp;source=gmail&amp;ust=1764815541452000&amp;usg=AOvVaw14RNxQ1wXVa1K6tMdR0X8a">Freelance Statistics: Global Workforce Trends</a></li>
<li>Pebl (2025).&nbsp;<a href="https://hellopebl.com/resources/blog/gig-economy-statistics" data-saferedirecturl="https://www.google.com/url?q=https://hellopebl.com/resources/blog/gig-economy-statistics&amp;source=gmail&amp;ust=1764815541452000&amp;usg=AOvVaw3FPuUyv7LF8uEae_vzdMXY">Gig Economy Statistics: The Rise of Independent Work</a></li>
<li>Jobstik (2025).&nbsp;<a href="https://jobera.com/gig-economy-statistics" data-saferedirecturl="https://www.google.com/url?q=https://jobera.com/gig-economy-statistics&amp;source=gmail&amp;ust=1764815541452000&amp;usg=AOvVaw0heysx3gTvRjGX0MpK_7eD">Future of Work Report: Career Autonomy and Diversification</a></li>
</ul>

The Portfolio Pod explores the future of executive careers and work. Hosted by Jacinta Whelan and Caroline McAuliffe, it’s a forum for experts and leaders to discuss how organisations and individuals are evolving. Focused on agency, empowerment, and readiness, the podcast supports those transitioning from traditional roles into portfolio careers. Each episode offers insight into how to be prepared, build market presence, and thrive in a flexible, purpose-driven career.

The Portfolio Pod explores the future of executive careers and work. Hosted by Jacinta Whelan and Caroline McAuliffe, it&rsquo;s a forum for experts and leaders to discuss how organisations and individuals are evolving. Focused on agency, empowerment, and readiness, the podcast supports those transitioning from traditional roles into portfolio careers. Each episode offers insight into how to be prepared, build market presence, and thrive in a flexible, purpose-driven career.

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