Expat Playbook

Alice Hong & Hayley Winchcombe
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Dream of a global career? Expat Playbook helps ambitious professionals design, launch, and grow international careers, with a focus on opportunities between Australia and Asia.

Episodes

  1. Oct 28

    Building a tech career across Australia, Singapore and London with Alice Hong

    Alice Hong knew from a young age that she wanted to work in international business. In 2019, Alice had a consulting job waiting in Hong Kong and flights booked through Singapore. When protests broke out in Hong Kong, Alice decided to stay in Singapore. Within one month she had secured a role in the technology sector, and a few years later she repeated the move in London. In this episode, Alice sits down with co-host Hayley Winchcombe to trace how she built a career across three cities. The conversations covers how Alice started as a career mentor for Hayley in 2020, when Hayley started a graduate role at Accenture Strategy and Alice took a half-hour call to give her advice. That call became a friendship through volunteering together at the ASEAN-Australia Strategic Youth Partnership, and now this podcast.  In this pilot episode, Alice explains why she set herself a deadline to build a global career in her twenties. Hayley shares why 4 exchanges across Japan, France, Spain, Singapore and Jakarta pointed her towards the growing economies in our neighbourhood of Southeast Asia. Alice then answers the question Hayley has wanted to ask for years: how do you get off the plane and get the job? Her answer comes down to 3 moves that apply in any city. Listen to find out what.  In the second half of the episode we unpack why an international career makes sense in 2026. Geopolitical risk is rewarding people who can read markets across borders, and digital nomad visas are spreading from Portugal to Malaysia. AI is raising the premium on human skills, personal brand and the ability to tell a commercial story.  Whether you are weighing a move to Asia, planning your first job search abroad, or deciding where to base a global career, this one is for you. 🎧 Listen to the Expat Playbook to get inspiration for your own moves abroad. Join your hosts Alice Hong and Hayley Winchcombe weekly wherever you get your podcasts. Chapters 00:00 Introduction 01:19 How Alice and Hayley met in 2020 04:26 The Hong Kong flight Alice never took 05:21 A deadline for a global career 06:38 Hayley's exchanges in Japan, Europe and Southeast Asia 08:54 Why Southeast Asia 10:52 Shanghai, Hong Kong and the case for Singapore 12:18 Increasing your surface area of opportunity 14:45 How to get off the plane and get the job 16:15 One month to a role in Singapore and London 17:34 Why now: geopolitical risk, connectivity and digital nomad visas 20:34 AI, human skills and personal brand 23:34 Work, live, retire: Alice on Singapore, London and Australia 25:30 Work, live, retire: Hayley on Malaysia, Indonesia and Australia 28:22 Closing and how to join the Expat Playbook community #ExpatPlaybook #GlobalCareers #SingaporeExpat

  2. Oct 7

    Penny Burtt on building an international career across the Asia-Pacific

    From diplomatic service to leading across Asia's most dynamic markets, Penny Burtt joins the Expat Playbook to unpack a career in which she most recently served as President, Southeast Asia at Boeing.  In a career spanning the business, government and nonprofit sectors, Penny Burtt has held leadership positions in the Asia-Pacific with global multinationals Visa Inc, the digital payments company and consulting firm McKinsey&Company, Stripe and Boeing. Penny led Australia’s leading centre for Asia engagement, Asialink at the University of Melbourne, as Group CEO.  A former senior diplomat, Penny represented Australia in Asia, and the United Nations in Geneva and New York. Penny is a passionate advocate for diversity and development, and has shared her expertise as an Executive Board Member with key business associations and nonprofits in Singapore, Australia and the United States. In this conversation, Penny shares why Singapore offers significant career options, how to think about opportunities in APAC, the difference between leading with authority vs influence, and why defining yourself beyond your day job is the best career move. Whether you are pivoting careers, building a business in Asia, or figuring out what comes next, this episode is for you. This podcast episode was created in collaboration with the Singapore Global Network. Interested in joining a community centered around Singapore?  Join the Singapore Global Network (SGN), a 250,000-strong community of changemakers, professionals and friends across 175 countries. SGN exists to connect people to opportunities that Singapore and its network of members have to offer.  Chapters 0:00 | Intro 0:53 | Penny's career journey  3:57 | Why Singapore?  9:55 | Australia-Asia investment and data centres 11:05 | Navigating diverse Asian markets  15:58 | Building trust with partners in Asia  17:27 | The power of showing up and staying connected  19:23 | From diplomacy to the private sector  21:35 | Leadership: authority vs. influence 23:00 | Choosing tech and staying relevant in the AI era 27:12 | Three tips for an international career 31:30 | Rapid fire round  34:53 | Thank you #ExpatPlaybook #Singapore #CareerPivot #Leadership #GlobalCareers

    Penny Burtt on building an international career across the Asia-Pacific

  3. Sep 30

    Launching into Canada's innovation ecosystem with Ronald Poon

    In this episode of the Expat Playbook, we sit down with Ronald Poon, a Hong Kong-born, New Zealand-raised innovation program manager who spent four years living and working across Montreal and Toronto before returning to Melbourne. Ronald shares how a two-week university study tour to Canada about data science and AI sparked a journey that took him from Montreal to Toronto, where he joined a startup consultancy running hackathons and innovation programs for major corporates including McDonald's, HSBC, and BMO.  His highlight was helping large companies "think like a startup" through running accelerator-style programs where employees pitched solutions to C-suite executives. We trace Ronald's path from a Bachelor of Law and Commerce at Monash, through his pandemic-era move to Canada, to his return to Melbourne's innovation space.  We discuss the cultural differences between North American and UK business cultures, and why building a network in a new country takes time. Whether you're an early-career professional considering a move abroad or are curious about what working in Canada is like, we hope you'll enjoy the discussion. 🎧 Listen to the Expat Playbook to hear more about Ronald's journey. Join your hosts Alice Hong and Hayley Winchcombe weekly wherever you get your podcasts. ⏱️ Chapters: 1:02 Introduction & tennis talk 2:43 Growing up: Hong Kong to New Zealand 5:04 From Melbourne to Canada 10:16 Finding work & building a network 13:46 Business culture: North America vs Down Under 17:49 Innovation programs & hackathons 20:43 Looking ahead: next steps & Canada advice 24:24 Montreal's hidden gems 26:26 Rapid fire 30:42 Final advice & wrap-up #ExpatPlaybook #Canada #Innovation

  4. Sep 24

    A professional placement within Singapore's innovation ecosystem with Antonia Robson

    In this episode of the Expat Playbook, we sit down with Antonia Robson, one of the first recipients of DFAT's Professional Placements Program under Australia's Invested: Southeast Asia Economic Strategy to 2040.  Antonia spent three months embedded with Padang & Co in Singapore, working on innovation programs that connect corporates and startups to accelerate the green economy across Southeast Asia. Her highlight was working on the Sustainability Open Innovation Challenge, delivered on behalf of Enterprise Singapore, in which thirty multinational corporates sought technology solutions to defined business challenges.  We discuss why Singapore's efficiency, infrastructure and clear government vision on innovation make it a natural launching pad into Southeast Asia. We also trace Antonia's path from a Master in International Relations at LSE, through consulting at Dragoman, KPMG and Asialink Business, to her current role.  Whether you're an early-career professional considering how to turn your degree into a career or an Australian curious about working on the ground in Southeast Asia, we hope you'll enjoy the discussion. 🎧 Listen to the Expat Playbook to hear more about Antonia's journey. Join your hosts Alice Hong and Hayley Winchcombe weekly wherever you get your podcasts. #ExpatPlaybook #DFAT #SoutheastAsia #Singapore #GreenInnovation

  5. Sep 16

    Building a career as a renewables lawyer in Australia and Southeast Asia with Mikaylie Page

    From an ACICIS university exchange in Indonesia to closing renewable energy deals across Southeast Asia, Mikaylie Page's story is anything but the typical lawyer pipeline. A Renewables Lawyer at White & Case, Indonesian speaker, and self-described "not a city gal," Mikaylie chose Singapore over London, learned Bahasa Indonesia from scratch in Yogyakarta, and built a career niche at the intersection of Southeast Asia, renewable energy, and cross-cultural work. In this episode, we unpack why Southeast Asia is one of the most exciting, and overlooked, career destinations for ambitious professionals. We also touch on how to build a niche that sets you apart, how Mikaylie handles navigating land tenure disputes in Laos and offshore wind deals in Taiwan, and how a double life between big law in Singapore and a remote Sumatran village reshaped her definition of success 🌏 Whether you're an early-career professional plotting your next move, a lawyer weighing London vs Singapore, or simply curious about life off the beaten path, this one's for you. 🎧 Listen to the Expat Playbook to be inspired by Mikaylie's journey.  Join your hosts Alice Hong and Hayley Winchcombe weekly wherever you get your podcasts. Chapters: 1. 0:00 — Meet Mikaylie Page, Renewables Lawyer 2. 2:50 — Inside the Day-to-Day of a Renewables Lawyer 3. 5:00 — From ESG to Contracts: Finding the Right Path 4. 8:50 — Why Singapore Over London 5. 11:00 — Renewable Energy in SE Asia: Challenges & Opportunities 6. 16:50 — Is Southeast Asia Overlooked by Australians? 7. 18:26 — The Accidental Exchange to Indonesia 8. 21:30 — Learning Indonesian & Life in Yogyakarta 9. 24:50 — Redefining Success Across Cultures 10. 27:00 — A Double Life: Big Law & a Sumatran Village 11. 29:20 — Advice for Aspiring International Lawyers 12. 31:12 — Wrap Up & Thanks #ExpatPlaybook #RenewableEnergy #SoutheastAsia #Singapore #Indonesia

  6. Sep 9

    A career in defence, risk and tech policy across Australia, Indonesia and Singapore with Aidan Hoy

    Aidan Hoy chartered a unique path from Perth to Indonesia, Timor-Leste, Canberra and Singapore through saying yes. From an ACICIS exchange in Yogyakarta and election scrutineering in Timor-Leste, these experiences built the groundwork for a career that saw Aidan return to Indonesia through his work in Defence; and later return to Singapore to work on election safety across Asia with a major tech company.  What does it take to build a career that spans Australia, Southeast Asia, and the tech sector? In this episode, we sit down with Aidan Hoy, whose 20-year career has taken him from political science studies in Perth to the Department of Defence in Canberra, and ultimately to Singapore, where he's worked across banking, geopolitical risk, and seven years at Meta (Facebook) managing elections and civic risk across the region. Aidan shares how learning Indonesian in primary school planted the seeds for a career in the region, how a semester abroad in Yogyakarta changed his worldview, and how volunteer election observing in Timor-Leste and postings with the Australian Defence Force shaped his understanding of geopolitics. He opens up about his pivots from the public service to the private sector, from compliance to risk, and from Australia to Singapore, and offers practical advice for young Australians looking to move to Asia. Along the way, we talk about Australia's unique people-to-people links with Southeast Asia, the art of cross-cultural relationship building, what a day in the life of a risk professional actually looks like, and why "benign leadership is debilitating." We wrap with a rapid-fire round covering favourite Southeast Asian dishes, underrated cities, Muay Thai, and three ingredients for leadership. Hosted by Alice Hong and Hayley Winchcombe.  Chapters 00:00 — Introduction 00:25 — Career Background 05:03 — The Singapore Pivot 06:48 — Indonesia & Yogyakarta 09:41 — Australia's Role in Southeast Asia 13:35 — Building Relationships Across Cultures 15:43 — A Day in the Life of Risk Management 20:23 — Timor-Leste 28:20 — Rapid Fire 34:59 — Leadership Wisdom 36:01 — Wrap up

  • 6 Episodes

About

Dream of a global career? Expat Playbook helps ambitious professionals design, launch, and grow international careers, with a focus on opportunities between Australia and Asia.

Information

  • Creator
    Alice Hong & Hayley Winchcombe
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2026 Expat Playbook
  • Show Website
    Expat Playbook

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