Our guest for this episode is Jennifer Upton - former British diplomat, now executive coach and founder of How to Diplomat
In this warm and deeply human conversation, Rebecca Rees and Caroline Bridge talk with Jen Upton - a former British diplomat who has been posted to some of the world’s toughest countries and now helps leaders and teams communicate, influence, and stay grounded when the pressure’s on.

As Jen says, she was “posted to places I wouldn’t get to see on holiday” - and some of those postings came with extraordinary challenges. She shares what it was like to evacuate twice with two small children and her husband, and to survive the Marriott Hotel bombing in Pakistan. These experiences gave her a powerful perspective on leadership, resilience, and how to stay composed when everything around you feels uncertain.

Now an executive coach and founder of How to Diplomat, Jen helps others learn the art of diplomacy in everyday life - connecting with empathy, handling pressure with grace, and leading through influence rather than authority.

Together, the trio explore:

• How to manage fear and uncertainty in high-stakes situations
• Why influence starts with curiosity
• How courage often looks quiet, calm, and deeply human
• The lessons diplomacy can teach us about work and life

If you want to work with Jen contact her by email:  [email protected]

If you want to follow her for more insights:

LinkedIn: www.linkedin.com/in/jennifer-s-upton

Diplomatic Dispatches newsletter:newsletter

Instagram: https://www.instagram.com/howtodiplomat/
Youtube: https://www.youtube.com/@howtodiplomat 

The views expressed in this episode are the personal reflections of our guest. They do not represent the official positions of the UK Foreign Office or any government.

Last week, Tom Bridge launched something new for us - the NVNG Top 3: three guiding principles or suggestions that help our guests when they’re facing new challenges or difficult situations.

Nothing Ventured, Nothing Gained is hosted by Rebecca Rees and Caroline Bridge.

Rebecca is an Executive Coach and Co-Founder of Peak 15 Coaching, passionate about how our brains work and helping people unlock possibility.

Caroline won BBC’s Race Across the World 2025 with her son Thomas - a series watched by over six million and shortlisted at the National Television Awards.

🎯 Our Mission: To help people pause, see beyond what holds them back, and discover new possibilities for greater happiness and wellbeing.

We’re rookie podcasters determined to keep going, keep improving, and share the adventure with you. Trying something new is rarely perfect - but it’s always real.

🎧 Creative Team : Angela Young – Podcast Production, Cambridge Podcasts, Zainab Uzair – Graphics, Logo & Cover Art, Gabriella Füzi – Portrait Photography

📩 Contact Us : We’d love to hear your questions, ideas, or stories of stepping outside your comfort zone: WhatsApp: https://wa.me/447375220027

Instagram @nothingventuredpodcast

👉 Please follow, share, and be part of the NVNG adventure — it all starts with daring to try.

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I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches.

You can also find me here:LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat

The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government.

This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

In this conversation, Carlos and Jennifer explore the complexities of life as a spouse in the foreign service, discussing the accountability paradox, the importance of adaptability, and the challenges of maintaining a professional identity while supporting a partner's career. They delve into personal growth, the dynamics of relationships in a foreign context, and the need for policy changes to support spouses. Carlos shares insights on navigating job markets, the emotional aspects of career transitions, and the significance of self-discovery in shaping one's professional journey.

Chapters

00:00 The Role of a Trailing Spouse

04:45 Marsupial Identity and Independence

06:53 Navigating Relationships and Autonomy

07:46 The Science of Relationships

09:32 Proximity vs. Emotional Connection

11:02 Adaptability in Foreign Service Life

13:18 Skills for Success in Foreign Service

14:49 Crafting Your Professional Identity

16:33 Reinventing Yourself in New Environments

17:57 Finding Your Core Interests

19:50 The Journey of Self-Discovery

22:03 Breaking Free from Attachments

22:51 Navigating Personal Growth and Change

24:55 Supporting Diplomatic Families: A Policy Perspective

27:58 Advice and Experiences as a Diplomatic Spouse

32:08 Reflections on Career and Identity

37:08 The Vocation of Diplomacy: A Call to Service

I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches.

You can also find me here:
LinkedIn: www.linkedin.com/in/jennifer-s-upton

Instagram: https://www.instagram.com/howtodiplomat/
Youtube: https://www.youtube.com/@howtodiplomat

The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government.

This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches.

You can also find me here:
LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat

Maria's contact details:

LinkedIn: https://www.linkedin.com/in/maria-brewer-b426b0180/

Website: https://paperbell.me/maria-brewer

The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the UK Foreign Office or any government.

This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

Chapters

00:00 The Calling of Diplomacy

04:58 Creating Community Abroad

07:13 The Journey to Diplomacy

09:44 Moments of Impact in Consular Work

11:46 Lessons in Listening and Understanding

14:32 Balancing Diplomacy and Motherhood

16:47 Navigating Crisis as a Parent

19:20 The Dynamics of Tandem Careers

21:46 Resilience in Diplomatic Families

24:16 Leadership Lessons from Experience

28:13 The Challenges and Rewards of Diplomacy

29:58 The Ambassador's Writing Style

31:36 Negotiation Techniques in Diplomacy

33:18 The Role of Ambassadors in Democracy

36:09 The Importance of Convening in Diplomacy

37:34 The Human Touch in Diplomacy

38:26 The Autonomy of Smaller Posts

40:08 Transitioning from Ambassador to Civilian Life

42:35 Embracing Change and New Beginnings

46:08 Coaching and Leadership Development

48:38 Authenticity in Leadership

52:41 Authentic Leadership and Strategic Intelligence

54:33 The Transition Paradox in Leadership

54:59 Overcoming Imposter Syndrome

I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly ⁠newsletter⁠, Diplomatic Dispatches.

You can also find me here:LinkedIn: ⁠www.linkedin.com/in/jennifer-s-upton⁠

Instagram: ⁠https://www.instagram.com/howtodiplomat/⁠Youtube: ⁠https://www.youtube.com/@howtodiplomat

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In this episode of the How to Diplomat podcast, I speak to Josue Castro, an experienced diplomat who shares his journey through the complexities of diplomacy, particularly during the Arab Spring in Egypt. We talk about the challenges of navigating moral and ethical dilemmas, the importance of personal growth through adversity, and the skills gained from diplomatic experiences.

Josue reflects on his transition from diplomacy to sustainability consulting, emphasizing the significance of leadership and personal development. The conversation concludes with insights on career choices and the unique superpowers diplomats bring to the private sector.

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Chapters

00:00 Introduction

02:25 The Journey into Diplomacy

03:05 Finding Purpose in Foreign Affairs

04:34 Balancing Idealism and Pragmatism

06:50 Navigating Human Rights and Trade Interests

07:57 Experiences in Cairo: The Dream Team

09:10 The Emotional Toll of Diplomacy

10:41 Personal Growth and Leadership Development

12:47 Staying Grounded in Intense Situations

14:50 Transitioning from Government to Private Sector

19:21 Navigating Leadership Journeys

19:55 The Importance of Reflection in Career Growth

21:55 Lessons from Diplomacy: Skills and Insights

25:12 The Value of Boundary Spanning in Professional Life

29:10 Systems Thinking: A Diplomat's Perspective

31:17 Advice for Future Diplomats and Leaders

34:16 Final Takeaways

The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of theUK Foreign Office or any government.

This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

In this episode, I chat with James a first-time British diplomat in one of the world’s toughest postings. We cover the life-changing but career-tightrope-walking art of vibe reporting (loved in capital, risky at post), how to keep calm when missiles are overhead, and why trust is the only thing that keeps a small embassy afloat. Plus: why he is my most nightmare of nightmare fellow travellers.

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I write more deeply about what I learn from my intervieweesalong with insights from 20+ years as a diplomat and army officer - in my weekly newsletter, Diplomatic Dispatches.

You can also find me here:
LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/Youtube: https://www.youtube.com/@howtodiplomat

The views expressed in this episode are the personalreflections of the guest. They do not represent the official positions of the Foreign Commonwealth & Development Office or any government.

This podcast shares human stories and transferable lessonsfrom diplomacy - not day-to-day operational details.

Chapters:00:00 Introduction

04:03 Navigating Anxiety: The Unknowns of a New Posting

06:21 Self-Discovery: Lessons Learned in a Foreign Land

08:29 The Unique Dynamics of Embassy Life

11:05 The Journey into Diplomacy: Expectations vs. Reality

13:23 Understanding Impact: The Role of a Diplomat

15:46 The Power of Storytelling in Diplomacy

17:13 Capturing the Vibe: Reporting Beyond Formalities

23:43 The Reality of Diplomatic Work

25:07 Skills Developed Under Pressure

25:50 Perspective and Big Picture Thinking

26:20 Trust and Team Dynamics in Crisis

28:54 Preparation for Crisis Scenarios

31:06 Emotional Intelligence in Diplomacy

35:40 Self-Care and Resilience

39:32 Getting Stuck In: Embracing New Experiences

41:31 Breaking Stereotypes of Diplomats

47:25 Building Trust in Teams

50:08 The Nature of Impact in Diplomacy

In this episode, I chat with John Constantine - former US Secret Service Agent, leadership pro, and someone I’ve (apparently) known for over a decade without realising it.
We cover leadership, ego, cultural diplomacy… and the time one of his colleagues elbowed me in the face in New York.

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I write more deeply about what I learn from my interviewees along with insights from 20+ years as a diplomat and army officer — in my weekly newsletter, Diplomatic Dispatches.

You can also find me here:
LinkedIn: www.linkedin.com/in/jennifer-s-uptonInstagram: https://www.instagram.com/howtodiplomat/
Youtube: https://www.youtube.com/@howtodiplomat

----------------------------------------------------Chapters

00:00 Introduction to John's Background

02:56 Joining the Secret Service: A Personal Journey

05:57 The Importance of Diplomacy in Security

09:36 Cultural Sensitivity in Operations

12:13 Navigating Cultural Differences

13:12 Decision-Making Under Pressure

15:52 Crisis Response and Decision Making

20:10 Surreal Experiences in the Field

24:33 Lessons from Political Leaders

29:04 The Journey to Personal Philosophy

32:18 Identity Beyond Profession

36:44 The Essence of Leadership

38:54 Navigating Identity Beyond Titles

Welcome to How to Diplomat!
I’m Jen Upton - former army officer and diplomat with 20 years in the field.

This podcast isn’t about the handshakes on red carpets or the headlines you already know.

It’s about the unsung heroes of diplomacy - the people who worked behind the scenes in revolutions, disaster zones, and tense negotiations. Ordinary people who found themselves in extraordinary moments.

In each episode, you’ll hear their stories. What they saw, what they learned, and the skills they used to connect, calm, and lead under pressure.

Because diplomacy isn’t just for diplomats. It’s about how we all navigate conflict, influence people, and build trust in a complex world.

Subscribe to How to Diplomat and and discover the tools that can help you connect and lead, wherever you are.