Jenny Wilcox reveals the hidden reality of diplomatic life—where managing powerful personalities, navigating male-dominated spaces, and leading through crises requires mastering the small details that make big outcomes possible.
From her early days in the Foreign Secretary's private office to serving as Deputy High Commissioner during international crises, she shares the unexpected skills that translate from diplomatic corridors to corporate boardrooms.
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.
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:
If you want to work with Jen contact her by email: jennifer@howtodiplomat.com
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.
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
------------------------------------------------------
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.
--------------------------------------------------------
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 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.
-------------------------------------
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.