Rory Stewart, a former British diplomat who recently returned to Yale, discusses his approach to teaching grand strategy — and offering hope in a bleak time.

In his career, Rory Stewart has held key diplomatic posts in conflict zones and participated in policymaking at the highest levels of the U.K. government, as a diplomat, cabinet secretary, and member of Parliament.

But a hike across Asia, completed during a break from the Foreign Service, informs his teaching as much as any of those experiences do, says Stewart, who in January joined the faculty at the Yale Jackson School of Global Affairs, where he’d previously served as a Senior Fellow.

In 2000 and 2001, Stewart spent 18 months trekking across much of Iran, Pakistan, and the Indian and Nepali Himalayas. In 2002, he completed the journey with a solo walk across central Afghanistan, shortly after the Taliban was toppled from power.

“I learned more by walking 550 days and staying in houses in 550 villages than I learned through the rest of my professional life,” said Stewart, who co-directs the school’s Brady-Johnson Program in Grand Strategy with Yale historians Arne Westad and Michael Brenes.

“It’s so rare in the modern world to get the opportunity to engage with raw local reality village by village. It gave me a totally different perspective on the world.”

Aside from his teaching, Stewart, professor in the Practice of Grand Strategy at the Jackson School of Global Affairs, co-hosts “The Rest is Politics,” the most listened-to podcast in the United Kingdom across all genres, with Alastair Campbell, former director of communications for Downing Street.

In a recent conversation, he discussed his approach to teaching grand strategy, the need to find hope on an increasingly bleak world stage, and his latest book, “How Not to be a Politician: A Memoir,” (Penguin Random House), a memoir of his nearly decade-long career in Parliament. The conversation has been edited and condensed.  

How are you enjoying teaching grand strategy?

Rory Stewart: It’s been great so far. Today, we’ll be discussing the Algerian War of Independence. Two weeks ago, we were teaching the Afghan War, and the week before that, the Vietnam War. We’re studying some of the most raw and interesting examples of political economic strategy coming together in contexts where there was an enormous human toll in killed and displaced. We’re trying to get students to understand the historical contexts in which these decisions were made.

For example, it’s very easy, looking back, to conclude rightly that the United States and its allies made serious mistakes in Iraq and Afghanistan. But it’s important to understand how those mistakes happened. How did smart, well-intentioned people trap themselves into thinking that poor decisions were sensible?

How has the Grand Strategy Program adapted to prepare students to grapple with today’s global challenges?

Stewart: The program remains an opportunity for students to engage energetically with policy, both international and domestic. As always, the hope is that this cohort of Yale students become leaders, whether as academics, business leaders, civil servants, politicians, or in other pursuits. And we hope to help them understand the perils of policymaking, including optimism bias and groupthink.  

I think the world changes and we must keep up with the world. The concerns of today are quite different from the concerns of 30 years ago. It’s very important that the course evolves, but that we do so in a way that preserves fundamental aspects of the program since its inception. For example, we still teach the Peloponnesian Wars between Athens and Sparta, which couldn’t be more traditional, but, at the same time, for our next class session we’re discussing the ideas of the political philosopher Frantz Fanon, who was a member of the National Liberation Front in Algeria and whose work has influenced post-colonial studies and critical theory. We’re engaging with many different perspectives, including issues of resistance and social justice, which I think the students appreciate.

What lessons from your experiences as a diplomat and politician do you draw on in your teaching?

Stewart: I think my experience equips me to help the students understand that, in policymaking, failure is often staring you in the face. People will think that failure’s not an option and then continue to dig themselves into deeper holes until it becomes manifestly absurd and anyone not in that bubble can see the madness for what it is. I’m trying to bring to light why bright and dedicated people can keep pushing ahead with flawed policy.

Now, I was very involved in Afghanistan before I entered politics. Later, when I was a member of Parliament, and considering events in Afghanistan from that perspective, I’d read military assessments by the U.S. Department of Defense that explained in detail why things would ultimately fail. The commander’s assessment would describe all the factors that were going wrong. And then suddenly it would reach a conclusion that had no relationship to what had preceded it. It’d end up arguing that another 40,000 troops were needed to achieve the desired result.

Now, of course, the students look at this and think it’s completely mad because they weren’t in that policymaking bubble. They’re perplexed by how a situation can be described so accurately and reach a conclusion that seems at odds with the description. What I’m trying to do is to try to clarify the factors that give rise to that circumstance. 

What are those factors?

Stewart: There are concerns about how the media and voters will react to decisions. An important factor is how much time politicians must spend really thinking about policy. Can they even find Afghanistan on the map or are they spending five hours a day making fundraising calls? When a politician issues a statement saying every Afghan is committed to a gender-sensitive, multi-ethnic, centralized state based on democracy, human rights, and the rule of law, are they really describing Afghanistan? If what they’re saying doesn’t really relate to Afghanistan, is that because they’re naive or are they dishonest? Or is it neither of those things? Are they just repeating words floating around out there that are designed to appeal to voters, but aren’t grounded in Afghan reality?

It’s difficult to explain these things except through case studies. You can tell students that when we’re intervening in foreign countries, it turns out to be all about us, not about the people living in those countries. But what does that really mean? How does it happen?

What kinds of global challenges will your students need to grapple with as leaders?

Stewart: I think that they will have to wrestle with a world where the assumptions that defined my early working life, which were about free markets and democracy, have begun to erode enormously. I grew up in the post-Cold War world of Francis Fukuyama’s “The End of History,” in which people thought that democracy was ascendant. The number of democracies in the world doubled between 1988 and 2004. There was an explosion of privatization, deregulation, and globalization.

Now we’ve entered a phase where the number of democracies is dropping and where protectionism and populism are on the rise. Democracy feels much more eroded and under threat, partly because of technology, partly because of the financial crisis, partly because of the failures in Iraq and Afghanistan, and partly because of the rise of China. The fundamental challenge for students is where to find sources of optimism and hope because the world looks very, very bleak right now. I cite case studies like the lasting peace in Northern Ireland to remind students that there’s always a reason to hope.

You established the Turquoise Mountain Foundation, a non-governmental organization that focuses on enhancing the Afghan craft industry. Your wife, Shoshana, is its chief executive. How has the foundation managed following the Taliban’s return to power?

Stewart: Like most organizations in Afghanistan, it went through real challenges when the Taliban took over. We helped many of our staff relocate to the United States and quite a lot of them settled in Connecticut through the amazing support from Integrated Refugee & Immigrant Services [IRIS], a New Haven-based non-profit that helps refugees establish new lives and become integrated in their new communities. People have been very welcoming to them, and I’m very grateful for that.

But we’ve managed to keep going in Afghanistan and in some ways expand, particularly our efforts working with rural women on carpet weaving and helping them get their products out to market. We’re able to provide them good-quality health care. Given the nature of the situation on the ground, we’re leaning into supporting traditional crafts. And in some ways security is improving, but’s still a tragedy and, particularly, a tragedy for Afghan women.

You recently published “How Not to Be a Politician,” a frank account of your political career. What did you learn about yourself while writing it? 

Stewart: The book was written when I was a fellow at Jackson before I came to take this new position. Being a fellow gave me the space to do the research for the book, which was, at times, very painful for me, but also wonderfully clarifying. It gave me a chance to be forthright about my own failures and consider the problems of working in a democratic system. I really tried to be honest about what it feels like inside to be a working politician.