NatSec@Work - National Security Workforce - September Issue

Leadership Lessons and Highlights

A Capstone That Almost Wasn’t McChrystal laughed when I asked him about setting out to write a book on character. “It was not,” he admitted, “there was not even going to be a book.” Originally, he explained, the project was just a series of reflections — “What I Think About the Things I Think About” — with no real throughline. But as he continued writing, one idea surfaced again and again: the link between conviction, discipline, and character. “Conviction times discipline equals character,” he said simply. That formula became the centerpiece of the book and the defining message of his career’s reflection. For McChrystal, this wasn’t an abstract idea. It was a principle sharpened by decades of high-stakes leadership, tough deployments, and hard-earned lessons. And while he may joke that the book is a capstone because his wife doesn’t want him to write any more, the truth is that it offers a summation of wisdom desperately needed in today’s environment — in government, in business, and across the national security workforce. Exhaustion in the Digital Era When we began the interview, I shared my own sense of exhaustion with back-to-back meetings, never-ending notifications, and the feeling of always being “on” in the digital era. McChrystal immediately agreed. “It’s exhausting,” he said. “You can go beyond your ability to maintain energy. At least I can.” This admission matters. McChrystal has long been seen as a leader with bottomless stamina — the kind of general who ran seven miles before breakfast and led at a relentless pace. To hear him acknowledge exhaustion is to be reminded that energy is finite for everyone, no matter the myth. For today’s workforce, this is more than relatable; it is instructive. Leaders cannot assume that simply because technology enables endless meetings, human beings can sustain them. Burnout is real, and without discipline — the second part of McChrystal’s formula — conviction can wither under the weight of exhaustion.

Doing Your Best in the Face of Disappointment McChrystal is no stranger to difficult outcomes. Reflecting on U.S. involvement in Iraq, Afghanistan, and even Vietnam, he did not sugarcoat the reality that many national security efforts ended in disappointment. “In each case, we ended up with disappointing outcomes,” he said. “The question is really, did we do our best? And if we did our best, you can sleep at night. If you didn’t do your best, you should feel guilty.” This perspective is particularly relevant in government and industry roles where outcomes are often shaped by forces far beyond individual control. Policy shifts, political tides, or global crises can undermine even the best-executed plans. For the national security workforce, McChrystal’s standard is clarifying: your responsibility is not perfection but effort. Did you show up with conviction? Did you apply discipline? Did you do your best with the tools, authority, and knowledge you had? Leaders who can answer “yes” to those questions can move forward without the paralyzing burden of regret.

By Lindy Kyzer

I n On Character , retired General Stan McChrystal distills decades of battlefield leadership and boardroom experience into a reflection on the moral compass that guides effective leaders. Far from a traditional military memoir, McChrystal’s work probes the essence of integrity, humility, and resilience, offering readers both cautionary tales and aspirational models. As someone immersed in the national security community, I see On Character as not just a book about leadership, but about how values shape decisions in the moments that matter most, whether in war, work, or everyday life. McChrystal challenges us to view character not as a static trait but as a discipline to be cultivated, tested, and lived. In his latest book, which he jokingly calls his “capstone,” McChrystal argues that the most important measure of

a leader isn’t found in their resume, their rank, or their achievements, but in their character. For him, character is the product of two variables: conviction and discipline. When those elements multiply, leaders can not only weather challenges themselves but also strengthen the communities and organizations around them. I had the privilege of sitting down with General McChrystal to talk about his latest work, in a conversation that spanned the exhausting pace of modern work, lessons drawn from Iraq and Afghanistan, and the enduring importance of community, whether in small towns or digital spaces. What emerged was a vision of leadership that feels both timeless and urgent, offering guidance for today’s workforce as it navigates complexity, connection, and constant change.