Lessons from the front lines from Obama Leaders

Two Obama Leaders share how military service shaped their approach to organizing, advocacy, and building power in communities.

This Veterans Week, our Obama Leaders offer crucial insights into what veterans uniquely bring to civilian leadership and why organizations should actively seek their perspectives. Read on for their three key pieces of advice. 

As a high school sophomore in South Carolina watching the Twin Towers fall, Brandon Upson , a Navy Junior Reserve Officers Training Corps cadet, immediately took the Armed Services Vocational Aptitude Battery test and headed to the Marine Corps recruiting table at lunch. He held his test scores in hand, a 90-something, which opened doors to specialized roles. But at 17, he still needed to wait.

That's when the Army National Guard recruiter grabbed him with an offer: “You can join when you're 17 and finish high school, and then, after high school, you can decide if you want to go to the Marine Corps, but we can get you in now.”

There was just one problem: “My mom would never let me do this,” Upson thought. So he hatched a plan. His mother worked two jobs, getting off late from her second shift. “I was like, 'Hey, if you come to my house around 9:30, I'll have her ready.'”

The recruiter showed up right on schedule and made his pitch. With Upson's high ASVAB scores, he qualified for chemical, nuclear, biological, and radiological specialist training, an ideal fit for a young man who wanted to be a chemical engineer. The recruiter sealed the deal with a promise that would prove spectacularly wrong: with that specialty, Upson's name would “always be at the end of the list” for combat deployment.

Within months of finishing his training, Upson found himself number one on the deployment roster to Iraq. “My friend, who had just come back less than a year ago from Iraq, volunteered to go back with me to ease my mom’s mind,” Upson recalled. He left South Carolina at 19 and came home at 21, having celebrated two birthdays in a war zone and volunteered for over 100 combat missions.

Christopher Purdy 's path to service followed a different trajectory but led to a similar destination. Coming from a military family—his father served in the Air Force, his grandfather in the Army—Purdy watched the Twin Towers fall and knew he needed to act. He joined the Army National Guard in 2004 specifically to serve his community through a state-based organization focused on natural disasters and emergencies. He deployed to Iraq in 2011 as a Combat Engineer and Sergeant.

Today, both men are part of the 2025-2026 Obama Leaders United States cohort, translating the leadership lessons learned in uniform into powerful tools for civic engagement and community organizing. Upson serves as executive director of the New Progressive South, organizing working-class communities across the region. Purdy founded the Chamberlain Network, mobilizing veterans as advocates for democracy and effective governance. Upson returned from Iraq in 2007 and eventually entered politics through Organizing for America in 2010.

“I really felt like I was moving from being in my Army Combat Uniform combat boots with weapons strapped around me to now putting on a different pair of boots into my community and fighting in a different way,” Upson explained. “Instead of organizing and moving soldiers, now it was organizing and moving community people. That structure, that discipline really from the military set me up to be effective.”

For Purdy, a crucial leadership lesson came during basic training. He was arguing with another trainee about how to tackle an obstacle when he suddenly stopped and said, “All right, I'm going to let you run the show here.”

“It wasn't that he was right and I was wrong, or I was right and he was wrong,” Purdy reflected. “It's counterintuitive to think that the army taught me how to think less like an autocrat.”

1. Mission over ego

Purdy learned during basic training that mission success matters more than individual correctness. When arguing with a teammate over an obstacle course approach, he realized the path forward was collaboration, not proving a point. "The most important thing was us coming together and doing things as a unit as opposed to somebody being right," he said.

Upson applies similar thinking to community organizing, crediting his Vietnam veteran sergeants who emphasized practical wisdom over credentials. Their unit completed dangerous missions across Iraq without losing a single soldier by prioritizing care and common sense. "The way they cared for us is the way I care for my people, even today," Upson said.

2. Adapt without fear of failure

Both leaders credit military training for their willingness to experiment and iterate quickly. During the 2020 pandemic, Upson saw opportunity in crisis and tried everything from QR codes on protest T-shirts to a full telethon-style "votathon" that registered 5,000 people in one day. "I'm not afraid of failing," he admitted. "We literally tried everything that someone suggested that was meaningful."

Purdy applies the same adaptability to building coalitions, putting ego aside to scale impact. His collaborative approach to a veteran poll worker program grew it from 1,000 participants in 2020 to 160,000 in 2024 by allowing other organizations to take the lead and build out the program using their skills and resources. "It requires people to be able to put their ego aside and try to build those relationships to break down the silos," he noted.

3. Empower others to lead

Through the Obama Leaders program, both men have deepened their approach to building distributed leadership rather than top-down authority. Upson recalls teaching power-building concepts to Miss Sharon, a Waffle House cook he's organizing, who became a "secret weapon" mobilizing both co-workers and customers. 

"I've just been able to be the conduit to give people the courage to try something crazy," he said.

Purdy focuses on equipping veterans with advocacy skills they can use independently.

“We're giving them the skills to go out and speak to their members of city council, their state house representatives, and their local elected leaders to effect change," he explained. The goal isn't to create followers but to develop leaders who can organize their own communities.

Perhaps the most powerful lesson both men carry forward is that the oath they swore didn't end when they took off their uniforms.

"The oath that I swore to protect this country is something I didn't discard when I took off the uniform," Purdy said. "Participating in America's longest war has a real emotional effect on a generation. That doesn't go away when you leave service."

His message to fellow veterans this Veterans Day invokes naval history: "Don't give up the ship. Don't let the things that we signed up to serve and defend go away. Now is not the time to be quiet. Now is the time to actually become loud."

Upson sees hope in the next generation.

"I know there's a generation coming up with the tools to get us to the promised land," he said. "Those of us who are of age right now, it's our job to hold the line and make it possible for them to enter the landscape."

Apply for The Obama Foundation Leaders Program. The application closes Friday, Dec. 12, at 12 p.m. United States Central Time (UTC-6).