194. Ten Years to be a Navy SEAL (Ret.) | Today CEO Trident Approach Leadership Consultant

Diego Ugalde

In episode 194 of the Transition Drill Podcast, retired Navy SEAL Diego Ugalde shares his powerful story of failure, redemption, and inner healing. Raised in a turbulent home, Diego joined the Navy after high school with dreams of becoming a SEAL. His first attempt at BUD/S ended in failure due to severe injuries and lack of preparation—an experience that haunted him for eight years. After leaving the Navy, he became a paramedic, but recurring dreams of that failure led him back. At 29, Diego re-enlisted, completed BUD/S with Class 246, and went on to serve at SEAL Team Two. He retired after 20 years, having risen to the rank of E-8. But even after success, he felt unfulfilled. Seeking healing, Diego turned to psychedelic therapy, where Ibogaine helped him confront deep-rooted trauma. That experience reshaped his purpose. Now, he’s a psychedelic integration coach, speaker, Diego also leads The Trident Approach, a leadership and cultural development consultancy, and is the co-founder of Warrior Side, a nonprofit supporting military veterans and first responders in healing from service-related trauma. Diego’s story is a testament that military transition is more than finding a new job—it’s about rediscovering who you are beneath the uniform.

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Diego Ugalde’s journey from a troubled youth to a determined Navy recruit wasn’t marked by ease or certainty—it was carved through chaos, brokenness, and raw ambition. Born in England while his father served in the Air Force, Diego moved stateside at a young age and grew up in Fairfield, California, near Travis Air Force Base. Childhood, for Diego, was anything but stable. The aftermath of his parents' divorce set the stage for a young man thrust prematurely into adulthood—his older brother, just eight at the time, became his caretaker amid a household ruled by tension and emotional rigidity.

This kind of upbringing isn’t uncommon among military veterans. Diego, like many service members, carried the invisible weight of unresolved childhood trauma—what he later recognized as one of the defining factors that led him to pursue a warrior’s path. But at 18, he couldn’t articulate it that way. All he knew was that he wanted to become a Navy SEAL.

Graduating high school in 1992, Diego entered the Navy through the Delayed Entry Program. He had his sights locked on the SEAL Teams—but the reality check came early. Though he passed the overall ASVAB, his score in mechanical comprehension fell just two points short of the SEAL requirement. The result: Diego would have to spend two years in the regular Navy before he could even attempt SEAL training. It was a bitter disappointment for a young man who already felt behind in life.

Still, Diego pressed forward. He trained, worked at a Navy hospital, and eventually entered Basic Underwater Demolition/SEAL (BUD/S) training with Class 199. But his first brush with the legendary crucible proved brutal. By his own admission, he wasn’t ready—not physically, not mentally, not emotionally. He’d trained inconsistently, abandoned his soft-sand conditioning, and assumed his football background and occasional long runs would carry him. They didn’t.

From day one, Diego found himself struggling to keep pace. He failed every single timed run. Still, he refused to quit. That refusal came at a price. The pounding of relentless training runs on the beach wore down his unprepared body, culminating in full fractures in both tibias. He was dropped from training just before Hell Week.

After being dropped from BUD/S just before Hell Week, Diego Ugalde didn’t ring the bell—but his SEAL journey was over. Injuries from relentless training had fractured both his legs. As a Navy corpsman, he still had time left on his contract. He was reassigned to work with Marine units and at Naval Hospital Camp Pendleton, finishing his enlistment far from the beaches of Coronado. When the Navy offered re-enlistment, Diego declined. He had joined with one purpose—to become a Navy SEAL. Without that, he saw no reason to stay.

In 1997, Diego left the military, stepping into a civilian world unrecognizable after years of structure. He pursued a dream that had quietly simmered beneath his military aspirations: emergency medicine. He went to bartender school and even flirted with becoming a cruise ship captain, but eventually, he returned to the calling that first led him to corpsman school—helping others. He earned his EMT and paramedic certifications, and soon began working on ambulances across Massachusetts.

For many military veterans, life after service is a winding path, filled with unexpected turns and pivots. Diego thrived as a paramedic, clocking 70- to 100-hour workweeks, working per diem at various stations across the state. His instincts were sharp, his passion undeniable. He even reported experiencing premonition-like dreams—visions of calls before they happened. The job wasn’t just a paycheck; it was purpose.

Eventually, Diego moved to Florida and continued working as a paramedic. On paper, he had what many transitioning veterans chase: a fulfilling job, a sense of impact, and the beginnings of a stable civilian life. But under the surface, something lingered. For eight years after being dropped from BUD/S, Diego had recurring dreams—three or more each month—where he relived the moments of failure, the moments of being yelled at on the beach, the moments of coming up short. They weren’t nightmares. They were heavier: persistent reminders that something unfinished still had a grip on his identity. Then one morning, he woke up with clarity. The only way the dreams would stop, he believed, was if he went back.

He was 28. At nearly 70 pounds overweight, he faced a mountain. But the Navy’s age cutoff for SEAL candidates was 29. If he was going to try again, it was now or never. With his wife’s reluctant blessing—driven by her fear of his eventual resentment if he didn’t try—Diego recommitted. They moved to Hawaii as planned, and while he worked as a paramedic on Oahu, he trained. Hard.

This time, he understood what had gone wrong. He didn’t just want to go back—he needed to earn his return. He ran soft sand, swam long distances, timed his workouts with park sprinklers for added grit. He chased pain as penance, not realizing until years later that it wasn’t just discipline—it was shame driving him.

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In 2002, Diego Ugalde re-entered the Navy with a single mission: make it through BUD/S and become a Navy SEAL. But this wasn’t the same 20-year-old kid who had failed his first time. He was now 29, a seasoned paramedic with years of life experience—and a battered body still carrying the memory of fractured tibias. This time, he was smarter. Diego rejoined the Navy under a reservist contract, ensuring that if he didn’t make it through BUD/S again, he wouldn’t be trapped in another active-duty role that had nothing to do with the SEAL Teams. But if he succeeded, his contract would convert to active duty. Everything hinged on that.

He classed up with BUD/S Class 246 and carried with him the kind of weight few around him could see. Every pushup, every sprint, every ocean dip was fueled by a cocktail of unfinished business and deep shame. His mindset wasn’t about pride or proving others wrong—it was about surviving the voice in his head that told him he wasn’t enough.

And it nearly broke him again.

Early in first phase, during a boat carry run, Diego felt a pop in his neck. The pain was severe, but quitting wasn’t an option. To protect his neck, he instinctively dipped his head—a move perceived by instructors as “ducking the boat,” a cardinal sin in SEAL training. The pain only worsened, but he endured, eventually developing a third-degree shoulder separation in second phase after a risky landing during an obstacle course run. Injured and behind again, Diego faced the very real possibility that he might not recover in time to meet the minimum physical standards. But this time, something had shifted. He wasn’t immature. He wasn’t delusional. He was deliberate.

Working closely with medical staff, he rehabbed just enough to pass the run times, complete dive phase, and meet the physical requirements—all with a separated shoulder and lingering pain from his past injuries. He never caught up to the class physically, but he never fell behind far enough to fail. He stayed out of the goon squad. He made the runs. He kept showing up. Finally, Diego Ugalde earned the right to wear the Trident.

Graduating BUD/S was supposed to be a moment of glory. Instead, it was quiet. There were no fireworks. No profound satisfaction. Just a numb, hollow acknowledgment that after a decade of chasing this title, he had barely made it—and that felt like failure to him.

Still, he pressed on. Assigned to SEAL Team Two on the East Coast, he stepped into life as a Navy SEAL during a time when the Global War on Terror was in full swing. He deployed to combat zones, made critical decisions under fire, and proved his worth again and again. By the time he retired, Diego had achieved the rank of E-8 and served a full 20-year military career.

He led missions, saved lives, and shouldered responsibilities far greater than most will ever know. But beneath the uniform, something remained unresolved. Even after retirement, Diego was still waiting for the moment when it would all feel worth it—when the identity he had fought so hard to claim would finally feel whole.

When Diego retired from the Navy after 20 years of service, he left behind more than the uniform—he left behind the identity that had defined him for decades. But like many military veterans transitioning into civilian life, Diego discovered that leaving the military didn’t quiet the war inside. It just changed its terrain.

Despite achieving what so many military veterans dream of—earning the SEAL Trident, serving in combat, rising to the rank of E-8, and leading elite teams—Diego still felt empty. He had been chasing a sense of fulfillment for over a decade. Yet, even in retirement, he was still waiting for the emotional payoff that never came. The celebrations were silent. The recognition, internal or external, felt hollow. And so, Diego—like many soldiers, sailors, airmen, and Marines—was left asking: Now what?

His answer began not in a VA office or a corporate job search, but in the unlikeliest of places: a psychedelic therapy session. Through Ibogaine, a powerful plant-based psychedelic, Diego experienced a radical confrontation with the trauma he had long suppressed. In that altered state, he saw not just the scars of combat, but the deeper wounds that started long before the Navy—childhood pain, identity struggles, and shame that had quietly fueled his drive. It was, in his words, the darkest and most profound moment of his life. And yet, it was the turning point.

Diego’s healing journey didn’t stop with that one session. Instead, it evolved into a new mission—helping others do the same. Today, Diego is an integration coach for other military veterans seeking transformation through psychedelic-assisted therapy. He has coached over 400 veterans, guiding them through their own emotional breakthroughs with empathy, honesty, and the wisdom of lived experience.

But perhaps his most impactful post-retirement endeavor is his work with Warrior Side—a nonprofit organization committed to helping veterans and first responders recover from the mental, emotional, and spiritual wounds of service. Warrior Side provides a safe and structured pathway for healing, centered around peer support, holistic wellness, and when appropriate, guided psychedelic therapy. The goal is not just to treat symptoms of trauma—but to reconnect each individual with their humanity and purpose. Warrior Side stands in direct contrast to the performative toughness often glorified in military and law enforcement cultures. Diego's role as a co-founder and core guide is deeply personal. The program reflects everything he wished he had access to during his own veteran transition—a place where vulnerability isn’t weakness but the starting point of strength.

Alongside this, Diego also leads The Trident Approach, a leadership and cultural development consultancy that translates elite team principles into the civilian world. Through workshops and speaking engagements, he now teaches what the SEAL Teams couldn’t: that the most elite form of leadership comes from self-awareness, empathy, and authentic connection. Diego Ugalde’s journey reminds us that life after service isn’t just about career changes or veteran jobs. For many military veterans, it’s about facing the war within—and choosing to heal. Warrior Side is proof that from that healing, a new kind of warrior can emerge.

The go-to podcast for military veterans, police officers, firefighters, EMTs, and first responders preparing for life after service. Hosted by Paul Pantani—a retired law enforcement leader with 30+ years of experience—Transition Drill features candid conversations with veterans from every military branch, as well as law enforcement professionals navigating career change, retirement, and the transition to civilian life. Guests share stories of mental health, post-traumatic growth, job search strategies, and what it really takes to succeed after the uniform. Whether you're transitioning from policing, firefighting, or military service, this podcast will help you lead the next chapter with clarity and confidence.

CONNECT WITH DIEGO UGALDE

WEBSITE: The Trident Approach

WEBSITE: The Warrior Side

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