Episode 269 of the Transition Drill podcast explores law enforcement, career transition, and rebuilding professional identity for veterans and first responders navigating life beyond the badge. You’ll hear former police officer and SWAT operator Bridget Truxillo on losing the career she thought would define her future, and what it takes to turn a painful transition into a new mission.

Bridget grew up in Louisiana before heading to the University of Florida with no clear career path. After graduating, she entered the police academy and joined the Alachua County Sheriff’s Office, where she moved from patrol into undercover narcotics, buying drugs and working investigations. Then she took another unlikely step, becoming the first female SWAT officer in her agency’s history.

But earning the position didn’t guarantee acceptance. Bridget talks openly about the internal battles, scrutiny, leadership failures, and feeling of betrayal that eventually pushed her away from SWAT and law enforcement. A planned path toward federal law enforcement also disappeared, leaving her approaching 30 without the career or identity she expected to have.

She started again.

Bridget entered law school, graduated in two and a half years, became an attorney, worked in asbestos litigation and investigative legal work, moved between Texas and New York, became a mother, and eventually realized conventional law practice wasn’t where she belonged.

Today, Bridget owns Lady Law Shield, where she represents first responders and public employees facing workplace and administrative problems. The experiences that once drove her from policing now help her protect people confronting some of the same battles she once faced.

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Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 268 of the Transition Drill podcast explores military transition and rebuilding a career after combat for veterans and first responders navigating life beyond service. You’ll hear retired Marine Corps Gunnery Sergeant Justin Rettenberger on leaving the identity and intensity of the Marine Corps behind, and what it takes to build a meaningful civilian life when your original transition plan falls apart.

Justin grew up in the Midwest, unsure what direction his life would take until a chance encounter with a Marine recruiter in 1997 led him into the infantry. He originally planned to serve four years and use the GI Bill, but September 11 changed everything. He reenlisted, joined the initial invasion of Iraq in 2003, fought in Fallujah, later deployed to Afghanistan, and completed eight deployments during a 16-year Marine Corps career. Along the way, he became a Bronze Star and two-time Purple Heart recipient and learned leadership from Marines including Doug Zembiec, whose challenge to “be a man of action” still influences him today.

Eventually, marriage, fatherhood, and a changing perspective on combat pushed Justin toward retirement. His carefully planned transition nearly collapsed when a lucrative contracting job disappeared before he left the Marines. With a new baby, a new house, and no clear career path, he went back to school.

College forced him to learn how to listen to people outside the military, challenge his assumptions, and redefine himself. He earned his bachelor’s degree and MBA, discovered occupational safety, and built a successful civilian career where he now leads others while continuing his education. His lesson for anyone preparing to transition is simple: have a plan, but always have a backup.

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Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 267 of the Transition Drill podcast explores law enforcement careers, undercover work, and life after retirement for first responders and veterans navigating the loss of identity and purpose that can follow service. You’ll hear Jenn Benjamins on the personal cost of letting the job become your life, and what it takes to rebuild relationships, purpose, and direction after the badge.

Jenn grew up in Las Vegas, played college softball, studied criminal justice at UNLV, and entered the Las Vegas Metropolitan Police Department without the lifelong dream of becoming a cop. What followed was a 22-year career that took her from patrol into vice, undercover investigations, and deep undercover work.

Jenn became LVMPD’s first female vice sergeant and later served as Director of Peer Support, helping officers through serious personal and professional crises. But while she was investing heavily in the job, her own family relationships were paying a price.

In 2022, a series of personal crises led Jenn to retire earlier than planned. Civilian life hit hard. The phone stopped ringing, her identity disappeared, and she found herself without a plan or purpose. A stint at Wynn Las Vegas followed, but rebuilding her relationship with her children and completing an emotional intelligence leadership program changed her direction.

Today, Jenn trains law enforcement professionals in undercover operations, created a women-led undercover school, speaks at police conferences, and is building a second career around preparing the next generation while staying present for the people who matter most.

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CHAPTERS

0:00:00 — Intro: The Three Versions of Jenn

0:02:49 — When Her Family Began to Fracture

0:13:37 — Brothers, Arrests and Different Paths

0:20:30 — Policing the City Where She Grew Up

0:27:48 — Undercover Is a Skill Set, Not a Look

0:30:47 — An Accidental Path Into Policing

0:35:31 — Entering the Academy Completely Naive

0:49:52 — When Police Work Suddenly Became Real

0:53:58 — 9/11 Changes the Reality of the Job

0:55:36 — Route 91: Responding to the Unthinkable

1:03:16 — Discovering Her Talent for Undercover Work

1:09:50 — Going Undercover to Target Pimps

1:24:53 — The Vice Case That Told Her It Was Time

1:32:58 — Living Undercover Beyond the Job

1:35:17 — When the Job Began Costing Her Family

1:40:24 — Retirement Exposes the Broken Relationships

1:46:36 — Ego, Promotion and a New Career Chapter

1:50:25 — Becoming Metro’s First Female Vice Sergeant

1:52:12 — Peer Support and Three Life-Changing Days

1:57:34 — Retirement, Isolation and Losing Her Purpose

2:02:01 — Building a New Mission After the Badge

2:06:00 — Rebuilding Herself and Her Relationships

2:10:01 — Be Present for the People Who Remain

SPONSORS:

GRND Collective: Premium, veteran-owned sportswear built for those who show up, outwork the excuses, and give 100%. Score 15% off your order at thegrndcollective.com using promo code TRANSITION15 at checkout

Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 266 of the Transition Drill podcast explores identity loss, combat trauma, and rebuilding purpose for veterans and first responders navigating life after service. You’ll hear Prime Hall on being medically forced out of the Marine Raiders, and what it takes to heal, reconnect, and build a mission beyond the uniform.

Prime grew up in and around the water in Corpus Christi and South Padre Island, Texas. After childhood abuse, family upheaval, military school, arrests, and years without direction, his grandparents helped him through an 18-month enlistment process. He entered the Marine Corps in 2005, struggled with anger, alcohol, and discipline, then rebuilt his reputation through relentless training.

That turnaround opened a path from artillery and the infantry to MARSOC. As a Marine Raider, Prime deployed to Iraq, Afghanistan, and the Philippines, worked in operational and intelligence roles, and trained Afghan forces. In 2012, an insider attack sent 12 RPGs into his compound. He survived blast injuries, concussions, and a damaged back, masking the consequences until an MRI triggered an abrupt medical separation after nearly 13 years.

Civilian life brought lost identity, medication side effects, chronic pain, and a difficult break from the military medical system. Relationships, mentors, emotional intelligence work, and alternative healing helped him rebuild. Today, Prime co-founded Deep End Fitness, helped create the Underwater Torpedo League, coaches elite athletes, and builds communities through breath, water training, trust, and accountability. In his book, Permission to Heal, he gives veterans ways to reframe trauma, avoid isolation, and create a meaningful next mission.

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CHAPTERS

0:00:00 — Intro: Relationships Are Everything

0:03:06 — When the Marine Corps Says You’re Done

0:07:36 — The Injuries He Tried to Hide

0:15:28 — Walking Away From Military Retirement

0:22:50 — Growing Up Around the Water

0:31:07 — The Water as a Microcosm for Life

0:35:12 — Check Your Ego at the Door

0:38:21 — The Power of an Outward-Focused Why

0:44:20 — Grandparents, Abuse, and a Different Path

0:54:07 — Military School Changes His Direction

0:59:00 — Lost, in Trouble, and Looking for Purpose

1:03:03 — Finding His Place in the Marine Corps

1:07:21 — Nearly Losing His Marine Corps Career

1:16:57 — The Road to Marine Raiders

1:32:16 — The RPG Attack That Changed Everything

1:45:40 — The Injuries That Followed Him Home

1:59:25 — Survival Ends, the Real Battle Begins

2:03:08 — Building Deep End Fitness Through Transition

2:17:16 — Don’t Let Someone Else’s Fear Stop You

2:19:14 — Vulnerability, Therapy, and Learning to Heal

2:30:16 — Building the Underwater Torpedo League

2:34:55 — Why He Wrote Permission to Heal

2:38:09 — A Lifeline for Those Struggling to Transition

2:41:07 — The Words You Use Shape Your Reality

Episode 265 of the Transition Drill podcast explores military transition, mental health, and renewed purpose for veterans and first responders navigating life after service. You’ll hear JD Dickson on leaving a 27-year Navy career, and what it takes

Born in Washington, D.C., and raised in Trinidad and Tobago, Dickson returned to the United States at 18 and entered the Navy in 1995. He began as an undesignated sailor before finding his place in aviation ordnance aboard the USS Independence in Japan. Mentors pushed him toward instruction and leadership. Marriage led him to make the Navy a career, with assignments in Pensacola, Brunswick, Rota, and San Diego, service aboard the USS Carl Vinson and USS Makin Island, and advancement from chief petty officer to chief warrant officer five.

Dickson speaks candidly about relentless operational tempo, his father’s death, accumulated stress, and the toll service took on his family. In 2022, he chose family over another assignment and retired. He immediately launched government-contracting and e-commerce businesses, but the nonstop work lacked the purpose he needed.

A family mental health crisis changed his direction. After experiencing brain-based treatment himself and seeing his daughter recover, Dickson joined Wave Neuroscience, where he now serves as director of veterans affairs. Today, he works to expand objective, individualized mental health care for veterans and first responders. His transition offers a direct lesson: leave the familiar circle, accept discomfort, build new relationships, and stay curious enough to recognize an unexpected opportunity.

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CHAPTERS

0:00:00 — Intro: Grace, Curiosity, and Transition

0:02:21 — From Trinidad to a Life in Uniform

0:05:26 — The Recruiter Who Changed Everything

0:11:34 — Leaving Trinidad for the Navy

0:15:01 — Thrown Into Aviation Ordnance

0:17:51 — Surviving Culture Shock at Sea

0:25:27 — Mentors Who Saw His Potential

0:28:37 — Marriage Changes the Mission

0:29:10 — 9/11 Changes Everything

0:40:52 — Learning to Lead People, Not Rank

0:44:02 — Becoming a Chief Warrant Officer

0:52:53 — The Deployment That Broke Through

0:54:36 — Stress Finally Shows Itself

0:57:36 — Transition Begins Before Retirement

0:59:54 — COVID Reveals a New Direction

1:09:19 — Choosing Family Over the Navy

1:13:24 — A Year of Loss and Overload

1:15:38 — The Opportunity That Changed His Path

1:17:08 — The Brain Scan That Changed His Life

1:39:08 — Get Uncomfortable and Stay Curious

SPONSORS:

GRND Collective: Premium, veteran-owned sportswear built for those who show up, outwork the excuses, and give 100%. Score 15% off your order at thegrndcollective.com using promo code TRANSITION15 at checkout

Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 264 of the Transition Drill podcast explores law enforcement retirement, Brazilian Jiu Jitsu, and career transition for police officers and first responders navigating life after the badge. You’ll hear Tom Chuckerel on leaving a 25-year police career without a clear second-career plan, and what it takes to turn skills, relationships, and genuine interests into meaningful work after service.

Tom wanted to be a Montgomery County police officer from the time he was six. He joined the department in 1994, spent years working patrol in the community where he grew up, became an FTO, and explored narcotics, surveillance, and SWAT before a medical issue unexpectedly redirected his career toward training.

That move became pivotal. Tom joined the police academy staff, helped modernize defensive tactics, and brought his growing Brazilian Jiu Jitsu experience into law enforcement training. He’d started training in 1997, eventually became a black belt, taught Jiu Jitsu and Thai boxing, and built a relationship with Rener Gracie while hosting Gracie Survival Tactics (GST) courses.

When Tom retired in 2017 and moved to Monterey, California, he still wasn’t sure what came next. He considered everything from X-ray tech school to becoming a butcher. Instead, years of training and relationships created opportunities. He ran a Jiu Jitsu school, worked private security and executive protection, and began teaching GST. Today, GST is his primary work, with roughly 150 classes led, allowing him to continue serving law enforcement through teaching, safer arrest-and-control tactics, and the work he genuinely loves.

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Johnny Collins Episode:

Apple: https://podcasts.apple.com/us/podcast/188-never-give-up-6-bud-s-classes-to-be-a-navy-seal/id1582888787?i=1000740317114

Spotify: https://open.spotify.com/episode/6z64p4xHrzZLB2rlWLy5AU

YouTube: https://youtu.be/ZT90jdj14ig

SPONSORS:

GRND Collective: Premium, veteran-owned sportswear built for those who show up, outwork the excuses, and give 100%. Score 15% off your order at thegrndcollective.com using promo code TRANSITION15 at checkout

Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 263 of the Transition Drill podcast explores military career transition and rebuilding your identity after service for veterans and first responders navigating the move into civilian life. You’ll hear retired Navy Senior Chief Timothy Henderson on leaving behind nearly three decades in uniform, and what it takes to turn military experience into a meaningful next chapter.

Tim grew up in Chicago’s Cabrini-Green projects surrounded by gangs, drugs, and limited examples of what life could become. After losing both parents young, becoming a father as a teenager, getting into trouble, and nearly losing his direction, a judge pushed him toward a military recruiter. He joined the Navy in 1997.

What began as one enlistment became a 27-year career. Tim went from an undesignated sailor to Gunner’s Mate, serving aboard ships, in San Diego and Japan, with Naval Special Warfare, in training commands, and ultimately in senior leadership. Along the way, mentors changed how he viewed education, leadership, professional development, and preparing for the day the uniform came off.

Tim didn’t wait until retirement to think about what came next. He built relationships, developed his network, and lined up civilian work before leaving service. Still, employment didn’t eliminate the challenge of separating Tim Henderson from Senior Chief Henderson.

Today, he’s a civilian department head at Navy Munitions Command while pursuing public speaking, mentoring, process-improvement consulting, and plans for a future business focused on ethical AI. His story shows why transition isn’t simply finding another job. It’s figuring out who you’re becoming next.

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CHAPTERS

0:00:00 — Intro: The Decision That Changed Everything

0:00:46 — Growing Up in Cabrini-Green

0:08:05 — Trouble, Loss, and Losing Direction

0:10:51 — Fatherhood at Seventeen

0:13:08 — A Judge Offers Another Path

0:20:30 — Joining the Navy in 1997

0:28:44 — Reenlisting Before 9/11

0:30:43 — Finding His Calling as a Gunner’s Mate

0:35:13 — Going Home Changed His Perspective

0:42:30 — Trouble in the Navy and a Second Chance

0:44:34 — Stop Living for Other People

0:47:24 — The Leaders Who Gave Him a Clean Slate

0:50:31 — Earning His Way to SEAL Team One

0:57:31 — Responsibility Changed the Sailor

0:59:30 — Finally Making Navy Chief

1:00:21 — Why He Stayed Beyond 20 Years

1:04:52 — Education as Personal Growth

1:11:32 — Preparing for Life After the Navy

1:15:16 — When the Uniform Is No Longer You

1:18:12 — Building the Next Mission

1:23:36 — Your Transition Is Your Own

1:26:27 — Outro: The Next Chapter Begins

SPONSORS:

GRND Collective: Premium, veteran-owned sportswear built for those who show up, outwork the excuses, and give 100%. Score 15% off your order at thegrndcollective.com using promo code TRANSITION15 at checkout

Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10

Episode 262 of the Transition Drill podcast explores reinvention, discipline, and rebuilding after major life consequences for veterans and first responders navigating life after a demanding career. You’ll hear GC Brown, author of SNIFF, on losing everything after business success, and what it takes to rebuild your identity, purpose, and future from the ground up.

Brown grew up working on his grandfather’s Indiana farm, surrounded by a family with deep military and law enforcement roots. A talented baseball player, he earned a college scholarship but chose work instead, quickly discovering he loved making money and building businesses. That drive took him across the country and eventually into real estate, restaurants, computer software, international flowers, and the diamond trade in Africa. By his early thirties, he’d built significant wealth, but his willingness to keep pushing into unfamiliar territory eventually collided with a federal investigation, a criminal trial, and a 20-year federal prison sentence.

Brown ultimately served 16 years. Several years into that sentence, he says he finally recognized what his success had always lacked: discipline, follow-through, and the willingness to change himself. Prison became the place where he began writing, developed the routines that still shape him today, and committed to a different life after release.

He returned home in November 2023 and went to work immediately. Today, Brown is an author, his first of a series, SNIFF, was released in November 2025, as well as co-owner of UpCup Koffee, a functional mushroom coffee company he built with a former cellmates.

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CHAPTERS

00:00:00 — Intro: The Turning Point in a Prison Cell

00:03:20 — Farm Roots and a Family of Service

00:09:37 — Baseball, Arizona, and a Scholarship

00:10:43 — Choosing Money Over College

00:15:29 — From Farm Kid to Serial Entrepreneur

00:18:25 — One Mobile Home to a $30 Million Empire

00:21:30 — The Miami Vice Lifestyle

00:25:06 — The $130,000 Diamond Scam

00:29:32 — Losing $470,000 in the Congo

00:32:14 — Turning $70,000 Into $7 Million

00:35:46 — The “Bloody Diamonds” Investigation

00:46:10 — Federal Trial and Firing His Attorney

00:53:59 — Conviction, Appeals, and Prison

00:57:04 — Gang Unit, Solitary, and Pennsylvania

01:06:17 — “240 Months”: The Sentence Becomes Real

01:14:39 — Discovering Writing Behind Bars

01:23:09 — Three Signs and a New Purpose

01:30:32 — Writing Sniff During COVID Lockdown

01:36:20 — Reinvention, Release, and UpCup Coffee

01:44:15 — Writing His Love Story Into Existence

01:47:19 — Words Are Powerful

SPONSORS:

GRND Collective: Premium, veteran-owned sportswear built for those who show up, outwork the excuses, and give 100%. Score 15% off your order at thegrndcollective.com using promo code TRANSITION15 at checkout

Blue Line Roasting: Premium, law-enforcement-owned coffee roasted to fuel the shift. A portion of every order directly supports law enforcement families facing line-of-duty injury or loss. Save 10% at bluelineroasting.com with promo code Transition10

Frontline Optics: Premium eyewear founded by a firefighter and built to withstand the job. Every single purchase helps support the First Responders Children’s Foundation, serving families who’ve paid the ultimate price. Save 10% off your pair at frontlineoptics.com using promo code Transition10