86. Marine Corps | Discharge - Failed Drug Test | Today CEO - LiboRisk Veteran Travel

Jess Quezada

In Episode 86 of the Transition Drill Podcast, Former Marine and LIBORisk founder Jess Quezada joins the Transition Drill Podcast to share her powerful journey of self-discovery, resilience, and transformation. Growing up in Dallas, Jess was immersed in art, creativity, and curiosity before unexpectedly finding her path in the Marine Corps as a photojournalist. She reflects on her service, the challenges she faced, and the pivotal moments that shaped her identity, including overcoming personal struggles, a DUI, and the life-changing coca tea incident that ultimately led to her separation. Jess opens up about navigating uncertainty during her transition, embracing minimalism, and redefining success by building a life rooted in passion and purpose. Through LiboRisk, she now helps veterans and service members reconnect with themselves, explore the world, and find healing through travel and community. Her story is one of courage, personal growth, and turning hardship into a mission of impact and belonging.

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Jess Quezada’s story begins in Dallas, Texas, where her childhood was shaped by complex family dynamics and an early exposure to art, creativity, and curiosity about the world. While her family life was far from simple, she found grounding in the deep bond she shared with her grandmother, a worldly and adventurous woman who became one of her most significant influences. Through her grandmother, Jess learned the value of exploration and self-expression. Museums, cultural experiences, and stories of travel became part of her upbringing, inspiring Jess to see beyond the boundaries of her immediate environment.

Her path toward art was a natural extension of her surroundings. Jess’s mother worked as a professional framer and possessed a creative eye, while her father was a talented charcoal artist, sculptor, and ceramicist. Growing up in a home immersed in artistry, Jess found herself drawn to visual expression from a young age. Her grandmother’s passion for museums and culture reinforced that interest, exposing her to creations that captured the beauty and complexity of the human experience. These early influences formed the foundation of Jess’s creative identity, where storytelling through imagery and design became central to who she was.

This passion eventually led Jess to Booker T. Washington High School for the Performing and Visual Arts, an elite institution known for fostering some of the most talented young artists in the country. While many of her peers pursued dance, theater, and music, Jess was captivated by visual arts and photojournalism. She immersed herself in her craft, thriving in an environment where students were encouraged to explore their artistic voices. The school’s reputation attracted students destined for institutions like Juilliard and other prestigious programs, and for Jess, being surrounded by so many gifted, driven individuals fueled her own growth as an artist.

Despite her thriving creative pursuits, Jess often felt out of place among her broader peer group outside of the arts community. While many classmates focused on sports and traditional extracurricular activities, she devoted her time to sketching, photography, and studying the power of imagery. Although she attempted volleyball and swimming, she admitted she was not naturally competitive and approached these activities as opportunities for personal well-being rather than performance. Her interest in physical activity would become more intentional later in life, but at this stage, art remained her primary focus and passion.

Jess also navigated challenges at home. Her relationship with her parents was distant, and her connection with her siblings remained limited. Without a strong sense of belonging within her family, she poured herself into her craft and leaned on the stability provided by her grandmother and her grandmother’s best friend, a woman Jess came to call her aunt. Through them, she built a sense of chosen family that provided support and encouragement during formative years.

By the time Jess graduated in 2012, she had developed not only her creative skills but also a deep appreciation for storytelling and visual narrative. She envisioned a future rooted in art and photojournalism, confident that her path would involve capturing the human experience through her lens. What she did not yet realize was that her journey would take her far beyond the gallery walls and art studios she imagined, leading her instead toward a uniform, a new identity, and an entirely different kind of storytelling.

After graduating from Booker T. Washington High School in 2012, Jess faced an important crossroads. While she had always envisioned a career in photojournalism, she quickly discovered that breaking into the field would not necessarily require a traditional college degree. Employers in the industry valued real-world experience, compelling portfolios, and unique perspectives over formal credentials. This realization pushed her to think differently about her future.

At first, Jess began exploring photojournalism programs and career pathways in the civilian world, but she quickly realized that opportunities were limited and highly competitive. Around this time, her older brother had spoken about wanting to join the Marine Corps. Though he ultimately went down a different path, his interest planted a seed. The idea of the military initially seemed incompatible with her background. She came from a liberal, art-focused environment where joining the armed forces was often viewed negatively. Yet as she researched further, Jess discovered that the Marine Corps offered a role she had not considered: military photojournalism.

The more she learned, the more the possibilities excited her. She discovered that the military could provide both unparalleled life experiences and hands-on training in photography, writing, and visual storytelling. Her first stop was the Army recruiting office, but the meeting left her feeling uninspired. Just next door, though, the Marine Corps office offered a different energy. Welcomed by recruiters who spoke passionately about the opportunities available, Jess felt an immediate connection. The conversation opened her eyes to the idea that she could merge her passion for photojournalism with service to something bigger than herself.

Taking the leap was not without resistance. Many of Jess’s peers, particularly those from her art school, did not understand her decision. Some teachers openly criticized the choice, framing military service as a path defined only by conflict and combat. Even her parents were skeptical at first, uncertain about what joining the Marine Corps would mean for her future. Jess, however, had always been determined. Once she decided on a goal, she committed fully. The lack of support from others only reinforced her resolve to forge her own path.

Before she could ship off to boot camp, Jess had to complete the initial strength test required for enlistment. At the time, the test included a mile-and-a-half run, a flexed-arm hang, and crunches. While she performed well on most components, the run nearly broke her. She finished last but still managed to pass. What stood out most, though, was what happened after the test. Every Marine who had already completed the run came back to cheer her on and run alongside her until she crossed the finish line. It was the first time Jess had experienced that kind of unconditional support and camaraderie, especially from people she barely knew. That moment crystallized her decision. She wanted to be part of a team where individuals lifted each other up rather than competed against one another.

In 2013, Jess officially enlisted in the United States Marine Corps with a guaranteed contract to train and serve as a photojournalist. Her high test scores, gender, and mixed ethnicity made her a strong candidate for the role, and she secured her preferred job assignment on the first attempt, an outcome she would later realize was rare. Training prepared her for far more than just taking photographs. The program covered writing, videography, media relations, crisis communication, and public affairs. Jess was captivated by the authenticity of military journalism, where integrity was central and misrepresentation was strictly prohibited. Unlike traditional media, there was little room for fabrication.

This new environment challenged her assumptions and gave her a sense of purpose she had never experienced before. She was no longer simply an artist; she was now part of an institution with a mission, a team, and an identity greater than her own. For the first time, Jess began to understand what it meant to dedicate herself fully to a cause, and that transformation would set the stage for everything that followed.

Jess began her Marine Corps career at Marine Corps Recruiting Command in Quantico, Virginia, where she covered national-level events and worked closely with leadership to support the recruiting mission. While the role provided incredible opportunities to document major operations and sharpen her storytelling skills, the environment was often isolating. Jess was still navigating her own social challenges, having grown up without strong family connections, and she found it difficult to develop close relationships early in her service.

After her time in Quantico, she received orders to Japan, where she served at an air station working alongside combat camera teams. This experience broadened her exposure to global perspectives and pushed her to expand her technical abilities as a photojournalist. She managed current and future operations for the unit, coordinating coverage for a wide range of events while capturing moments that highlighted the Marine Corps’ role in the Pacific region.

Her final assignment brought her to Orange County, California, where she stepped into one of the most unique roles of her career. Instead of remaining strictly behind the camera, Jess transitioned into a billet where her photojournalism background merged with marketing and public affairs. She became responsible for supporting the Marine Corps’ recruiting efforts by creating promotional campaigns, developing strategies to reach potential recruits, and managing digital storytelling across multiple platforms. Her ability to communicate visually and strategically made her an asset to the mission, and she began developing the business and branding skills that would later become foundational to her entrepreneurial journey.

Throughout her time in uniform, Jess experienced the unspoken divisions that sometimes arise within the military between those in combat roles and those in support positions. As a photojournalist, she was occasionally dismissed as someone who was simply “taking pictures,” but Jess understood the critical role storytelling played in shaping public perception and preserving the history of the Marine Corps. She came to embrace the philosophy that every Marine, regardless of specialty, contributes to the broader mission. While the front-line operators risked their lives in combat, those supporting them ensured resources, logistics, and communication flowed seamlessly. The recognition of that interconnectedness became an important part of her personal and professional growth.

However, the Marine Corps was not without challenges. Jess’s personal struggles, many rooted in her early life, began to surface during her service. Growing up in a difficult family environment, she had never fully processed past traumas, and those unaddressed experiences affected her decision-making at critical moments. She found herself turning to alcohol as a coping mechanism, something she had rarely encountered before joining the Marines but which became deeply ingrained in the military culture around her.

The issue came to a head when Jess received a DUI, a moment that she describes as a turning point both personally and professionally. While she initially tried to manage the consequences quietly, the reality caught up with her, and she faced administrative and financial penalties as well as the weight of her own disappointment. In the aftermath, she began reflecting on the broader cultural challenges around alcohol within the military. She recognized how normalized drinking had become and how rarely conversations addressed the underlying struggles service members were facing.

This period marked the beginning of a deeper internal transformation for Jess. She started asking harder questions about identity, fulfillment, and personal growth. At the same time, she continued to excel professionally, becoming highly efficient and autonomous in her work, which at times masked the personal battles happening beneath the surface. While she carried the pride of her accomplishments and the meaningful relationships she built along the way, she was also starting to confront the emotional weight of her journey.

It was during this chapter of her career that Jess realized the Marine Corps had given her a platform to tell stories, but she still needed to figure out her own. That awareness would set the stage for a series of life-changing events that tested her resilience and eventually pushed her toward redefining her purpose beyond the uniform. 

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After rebuilding momentum following her DUI, Jess found herself facing an unexpected setback that would ultimately alter the trajectory of her Marine Corps career. During a trip to Colombia, she participated in a multi-day jungle trek, immersing herself in the rich cultural and natural experiences the region had to offer. Along the way, she purchased coca tea, a common local product widely consumed in South America, especially by hikers seeking relief from altitude sickness. For locals, coca tea was as normal as coffee or green tea, and Jess had no idea it could present any future issues.

She returned from the trip unaware that the tea could trigger a positive urinalysis, and because the product was sold openly and consumed publicly, she kept it without hesitation. Nearly a year later, she brewed the tea without realizing it contained metabolites that would register as a controlled substance on military drug tests. When her results came back positive, she was called in by her sergeant major and informed of the findings. The revelation was shocking, not only because of the result itself but also because the Department of Defense travel briefings at the time did not include any warnings about coca tea.

Despite the fact that coca tea was legal in Colombia and commonly consumed by travelers, the Marine Corps treated the incident as a policy violation. Jess had the documentation from her trip, including records showing she had attended all required briefings, yet none of those materials mentioned the product or its risks. While she hoped to challenge the circumstances, the presence of the prior DUI on her record complicated her case. Both incidents had occurred during the same enlistment period, and together they painted a picture that made it difficult to secure command support for retention.

Working with both a JAG attorney and a personal lawyer, Jess evaluated her options carefully. Her legal team explained that while she could attempt to fight the separation, her chances of reenlistment or returning to her desired career track were slim. More significantly, the incident closed the door on her long-time goal of becoming a Marine Security Guard, a specialized and highly competitive program she had worked hard to be approved for. That approval had been granted, then later revoked without a clear explanation, and combined with the urinalysis result, the opportunity was no longer viable.

The realization was devastating. For years, Jess had poured her energy, identity, and self-worth into being a Marine. Much of who she believed herself to be was tied to her role, her rank, and the uniform she wore. Now, with the possibility of separation becoming real, she faced a reckoning. The career she thought she would build within the Corps no longer existed, and she needed to decide whether to fight to stay or begin preparing for life beyond military service.

After much reflection, Jess chose to accept a general discharge under honorable conditions. While the decision was difficult, she began to recognize that her time in the Marine Corps had reached a natural conclusion. What initially felt like a painful ending slowly began to reveal itself as an opportunity for a new beginning. She realized she needed space to heal, to grow, and to redefine her identity outside of the strict structure of military life.

The coca tea incident became a pivotal moment in Jess’s journey, one that forced her to confront deeper questions about purpose and resilience. The uniform that once defined her was being set aside, and the stability of her life in the Marines was coming to an end. She stood at a crossroads, carrying lessons from her experiences but facing an uncertain future without the clarity of a mapped-out plan. The next chapter would require rebuilding from the ground up and creating a new sense of meaning outside the world she had always known.

Jess began preparing for her separation from the Marine Corps during one of the most unpredictable times in recent history. In 2020, at the height of the COVID-19 pandemic, the uncertainty surrounding her administrative process added another layer of stress. Facing the possibility of leaving the military without benefits, she knew she had to plan for every worst-case scenario. With no family home to return to and few financial safety nets, Jess made the decision to take control of her situation and create her own backup plan.

She started working two jobs while still on active duty, dedicating her free time to saving as much money as possible in anticipation of what lay ahead. One job was at a chiropractic office, while the other involved co-owning a small lumber company with a Marine Corps veteran. This partnership proved invaluable, as it gave her access to the tools and resources she would later use to build a converted school bus into a livable home. The idea came after considering the affordability and independence of van life. Purchasing the bus before her separation paperwork was finalized allowed her to secure a place to live regardless of the outcome of her discharge process.

While this period of transition was filled with pressure and uncertainty, Jess approached it with determination. She learned to embrace minimalism, focusing on what she truly needed rather than what society told her she should have. The bus became more than a place to live; it represented freedom and resilience, a physical symbol of her ability to adapt and create stability in the face of chaos.

During this time, she also experienced a shift in perspective. Much of her identity had been tied to her rank, role, and responsibilities as a Marine. Without the structure of the Corps, she was forced to confront deeper questions about who she was and what she wanted her life to represent. Jess began turning inward, reflecting on the challenges she had faced, the mistakes she had made, and the lessons she had learned along the way. She realized that personal growth required confronting her past, embracing vulnerability, and finding meaning beyond titles and achievements.

Living in the bus gave her the flexibility to slow down, simplify, and reset. She began dedicating more time to learning, reading, and listening to podcasts focused on self-improvement and personal development. Travel became an important outlet, allowing her to reconnect with her adventurous spirit while creating space to process everything she had experienced in the military. Through these explorations, she found a sense of healing and perspective that helped her begin to rebuild her confidence and clarity.

Jess’s separation from the Marine Corps was finalized with a general discharge under honorable conditions. While many would have viewed the circumstances as a setback, she chose to see it as an opportunity to reinvent herself. The independence she developed during this period became a cornerstone of her post-military life. She learned that self-reliance did not mean isolation but rather taking ownership of her choices and creating a foundation strong enough to withstand unexpected change.

It was during this process of redefining her identity that the earliest ideas for her future began to take shape. Her passion for travel, combined with the leadership, storytelling, and operational skills she had honed in the military, pointed her toward a vision she had not yet fully articulated. This was the beginning of an entrepreneurial journey focused on building community, creating opportunities, and helping others navigate their own transitions by reconnecting with purpose and possibility.

As Jess moved forward from her military career, she began shaping the idea that would become LIBORisk, a purpose-driven company designed to combine her passion for travel, storytelling, and community-building. The vision began forming during her time in Japan, where she frequently took advantage of long weekend periods to travel across Asia. Whether visiting Thailand, Malaysia, Borneo, or exploring Japan itself, she constantly received questions from other service members about how she planned her trips, managed the logistics, and made international travel affordable on a military schedule and budget.

Through these conversations, Jess recognized a gap. Many service members and veterans wanted to travel, but there were few resources that made it approachable and accessible. Most retreats or curated experiences available to the community were prohibitively expensive, designed as insulated all-inclusive vacations rather than opportunities for genuine cultural connection. Jess envisioned something different: an ecosystem built around affordability, purpose, and belonging. She wanted to create spaces where veterans and service members could reconnect with themselves and others through shared experiences while rediscovering their identity outside of the uniform.

LiboRisk, a name drawn from the Marine Corps colloquialism “liberty risk,” reflects this mission. In the military, the term refers to someone who tends to get into trouble during liberty periods, but Jess reclaimed it as a symbol of intentional risk-taking, personal growth, and adventure. Her belief is simple: through travel and shared experiences, people can push beyond their comfort zones, learn about themselves, and reconnect with their humanity.

Her retreats and events are designed with this philosophy in mind. Each experience prioritizes three core values: safety, vulnerability, and purpose. Jess ensures participants understand community expectations from the beginning, establishing guidelines that foster respect and connection. By creating these intentional spaces, she has seen attendees open up about their journeys, engage in meaningful conversations, and form bonds that extend beyond the events themselves. LiboRisk events are not just about traveling to new places; they are about healing, rediscovery, and transformation.

Jess structured LiboRisk as a for-profit company, but her goals go far beyond revenue. In addition to selling merchandise and operating as a certified travel agency, she uses profits to subsidize retreat costs and make experiences more affordable. She partners with companies to secure group discounts, which allows her to keep prices accessible while still delivering high-quality, impactful trips. She does not position herself as a guide or influencer. Instead, she acts as a connector, curating opportunities and fostering the environments where meaningful engagement can occur.

Looking ahead, Jess has ambitious plans for LiboRisk. Her long-term vision includes developing a global platform where veterans and service members can connect directly with one another. The app she envisions would allow users to share itineraries, exchange local travel tips, host fellow service members, and participate in curated cultural experiences worldwide. Alongside these technological goals, she plans to expand retreats into new destinations, partner with veteran-led organizations, and continue advocating for travel as a powerful tool for mental health and personal growth.

For Jess, LiboRisk represents far more than a business. It is the culmination of her journey, shaped by the lessons of her early life, her service in the Marine Corps, and her personal evolution after leaving the uniform behind. By transforming her passion for travel and storytelling into an opportunity to serve others, she has created a platform where healing and exploration intersect. Through LiboRisk, she continues to help veterans and service members rediscover who they are, embrace new challenges, and reconnect with the deeper meaning of community, belonging, and purpose.

CONNECT WITH JESS QUEZADA

Website: LiboRisk

Instagram: LiboRisk

LinkedIn: Jess Quezada

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