This is part 1 of a 3-part series sharing Jarrod Matteson's story about why he left his successful career in big law—and why he joined Prasada. Read part 2 of the series here.
A Story of Success
For nearly two decades, my life was what some would consider a story of success. Climbing the professional ladder, I built a thriving career in big law, navigated complex real estate transactions, led high-stakes deals, and became a partner in a global law firm. I was surrounded by brilliant colleagues, entrusted by successful clients, and rewarded with the security and recognition that comes with becoming a partner at a large law firm. On paper, according to all accepted expectations, I’d achieved everything I had worked hard for.
Though underneath that story of achievement, a more subtle story was developing—one that was far less certain. It started as a gentle, persistent, whisper in the form of a pressing question: Is this my purpose in life?
At first, I dismissed this question as fleeting doubt, creeping in from the pressures and expectations of a professional career. Even before law school, I had developed a meditation practice that taught me to allow thoughts to arise and let them pass, without clinging to them. So, that’s what I did. I allowed that doubt to drop away in the background and not let it dominate my inner monologue.
Besides, I wasn’t unhappy. There were parts of my work as a lawyer that I enjoyed. It was fulfilling to lead a complex transaction to a successful closing, experience the camaraderie of collaborating with clients and colleagues, and mentor junior attorneys as they found their footing along their career paths. I was living out the expected path according to plan.
Still, the whisper persisted—subtle yet unwavering.
I turned to my inner work practices and used this fleeting doubt as a new inquiry for self-discovery. Maybe this whisper was an echo of some childhood memory causing self-doubt. After all, it appeared to be encouraging me to give up a successful career that I decided years earlier to pursue. I’m not one that gives up easily. I was proud of the career I built through years of hard work and wasn’t about to throw it away because of what I thought was just some negative self-talk. But still, I felt a part of me longing to explore beyond this expected life path.
As a child, I was curious and eager to learn. Curious about why we are here, human behavior, and what unseen forces drive people. Before law school, I was a mathematician studying twist maps and trimming operators in graduate school. Math felt isolating to me as my graduate school colleagues and I became increasingly specialized in our studies, making collaboration difficult. At first, my legal career provided more of the connection I was seeking, though I quickly had to prioritize the transactional nature of the work—the technicalities of leases, contracts, and structuring deals. Even though I had frequent opportunities to collaborate with colleagues and clients, with the transactional nature of the work again I started craving more of the connection that led me to law school in the first place.
Curiosity, love of learning, and connection
Curiosity, love of learning, and connection were useful traits for me as a lawyer, but I felt the pressure of the legal world’s more valued traits of decisiveness, certainty, and efficiency. The space for exploration—for asking “why?” when I was expected to deliver “how”—sometimes made me feel frustrated that I wasn’t able to bring all of myself to the job.
In the flurry of the busyness of the work environment, my superpower was compartmentalizing. I led with competence and precision outwardly, while inwardly I guarded the seeker, the listener, the student of life—safeguarding that part of me like roots quietly growing beneath the surface, unseen but anchoring me for future growth.
By compartmentalizing, I divided myself into two parts. On the exterior was the successful lawyer, but on the interior was the part of me looking for more and the whispering questions I could no longer ignore. Slowly, the line between these two parts began to blur as I began to find myself in deeper conversations with others who gravitated to me not just for legal advice but for something deeper. They wanted to share about navigating uncertainty, finding balance in the unrelenting demands of life, and how they felt burned out. I slowly started sharing my personal growth practices and what had been helpful in my journey—mindfulness practices, breathwork, and the Enneagram. What began as side conversations became moments of shared humanity, like what I had been seeking.
Each of these conversations was a moment of connection. I was not able to see it at the time but later realized that with each conversation, with the space and attention I made for deeply listening to others’ experiences, my own sense of purpose was coming to the surface of my awareness.
These shared moments became a new inner work practice for me. I slowly remembered something I had seemingly forgotten: Work is important, but how we live within our work matters even more.
The Turning Point
This was all unfolding, preparing me for the turning point—the retreat.
I signed up, unsure of what to expect but feeling that familiar tug of curiosity. Most of my inner work journey, was on my own, unlike the group setting of the retreat. It was a space unlike any I had experienced before—a place where external success took a back seat to the pursuit of internal truth. Where vulnerability was not a liability but a source of true strength. People spoke openly about their fears, grief, and longing for something more. And where the facilitators didn’t rush to fix or advise—they simply held space, with the kind of compassion that strips away pretense and allows what is real to emerge.
For the first time in a long time, I felt fully seen—not as a lawyer, not as a professional, but as a human who struggles just like everyone else. It was incredibly powerful to be in a community of people brought together by their desire to heal and grow. I felt seen, and for the first time, I fully saw myself. That whisper, which I had protected in the margins of my life, became a yell. Quite literally.
I realized the deep connections within this shared group container supported each person’s inner journey.
The whisper wasn’t asking me to abandon what I had built. It was not a rejection of ambition. It was an invitation for an evolution into the fullness of who I was becoming. I realized that I didn’t want to just attend these spaces. I was motivated to create them. This was the work I was called to do.
But clarity doesn’t erase fear. If anything, it amplifies it. Yet in the amplification, like looking through a microscope, we see more.
The whisper grew louder, and the questions rippled further:
What if I fail? What if I let my family down? What will my colleagues think? Am I throwing away security for nothing more than a fantasy?
Those fears crept through my thoughts in the quiet moments between conference calls and client meetings. The weight of my responsibilities, to my work, to others, and to myself crashed against each other.
Stepping into the Unknown
Yet, alongside the tension of fear, a new softening emerged: compassion.
Compassion for myself—I could see the part of me that was terrified, clinging to the part that was hopeful and inspired. Compassion for my friends and colleagues—many of whom carried their own whispers in silence. And perhaps most profoundly, compassion for the younger me—the one who had stepped into the professional world bright-eyed and ambitious, not yet aware that the real journey would be through my own inner world.
By embracing and stepping toward the whispered questions, I allowed compassion to grow into a willingness to step into the unknown. I had protected the parts of me that had bigger questions and bigger dreams.
It was uncomfortable, like standing at the edge of a cliff, heart racing, unsure of what’s below. I was ready.
Are you willing to stand at the edge of the unknown?
Have you ever felt a quiet whisper urging you toward something different?
What did you do with it?
What might it look like to listen to that voice with compassion and explore where it leads?
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