A Year of Practice
reflections from a year of practice, learning, and becoming
Last December marked the end of a full year without a paycheck. After twelve months of wandering, physically across continents and mentally through possibilities, I found myself ready to embrace a new adventure of uncertainty. While my sabbatical had led me through various creative projects, an unexpected path had emerged: coaching.
At my mom's place, winter gear appeared from storage as summer clothes disappeared into closets. Between sorting through city sneakers and dusty ski boots, each item represented a chapter in my chosen lifestyle - one without a fixed address but rich with intention. Despite the uncertainty ahead, I felt a calm reassurance about flowing with whatever changes would come.
Though I had no concrete plans, mysterious trailheads of apprenticeship and coaching beckoned. Twelve months earlier, coaching had been just a whispered possibility. Both Downshift, the coaching organization I'm now part of, and my own practice were seeds waiting to sprout. The path ahead held more questions than answers, but I was learning to leave space for emergence.
This year delivered plot twists I never saw coming: my first broken bone, a stint in a Manhattan penthouse, and after five years of nomadic living, a surprising desire to put down roots. While my passport gathered dust for the first time in a decade, the real adventures unfolded internally—in coaching sessions, deepening relationships, and the continuous practice of presence.
Now, at the completion of this year, I find myself holding both grounding clarity and beautiful mystery, knowing I'm heading in the right direction while remaining open to what unfolds. As I continue this ritual of annual reflection, I'm struck by how naturally this year divided itself into four seasons of three months each:
❄️ Wintering (January to March)
🎓 Apprenticing (April to June)
🏃♂️ Venturing (July to September)
➿ Integrating (October to December)
Seasons of 2024
❄️ Wintering (January - March)
Winter in the mountains has its own heartbeat. While most retreat indoors to fireplaces and cozy conversations, I've always moved in the opposite direction - clearing my calendar for powder days and dawn patrols. This year was no different. Our cozy Tahoe ski lease, shared with five other snow-obsessed souls, felt like the perfect launching pad for another big ski season.
January flew by. Although my schedule primarily revolved around skiing—and by extension the weather, I still made time to write, meet with people virtually, and write both my blog and climate newsletter. Sheltered in our little ski chalet with boots, gloves, and jackets strewn everywhere, I was stoked for another couple months of chasing powder, followed by an eventual return to NYC.
But the universe had other plans. In February, I suffered a fluke accident that wasn’t even a double-black diamond run or an off-piste daredevil line. I somehow skied down the mountain unknowingly with a broken ankle, and then was pushed in a wheelchair with giant snow wheels to the village clinic, forced to sort out a health insurance debacle before getting an x-ray. I didn’t know it at the time, but I was entering a one-legged, bed-ridden rut. My ski season was cut short, bringing bouts of frustration, sadness, and self-loathing.
What was supposed to be three months of high-energy skiing turned into an internal wintering. My world contracted to 300 square feet of cabin space, marking slow journeys between bed, desk, bathroom, and kitchen on crutches. As fresh powder accumulated for all the non-injured residents to enjoy, I languished inside, oscillating between resistance and acceptance that this was now a season of rest and recovery.
Beyond the injury, I was being patient and sitting with uncertainty with my work. I had just begun to have conversations with Steve about forming a potential apprenticeship, and Downshift was a seed of an idea, waiting to be nurtured into a full-fledged company. I knew I wanted to coach, but I didn’t know how to begin or where I would end up.
Other than the newfound curiosity in coaching, I was still pursuing other ventures: an apartment subletting platform and my climate newsletter. Between feeling less excited and not seeing significant external traction, I decided to wind down the subletting project and pause my climate newsletter. In the past, I would’ve resisted and delayed these decisions far longer, but this time, there was grace and ease. While I wished every experiment could be a resounding success, I recognized that letting go created space for new possibilities. I trusted that if those previous missions were truly meant for me, I could always return to them with renewed purpose.
By the end of March, I was ready to complete my season of wintering. My ankle was making a full recovery, I had begun my apprenticeship with Steve, and we were working to create a transformational experience for the inaugural Downshift cohort. With a thick ankle brace, I could finally walk without a boot or crutches—perfect timing for my return to the pulsing energy of NYC.
Plants and animals don’t fight the winter; they don’t pretend it’s not happening and attempt to carry on living the same lives that they lived in the summer. They prepare. They adapt. They perform extraordinary acts of metamorphosis to get them through. Winter is a time of withdrawing from the world, maximizing scant resources, carrying out acts of brutal efficiency and vanishing from sight; but that’s where the transformation occurs. Winter is not the death of the life cycle, but its crucible.
- Katherine May, Wintering: The Power of Rest and Retreat in Difficult Times
🎓 Apprenticing (April - June)
I call this the apprenticing season not just because of my role at Downshift, but because I became an apprentice in life itself. The origins of the word all point to learning, and indeed it was the first time since my first job that I felt like learning was my primary modus operandi. I was in a state of full immersion learning, steeped in novel contexts with new challenges to navigate.
Even as I embarked on a new path of work, I found comfort in returning to Sunset Park, Brooklyn. After months away from NYC and recovering from my ankle injury, I was eager to work hard, move freely, and see people again. Living in a middle-class immigrant neighborhood and subsisting off Costco was fitting for where I was at: a humble tadpole starting at square zero of an infinite board. This environment perfectly mirrored my internal state: humble, focused, eager to learn.
My first real opportunity to coach came unexpectedly. With the announcement of my apprenticeship, a couple people initially reached out for coaching with me. Despite not having a website, a bio, or even suggested rates, I began coaching a few people while still prioritizing my self-guided coach studying. One client could only afford $50 a month for two sessions, which tested the quality of my intentions with coaching. I sensed my willingness and excitement to help them, reaffirming my desire to coach, regardless of the financial reward.
As I began to help Steve with Downshift, I immersed myself in the craft of coaching. In a normal school, everyone sits at their desks and listens to the teacher regurgitate the same information over and over again. Being out of the education system with no desire to go back, I forged my own curriculum in the realm of coaching and allowed my mind to freely roam. I began reading coaching textbooks, taking notes on presence, deep listening, and the art of asking empowering questions. I brought my questions and insights to my sessions with Steve, creating a powerful feedback loop that accelerated my learning and fueled my curiosity.
When I wasn't reading or talking about coaching, I was listening to podcasts while walking around NYC, each conversation adding another layer to my understanding. Between books, podcasts, 1:1s with Steve, Downshift, and my first coaching clients, my days became the equivalent of entering a foreign language immersion school—except instead of conjugating verbs, I was learning the language of human transformation.
This immersive initial sprint of learning culminated in the first Downshift cohort in mid-April at our retreat upstate, surrounded by budding spring trees and fellow seekers. Over the next eight weeks, we moved through virtual workshops, each session furthering my understanding of transformation and human potential. My role as an apprentice felt right—I had just enough responsibility to contribute meaningfully while still absorbing the wisdom from Steve, David, and our guest lecturers.
During this season, I didn’t have the bandwidth for many additional commitments, and that was intentional. After a year of exploration - four different projects, varying degrees of success, and zero income - I was ready to find work worth dedicating decades to. During this period, I had a hunch that I was on the right path. Now, as I embark on my second year of coaching, I’m glad I heeded the call.
The goal of an apprenticeship is not money, a good position, a title, or a diploma, but rather the transformation of your mind and character—the first transformation on the way to mastery
- Robert Greene, Mastery
We find the core essence of work, firstly through its fear-filled imagining, secondly, in the long necessary humiliations of refusal, courtship and apprenticeship, thirdly in the skill and craft we learn by doing and finally in the harvest of its gifting and then, the surprising ways it is both received and rejected by the world and then given back to us.
- David Whyte, Consolations
🏃♂️ Venturing (July - September)
After the first Downshift cohort completed in June, I took time to reflect and recalibrate. My coaching website sat ready but unannounced for weeks—a testament to my hesitation. Through deep self-inquiry and conversations with friends, I realized I had been putting off announcing my coaching practice because it felt like such a big one-time opportunity. Rather than downplay the gravity of the situation, I leaned into it. Coincidentally, Kelly, a creative embodiment coach, invited me to join a weeklong creative challenge with other digital creators. It was the nudge I needed.
Two days before I planned to announce my coaching practice, I made a list of friends, colleagues, and acquaintances and DM'd all of them, asking for support while keeping it low pressure. On the day of, the coordinated pre-launch paid off with social media posts receiving views in the tens of thousands. Although a singular shallow metric, this translated into strong initial demand with my calendar getting filled with intro sessions for the following weeks.
My reaction was unexpected. I was happy, but not ecstatic—it was almost as if subconsciously this was something I had been working towards all along. After six months of immersion on the coaching path, the outpouring of interest meant it was time to buckle up and get to work. Gone was the excuse of "If only I had more client leads..."
As my coaching practice was taking flight, I was also coming up on 18 months of living off savings. Sensing a desire for more stability, I began exploring other work possibilities that would complement my primary pursuit of coaching. Coincidentally, an opportunity fell into my lap without having to update my resume or rigorously prepare for interviews. Without much diligence, I started consulting at an early-stage startup as a part-time product manager, accepting the offer on the same day I announced my coaching practice.
Making good money again was comforting. Beyond enjoying more meals out, the greatest benefit was seeing my time horizon expand across all dimensions of life. I approached coach training programs with less urgency and felt a greater sense of ease in my coaching sessions.
However, the trade-offs emerged quickly. Context-switching became difficult, and being fully present grew challenging. Between coaching, writing, Downshift, and this new gig, my mind was constantly racing. After over a year of self-discovery and working on my own projects, I found it challenging to conform to the rigid rigor of a small startup. Perhaps one consequence of inner work is losing the ability to bullshit yourself—to simply put your head down and grind. When I was ultimately let go, it felt less like a failure and more like a course correction back to my path.
Unlike my 2020 layoff from my dream company, this firing brought neither pity nor judgment from others—nor did I seek it. The timing felt meaningful: I had accepted this role the same day I announced my coaching practice, before knowing if anyone would even want to work with me. It felt less like a failure and more like a gentle nudge from the universe back to my intended path. I don't regret this experiment—it gave me both a taste of financial stability and clarity about its potential costs. As I look ahead, I remain open to similar opportunities, but with a sharper eye for alignment from the start.
As I retold this story over breakfast to a wise elder, she reframed it as an act of seduction, which I resonated with. I had a desire for more money, and the first opportunity that came my way was tempting. This experience reveals how we often rush to solve our discomfort instead of sitting with it. We rush to answer difficult questions with problem-solving and advice-seeking. In these pockets of emptiness, new possibilities often emerge as the environment transforms around us.
Through these months of professional evolution, adventure wasn't something for 'after work was done'—it was embedded naturally into the fabric of my days. This summer season, already eventful with work, was also expansive as I embraced the warm weather and long days. I enjoy learning about coaching, spirituality, and consciousness, but I often find that communing with nature teaches me just as much as the deep stuff. After missing a year of backpacking, I reconnected with wilderness in Yosemite summiting Half Dome at sunrise and basking in the quiet wind-free solitude. My girlfriend and I kayaked and biked in Tahoe, where she had cared for me during my injury just months before. In Colorado, I joined my friend Parker for white water rafting and a roundtrip Denver-to-Boulder bike ride, stopping to hike the second Flatiron and devour a massive smothered burrito. My summer adventures concluded with three weeks in Hawaii, where I reconnected with friends and hiked the Na Pali coastline again before returning to NYC.
The goal is to connect to a world outside of us, to lose the obsessive self-focus of self-exploration and, simply, explore. One quickly notes that when the mind is focused on other, the self often comes into a far more accurate focus.
- Julia Cameron, The Artist’s Way
The only way to make sense out of change is to plunge into it, move with it, and join the dance.
- Alan Watts
➿ Integrating (October - December)
We spent October in a Brooklyn brownstone's ground floor apartment. The warm lamps and houseplants created a cozy hideout from the city's bustle, while my walks around Prospect Park offered a natural rhythm to my mornings. Surrounded by a field of frolicking leash-free dogs, I watched as the leaves gradually turned into autumnal gradients.
The well-furnished, intimate apartment helped me ease into a routine. Mondays brought Downshift team meetings and my Artist’s Way group complete with exercises, morning pages, and artist’s dates. With coaching sessions clustered mid-week and Downshift workshops on Tuesdays and Thursdays, I had the flexibility for spontaneity and socializing.
Fall began with our second Downshift cohort retreat nestled in the Catskill Mountains. Amid peak foliage, the simple, yet spacious venue created the perfect cradle for a container of new participants and also a new team. As a facilitator and witness, I observed how the full spectrum of human experience was made visible, relatable, and held with compassion. This moment reaffirmed my path in coaching while also revealing new areas for my own journey.
I left NYC on November 1st, earlier than my usual mid-December departure. After months of intensity, I craved the simplicity of suburban life. This wasn't just about timing or logistics—it reflected a deeper shift. The more I immerse myself in coaching and witness my own transformation, the less I need intense external stimulation. Where I once thrived on the city’s endless possibilities—its constant buzz of people, culture, and spontaneous adventures—I now find myself drawn to quieter spaces.
The city still pulses with unlimited potential, but I've discovered something more compelling: the infinite landscape of self-discovery and human connection. This coaching work demands a particular kind of presence that feels increasingly at odds with NYC’s relentless rhythm. While its magnetic pull endures, I'm accepting that it may no longer be my primary home—perhaps just a place for periodic reconnection, inspiration, and Lucali1.
My coaching practice has evolved swiftly, though without clear benchmarks for success as a newcomer. Every few sessions brought fresh revelations—whether encountering a growth edge or discovering a new way of relating. As I examined these experiences in my mental learning laboratory, I discovered new insights and depth. While books and podcasts had laid the foundation, true understanding emerged only through practice, where theoretical knowledge transformed into embodied wisdom.
After months of movement on adventurous road trips and in NYC, I've welcomed the slower pace of winter solstice season—a time when my annual review2 reveals how I’ve grown and transformed while still remaining true to myself and my roots. This season of integration has shown me how inner change reshapes our environmental needs, while making the path ahead feel both clearer and more spacious, guided by an ever-strengthening inner compass.
📅 Lessons Learned in 2024
The Human Behind the Label
As my coaching practice evolves, I've experienced numerous limiting beliefs about who I can serve. Through self-inquiry and direct experience, I've worked with clients across every dimension I once doubted—people older than me, wealthier, more senior in their careers, parents, and those of different race, gender, and sexual orientation. Each engagement reinforces a fundamental truth that aligns with my vision of the More Human Possible: beneath our surface differences lies our shared humanity. Behind every label, title, and life circumstance exists a whole human with universal needs and infinite possibilities. While new challenges will emerge, I'm learning to meet them with curiosity and openness rather than resistance and constraint.
We Are Our Relationships
The individualistic model prevalent in modern society, especially among Americans, emphasizes personal agency while falsely suggesting we can ever fully control our reality. As I explore spirituality, consciousness and systems thinking, I'm recognizing a more interconnected view of identity.
Rather than seeing myself as an isolated entity, I now understand my "self" as a dynamic network of relationships. My identity isn't fixed, but emerges from my interconnectedness with people, places, and nature. This manifests in simple ways: a bad day can result from an argument, just as a good day often includes quality time with a loved one.
Beyond surface-level differences, we are united by our core human needs for connection, meaning, and belonging. Our sense of self is not something we possess, but something we continuously create through our interactions and bonds.
The Power of Empty Space
My tendency to overcommit stems from a deeply ingrained belief that constant activity equals progress—as if doing more makes me more worthy. Yet true transformation occurs in the spaces between actions. Change is always happening, whether we notice it or not. But the noticing itself—the awareness that allows us to integrate and learn from change—can only emerge in moments of stillness.
This year taught me how scattered attention and digital noise prevent deep focus. Habitually filling quiet moments with texts, emails, and social media, I often failed to preserve the spaciousness that is required to allow for the mind to wander and wonder. The finitude of life reveals a paradox: to make the most of our limited time, we must create space for emptiness.
Pure aligned achievement isn’t about constant doing, but about creating room to simply be. This is easier written than lived. Creating emptiness requires tremendous self-trust—faith that novel possibilities will emerge even when our calendars feel sparse. Emergence, the appearance of something that wasn't there before, often arrives precisely when we create the conditions that allow for it. Like a garden needs space between plants to flourish, our lives need intervals for new insights to take root.
Presence Above All
This year's lessons were powerful reminders. I learned the importance of presence in a myriad of methods, including the the hard way when I broke my ankle while skiing. Injuries aside, I’ve seen how my presence shapes the quality of my experience. The quality of each experience, from epic adventures to quiet moments, depends on my ability to be fully there. Even mundane activities become meaningful through presence, while anticipated highlights fall flat without. Continuously living this lesson requires daily practices that cultivate mindfulness, embodiment, and self-awareness.
🌠 Intentions for 2025
Making More Money
The past two years have transformed my relationship with money. I once used money to cope, numbing myself to the drudgery of unfulfilling work by buying things I thought I wanted, influenced by others. My year without income taught me that while I could live off savings again, it wouldn't serve me as it did before.
This year marked a shift towards earning money in more empowered, self-directed ways. After this reorientation, I appreciate money as a means to create abundance. I view it as a tool for creating the life I want, playing a central role in my purpose and service. I’ve learned that desiring and possessing wealth is neither immoral nor wrong. More money could serve me by providing comfort, safety, and security, while also helping me plan for a family and pursue more ambitious, higher-risk ventures.
Regardless of the future, my perspective on money has shifted. Instead of solely focusing on my individual wants from a place of lack, it's now about how it can serve me, my loved ones, and my purpose. This new outlook stems from ambition, abundance, and growth rather than sloth, scarcity, or stasis.
Creating Authentically
This year has taught me about the delicate balance between authenticity and creativity in the digital age. With social media being the predominant medium that creations get shared, I’m finding that there’s a fine line between creating what I want vs. creating what I think others want. While it isn’t black-and-white, truly resonant content must be created from a place of authenticity.
As a coach with my own practice, I recognize the importance of marketing my services. However, this can sometimes lead to a slippery slope of creating what I think others would engage with rather than what I truly want to create. I've seen this happen multiple times with friends who are digital creators. They start sharing their passion online, grow an audience, and then at some point, their passion gets twisted by the pull of algorithmic incentives and the allure of financial success.
In 2025, I intend to express myself more authentically through my creations. While it won't be without challenges and tradeoffs, I aim to strike a balance between building a sustainable business and creating what I'd like to see more of in the world, even if it doesn't have immediate ties to my coaching practice. In the year to come, I'll create content and write essays that are not only fulfilling for me, but also helpful to those who view them. The reward for expressing my creativity will be the act of creating itself.
Living in Spaciousness
Spaciousness is a feeling, a state that is more easily felt than understood and observed. It’s about not constantly rushing or oscillating between overwhelm and barely getting by. Living a life of spaciousness doesn’t mean neglecting responsibilities or offloading errands. It means creating boundaries, taking breaks, and resisting temptations.
Ironically, I accomplish more and enjoy life more fully when I do less. As my calendar gets crowded and meetings start getting booked weeks in advance, I’ve learned to recognize the mental flare warning me that my sense of spaciousness is contracting. This often coincides when I find myself checking my devices often and things start to feel urgent, even though real emergencies are rare. Boundaries begin to erode as I reluctantly enter a self-inflicted vortex of saying yes to too many things.
For 2025, I’d like to improve in this area. I’ve seen how energizing and productive spaciousness can be, despite initial hesitancies. I’ll set boundaries, say no, and consume less as I work diligently to make space for joy and presence. While none of these are easy or guaranteed, they are well worth the intention. In practice, this means protecting my mornings from meetings and social media while embracing unstructured days for either deep work or rest, play, and spontaneity. These aren't just scheduling preferences—they're intentional choices that create the conditions for sustained flow.
Pursuing Depth
In my journey toward depth, I've confronted my own patterns of shallow engagement, like getting caught in social media's undertow or creating aspirational overwhelm with my ever-growing reading list. The truth is simple: those who read deeply make time for it.
Meaningful learning demands sustained attention. This means allergically avoiding the tempting tentacles of social feeds. It means choosing the quiet focus of a book, trading the illusion of being informed for the reality of being transformed.
With my coaching practice, I’m following a similar arc of prioritizing depth in the new year by pursuing my first formal training program. Initially, I felt resistant to committing to an expensive investment without the lived experience of coaching. I explored several training programs, but none resonated deeply enough.
With the learnings of my apprenticeship and my own coaching practice, I’m ready to deepen my practice. After sampling various coach trainings and therapy modalities, I'm excited to begin a one-year training starting in January with Hakomi3, a mindful somatic psychotherapy method. This decision reflects where I am in my coaching journey—I've gotten enough reps to identify my natural gifts as well as areas for development. It feels like the right time to immerse myself as a student again.
Conclusion
Last year was "A Year of Zero", a conscious choice to earn nothing while exploring everything. This year emerged as "A Year of Practice," where exploration crystallized into commitment. Through my apprenticeship, coaching work, and continual learning, I've discovered that practice isn't just about repetition or mastery. It's about showing up with presence, curiosity, and openness to what each moment holds. The discipline of practice has given shape to what began in the emptiness of zero.
Yet, as I mark this as my year of practice, I recognize that practice itself is infinite. This year has taught me that becoming is not a destination but a continuous unfolding - we are simultaneously who we are and who we are becoming at every moment. While zero created the space for possibility, practice has revealed the art of conscious becoming, showing me how to move forward with intention while remaining open to the mystery of what lies ahead.
Stay tuned for upcoming Downshift offerings here.
To learn more about coaching with me, check out my website.
The best pizza in the city. Apparently Jay-Z and Beyonce’s favorite restaurant in Brooklyn.
It’s still not too late to do your own annual review! If you’re looking for a template, check out Downshift’s Annual Review.
I’ll share more about my training explorations at some point! I surveyed and sampled across a wide variety and learned a bunch through this process.
I really loved walking with you as I read your journey Matt… the ups and downs of it all and the insights you gain which feel so relatable. Thank you for your honesty.
As an aspiring coach, id appreciate you sharing your self-guided coaching curriculum! 🙏🏼