March 2025: Seasons

in the midst of some turbulent, yet pivotal few months

I've been enjoying writing these monthly recap blogs in part because they're a forcing function to sit down and reflect on the past few weeks, but also because it gives me permission to riff on a cluster of different ideas rather than focusing on one central concept. While significant changes are unfolding in my life right now—some already happened, others in motion—what's most interesting to me is documenting the experience of transition itself. There's plenty happening in my internal landscape worth exploring, even if certain external details remain private for now.

At this point, it's abundantly clear that I'm going through a transition. In the past, transitions were really hard for me. New difficult emotions would arise and I wouldn't know how to process them or be with them. Now I still experience anxiety and worry about the future, but I notice these feelings much sooner. Instead of weeks of anxiety, it's now more like two days, followed by an "oh shit" realization which usually involves a difficult conversation I've been putting off or reeling back from trying to do too much.

This transition, whether by nature of being shorter in duration, or because I am far more prepared to navigate it now, feels more like a micro-transition. Quitting my job took me over ten months, my sabbatical lasted a year, and it took me six months to actually start my coaching practice. This shift isn’t as big of a deal as going on sabbatical or starting to coach; there's far more continuity and integration going on right now and it’s happening within a larger movement between life phases.

The discomfort of transition stems from newness itself. I observe this pattern repeatedly. The high-achiever granted freedom to pursue anything becomes paralyzed by possibility. The successful founder post-exit writhes with internal conflict when refusing investment opportunities and networking calls that no longer resonate. Clinging to old identities keeps us playing games we've outgrown, while speedrunning to escape discomfort only perpetuates it. The only way forward is to sit—patiently inhabiting the mysterious fog that will clear in its own time, according to its own wisdom. I'm getting better at sitting in this fog now, with more tools than I had in previous transitions.

Seasons of A Man’s Life

I'm becoming increasingly aware of which season I'm in—the phase right before settling down. It carries a distinct feeling of urgency, purpose, and motivation. There's pressure, but it's not entirely unwanted; it feels like a natural progression.

My internal assessment aligns with psychologist Daniel Levinson's work in The Seasons of a Man's Life. His research team at Yale interviewed 40 men across different walks of life and identified throughlines in their stories, developing a theory of the "life cycle and its seasons." I'm particularly drawn to two phases: "Entering the Adult World" (ages 22-28) and "The Age 30 Transition." While the book was published in 1978, and the exact age ranges have likely shifted with people marrying and starting families later, the core principles have withstood the test of time.

In exploring Levinson's work on life seasons, I'm struck by how he nails the fundamental conflict guys like me face in our twenties. We're caught between wanting to keep our options wide open while simultaneously feeling the pull to build something meaningful and take on grown-up responsibilities.

As we edge toward our late twenties, there's this growing awareness that the window for major life changes is starting to narrow. This creates the urgency that defines the whole Age Thirty Transition. We start seriously questioning our current path—career, location, relationships—realizing that decisions we make now will shape decades to come.

One of Levinson's spot-on insights is that life forces us to make huge decisions before we're actually ready for them. He writes, "One of the great paradoxes of human development is that we are required to make crucial choices before we have the knowledge, judgment, and self-understanding to choose wisely. Yet if we put off these choices until we truly feel ready, the delay may produce other, greater costs."

Moving into our early thirties, the main task becomes commitment—narrowing our focus to go all-in on what truly matters. The scattered exploration of our twenties gives way to building something substantial in our work, relationships, and community.

What resonates most with me is Levinson's concept of "the Dream"—that personal vision guiding our life choices. This concept beautifully complements what Joseph Campbell explores in "The Power of Myth," where he shows how myths aren't just ancient stories but living frameworks that help us understand our place in the world. Like Campbell's hero's journey, Levinson's Dream serves as our personal mythology, the story we tell ourselves about who we are and what we're here to do.

It's taken me nearly four years to get clear on my own vision. Looking around, I notice many friends still don't have this north star. Back in 2021, my supposed vision involved living nomadically in a van with a partner and maybe a dog. Looking back, this wasn't actually about my future—it was about wanting freedom and adventure within a relationship at that specific moment in time.

Levinson beautifully describes this concept: "A man's Dream is his personal myth, an imagined drama in which he is the central character, a would-be hero engaged in a noble quest." He quotes Goethe's insight that "For a man to achieve all that is demanded of him, he must regard himself as greater than he is."

One of the biggest challenges I've found with developing this Dream is finding the sweet spot between commitment and flexibility. I need a vision strong enough to organize my life around, but holding it too rigidly leads to disappointment and missed opportunities. The challenge is to create a Dream with enough structure to guide myself while leaving room for it to evolve as I do. It's less about executing a fixed plan and more about following a living, breathing vision that remains open to life's unexpected turns.

The stakes of this transition are surprisingly high. A failed transition can mess you up, as you might struggle to see meaning in life beyond this point. On the flip side, as Levinson notes, "Those who build a life structure around the Dream in early adulthood have a better chance for personal fulfillment, though years of struggle may be required to maintain the commitment and work toward its realization."

What makes the Age 30 Transition so pivotal is that it represents a "second chance" to create a life that actually works for you. There's both opportunity and urgency—a recognition that while change is still possible, the window is closing. The carefree vibes of our twenties are ending, and life is becoming more consequential. As Levinson says, by age 30, there’s "a stronger sense of urgency to 'get serious,' to be responsible, to decide what is truly important and shape his life accordingly."

I'm learning to balance these opposing forces. Taking my life choices more seriously while refusing to sacrifice playfulness and wonder. When I make decisions now, I'm not just asking "Is this responsible?" but also "Will this keep me curious and energized?" I'm navigating the challenging leap from big kid to serious adult while fiercely protecting that sense of childlike joy and wonder that makes everything worthwhile.

On Change and Transformation

I've been noticing subtle but significant shifts in myself lately that align perfectly with what Levinson describes. My once-insatiable appetite for travel has mellowed. Instead of constantly searching for the next adventure, I find myself craving routine and stability—a predictable rhythm to my days that allows for deeper work and more meaningful connection.

What's interesting is how good it feels to embrace the role of the seeker again. Being in pursuit of something carries a certain energizing quality. There's a youthful vitality to actively working toward change and growth, whether in the gym or in my career. The state of being in pursuit feels deeply natural, almost primal. We were born to be in pursuit of something.

This pursuit creates an interesting tension with the Buddhist principles I've been exploring. On one hand, Buddhism teaches acceptance and non-attachment to desires. On the other, having direction and purpose feels essential to a meaningful life. I'm learning that these seemingly opposing forces can coexist—the challenge is discerning which desires are genuine expressions of my deeper self versus those I've absorbed from others or society.

Western individualism conditions us to reject others' expectations as inherently constraining, but I'm finding that sometimes wisdom comes from listening to what people or our environments are telling us. The real skill isn't blindly following my desires nor ignoring them completely—it's developing the discernment to know which ones merit attention and commitment.

As I lean into this season of commitment and clarity, I'm reminded of another Campbell idea that keeps coming back to me: "We must be willing to let go of the life we planned so as to have the life that is waiting for us." The Age Thirty Transition isn't about figuring everything out once and for all—it's about developing the courage to commit to a path worth walking while maintaining the wisdom to adjust course when necessary.

Other Musings

Tending To A Garden of Relationships

Being back in NYC, specifically the Upper West Side for the next month, has reminded me just how important relationships are. I've been reconnecting with people and realizing that I actually have a lot of genuine, real connections here.

I've developed an interesting pattern from my years without a lease—I'm always the one who reaches out first, and it works. While many people hesitate to contact friends (not wanting to be a burden or fearing rejection), I've never struggled with this. Since I'm constantly on the move, people don't know where I am, so they expect me to initiate. This structural dynamic makes the "uneven" reaching out feel completely natural.

It's been rewarding to not only reconnect but also to experience the reciprocity of help from people I've supported in the past. I'm starting to appreciate just how long life is and how many re-encounters we have with people, even after one chapter ends.

Morning Rituals That Ground Me

I've settled into a morning routine that helps me start each day with clarity: stretching → meditation → walking around the reservoir → decaf coffee + one page of morning pages.

I've noticed that meditating after some movement allows me to drop deeper than if I were to start meditating immediately. There's something about getting embodied first through physical movement that creates a noticeably different meditation experience.

The reservoir loop in Central Park has become a special place—the one-way path means everyone moves in the same direction, creating a peaceful flow without the need to navigate oncoming traffic. It's meditative in its simplicity.

I've intentionally scaled back my morning pages to just one page instead of two—a practical trade-off that keeps my morning routine from consuming two hours. For ad-hoc reflection, I've been using Lightpage for voice journaling during walks, which has been a game-changer.

new daily walk

Questions I'm Sitting With

As I navigate this transition, several questions keep surfacing:

• What would it look like to integrate the human work I do in coaching with technology work?

• As an Enneagram 6 who struggles with self-trust and anxiously tries to forecast the future, how can I navigate this next chapter with more openness and patience?

• What is my environment trying to tell me, and how can I act in accordance with that? (Whether "environment" means the universe, a higher power, or simply what I observe outside myself that resonates)

• How do I balance enjoyment and work? Rather than seeking ways to work less and play more, I'm curious about how to enjoy the process of working—integrating play and work in a way that isn't common but feels right for me.

These questions keep me company during this seasonal shift. I feel the pressure of decisions that will shape my coming decade, yet find satisfaction in finally committing after years of keeping options open. Understanding these life seasons helps me see this not as random anxiety but as natural development. The uncertainty remains, but I'm learning to see it as a companion rather than an enemy. This balancing act and intentional shift embodies the essence of navigating life's seasons.