Reflections at 44

Musings from the depths of midlife

Hello from Stone Ridge! It feels refreshing to be back home in the woods after a hectic but energizing few days in NYC. My time there was a whirlwind of seeing coaching clients, reconnecting with old pals, and supporting a few guys from my men’s group. And yes, I managed to treat myself for my birthday—a slice of “Brooklyn Blackout” cake from the Little Cupcake Bakeshop. Trust me, it's hands down the best chocolate cake in the US.

Yup, today’s my 44th birthday. Just before sunrise at 6:20, my identical twin brother, Dave, and I completed our 44th trip around the sun. Seeing that number is somewhat surreal, and while a part of me finds it hard to believe that I've reached this ripe age, there are moments where I genuinely feel the weight of those years stacking up. With each passing year, I’ve come to cherish my birthday with increasing depth and appreciation, recognizing the sheer wonder and preciousness of life. I can’t help slow down to reflect on my journey and celebrate the miraculous gift of time.

As I peer into the depths of my closet and dresser, I realize that I’ve owned many shirts and jackets for over a decade, some even surviving several decades. Notably, holes and frays have begun to appear on some of my treasured staples, silently mirroring the aging process that I’m also undergoing. While a few hold deep sentimental value, there's an increasing urge within me to let go of stuff that I no longer use or don’t value much. My instinct to shed and simplify isn't limited to material belongings—it extends to routines, hobbies, mindsets, relationships, career pursuits, and social media. I find myself increasingly drawn to a life distilled to its essence, filled only with what's truly meaningful and cherished. 

With enough time under my belt, I’ve become acutely aware of the many doors that have softly clicked shut behind me. Some, like the venture capital profession and my bachelor days in NYC, have locked, unlikely to open again. With every step forward and decision I make, there's an intricate interplay of doors—both seen and unseen—simultaneously swinging open and shut. Each closed door leaves a bittersweet taste in my mouth, causing me to grieve untapped potentials while also moving towards new possibilities. They are reminders of the impermanence of moments and opportunities, and the importance of cherishing every stage of my ever-unfolding journey.

At 44, I can see my life in its totality, accepting who I am, where I am, and what I have. Yes, certain elements can be changed, but in many ways, the foundation for the foreseeable future has been laid. I have my body and mind with all of its capabilities and limitations. I have my personality and values. I have my wife and kids. I have my home. I have a profession and a craft that I’m committed to for the long haul. While there's room for tweaks around the edges, the prospect of large, sweeping changes no longer feels possible with family in the equation. From time to time, I catch myself playing Monday morning quarterback, reviewing past decisions and asking “what if”, only to be jolted back to the present, realizing that I’ve never had more balance, presence and satisfaction at any point in my life. I’m becoming content with what I have and confident in who I am, yet I remain open to the boundless possibilities and unknown potentials that sill await me on the horizon.

Time is a limited and precious resource, especially now, with young children and a partnership rooted in co-parenting. Each passing day underscores the importance of making deliberate choices about where I channel my time, energy, and attention. As new opportunities and aspirations surface, I'm compelled to ask: What’s really driving this desire? What do I really want? Am I willing to dedicate the necessary time and effort towards new pursuits? How do these align with what I value most? How will this contribute to and impact the totality of my life?

I find myself increasingly stepping into and embracing my roles as both a husband and parent. This has become the top priority in my life, surpassing career and status games. The mental, emotional, and physical demands of fatherhood are more intense and rewarding than I anticipated as a newlywed. Being fully present—emotionally and physically—for my girls feels like a divine calling in this season of life. They need their father. And in many ways, I need them just as much. It’s primal. They give me a reason for being, and infuse every day with purpose, even if some of those days are damn exhausting and difficult. But they constantly remind me that I’m responsible for and a part of something much greater than myself.

My perception of time is also shifting in subtle yet profound ways. Months now seem to pass as swiftly as weeks. Every November, I find myself turning to my wife and asking, "How is it already Thanksgiving?” My younger self liked to measure life in weeks and months, rarely pausing to consider longer arcs of time. In my teens, twenties and thirties, the ebb and flow of days and the procession of age rarely crossed my mind. But now, perhaps for the first time, I notice myself thinking in years, even decades. The realization that a mere decade from now I'll be in my mid-50s, with my girls entering middle and high school, is humbling and hard to fathom.

While being a father is the most important role I’ve ever held, I have a highly ambitious part that yearns to scale my coaching business and write a book, and a freedom-seeking part that craves autonomy to drive cross-country solo and attend countless retreats. These pursuits feel momentarily out of reach given my responsibilities and commitments, but I’m increasingly trusting and honoring the natural progression of life. I’ve come to appreciate that now isn’t the season to prioritize and chase career milestones and achievements, as I have for nearly two decades. Rather, it’s my family, my health and wellbeing, and my coaching clients that I want to devote my time to. With unwavering faith, I believe I’m exactly where I’m meant to be and my path will unfold in beautiful, mysterious ways. I trust that one day I’ll be able to throw myself fully into career, creative expression or other unforeseen pursuits, but for now, my heart is at home. 

For my 44th birthday, I imagine a relaxing morning where time seems to stand still. The gentle rays of the sun stream into our dining room, filling our home with a warm glow and geometric patterns of light and shadow. I settle into my favorite chair, a book in one hand and a freshly brewed cup of coffee in the other. The pages transport me to a different land and era as I take that first sip, savoring the its depth and complexity. Just then, the playful giggles of the girls emerge from our living room. Their laughter, innocent and unrestrained, cuts through the stillness, grounding me deeper in the moment. It's a sound that speaks of joy, of childhood wonders, and it serves as a powerful reminder of the rich, colorful tapestry that is my life. I can't help but smile.

🙏 My Birthday Request: Subscriber Survey

Since today is my birthday, I have a special request that would be a huge help. WTRB has been a labor of love for nearly two years, and more than 5,500 of you have joined me on this journey. However, I have to admit, I wish I knew more about each of you and what you seek from my writing. In an effort to better serve you and create content that deeply resonates, I’ve put together a brief survey to know you better. It will only take a few minutes to complete.

As a small gesture of appreciation for sharing your thoughts, one lucky respondent, chosen at random, will receive a complimentary month of coaching from yours truly.

🌲Mindful Leadership Retreat: Transitions & Growth

Peter Corbett and I invite you to a transformative retreat tailored for leaders in transition. From November 2nd to 4th, immerse yourself in community and the tranquil beauty of the Hudson Valley. Set against the breathtaking backdrop of Eldred Preserve, our retreat—just a two-hour journey from Manhattan—spans 3,000 acres of rejuvenating landscapes coupled with modern comforts and amenities.

We've curated a blend of silent meditation, breathwork, solo nature explorations, and intimate group workshops. This experience is designed for:

• Founders seeking inspiration post-exit

• Executives planning or undergoing a transition

• Leaders yearning for rest, a reset, or rejuvenation

There are only a few spots remaining! We have an impressive crew of leaders already committed to this journey. Learn more and request an application here.

🤔 For Contemplation

A few days ago, I listened to a short yet profound musing from Krista Tippett on the magic of “taking a long view of time.”

In this talk, Tippett makes a compelling case that embracing "a long, reality-based view of time has a power to replenish our sense of ourselves and the world."

Through her introspective lens, she underscores that true change often doesn’t erupt suddenly but rather "ferments" slowly over expansive arcs of time.

With that in mind, here’s a question for reflection: What change in your life is currently fermenting, gently and steadily rising to the surface of your awareness? How do you know?

👐 Community Corner

Here are some announcements and updates from friends and members of the WTRB community. I believe in the power of lifting others up and paying it forward. So, if you ever have news or updates you'd like me to share, don't hesitate to reply or send me an email. 

👨🏻‍🔧Manuel Saez, Executive Coach

My dear friend, Manuel Saez, is not just an incredible designer and serial entrepreneur; he's now launching his founder coaching practice. Over the span of fifteen years, Manuel has navigated the complexity of building two companies, securing venture capital, leading high performing teams, and surmounting significant emotional challenges. Through it all, he has come to recognize that the right mindset is the cornerstone of true success.

While he has informally coached and advised founders and executives for years, his recent training with Aletheia has greatly expanded where he can take a client. If you’re on the hunt for a coach who genuinely understands the entrepreneurial journey, I can't recommend Manuel enough. Any founder or executive would benefit immensely from his wisdom, guidance and support. Beyond his skills, he’s a truly remarkable humanbeing. You can learn more about Manuel at manuelsaez.com or reach out directly to manuel@manuelsaez.com.

🌱Seeds of Change

Here are some pieces I’ve enjoyed and have been contemplating over the past few weeks.

1. In today’s age of relentless self-improvement, climber and philosopher Francis Sanzaro offers a contrarian view on the dangers of over-optimization and the elegance of simplicity:

“The tactic of subtraction goes against the grain of the so-called mind-set revolution, in which it seems everyone is adding this or that quality to their mental approach. The growth mind-set. The abundance mind-set. The gratitude mind-set. But in this genre of self-optimization, if it can be called that, we are adding more and more duct tape to something that isn’t broken—our mind—until it is so covered we lose sight of the beautifully designed machine underneath it all and it thus becomes, in fact, broken.” 

2. My friend Holly, the force behind “Quit Like A Woman” and the “Recovering” Substack, recently texted me a profound talk by Gil Fronsdal on the concept of “being lost.” His words highlight the strength and wisdom found in stillness, especially during those uncertain moments when we’re unsure of our direction or next steps.  

3. With October’s arrival, we turn the page on the summer and welcome in a new quarter. It’s not too late to reflect on the past three months and set intentions for the remainder of the year. In other words, there’s still time to complete the Ultimate Quarterly Review and end 2023 with more intention.

4. For those curious about Ayahuasca, particularly through the lens of a Western medical professional, I highly recommend The Fellowship of the River: A Medical Doctor's Exploration into Traditional Amazonian Plant Medicine. I'm currently halfway through and finding it incredibly insightful as I consider working with this medicine. A big thank you to Alex Olshonsky of DeepFix for pointing me to this illuminating read.

5. In the latest issue of GQ, an evocative quote from the 80-year-old Martin Scorsese stuck a chord with me–my heart skipped a beat. As he nears the twilight of his life, the iconic director reflects on the profound weight of relationships, the fleeting nature of time, and his looming mortality: 

“‘I saw an old friend a few weeks ago here; my God, we’ve known each other since 1970,’ he told me. ‘I hadn’t seen her in years. But by the time she left, we embraced and held onto each other for, like, 10 minutes, not knowing if we would see each other again. But couldn’t say more. But that’s good. It’s narrowed down.’”

6. Looking for insights on transitions, purpose, and the quest for a deeper calling in life? This powerful thread by Morning Brew's co-founder, Alex Lieberman is a vulnerable and sincere take on being lost, losing an identity, and searching for one's "second mountain.”

7. If we’re lucky enough to live a long life, the challenges of old age await us all. Here’s an honest and comical musing from Roger Rosenblatt, an 83-year-old New Yorker, on what they don’t tell you about getting old.  

8. For those of us devoted to personal growth and learning, the process of how we learn is equally as important to what we learn. Earlier this week, I was captivated and inspired by this thought provoking discussion—“How Learning Really Works”—featuring Dr. Theo Dawson. She “explores the central problem of the educational paradigm, how learning actually works, and the relationship between context and performance.”

9. During a recent coaching session, my teacher, Steve March of Aletheia, shared a simple yet powerful truth:

   “The locus of transformation is not the self, it’s the complex ecosystem the self is within.”

   This underscores that authentic transformation doesn’t occur inside a self-constructed bubble, detached from our environment. Rather, it unfolds when we actively engage with what life presents, being in contact and in relationship with reality. This entails being attuning to our environment and how that shapes our thoughts, emotions, sensations and behaviors.

10. As I move deeper into the craft of writing, I’m drawn to literature for inspiration and guidance. One such gem I recently devoured is A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life by George Saunders. This delightful book expanded my perspective on storytelling and the art of writing. It's one of my favorite reads of the year.