Becoming an Apprentice 📖

how I arrived at my next chapter

I’m stoked to share that I’m starting an apprenticeship with Steve Schlafman! Among other roles, Steve is a coach with a focus on guiding high performers through work-life transitions. I’ll be helping him with some exciting projects that will be announced soon! I have a lot more nice things to say about Steve and the story of how we met, but that’ll come later on.

It might seem like a surprise to be reading about my first step into coaching, since I’ve never mentioned it all before, but this has actually been the culmination of years of wandering and more recently, a few months of intentional exploration within myself and of what life is asking of me. In this essay, I’ll share how I landed on coaching, why I decided to seek out an apprenticeship, and ultimately why I reached out to Steve.

As I replay the key moments from last year, I can’t seem to trace a precise throughline. Most of the time, I felt like I was enveloped by uncertainty. As I wandered through the fog, the only thing that guided me was the faint pull from an invisible thread of curiosity.

Throughout this journey, I’ve been an archaeologist of my own inner landscape. Years of following other people’s blueprints and society’s scripts led to my own compass being buried. I didn’t expect there to be so much unexplored territory! With plenty of time for stillness and introspection, I excavated artifacts of self-discovery, but they were often initially indecipherable, like hieroglyphics. But I kept digging. Then one day, I found it. My version of the Rosetta Stone.

Bumping into Coaching

When I started my sabbatical in January 2023, I had no plan. From the outside in, it probably looked like I had my shit together because once I quit, I immediately launched my climate newsletter and started a podcast. But on the inside, I felt lost. It was the first time in my life that I didn’t have tangible achievements to strive for.

Despite not knowing what would unfold, I felt compelled to share a reflection on why I quit my job. That essay caught Steve’s attention and it also led to random strangers DMing me and thanking me for sharing my story. I was surprised that my story resonated with others and I happily took every single call. During a long solo drive from Lake Tahoe to Salt Lake City, I distinctly remember one stranger tell me that I understand him more than his own family and friends.

At the time, I wasn’t even aware that coaching was a thing. A few months went by. I deliberately stopped writing about my sabbatical because I didn’t want to be known as the guy who quit his job and won’t stop talking about it. It also felt a bit icky to promote the idea of taking a sabbatical before actually knowing how my own would be. So off I went. To work on my climate newsletter, my podcast, and myself.

About three months in, I still had no idea what I was doing, but it became clear that I wasn’t going back to my past life as a product manager. It wasn’t that my skills had atrophied. Rather, my tolerance for the work had all but disappeared. As my workweek was now just “the week”, I spent my time noticing new interests, but I wasn’t aware of any job titles to map them to. Meanwhile, I asked myself questions about my identity, what work I want to do, and what kind of life I want to live.

I didn’t think about the actual term coaching until June when a series of serendipitous events beckoned me to explore this new path. First, a coach emailed me asking for an interview for her blog. Less than a week later, I was asked to come on a podcast to talk about how to quit your job. Then, an executive coach reached out to chat. If these moments were dispersed across the entire year, I might’ve shrugged it off. But the fact that this all happened within a couple weeks compelled me to ask why were all these people asking to talk to me. Me — an unemployed dude in his 20s who just a month ago was surfing in Indonesia, living off of $25 a day.

It took a couple months for me to piece together the puzzle. I had never thought of myself as a coach and even in those moments when I was being interviewed, I still didn’t think of myself as one. But what I’ve come to realize is that I think about the same things that coaches think about. Not just think. I contemplate, explore, obsess over, and struggle with the same set of ideas and problems that coaches are fluent in. Encountering this potential path felt right to me because it came together organically, but I also sensed that I had my work cut out for me. I didn’t know what coaches actually do, where to find them, or if I could actually see myself as one.

For the next few months, I researched coaching as a potential path. Anytime I came across a coach, I would note their name in my Notion page and include a link to their website. During this time, I spoke to over a dozen coaches across a variety of disciplines (life, career, leadership, executive, transition). Throughout these conversations, I was trying to understand what coaching actually means, but also identify the characteristics in these coaches that resonate with me. Over time, I started to view becoming a coach as a fulfilling path to help people build self-awareness and achieve their full potential. I also saw how coaching wove together my interests in philosophy, spirituality, psychology, and performance and put it all into motion grounded by tangible change as opposed to abstract wishful thinking.

Alongside those conversations, I pursued my own self-directed curriculum by listening to podcasts like The Art of Accomplishment and reading books such as The 15 Commitments of Conscious Leadership. I also referenced Steve’s comprehensive guide for aspiring coaches on a nearly weekly basis. I was having a great time absorbing everything, but I was also unclear of how to proceed. It seemed like all the best coaches were over a decade older than me and had their own unique story of how they naturally started coaching. I attempted to chart a similar journey and began informally coaching a couple of my friends who run startups. Although I got over the initial hump, I was still unsure of this path so I didn’t announce anything.

Why an Apprenticeship?

The fundamental learning situation is one in which a person learns by helping someone who really knows what he is doing.
– Christopher Alexander, A Pattern Language

Thanks to my journaling habit, I can trace back the realization of pursuing an apprenticeship to July 24th. By this point, I had already ruled out the possibility of returning back to my previous work, let alone any normal 9-5 job. But in crossing out the most common type of employment, I was left with few options. It had already been months of flying solo and cranking out blogs, newsletters, and podcasts. I wondered if preserving my freedom and creative expression had to be coupled with a lone wolf mentality. I wondered what lay between the spectrum of sole proprietorship and mega corporation which reminded me of concepts such as cooperatives, collectives, and liquid teams. While these options seemed appealing because they balance collaboration and ownership, I didn’t have a clue what the first step might be.

On July 24th, I was reading Mastery by Robert Greene at Book Club, a bookstore in the East Village that serves coffee by day and wine by night. Greene analyzes the lives of masters like Benjamin Franklin, Leonardo da Vinci, and Albert Einstein to weave together a narrative about how each of us can achieve mastery. I read about how each of these remarkable individuals apprenticed under a master before becoming one themself. I was only a couple chapters in, when I decided to pursue an apprenticeship myself.

Leading up to this moment, the word apprenticeship had been in my vocabulary, but I associated it with medieval craftwork like making pottery or smelting iron. The only time I came across the term was in history class, Medieval Times (quite the field trip), and Runescape. I thought I didn’t know a single living person who had done an apprenticeship until I realized that nowadays they’re just called something else. To become a doctor, medical students complete clinical rotations and several years of training during residency. In the restaurant industry, an aspiring chef will stage, immersing themselves with new techniques in exchange for free labor. In fact, the trades, such as carpentry, plumbing, and HVAC rely on the apprenticeship model to train novices.

By this point, I was exploring both coaching and the apprenticeship in parallel. As I gained more exposure to both the breadth and the depth in coaching, the path became more exciting, but also more daunting. I became firmly aware that I was starting at square zero and that the road ahead was long, but rewarding. Viewing the apprenticeship within the context of coaching started to make more sense to me. Coaching, in the literal sense, is basically a series of one-on-one conversations between the coach and the client. The intimate, confidential nature of these sessions is what makes it so valuable, but also makes it difficult to record or simulate. Unlike other disciplines that can be learned through YouTube tutorials and self-paced exercises, coaching demands immersion in reality.

While I did consider training programs, there were so many that it felt overwhelming. Also, the lack of specificity on who the teacher would be made it difficult to feel a strong connection with any of these organizations. Even if their name was listed, I didn’t know anything about them. I wanted to learn from a real human, not a business. Although I hesitated to seek out formal training, I’m almost certain I’ll participate in them some day. I recognize that these training programs offer valuable teachings and that I might just need some time to familiarize myself with them.

As I explored coaching further, the idea of an apprenticeship became more appealing to me. Although I would start from scratch, I felt excited to be a beginner again. After living off of savings for an entire year, I was already used to humble and scrappy living. I also had a feeling that even though I would be coming in with little experience, I could still help. I learned this lesson from writing this blog. I never would’ve imagined that sharing my stories would help people get unstuck and navigate their own transitions.

So with that in mind, all I had to do was figure out who to ask.
Fortunately, it was immediately obvious.

Reaching out to Steve

In the past when I sought out work, in the form of an internship or a job, I employed a mechanical, almost manipulative approach. Every fall semester, I sprayed-and-prayed hundreds of applications into the ether. When a company required a cover letter, I would simply swap out the company name in my template and rename the file for maximum efficiency. During interviews, I would BS a half-decent explanation for why I was interested. Part of me felt wrong for doing this. The other part of me could see that the interviewer was doing the exact same thing. I think I am far from alone on this.

This time around was different. Prior to reading Mastery, I was already reaching out to coaches out of pure curiosity. In these conversations, my primary motive was to learn, but I was also observing how these coaches carry themselves. Like a sponge, I soaked up every bit of information. Everything was relevant to me. Things like friendliness, energy level, body language, and even word choice. Before any thought about apprenticeships, I had already begun to piece together a model for what coaching is.

By the time I was ready to seek out an apprenticeship, I was familiar with over 70 coaches and had met over a dozen of them. In some sense, this could be interpreted as just another job search, except this time around, instead of spraying-and-praying, I only reached out to Steve.

I first came across Steve’s work through his Ultimate Annual Review over four years ago when I conducted my very first annual review for 2019. From then on, the exact sequence of events starts to get a little fuzzy. I vividly remember his essay on burndown, the feeling of being out of alignment, and feeling seen during a time when I felt lost, guilty, and ungrateful for no longer wanting to stay in my well-paying tech job. Fast forward to January 2023 when I wrote about quitting my job and I was pleasantly surprised to see my essay linked in his newsletter.

Despite coming from different backgrounds and being in different stages of life, we share some similarities. We’ve both navigated and written about our respective work-life transitions. For Steve, he achieved the coveted Partner role in VC before realizing it wasn’t his calling. For me, I got promoted to Senior PM in less than two years and came to a similar conclusion. I’ve always appreciated Steve’s willingness to openly share his most vulnerable moments. It’s these types of stories that resonate the most with me. And when it comes to coaching style, I prefer his grounded approach that still leaves room for free-spirited contemplation. It’s how I’d like to model my own coaching practice.

We met up over bagels in NYC in December and kept an open dialogue as one year transitioned into the next. A few conversations later and here we are. While I’m super excited for this apprenticeship to unfold, I’m trying my best to view it as an experiment, like with anything else that feels energizing, important, and also uncertain. From my prior experience with uncertainty, I’m learning to trust that things have a way of working out and accept that not knowing is not bad.

I’m intentionally beginning my coaching journey this way because I have a ton of respect for the discipline and I’ve seen what it looks like to excel at this craft. I humbly recognize that the journey is long which is why I’m taking a learn-first approach from someone who knows what they’re doing. Taking this first step is also a commitment to continue “doing the work” myself. I may have already figured some stuff out, but I also recognize there’s still so much to experience.

Over the coming months, I intend to explore and launch my own coaching practice. Whether you’re new or have been following my journey for a while, if you’re interested in working with me, please don’t hesitate to reach out! I’m currently coaching a small handful of high performers and am looking to gradually expand my practice over the next few months.

In the meantime, I’ll continue working on my existing projects and begin helping Steve with an exciting new project that will be announced shortly. I’ve taken a sneak peek and believe this is something much needed in the current world we exist in. I’m grateful to Steve for the opportunity as well as all the other coaches who played a role in my explorations.