coaching / coaching-journey · article
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Jason's Coaching Journey

Jason's path into coaching was not planned. It began through openness and circumstance — a volunteer shift at a free coaching event, a chance to sit in on a session — and unfolded over more than a decade of being coached, watching coaches work, and eventually coaching others. Each coach he encountered taught him something different, and not always what the coach intended. The journey from first client to professional practice is a case study in how conviction is built: slowly, through real experience, through failure, and through the willingness to sit with discomfort that has no easy resolution.

Coach 1: Caryn (2010)

In 2010, Jason was working at an early-stage startup in San Francisco, sharing an apartment with co-founders, making around $60,000 in one of the most expensive cities in the country. Craigslist was hosting a mini-conference, and his roommate Kalvin figured out that volunteers got in free. Jason ended up checking people into a free coaching station — rows of white chairs, one for coach-in-training, one for client.

At first he assumed it was career coaching. When the coach he sat down with clarified that it was simply coaching, his curiosity was piqued. He started asking questions about the process, and the coach redirected him: "This session is really supposed to be about you, not me." Within minutes, he had set an intention for himself: before he could be something, he probably needed to experience it firsthand. He asked if he could sign up for a session of his own.

He found Caryn through a form posted by coaches-in-training offering affordable rates. Co-Active coaching. He reached out to a couple profiles and chose her quickly — partly because her voice made the decision easy. He described it as "the late-night FM DJ voice that FBI hostage negotiator Chris Voss talks about" — low, warm, alternately curious or firm, a voice that communicated presence and safety in equal measure.

Sessions ran every few weeks, just twenty minutes at a time, by phone. He would take the calls walking through San Francisco with wired headphones, sometimes from a rooftop he wasn't supposed to access, gazing out toward the Mission and Dogpatch. The constraints were severe enough that each session demanded a focused intention. Progress required both parties to cut to what mattered.

What they worked on over two years: family anger patterns, particularly with his mother; dating and the feeling of being left behind as friends started companies; and professional ambition that had not yet found its container. Two sessions stand out.

The first: Caryn challenged him to quit his job and start a company within three months. He pushed back, asked for more time. He ended up launching a startup six months later. The challenge came at exactly the right moment — not because it was news, but because having a trusted person articulate the move and put a stake in the ground made it real. The well-timed challenge from someone you trust has a different quality than a decision reached alone.

The second: a Future Self visualization. He imagined himself in a high-rise apartment in New York City, married, with a daughter, working from home. Six years later, most of it was true. The exercise was not magic — it worked because it made a concrete picture out of vague aspiration, giving him something to navigate toward rather than just away from.

Key learning: coaching begins before the technique. The quality of presence and voice that made him trust Caryn in the first five minutes is what made every subsequent session useful. "People will forget what you said but they will always remember how you made them feel." He carried this forward.

Coach 2: Hamilton

Hamilton was a Y Combinator peer — Harvard Law to founder to coach. The model was simple and transactional: $150 per session, focused on concrete business problems.

The practical value was real. Hamilton helped with product-market fit thinking, fundraising positioning, and investor prep. He conducted a 360-degree leadership assessment, interviewing a co-founder, an employee, and an investor to surface Jason's blind spots. The structure was clean and the focus was useful.

But something was missing. Jason's own phrase: "I yearned for a greater sense of depth." He asked Hamilton directly to challenge him more. The challenge did not come. The sessions continued to be useful but stayed at the level of strategy and execution, never going deeper into the psychology beneath the decisions, the patterns beneath the behaviors, the identity questions beneath the business questions.

This experience clarified something important: the ingredients of effective coaching are not reducible to competence and structure. A coach who is technically skilled but unwilling or unable to push into uncomfortable territory provides a useful service but not transformative coaching. The willingness to go somewhere the client hasn't asked to go — and to do so with care rather than aggression — is a distinct skill, and not everyone has it.

Key learning: support and structure are necessary but not sufficient. The difference between a good advisor and a good coach is the courage to engage with what the client is avoiding.

Coach 3: Shruthi

When Jason was looking for a third coach, he had two finalists. One was a self-described "performance coach" with a spreadsheet-heavy system for tracking goals and habits. The other was Shruthi: a former PwC consultant, coaching from India, with a quieter and more exploratory approach. He chose Shruthi over the spreadsheet because, as he put it, "I couldn't see myself getting excited about a spreadsheet." The preference itself was revealing — he was choosing feeling over systems, presence over process, which turned out to be exactly what he needed.

The Kay Supervision Case

The richest and most psychologically complex material in Jason's coaching development came from Shruthi's supervision of his work with Kay. Kay is an autistic and ADHD founder — a former co-worker, a fellow founder who raised from the same investors, a sibling in the portfolio. She reached out to Jason partly because he had been open about his own ADHD, and that disclosure had signaled that she would not be judged.

Jason's default when Kay presented challenges was to bring ideas, frameworks, and paths forward. He was trained by his own history to see a problem and generate solutions. Shruthi challenged him: what might it look like to support Kay without diagnosing the situation, without suggestions, just asking questions?

The question hit immediately. "I feel stuck now. Frustrated. Like I don't know what to do. I don't have an answer." He recognized in his own reaction the exact discomfort he was trying to relieve in Kay. He felt like this was a test, and as a coach he was supposed to know how to do this — but he didn't.

What Shruthi surfaced through this challenge was a pattern of identity-specific obligation. When Jason coached his corporate executive client — someone from a different industry, a different level, a different world — he was comfortable not having answers. He wasn't supposed to have them; his job was to be a partner and ask good questions. But with Kay, the shared markers (neurodivergent, YC, founder, immigrant experience) created an implicit expectation: someone like me should be able to help someone like her. The comfort with not-knowing was conditional on not-belonging to the client's category.

This paralleled something real in Kay's own team dynamics. Kay often had a system in mind and was willing to consider alternatives, but suggestions sometimes got batted down and no one knew what to do next. The circle of struggle: Kay didn't know, her employees didn't know, Jason didn't know. Maybe Shruthi didn't know either. The question was what to do in that conundrum.

Shruthi's framing: "To have an answer is to close your mind to what is possible." The right question, held open, forces harder thinking than any answer. Answers foreclose possibility; questions extend it.

A shame sequence opened during this session that Jason described in striking detail. He recalled a moment helping a friend review materials: he hadn't read everything closely, and some recommendations he made had already been addressed in sections he skipped. It became obvious. The feeling that followed was "a big sinking hole in my chest — an inky blackness that led to a swamp of goo." The shame of not being good enough, not having done the work, not deserving the trust. The intensity of this reaction in a relatively minor situation revealed how much of his coaching identity was bound up with the need to be competent and prepared.

The breakthrough was practical rather than cathartic. They developed a checklist: six questions Jason could ask himself to assess whether he was doing a good job as a coach. The list shifted the standard from "did I have an answer?" to "am I operating according to my own standards?" If the answer to those six questions was yes, he could be at peace with not knowing. The checklist was not a solution to the problem of not-knowing; it was a way to be okay with it.

Key learning: the places where you feel you should know are the places most worth examining. The obligation attached to shared identity is a specific kind of pressure that creates specific kinds of distortion. And presence without answers can be more valuable than answers delivered without full presence.

The First-Year Drought

The first year of Jason's coaching practice ended with a two-and-a-half-month drought between new clients, accompanied by two existing clients requesting pauses. Both cases taught him something.

Talget — an ex-Google, Amazon, and TikTok founder — paused the engagement. Jason suspected he had pushed too hard for results, had been too drill-sergeant when Talget needed more space. The relationship had not broken; it had strained under the wrong style of engagement.

Amit — a weight loss coach — left a voice note that hit harder. He said Jason reminded him of his father, and not in a good way. The directness that Jason understood as a coaching strength had felt, to Amit, like something more controlling and critical. A style that works well with clients who want someone to push them is actively harmful to clients who need to be met with more gentleness first.

The drought forced an honest reckoning: adaptive coaching style is not optional. Some clients want a drill sergeant. Others need a thought partner who will follow rather than lead. A coach who does not modulate approach will reliably push the wrong clients too hard and under-serve the ones who needed more.

The learning did not require abandoning directness — directness is one of the consistent things clients value. But it required pairing directness with better calibration of what each client actually needs, and being willing to ask rather than assume.

Trust as Foundation

Every coaching relationship Jason describes — being coached or coaching — was built first on trust. Caryn earned it through the quality of her presence and voice in the first session. Hamilton earned it through shared context and YC experience. Shruthi earned it through her willingness to challenge him precisely where he most resisted being challenged.

His own client attraction mirrors this understanding. He leads with personal disclosure — ADHD, immigrant background, startup failures — not as a marketing tactic but because clients who identify with those markers are the ones for whom trust comes quickly and coaching can work. Fit is not a nice-to-have; it is the prerequisite through which all other value is delivered.

The through-line across all three coaches and all the client relationships: the most powerful interventions happen inside a relationship where both parties feel genuinely present with each other. Technique follows trust. See coaching-philosophy for how these experiences shaped Jason's beliefs about the work.

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