On Becoming The Seeker Again

the challenge of integrating money and meaning

After months of debating and contemplating different paths towards long-term financial wellbeing, I've found myself in a state of boundless exploration that feels both exhilarating and frightening. Over a month ago, I began looking for new work opportunities to complement my coaching practice. I say "work opportunities" instead of "job" because although I'm open to getting a full-time job again, I'm also exploring things that don't fit in the traditional box of what a job is. When I made this decision a few weeks ago, I hesitated to write about it. The vulnerability felt uncomfortable, but wise advice¹ encouraged me to lean into that discomfort and share my experience openly.

The Journey to This Point

My actual sabbatical took place in 2023, but it feels like I'm on sabbatical again. The only other time I felt this way was in spring 2019 during the liminal space between having graduated but not yet having started my first job. In 2019, with the security of a job lined up, the time wealth of an empty semester, but also a somewhat empty wallet, I ventured outwards to see the world. As I visited China, Taiwan, Peru, Patagonia, and Indonesia, there was a desire to seek, understand, and immerse myself in experience.

After a yearlong sabbatical, I ventured into the world of coaching. It's hard to pinpoint exactly when I knew coaching was the path I wanted to be on. I don't think I ever knew, so maybe hoped is a better word? The reality was that cold hard facts and lack of evidence should've deterred me, but curiosity pulled me forward because it was as exciting as the first time I put a blindfold on trying to hit a piñata at a birthday party or when I tried to paddle for my first wave. I was so fervently focused on learning about coaching everyday that the inability to see where this path would lead disappeared from my awareness. In other words, at some point, I stopped worrying about the future.

As I danced with uncertainty and eventually stumbled into coaching, I never once sat down to write a business plan for how this new venture would fully sustain my lifestyle. I'm actually glad I didn't because it was my youthful naiveté that allowed me to continue down a path that many don't dare to explore until much later in life. The same naiveté, however, meant that I gave little thought to my financial future. I simply assumed that coaching meant being a solopreneur with my own business.

Fast forward 18 months to today and a lot has happened. I've completed an apprenticeship, started my own coaching practice, and also begun training in somatic psychotherapy. I'm proud of the progress I've made, yet also aware of the practical desires I have. I'm currently earning enough to cover living expenses with a tiny bit leftover for savings, and that feels pretty good considering I started my own practice less than a year ago. But it also doesn't feel like enough to be completely comfortable and that results in a complex blend of emotions.

Making the Decision to Recalibrate

I feel excited about where my coaching practice is headed, but I also worry about money. There's a sense of satisfaction with my coaching practice and a dissatisfaction with my coaching business. I think it's better to be brutally honest with myself and take the nail out of my head² rather than parade around in a mirage of delusion. But the quality of the dissatisfaction comes along with acceptance and surrender. It's like being in a kayak. I must flow with the river while remembering to paddle intensely at times³. I think it's okay to not be okay with certain aspects of life as long as that's met with a sense of agency and trust (in oneself and the universe/choose-your-god). Sugarcoating problems only leads to avoidance.

My original plan was to wait until I had a new gig figured out to share the news. But as I kept pressing down on the gas pedal, it felt like I was fighting gravity in a vacuum chamber of compressed time. As I turned inwards and felt the resistance, I uncovered subtle layers of shame and sadness. I worried about being perceived as if I'm quitting or failing. I’d often oscillate between blindly hoping for a miracle or telling myself I needed to lock in, turn to growth hacks, and sell sell sell. I’m aware that it’s a false dichotomy, but I just felt something needed to change. The financial reality is undeniable. I haven't generated the income I need to sustain my lifestyle long-term.

As I've unpacked this, I've come to see how I was projecting other people's opinions onto myself. After all, aren't we all looking for a great story? The story of the underdog who surmounted great odds or the boy who left home on a grand mission and returned as a hero. Whether I like it or not, the storyline can only be seen in hindsight. In the present moment, it's messy, ambiguous, and unpredictable.

Approaching the Search Differently

So this time around, I'm really letting myself freely wander. I've been having many conversations with friends, former colleagues, and total strangers, with topics ranging from AI therapy to agentic coding to transformational communities. At first, I approached each specific topic or opportunity with a narrow self-presumed role like product manager or coach. When I felt like I had to choose a partial identity to present myself with, I felt like I was wearing a mask, which led to frustration at both myself and the other person for me not feeling fully seen. It's an ongoing process, but I'm learning to show up as my full, whole self which is daunting, but also essential.

Dropping seemingly unrelated little bits of myself in conversations has led to some unexpected twists and turns. For example, I mentioned to a recruiter that I was learning about the senior caregiving industry and then she told me about how her mom used to be a hospice worker and since her dad traveled often for work, as a little girl she'd go with her mom on late night visits to patients. Even though she focuses on recruiting in the tech industry, we ended up talking about skiing and coaching too. This openness creates authentic connections that transcend transactional networking.

This period has also helped me reconnect with my intellectual curiosity for how to solve big problems with tech. When I step back and look at my arc for the past few years, I spent my early career in tech, but without many human skills. Since leaving the tech industry, I've been more focused on what it means to be human, both from a personal perspective, and also in my coaching work, which is human-to-human with minimal tech. The next chapter of my career is about integrating scalable problem-solving with deeply human, relational work.

In my free time, I've been learning about AI and heavily using tools like Claude, Perplexity, and Lovable. What's most fascinating is the speed at which all of this is happening. When I was an EECS student at Berkeley, I enjoyed learning computer science as theory, but could never get myself to enjoy coding because of how frustrating it was to debug and meticulously ensure there were no syntax errors. So much of what kept me from pursuing a career in programming has now been abstracted away by AI. The gap between idea and creation is only getting smaller, and that excites me as someone who has a lot of ideas, but not a ton of patience for getting every little detail figured out. The rapid change we’re seeing now in technology, politics, and the economy align with my personal evolution. As the world increases in chaos and complexity, I’m intentionally positioning myself to be adaptable, resilient, and agile.

Navigating Uncertainty Mindfully

Wading in the knee-deep murky waters of uncertainty is still challenging despite my familiarity with the unknown. With my Enneagram 6 and 8 personality, I instinctively believe I can control outcomes through sheer willpower and grinding harder, but that approach consistently fails me. What actually works is opening myself to possibility through concrete actions: asking for help, reconnecting with people, and documenting unexpected opportunities as evidence that my predetermined plans rarely manifest as expected. When I first entered this transition, I reflexively set deadlines and timelines, trying to minimize uncertainty just as humans have evolved to do. But the complexity of finding meaningful work in 2025 defies this caveman-like approach to problem-solving. Instead of fighting this reality, I'm accepting that I'm not fully in control while maintaining forward motion through an easeful yet deliberate pace. Rather than letting stress and fear propel me, I'm anchoring myself in the deeper meaning and purpose behind my endeavors.

At the start of my search, I caught myself replaying a past pattern of making the job search more stressful than it needs to be. I’ve only had to look for a job twice. The first time was during senior year of college when I was dealing with betrayal that resulted in me wanting to graduate college ASAP with something to show for. The only other time was during the peak of the pandemic after I got laid off with less than a full year of experience. With the awareness that this time doesn't need to be like the past, I’ve begun to look at this next chapter with fewer assumptions. Instead of being default driven by anxiety, I’ve taken a step back and recognized this period for what it actually is: a blank canvas opportunity to find meaningful work that supports me while allowing me to contribute with my unique strengths and skills.

Money and Meaning: A New Relationship

It's hard to explain what I'm going through right now. I'm not winding down a failed startup or quitting a passion project. What I'm experiencing isn't so much a transition as a recalibration. I'm releasing the pressure to earn a full-time income from coaching, but the practice and it’s meaning in my life continues uninterrupted. I'm intentionally choosing to create space between money and meaning.

This separation feels like a necessary step in the evolution of my practice. By creating distance between the practice itself and financial constraints, I’m creating room for growth. I get inspired just thinking about what might emerge given a few years to incubate, develop, and nurture my practice in a conducive environment. I’m focusing on the present situation, but I have a clear vision for where I’d like to steer towards, in terms of work and how I want my life to be.

It's also strange because I sort of did it out of order. Usually people start to explore ideas and tinker with experiments when they're still employed. With the stability of a job, they spend their nights and weekends bringing something to life and seeing if it "has legs". My friend who's a full-time content creator was posting TikTok videos for over a year before quitting his job. Other friends who have started their own companies don't leave their jobs until they've secured funding.

In my case, with the benefit of hindsight, I don't actually see how that could've been possible for me. It's almost like I had to leave full-time work for two years in order to get to where I am now. I was carrying a heavy backpack of frustration, confusion, and hopelessness, a burden that only began to lighten once I stepped away and consciously set it down. Towards the end, I internalized resentment towards other people and the company. It took time and space to unwind that and realize that all the negative emotions I was experiencing were self-created. With this newfound clarity, I've come to appreciate everything that I had in my previous jobs while also accepting that it was the right time to leave.

By seeing how I was the creator of my mental prison, I've been able to own what's mine and absolve the externalities from blame. There's nothing inherently wrong with working a full-time job or being a product manager. Having walked this path myself, I now understand what it takes to navigate similar terrain. This firsthand experience is essential, as there's no other way to guide people in the wilderness without having spent time in the wilderness yourself.

At its core, what I’m going through right now reflects what I see so often in others. We think it’s the job we work, partner we date, boss we report to, or city we live in. But it’s so often not just the external thing that is creating the problem. It’s how it’s paired in combination with the inner conflict. That’s why when we actually get what we want, whether it’s the addition of something new or the removal of some existing thing, it rarely feels as good as we imagined. That’s because the essence of what we actually want is a feeling of safety, security, belonging, and freedom. It gets down to our beingness⁴, the quality of our present experience. And that’s something I’ve had to remind myself over and over again during this period.

The Beauty in Uncertainty

With the speed of modern society, it can often feel like we need to approach liminal spaces with a specific objective and timeline, but from the past month, this strategy has only led to urgent grasping and unnecessary suffering. I'm learning that this recalibration isn't about failure, it's about adjusting course on an uncharted journey. The path I sought with coaching looks different than expected, but that's okay.

Staying on the path means being brutally honest with myself about what is actually not working while also not shaming myself or sulking in gloom about it. I'm creating space between money and meaning, not because there's anything wrong with trying to monetize meaningful work, but because forcing it has created friction that doesn't serve me. By allowing some separation between financial demands and my coaching practice, this craft I intend to practice for decades has room to evolve naturally.

What I'm discovering is that coaching skills aren't confined to formal sessions. It's a way of being I can bring into any workplace or conversation. This integration of tech knowledge with human understanding feels increasingly important in a world where these domains are often separate.

As I continue my search, I'm focusing on contribution rather than urgency. What can I offer? How can I serve? These questions feel more authentic than anxious timelines or expectations. The uncertainty is still there, but so is the possibility.

For me, this isn’t about escaping discomfort. It's like hiking a challenging trail where I've accepted the blisters and unpredictable weather as part of the experience. Some moments I'm catching my breath, other times I'm standing in awe at a vista I never expected to find. I still feel the uncertainty of what lies ahead, but there's also a strange sense of beauty in the depth and richness of seeking something new. I'm learning to trust my footing even when the path isn't clear. Coaching has evolved from a casual walk to a never-ending adventure, challenging and rewarding in ways I couldn't have imagined. The mystery is the invitation, the rawness is the teacher, and the wonder comes from embracing both.

1. Thank you Tom for the conversations and also for putting yourself out there!

2. I’m referencing Graham Weaver’s talk: How to live your life at full power

3. This metaphor of balancing action and surrender is very Taoist and I’ve heard of it from multiple people, including Andy Johns and Ling Lam.

4. For more on beingness, check out this podcast episode.