Inspired by our insight that conviction is fundamentally based on building intuition, and while objective reason and logic can help facilitate the building of intuition, they aren’t enough on their own, we set out to accelerate people’s existing methods for building intuition.

One common approach we discovered was reaching for Apple Notes or Notion right away whenever they feel anxious, uncertain, or overwhelmed due to low conviction. People would dump their raw thoughts into a note, and then iteratively edit and restructure the note as a means of organizing their thoughts. Once their thoughts were organized, they’d often share their thoughts with others for validation and perspective, before returning to update the same note.

Inspired to meet users where they are and not require any new behaviors, we began designing and building a notes app that processes and reorganizes your raw thoughts for you, validates your reasoning that makes sense, flags your assumptions that should be questioned, connects your thoughts back to past notes to keep yourself honest, and suggests new perspectives and approaches, all to accelerate the rate of intuition building.

This is an active work in progress!

After observing that 90% of users across Pondry, Forge, and Coaching were grappling with their career direction, we began building CareerRPG, a product that conversationally understands your latent career motivations and values, before recommending a career direction tailored to the user.

By tailoring the experience specifically to career direction, we were able to give the product a clear identity that users could intuitively understand, and also tailor the questions and follow-ups asked during the initial context-gathering phase to be extremely high-signal and relatively low effort.

The main user feedback validated this move, with users remarking that CareerRPG was fun and delightful to use, taking at most 10 minutes to share context about their current career situation. In addition, the inferred career values that were returned strongly resonated with many users.

The values it identified are actually very good. I read it and felt ‘ok, this is actually how I feel.’

It extracted core values from my rambles, some of which surprised me because I hadn't articulated them before, but resonated with when I saw them laid out.

However, not every career direction suggestion was compelling, and even when they were compelling users did not leap into pursuing them.

We realized from user feedback that CareerRPG is compelling because it promises to turn a traditionally subjective question (“What career direction would I feel fulfilling to me?) into an objective question with an objective, “best” answer that can be “rationally deduced.” All our users were people who instinctively build their intuition through reason and logic, rather than trusting their gut and intuition.

We also realized that even when CareerRPG was able to suggest a compelling career direction, users never seemed to gain the conviction needed to take action. After investigating more, our takeaway is that conviction is fundamentally based on building intuition, and while objective reason and logic can help facilitate the building of intuition, they aren’t enough on their own. Thus, CareerRPG needs to be supplemented by a method to rapidly build intuition.

We focused on preserving Forge’s ability to identify remarkable resonant core values, while making the experience of sharing context much more light weight and conversational.

We went through four rounds of user feedback and iteration before reaching a state where users reported enjoying talking to Pondry, and viewed it as a “neutral and objective third party” to talk to and build conviction with.

The main breakthrough was making sure the flow of conversation is primarily led by the user instead of by our product’s prompts/questions, while still nudging users towards the remaining topics we need them to cover to infer their core values.

We were starting to run into inefficiencies in the user experience that stemmed from trying to keep the product generic. It was becoming clear that further leaps in user delight and ease while sharing the context required to infer values would only be possible if we began tailoring the experience to specific types of decisions.

When we checked, we observed that over 90% of usage across Forge and Pondry could be summarized as “what should I do next in my career?”, even though both tools were framed as generic aids for building conviction in life.

We recognized that the most consistently valuable step for users across all our work so far was helping them uncover and understand their latent motivations and values.

We also recognized that because core values are latent, they are most effectively identified through inference upon detailed context gathered about specific situations that are being impeded by low conviction.

We then first derived a series of high-signal questions, and then set up an LLM to infer values from the answers. Both steps heavily incorporated on our insights from coaching, the handbook, and the workshop series.

After several rounds of user feedback and iteration, we shared the product publicly at MIT PI Reunion in Vegas (July 2023). We had 300~ visitors to the side with a <50% bounce rate, and average duration of usage above 40 minutes, which felt strong for a new single-player experience.

The main pro we heard was that the core values uncovered and returned felt remarkably resonant.

The main con we heard was that the 30-60 minutes of responding to introspective prompts that was required to generate those core values felt very painful, almost like forcing themselves through an intervention.

Another con we heard was that it was unclear how to practically apply their newfound understanding of their core values.

So our next step was to shrink the time and effort required to uncover the user’s relevant core values to lower the friction.

Working on the Inner Compass Handbook meant we had more structure to our exercises, and needed to be less hands-on when guiding an individual through our coaching framework. Thus, we wanted to explore how effective our conviction building method was in a one-to-many group setting.

We hosted a four-part workshop series where we would focus on contextualizing introspective exercises, sharing examples, and then giving participants time to try to the exercise themselves, before reconvening as a group to share insights and answer questions.

The workshop series had strong attendance and retention across the four parts, and solid ratings afterwards. Most attendees reached out asking to be included in our user research sessions for future prototypes.

The workshop was effective for people, even though the experience was not personalized for each person 1-on-1. This revealed to us an opportunity to deliver an impactful experience through a semi-structured experience.

We repackaged our Inner Compass framework that we developed for our life and career coaching service as a self-serve handbook with explanations and interactive exercises.

Went through two major iterations based on feedback from user-research sessions, which led to improving the framework contents itself, the pacing and structure of the handbook, and the quality of the exercises.

Many people bookmarked the handbook, but few moved through it quickly. We realized that building a handbook for conviction building was akin to asking someone to self-study a subject from a textbook without any assistance or guidance.

To make our approach more approachable, people need a guide to walk them through the material, hold them accountable, and ensure they internalize each step before moving on – similar to a tutor or TA for an academic class.

Using our essays from the Inner Compass Blog as a top-of-funnel, we launched a life and career coaching service to help compelled readers apply these principles in their lives.

We built a multi-step framework called “Building your Inner Compass” for uncovering your latent motivations and values and understanding how to incorporate them into your life decisions.

We regularly met 1-on-1 with several clients for a few hours a week to guide them through our framework, and also gave take-home exercises and reflections between meetings.

Based on feedback from each meeting, we iterated and improved our framework and its materials.

When it comes to building conviction, working with people 1-on-1 is crucial to bridge the gap from general and theoretical to specific and actionable.

However, the economics of 1-on-1 coaching are hard to sustain, and create incentives to work more with wealthier clients (such as CEOs).

Also, the form-factor of 1-on-1 coaching is not as reactive as clients would like. When they experience acute moments of stress, uncertainty, or overthinking due to low conviction, their coach is not always available.

To bridge this gap, people need affordable, self-serve methods to get similar value.

After shutting down KAP, we wrote essays about the core insights that were most prevalent in our psychotherapeutic materials.

We circulated the pieces to our network, and they spread organically.

One specific piece was particularly well received (How to make decisions when there’s no best answer) – multiple people I didn’t know wrote in to express gratitude, and I learned that a group of friends had held a dinner party to discuss it.

People resonate with the need to find better methods for building conviction.

Writing is an effective top-of-funnel, but it’s often not enough to change people’s behavior. To bridge the gap, people probably need personalized, hand-held support to navigate their personal circumstances causing them low conviction.

Inspired by the rapidly emerging clinical research and evolving policy around psychedelic medicine, we set out to build At-home Ketamine-assisted Psychotherapy to help people navigate acute existential crises.

Operationally, I fully set up Resa to offer KAP, including onboarding key medical doctors, establishing an MSO-PC corporate structure, establishing our medical protocol, getting foreign-qualification in three states (FL, NY, MO), securing corporate and medical insurance, securing a partnership with a reputable compounding pharmacy, hiring MAPS-certified LCSWs to deliver state-of-the-art psychotherapy guidance for KAP patients, etc. On the technology side, I built out an in-house, fully-compliant EHR and online patient portal to support and guide the entire psychological patient journey through Ketamine-assisted Psychotherapy, complete with KAP-specific introspective exercises.

Began fundraising with VCs. Had many meetings, and the thesis resonated as something clearly needed. But the concerns were around whether KAP was the right solution for this problem, and the legal and compliance risk.

Launched a waitlist. Reached 1000+ signups, but most signups were here because they saw a documentary on Ketamine and wanted access to Ketamine, with no interest in the accompanying psychotherapy support.

Consumer perceptions of Ketamine and psychedelics are too noisy to build a focused service for building conviction and finding purpose. Also, the regulatory landscape became difficult as the relaxed regulations around the remote practice of medicine were reverted.

Decide to wind down KAP and take the insights we had amassed on the psychotherapy front to explore other paths.