Beginning to dream again

a dialogue with myself

I’m sitting in my favorite coffee shop, Qahwah House on Bedford Ave, remembering how to dream.

I’d like to begin dreaming again, now that I know the power of competence and skill. The goal is grounded idealism. Tactical and imaginative.

I think over the last two years various voices have been at war within me, keeping me from dreaming. Let’s bring this onto the page. I’ll structure this as a dialogue.

***

Voice (multitude): What does it mean to dream? What will dreams bring you?

A sense of purpose. A sense of excitement. That my work matters. That I know what I am to be and do on this earth.

Voice (spiritual): Your assumption that there is one purpose for you on this earth is myopic, and your restlessness is something to heal, not something to listen to. Be part of this moment.

Voice (unknown): Your sense of what is meaningful to you has changed over many years. What makes you think you can even find it?

Yeah, you’re right. Maybe there isn’t one. But… still, I know there are times in my life where I’ve felt fulfilled by my work, and times where I haven’t.

There seem to be two kinds of fulfillment - the fulfillment of busy hands weaving and crafting, and the fulfillment of dream and vision.

I remember the latter has come most alive when creating the CommonHealth Project. I literally was working all hours, all ways, and all of my skills came alive. I was talking to so many people, dreaming and leading and convincing and executing. And it’s probably my proudest achievement to this day. I knew what I needed to do. And in fact, I burned out and got depressed when we lost control over our own destiny, when it became routine, and also probably because I was staring medical school in the face.

Seems like the question that I’m asking is:

Voice (unknown): If you were so fulfilled, why did you burn out?

Voice (distraction): This is getting pretty uncomfortable, you should switch windows and go down a rabbit hole about Chamath Palihapitya, starting with “below my line.” Wikipedia says that he moved to California to follow his wife, and then they divorced, and now he’s married to a young model - what a messy situation wealth puts you in. If I was ever that wealthy, would my relationships be a wreck? I wouldn’t want that to happen with S. We’re doing the work right now to forge a strong relationship.

Phew. Felt really good to own that. Anyway. This coffee is really hitting huh?

What scares me so much about examining that period? Is it because I haven’t felt that energized about a project ever since? I wonder what M, what S would say to that. I wonder what would happen if I asked them about it, if it’s really true.

Actually, I think I did ask them about it, back in 2023 during my sabbatical. I asked them when they’ve seen me come alive.

a response from M

It’s not quite the same as what I’m examining now. For better or for worse, I’m trying to examine the moments in my life where it has felt like my entire body and soul was aligned toward a mission. It’s not the same as the joy of busy hands crafting. I’ve observed that at many jobs - as a product manager writing briefs, as a designer creating prototypes, as a software engineer shipping code. Here are moments of creation and work that I love:

Modeling systems and problems. Mathematics, software engineering, electrical engineering, computer science, control systems. Holy shit I absolutely love planning an app, where I start with the data models, then the controllers, then the routes, then the frontend components, and the APIs, etc., until I’ve essentially built the full representation of the application on pen and paper. I absolutely love describing problems as a system of equations (although I don’t do this enough and want to get better at it) like when I completely over-engineer growth pipelines at multiple companies.

from my notes from the other day

Taste-driven, opinionated curation. Making a playlist in Spotify, making a design in Figma, making music in Ableton, jamming with friends. I love that completely intuitive process where the words and gestures and decisions leap from my gut. “this goes here, this goes here, this goes away, not at all, bring me more of this, i love that, thank you that’s perfect.” Jon Bellion in his studio is who I want to feel confident enough to be.

from my twitter

Creation and publication - delivering something from start to finish. Game dev, software engineering, design, professional and personal writing. I love the process of bringing something to life and showing it to other people. I love to ship demos and post about them on Twitter. I make killer product briefs with awesome diagrams.

from my blog

Connection, humanity, teaching - being raw and opened, in contact with what is so beautifully and messily human, learning from experienced people how to connect with and guide kids during their development. I’m chasing the deepest human questions, and what binds us - it has everything to do with On Being, Priya Parker, the documentary HUMAN, clowning, StoryCorps. There’s a podcast for me to start, an interview series, a documentary.

from my twitter

Nature, art, cybernetics, Ways of Being - the beauty and awe, the sense of dissolution that I have when I’m in nature and in connection with some deeper truth of the world. A reminder that I was born a part of something greater than myself. Ways of Being has inspired this most deeply - the antidote to alienation from myself and from technology. I feel tension in my face loosen even when revisiting my old creations here. There’s something stable and true for me here, a deep lodestone.

from a small digital installation

Voice (fear): How do you know you will ever find that mission again?

Voice (problem-solving): How do you set yourself up to be struck by a mission once more? How did you do it last time?

Definitely did not sit on my hands and wait for it to come. It was the right confluence of an impactful moment, a team and people that I had already connected with, a skillset and an orientation. The first startup I worked on at our university incubator was called Ember - futzing around with “Twitter for ER docs” and worrying chiefly about the name and equity split of the company. As soon as the pandemic kicked off my team dropped it immediately to work on the CommonHealth Project. We were in the right place, with the right people, to respond quickly.

Voice (problem-solving, impatient): So how do we get lightning to strike twice? Is it more… waiting around? You’ve kind of done that so far and it hasn’t hit you yet. How will you know?

I think an important observation to make here is that there’s no one thing I’ll want to do for the rest of my life. That’s an unfair expectation to place on any mission I’m excited about.

Also important to delineate here between Mission and my Purpose. My Mission is a specific manifestation of my deep, inner Purpose. I might be excited about a particular Mission for several days, months, or years, but it’s a product of external circumstances combined with an expression of my deep Purpose, what my unique gift is to give on this Earth.

But an expectation I do want to place is that my mission will bring me alive. For J at ESAI, she said that she was pretty much manically focused on bringing it to life. I see it with M, too, for our potential company. Me and J are kind of half-in, half-out right now. Maybe this could change, but… this is the Mission that M wants to accomplish, and that’s not how it feels for me at all. I guess it’s possible that I could fall in love, or that there are other kinds of blockers that keep me from embracing it.

Voice (skepticism): Remember when you were “on sabbatical” or “taking a break” and just didn’t do much of anything at all? You felt resistant to work. Bootcamp, though scary and uncertain, ended up being the right choice after all. If you trusted your feeling of uncertainty too hard maybe you wouldn’t have done this awesome thing and would have floated around.

Yeah, maybe, but also that feeling of uncertainty was ultimately overpowered by the strong desire to get up and go do something, and by a bet on my desire to create. Maybe what I’m trying to say is… everything in its own time.

Voice (skepticism): But I’m trying to tell you that you might be throwing an opportunity away to build something really awesome.

Yeah, I guess that’s true. Idk. What’s another question I could ask here so that we can approach it differently?

What would have to happen for me to commit my life to this mission?

It would have to be building something really fundamental for patients, completely transforming their experience of the healthcare system. It would have to be a consumer app for patients. It would have to be in care navigation, or at least damn close.

Voice (shadow): And I would have to be CEO.

??? This is distressing. Why?

Voice (shadow): Because I’m afraid that I’ll get left behind in the exponential growth of startup success if I’m not a CEO. That I won’t build the investor relationships or the business skills required to succeed at future endeavors. That I’ll be in a lower agency position. That the “real person” that people will respect and want to do future business with will exclusively be the CEO.

Hmmmm. Is this actually true? The reality is that I come most alive as a leader and as a creative when I’m doing something I’m incredibly passionate about. Idk, I think that being CEO entails an attention to certain kinds of details that are just not as interesting to me and much better fit to M’s profile. He’s able to handle some of the hard stuff differently than I do. This is more of an ego thing. I feel like having a different title means I’d be less important. In reality I think that has much more to do with how we set up our relationship within the company.

But also, this gets at something - I need to feel like I can take up space. Like I have a mandate. For me, “CEO” is short for being able to think as big as I want, and be as opinionated as I want in my team. I notice that I can access those two things independent of the title. And I have other desires - like respect amongst my peers for the work I do and to build a network for future levered bets. I don’t need the CEO title to achieve this, I can just grab it on my own. The important piece is communicating my desires and intentions with my cofounders.

I’d like to take big swings in my life. Work on what matters to me. What else is my work for?

***

This is getting to be a long one. Open questions for next time:

1. What would it take for me to dream?

2. What would I dream about?

3. If I had to guess, what are three missions that could completely hijack my whole self for the next several months/years?

4. What makes me want a mission so badly? What makes it so I only reach my fullest expression when working on a Mission?

5. Notice that we started talking about dreams and now we’ve gotten to Missions. Let’s pause and take stock of that.

6. M responded and said that he hasn’t seen me come alive since the CommonHealth Project. Time to unpack that.

7. If I had to guess, what are three dreams that I can nurture for myself, outside of or part of my career? Completely separate from the question of how I would financially sustain myself. And engage in the full dialogue here.