Flight Lessons

aren.na block

“What’s the largest conversation you can have with life?”

– David Whyte

The call to adventure

Earlier this year I had a dream.

I was walking through downtown SF on my morning commute to work. The day was overcast and the surroundings were grim– far more intense than downtown has actually been recently. I arrived at the door to my office and as I reached for the handle I heard a voice. It said,

“Why spend the day in there when you could fly?”

Without hesitation, as if spring-loaded, I shot upwards through layers of fog, finally breaking through that gray blanket to feel the warmth of the sun on my skin. I spent the day soaring over SF. Cutting between skyscrapers. Reveling in the freedom of flight. Towards the end of the day, as the sun dipped towards the Pacific and bathed SF’s hazy air in a golden glow, I flew to Coit Tower and landed to watch the sunset. I felt there another being, hidden from sight. They conferred to me a degree– this was a graduation.

Then I woke up.

---

Later, while journaling at a cafe, I wondered at the significance of the dream. Did it have something to do with leaving my job? The question was like an undertow, pulling me out from shore, towards an unknown. Yes. The time had come, unexpectedly, to leave. Next I was hit by a wave of fear. I wasn’t ready.

I’d been leading design at Modern Treasury for over 4 years¹. Momentum was solid and I liked my team, my coworkers, and the problems we were solving. It was an exciting time and there was still more I wanted to do within the organization. But the undertow pulled at my heart. A line of questioning had begun to crystallize: “Am I holding myself back? What possibilities am I not seeing right now? What would a life of flight look like?”.

Fortunately the dream had come at the start of a weeklong vacation. I spent that week reading², writing, reflecting, and talking things over with my wife.

I was torn. The joy of flight sounded great and all but the fear of the unknown kept me clinging to a life I knew. What would happen if I let go? I didn’t even really know what I would do with my time. Surely I should know before taking this sort of leap? And what about finances? Bills? Healthcare? Fears around security and safety came up in full force.

I’m grateful for that week. I had the time and space to sit with my loops, parts of myself working hard to keep me safe. I had the space to attend to these parts. To be with them, to look at them, to understand them.

As I sat with the fears that kept me in the nest, along with the possibility of flight, something began to shift: for all my fears, I wondered, would anything be quite so bad as looking back at my life with the knowledge that I turned down this call to adventure? That I’d turned down the call to discover and live into the fullness of my being? How many years would I continue to choose safety? I longed for authenticity and knew that to fly, I’d have to start with a leap into the unknown.

are.na block

“Tell me, what is it you plan to do

with your one wild and precious life?”

– The Summer Day, Mary Oliver

At this point, it’s worth acknowledging who I am in the world. As a white man, I’ve been afforded privileges that many don’t have, specifically, freedom from institutionalized discrimination and significant access to all manner of support. So who am I to write about pursuing authenticity and purpose in work? What role does privilege play in this exploration?

I’m writing this because I believe that our human community– from the local to the global– would be bettered if more people listened to and followed their hearts. Instead, we live in a world where incredibly privileged individuals, disconnected from their hearts, cause an inordinate amount of suffering. If it’s easier for those with privilege to follow their hearts, why do there seem to be so few doing it? I’m not altogether sure.

That said, I do believe that each of us, at our core, possesses an innate sense of shared humanity. I believe that, in our truest selves, we would naturally hold one another with compassion and care. I furthermore believe that those with privilege ought to use that privilege for good. In fact, on a deeper level, I believe that if each and every one of us were aware of and connected to our truest selves we’d act naturally from a sense of love and fellowship.

I’m reminded now of bell hooks’s definition of love: the will to extend oneself for the purpose of nurturing one's own or another's spiritual and emotional growth. That will exists in all of us, and the path of authenticity is one of embodied loving.

All that’s to say: this essay isn’t a promotion of hedonism or a clarion call for everyone to quit their jobs. I don’t presume to know what your path is– I barely know my own. I do have a sense though that the path of authentic work is not self-serving. Rather, it’s liberative in nature, both personally and collectively.

As the saying goes, no one’s free till we’re all free.

are.na block

What follows is a collection of stories: challenges I’ve faced as I tested my wings, so to speak. There are 4 parts, laid out more or less as I’ve experienced them over the past few months. They are:

1. Navigating fear

2. Feeling my way

3. Trusting don’t know

4. Finding flow

Navigating fear

A card by Johnnie Jefferson that Miche got me around the time I took my leap of faith, available for purchase at Open Editions.

Inside of me there seems to be a steering wheel, along with a duality of self³: at my core there’s the me that’s calm, curious, compassionate, playful, present. In another word, there’s the me that’s love, that’s loving. Then there’s the fearful side: my limbic self, the parts of my psyche that are powerfully tuned towards survival. Fight, flight, freeze, fawn. When something triggers these parts, even something that is no threat to my survival, Fear flares up and reaches for the wheel.

While courage had helped me quit, I found that the fears didn’t disappear. For the first few months after quitting, fear was steering the ship. I white-knuckled my life. Stacked my calendar. Sprinted to get... somewhere. I created projects for myself, spun my wheels, but things didn’t feel right. Surely this wasn’t flight.

During this time, my therapist shared the poem “Lost” by David Wagoner, which ends with the lines, “You are surely lost. Stand still. The forest knows where you are. You must let it find you.” In the same week, another friend told me that, based on my Enneagram type, I shouldn’t rush into anything⁴. It’s all too easy for me to choose paths that would garner praise but are ultimately disconnected from my deepest desires. This struck a chord (or, more accurately, a nerve). I felt torn: there was a deep discomfort with staying still, but moving forward felt equally uncomfortable. What was I to do?

Naturally, I continued to I try to force things. I tried to manipulate the external so as to pacify the storm I felt within. I pushed on projects and collaborations and got nowhere. My efforts were stymied again and again. Creative choices would show their flaws in such rapid succession that I became discouraged, frustrated. None of the “work” I pursued felt like it was working. And in the sense of failure, of mounting pressure, I spun ever more.

People would ask me: “So what are you doing these days?”

By this, they wondered what I was doing for work. And I couldn’t quite say. If I was being honest, I’d have told them that I was lost. That I didn’t know what I was doing. But to admit that filled me with dread. To not know was to be in free fall. Out of control. I should know, I thought. The fact that I didn’t was wrong. So I’d say whatever I’d busied myself with that day– and I could sense the lack of resonance, internally and externally. More spinning.

Finally, one week at my meditation group, the speaker started her talk with a story about hikers lost in the woods. When hikers realize they’re lost, the majority of them push forward out of fear. However, the speaker continued, studies⁵ show that more often than not, rescues are successful when a hiker has been able to stay still, allowing rescue teams to more easily find them. The poem echoed in my mind: “You are surely lost. Stand still. The forest knows where you are. You must let it find you.”

So, frustrated, tired, and getting hit on all sides with messages to stop running, I made a resolution to stay still– to really get a sense of the woods around me.

Ok. I figured. Nothing is working. I’ll stay still until the path was clear. Until my fears pass through me. Until the woods find me.

are.na block

As it turns out, stillness, especially when working with fear, is a very active practice. Fearful emotions swelled and crashed like great waves on the beach of my being. Sometimes I was able to ride these waves, but more often than not I was wiping out, thrashed in the painful churn of fear.

But the more I remained in stillness, the more I got a sense of the waves. I started to see why staying still was so uncomfortable. In this time, I became more familiar with my fears: fears of not knowing, fears of financial insecurity, fears of loss, fear of loneliness, fears of fucking up. I started to see how much I’ve lived in fear. How I’ve sought pleasure to escape fear. How fears have kept me caged. It was hard to sit with. I was upset as I saw the ways I’ve lived from fear– the ledger of my life: debits and credits, fear and love. But over time, I also saw how, in trying to keep me safe, the fears themselves were acting from a sort of unaware love. As challenging as the individual fears are, the root relationship to fear– to avoid or to be with– may have been the most important shift. No blame, no vilification, no rumination. Just being with whatever comes up: fear, grief, pain.

I’m still learning how to ride the waves. A few practices and systems have been immensely helpful in the process of navigating fear:

• Meditation: Our actions dig the grooves of our being. Repeated over time, they create canals where we flow more easily. Meditation digs grooves of curiosity, equanimity, loving-kindness, self-compassion– indispensable qualities when exploring fear. Viktor Frankl said, “Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” Meditation makes more space.

• Internal Family Systems: The psyche is not a monolith. In fact, it’s fractal: a wholeness, made of parts, which themselves are made of parts. It’s parts all the way down! Internal Family Systems has given me language and methods for exploring and integrating the parts of myself, both in a therapeutic setting as well as in solo sessions. This podcast and this one are great ways to dip your toes in, as is the book No Bad Parts.

• RAIN: Recognize, Allow, Inquire, Nurture is a meditation practice for cultivating self-compassion. Combining this with parts work has led to some wild experiences and insights– frankly, it’s been psychedelic. Tara Brach has a ton of great talks and meditations if you want guided experiences– this is one of my favorites.

• Enneagram: The Enneagram is a personality system that, in the words of Josh Keefe, “doesn't put you in a box, but shows you the box you put yourself in and how to get out." For me, it’s been an incredibly helpful tool as I’ve sought to better understand and integrate my fearful parts.

• Open water swimming: Swimming in the frigid water of the bay– out where there are sea lions, whales, and sharks– kicks up some deep seated fear responses. I remember someone in the Dolphin Club sauna joking that open water swimming is like hopping back in the food chain. It feels that way sometimes. But it’s not nearly so dangerous as it feels, statistically speaking. Finding a practice that allows me to safely work with fear has been very helpful in building my connection to courage.

---

I recall now a teaching around stillness. I could have sworn it was from Alan Watts but I can’t seem to source the original. No matter. The gist was that, when you aren’t sure what to do, consider letting yourself pool as a mountain lake does. Do nothing but fill the present moment with your awareness. Explore the fullness of your being. Fill up completely through the expression of present-moment interests and desires. If you limit yourself you block the possibility of flow, so be wholly you. Lovingly erode the barriers that prevent your fullest expression– the ways in which you get stuck. It is in your fullness that you will find the flow of life, as a mountain lake finds the path of least resistance and flows again only once it’s reached its furthest boundaries.

That phrase– the path of least resistance– strikes a chord with me now. Flight must surely feel like the path of least resistance– there’s hardly any resistance at all while airborne, no? Compare that to the default mode so many in the tech live in and praise: the grind.

What a phrase. To grind, to wear down. An engine that is grinding is in poor condition. In desperate need of attention. Yet we praise the grind. Why?

For years and years and years I grinded. Maybe it’s what I needed. Like a rock in a river, I was being ground down, till finally, a deeper version of my being began to emerge.

are.na block

Feeling my way

When not working on fears, I flipped between modes of playful work and rest. I asked, “When I was a child, what did I love? What did I dream of?”. I explored those areas: Inventing gadgets, making music, designing buildings, swimming, writing, connecting with others. I experimented and explored. In all forays, I turned my attention toward the felt sense that accompanied my actions. Moment-by-moment body sensations became my guide– a sort of somatic compass.

The more I turned my awareness inwards, the clearer the signal became. Agitation from boredom, fear, or anger was a call for attention. A call to return to stillness. Stop! Recognize what’s happening! Welcome it as a visitor, if at all possible– it’s here already, after all. Inquire, nurture, then proceed. Conversely, when I felt good, I did my best to listen to and deepen those states. To chase my natural curiosities. To follow my joy⁶.

During this time of free exploration, a concern arose. While I was expressing all sorts of interests, I couldn’t figure out how they wove together. I wrestled with myself. I need to choose! I need to focus! If I don’t then none of this will amount to anything! I was following a trail without a known destination. That lack of knowing filled me with anxiety. There was still more fear to unwind.

We live in a goal-obsessed culture. The prevailing ideology is intensely focused on objectives– getting somewhere you’re not, acquiring what you lack, proving yourself. Folks in tech extol the need to focus if you want any sort of return on your actions⁷. Only through focus can you power a flywheel of momentum. Only a flywheel of focus can create compounding returns on your actions. Only through compounding will you become a success. But what sort of success is it that leads us to live half-lives, severed from the fullness of our being by a focus that cuts like a knife?

Don’t get me wrong– with focus you might be able to achieve the goals you set for yourself. All I’m wondering is this: what if your most expansive and interesting future lies outside the objectives you’ve imagined? If you achieve a goal that falls far shorter than your greatest potential– your fullest expression– will you have succeeded?

I wrestled with the question of success. My inherited notions that reputation, achievement, and possessions clashed with a success rooted in living fully. How did I want to live? Would I cut away parts of myself in service of objectives or would I embrace my fullness? I wanted to live a life of wholeness⁸, but how was I to, when fear (and my aversion to those fears) kept me in a state of division?

Two quotes– both attributed to multiple sources– became my daily companions:

1. The problem is not desire. It's that your desires are too small.

2. Discipline is choosing what you want most over what you want now.⁹

What did I want most? I wondered.

One perfect autumn afternoon, in the dappled light of Brooklyn’s Prospect Park, I tried to answer the question: What’s the best that could happen? After weeks of pressure, I wanted to get to the root of an inner conflict– to feel some sort of knowing about my objective. I wanted a life of flight, so what would that look like?

I sought to imagine the ways the world would need to arrange itself to satisfy the question but I faltered, again and again. I’d come up with an idea: a dream collaboration, an ideal opportunity. Immediately after, I’d be hit by doubt. How could I know for sure that that was the best that could happen? The question, it turns out, is limitless. Seek satisfaction in externalities– things, experiences– and no matter how much you acquire, you’ll find there’s always something else that’s just out of reach. I’ve heard that, when asked how much money was enough, J.D. Rockefeller (the world’s first billionaire) replied, “Just a bit more”.

So I looked for a lateral move. Though I couldn’t imagine the best arrangement of external circumstances, I found I could articulate the best possible feelings, and to my surprise they were accessible in the present moment. I wrote:

I feel soaked in gratitude, like a plum in sangria.

I feel rooted in a vast and joyful abundance.

I feel lit up by enthusiasm as I explore the fullness of my being.

I am engaged in creatively playful collaborations with beings of enthusiasm and integrity.

Life feels spontaneous, spacious, and serendipitous.

I love my life.

I found I could intentionally connect with each feeling in the present moment. They already existed! They were like acorns– potentials longing for fuller expression.

I’d found a map for my somatic compass. Like any map, it’s not the territory and I expect it’ll change over time. No problem. The somatic compass stays true, even when the map needs updating.

Trusting “don’t know”

are.na block

Though I’d found a compass and map, my internal wrestling match continued: on one hand, there was the desire to be fully myself. On the other, there was my inherited mental software of focus & objectives– ultimately, a cultural programming I’d picked up that defined ideas of success. I found that I still longed for a destination– to know where the hell I was going. That is, until October 17th, 2024– the night of the Hunter’s Moon.

“Don’t people do something on full moons?” I asked Miche, my beautiful genius wife, “There’s a ritual, right?”

“Yea, it’s a time of letting go. People release stuff. To be honest, I wish I had a better ritual around it.”

Hm. “I don’t really even know what I would release.” I responded, stumped.

She paused, then offered, “So... release the need to know.”

A tuning fork. That was something. Later that night, I wrote it down in my journal: I release the need to know.

In the days that followed, I noticed when I sought to know and invited those parts to let go of the inclination. I mindfully worked to shift my seat of awareness from my head to my body, continuing to deepen my connection with the somatic compass. In the don’t-know state I consistently discovered a different sort of relationship with the present moment. More alive. Like the cells in my being were lighting up. A feeling of being in the right place at the right time.

In Zen, there’s a teaching story. It goes like this:

Dizang asked Fayan, "Where are you going?"

Fayan said, "Around on pilgrimage."

Dizang said, "What is the purpose of pilgrimage?"

Fayan said, "I don't know."

Dizang said, "Not knowing is most intimate."

Finding flow

are.na block

Things felt like they were clicking. Actions flowed through me. Was this the wu-wei I’d read about in the Tao te Ching? Freud’s oceanic feeling? Whatever it was, it became another state I looked for in my somatic compass.

Fears continue to crop up. These days, I see them as invitations to tend to my inner garden. Thinking of them as problems– as enemies– is just another way of knowing. It makes sense they’re arising. Exploring without knowing where I’ll end up is fairly new! “Isn’t this irresponsible? What if this is a huge mistake?” ask the fears. The rational mind isn’t used to dropping control. I told Miche about these fears and she hit me with an absolute banger: “It’s makes sense you’d feel like you were in free fall as you learn to fly.” Damn. I’m grateful for her.

While on a meditation retreat this past summer, the Abbott of the monastery gave a talk about the mind. He said, “The mind isn’t the HQ. It’s the branch office. The gut– now that’s the HQ. When the mind thinks it’s in control, things get out of control. The mind can’t really see things as they are. But it’s a great branch office! So helpful!”

I’ve found this to be true. The mind is an amazing collaborator. I can ask my mind for examples of when I’ve trusted it over my gut. It’s happy to oblige, providing all sorts of occasions: jobs chosen, relationships prolonged, candidates hired… the list goes on. It turns out my gut was right in every example! Ha! In the past, I just couldn’t square trusting a feeling without some sort of rationale. Whoops! I’ve heard it said that the same situations will continue to arise in your life till the lesson is learned. OK, I figured, let’s try trusting my gut. Let’s see where the somatic compass takes me.

Here’s a story from this time: I’d told a friend that I was writing this essay and that I’d have a rough draft done by a certain date. The deadline day came, and as evening fell with the draft uncompleted, I found myself totally zonked and wholly unmotivated to write. It’d been a long week of joyful exploration and I was dog-tired. In my tiredness I believed that I didn’t have it in me to finish the draft when I said I would¹⁰. I felt like I’d failed. In the past this feeling of failure would’ve prompted me to dig deep and grind to get the thing done. Would it have been good work? No. But I’d be able to check the box saying I’d completed it. Good enuf. But that night I listened to my somatic compass and moved fully into rest. I did exactly what I wanted to do, even though a part of me saw it as an undeserved indulgence. In the past I’d have felt guilty about this. Why should I reward a failure with rest? In the logic where rest is a reward, is work a punishment?

Trusting dont-know and my somatic compass gave me the space to try resting completely.

An hour later I felt myself getting antsy. I pulled up twitter, multitasking. I’ve found that multitasking masks an urge to escape. It’s a sure sign that I’m not at peace, that something needs to be tended to or changed. I put my phone down. Paused. Checked in with my body. Realized I was no longer tired. In fact, I felt a wellspring of energy! I wanted to write! So I wrote, and before I knew it I’d finished the draft. Color me surprised. I’d done the thing I’d said I’d do without forcing anything! This was new territory.

"Don't go where the path may lead, go instead where there is no path…and leave a trail."

– Ralph Waldo Emerson

Towards flight

are.na block

The more I follow my somatic compass, listening to the tuning fork of my being, the more lit up I feel. There’s more energy now that I’m letting all parts flow. Is this flight? Maybe! Who knows!

I still get thrown for loops. I’m still rewiring my definitions of success, still unwinding deep-seated stories around self-worth. In that process, I’m becoming more comfortable being a work in progress, not having things figured out. In fact, I’m finding that not knowing opens the aperture of my awareness. There’s more wonder, more appreciation. I feel a deepening dedication to living a life of integrity, of wholeness. Recently, watching the Simone Biles docu-series, when asked what she was most proud of– this, the GOAT with dozens of olympic medals to her name– replied, “that I stayed true to myself.” What an inspiration. Perhaps being true to oneself is the greatest success.

In addition to writing this, here are a few other things I’ve been up to recently:

✅ Visited the Farralon islands, the most distant land that’s still technically San Francisco.

✅ Attended a meditation retreat at Tassajara. Bucket list item. Incredible. A version of how we could relate to one another. Eutopic.

✅ Sat on park benches and participated in the environment, reveling in the golden glow of sunlight held in the marine layer, sucking the bright mustiness of eucalyptus through my nostrils, appreciating the activity of my neighbors. God, San Francisco is gorgeous.

✅ Learned to whistle super loud without fingers. According to a gristled old-timer in the Dolphin Club sauna, this is a good method for calming playful seals when open-water swimming.

✅ Reread my favorite books and a few others that have helped in this process: Zen and the Art of Motorcycle Maintenance, The Bhagavad Gita, The Initiates, Asterios Polyp.

A handful of explorations are ongoing:

🌀 I’m meeting with resonant individuals. I’ve been surprised and cheered by how many people are in similar boats, navigating the waters of purpose, meaning, and authenticity. These conversations have been so much fun and have lit me up like nothing else. So, if you resonated with this, I’d love to connect. Send me an email at duncan@superbloom.so.

🌀 I’m designing a physical, sculptural meditation timer. Read: not an app! I’ve used apps on my phone for over a decade and for years I’ve longed for something better. I can’t tell you how many times I’ve found myself sitting on my meditation cushion, checking email or flipping through social media. The last thing I want to interact with before, during, or after my meditation is the little black box that distracts me throughout the day. So I’m making what I wished existed: beautiful devices that invite deeper presence. You can follow along here.

🌀 I’m exploring ways that I can support deeper human flourishing. If you’re working in spaces like meditation, mental health, climate, creative expression, education/tools for curiosity, the exploration of consciousness, worker cooperatives, or similar endeavors, I’d love to connect. Send me an email at duncan@superbloom.so.

Thank you for your time– I hope this was helpful in some way. 🙏

Much gratitude to those who provided feedback on early drafts: Miche, Liam, Amanda, and Sarah. This essay was overwhelmingly improved by your insight and care. Thank you.

1. MT is a special place. The folks there are insightful, driven, and dedicated to creating an environment for personal and professional growth. If you’re looking for your next role working on complex problems with talented people, you should check out their open roles.

2. I’d been recommended David Whyte’s Crossing the Unknown Sea and had brought it on the trip. Now, looking back, I see with clarity the way this maps to Joseph Campbell’s monomyth sequence– the dream, my call to adventure; the fear, my refusal; this book, my mentor.

3. Ultimately, duality is just tool of the mind: an abstraction to make sense of the world, lacking reality. As Heraclitus says: “All being comes from the conflict of opposites, and the whole flows as a stream.” Duality only works when one is rooted in the non-dual.

4. fwiw, I’m a 3, otherwise known as The Achiever.

5. I haven’t been able to source these studies, but it’s a nice story nonetheless, and apropos for a practice that’s all about just staying still and noticing what’s present.

6. I once read Eckhart Tolle’s Power of Now and he talked about a of ladder of presence: beginning with Acceptance, which naturally gives way to Joy, which then becomes Enthusiasm. It’s been a helpful scaffolding for me.

7. This, even though much of the novel innovation or breakthroughs we’ve achieved has come about not by working backwards, but wandering, exploring what interests or excites us most.

8. I’m a nerd for etymology and I love that the Latin root of integrity means “wholeness”. Can one live in integrity without being wholly themselves? Additionally, to heal is to be made whole.

9. There’s a unresolved question I still hold here: what about rabbit holes? I’ve found it all too easy to take systems and mental models too far. An idea of discipline that dulls my sense of wonder and the joy of exploration is a poor tool. But perhaps what I want most is to be enthusiastically engaged with this life! Then fine! Bring on the rabbit holes! Maybe what I want most is to be whole! Rabbit holes and all!

10. Attentive readers will have caught the knowing baked into that belief. How was I to know what was possible? All I really knew was that I was too tired to write at that time.