In the 1970’s, researchers showed a split-brain patient’s right hemisphere a card that said ‘walk’. When the patient stood to leave, the researchers asked ‘Why did you stand up to leave?’

The patient’s speaking left hemisphere answered confidently ‘I wanted to go get a Coke’.1

This study reveals an extreme example of a concept that has been borne out by modern cognitive science over the past 60 years; the brain can often act, feel, or believe and then create reasons for that mental state.

If this reverse reasoning happens subconsciously, how can we trust more subjective kinds of self-knowledge like who we are as a person?

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We often believe introspection offers direct access to who we are. But what if the self is not something we uncover—but something we construct? This essay explores how cognitive science, philosophy, and language reveal a more active, observable path to self-understanding—one built through action, reflection, and creation.

Introspection is a Funhouse Mirror

The term introspection illusion refers to a cognitive bias in which people believe they have direct, reliable access to the causes of their own thoughts, feelings, and behaviors. In reality, as we’ve already shown, they do not have access to their own thoughts.

People under the spell of the introspection illusion are liable to mistake their own confabulations for genuine insight.

Emily Pronin, who coined the term introspective illusion, says the illusion has four main components:

1. People use introspection to assess their own mental states

2. People use behavior to asses others’ mental states

3. People trust introspection even when it’s misleading

4. People do not apply the same skepticism to their own introspections as they do to others’ behavior.

In The Opacity of Mind, Peter Carruthers defends the claim that we possess a single mental faculty for assessing the mental states of both ourselves and others.

This suggests the self-knowledge we gain through introspection isn’t a special kind of knowledge. It’s better to view it as a deceptive kind of half-data-point that needs to be grown into a whole idea before it’s truly useful.

But how do we actually grow our introspection into full self-knowledge?

If introspection is vulnerable to illusion, and behavior is prone to misinterpretation, then perhaps self-knowledge isn’t found in any one moment or modality—but must be triangulated over time: through what we say, what we do, and how we reflect.

Revealing the Self Through Action

Start close in, 
don’t take the second step 
or the third, 
start with the first 
thing 
close in, 
the step 
you don’t want to take.
...
—David Whyte, Start Close In

Action helps us observe our patterns.

Our patterns reveal what we really believe, what we really value, and what we truly want.

John Dewey, perhaps the most famous pragmatist philosopher, argued that we don’t start with a clear sense of self that acts. We become ourselves through action—by how we navigate the world, respond to consequences, spend our free time, and revise our habits.

“We do not learn from experience,” he wrote, “we learn from reflecting on experience.” Self-knowledge is not a passive uncovering of what’s inside us that’s meant to inform future action. It’s an active process of engaging, adjusting, and reflecting. The self is not hidden deep within—it’s written across the arc of our behavior.

The self is a ghost in abstract.

Cognitive scientist Daniel Dennett offers a complementary lens. He frames the self as the “center of narrative gravity.” In this view, our identity isn’t something we have, it’s something we construct by observing what we do and telling ourselves stories about it.

He frames the self as several parallel drafts driven by split-brain experiments—constantly stitching parallel narrative drafts that are sometimes accurate, sometimes not. The fact that this narrative is unconsciously created may seem to make it meaningless.

On the contrary, the act of narrating—of giving scaffolding to action—is how the self coheres over time.

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Learning Our Own Thoughts Through Language

...
To hear
another’s voice, 
follow
your own voice, 
wait until 
that voice 

becomes an 
intimate private ear 
that can 
really listen 
to another.
...
— David Whyte, Start Close In

Language helps us observe and complete our thoughts.

“Thought undergoes many changes as it turns into speech” as Vygotsky puts it.

When Cheryl Strayed began writing Wild, which eventually became a bestselling memoir, she was a heroin addict trying to outrun herself. By her own account, she was lost. As she wrote, the very act of turning her experiences into language alchemized them—in her own words: “Writing Wild was not about remembering who I had been, but about becoming someone who could bear to look back. The story didn’t live in the past. I lived in the words.”

Joan Didion, perhaps the most famous personal essayist of all time, famously stated, “I write entirely to find out what I’m thinking […] Had I been blessed with even limited access to my own mind there would have been no reason to write.”

These and many other great minds have noticed that the brain seems to be a mess of half-thoughts masquerading as whole ideas. Articulating our thoughts doesn’t expose them so much as it remodels them in real time.

Seeing what we’ve written is one way of discovering both what we truly think, feel, believe, and the reasons behind it.

Conclusion

...
Start right now 
take a small step 
you can call your own 
don’t follow 
someone else’s 
heroics, be humble 
and focused, 
start close in, 
don’t mistake 
that other 
for your own.
...
— David Whyte, Start Close In

If all you do is consume and ruminate, you’ll remain a mystery to yourself.

Creation is how you come to meet yourself. Your own actions are evidence of what you truly believe.

Taken together, these thinkers point to a consistent pattern: our introspections are fallible, our behavior often says more than we realize, and our self-understanding emerges over time—through action, narration, and reflection

You must take the action. You must observe yourself carefully. You must come to view yourself as neither fully transparent nor fully knowable and act accordingly.

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In the next section, I’ll talk more about examples of effective frameworks for this type of structured introspection, which leads to durable self-knowledge that can form a basis for self-cultivation.

The point of all of this is to arrive at the meaningful life that is centered in the true you. The one you can’t see without looking from the outside in.

The Problem With Outcome-Oriented Living

One of the hardest lessons I’ve had to learn (more than once, unfortunately):

It’s possible to sacrifice meaning to achieve a big goal—and still lack meaning when you reach it.

An old friend of mine bought a business to run. It’s what he thought he’d always wanted. He was stepping into his dream.

The business was failing, but he knew that going in. He had a strategy and wanted the challenge.

After about a year, his strategy was working—he was succeeding at his dream. The company was more profitable. They had found clearer paths to further growth. But there was a problem: he found himself stuck in an HR role that he despised.

We met for lunch one day while he was in the rough and tumble, and it became clear that the fix wasn’t as simple as hiring an HR manager. I asked him out of concern, “What’s your ultimate goal here?” He thought for a moment before saying, “I really just want to grow the business enough to sell it so that I can open an orphanage in Africa and help kids.”

He wasn’t after a different role. He’d virtually accomplished his goal, and he realized he wasn’t going to get the sense of meaning he’d been craving. As a result, he was after a completely different way of living.

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Goals Don’t Produce Meaning

In effect, a goal is a strategy that says:

Conform your actions to the requirements of an outcome until you achieve it.

A goal is an effective tool for producing outcomes.

A goal is not always an effective tool for producing meaning.

This is because meaning isn’t exactly an output; it’s more of an emergent property of lived engagement.

Two foundational papers from the 90’s1 established that cognition is more than abstract calculation—it’s an embodied process grounded in action and feedback within an environment. A goal is an abstract proxy for a lived reality that will remain, to some degree, opaque until it becomes embodied. When we focus on abstract outcomes, we risk cutting ourselves off from the embodied context that true meaning depends on.

Trying to project meaning ahead of experience is like trying to reverse-engineer joy from a blueprint.

The core problem isn’t often that we haven’t thought enough about the destination, it’s that we can’t fully perceive a life we’ve never lived.

A goal can become a caged elevator—mechanically sound, upward-moving, but sealed off from the very terrain it’s trying to reach.

Self-as-Action

Daniel Dennett, famous for framing the self as the “center of narrative gravity”, makes the case that the self is not something inside you, it’s something you do. Just as the center of gravity emerges from but doesn’t exist separately from a physical object, your self emerges from the ongoing story you construct through your actions and choices.

I wrote in another article about how anchor questions can help us draw meaning toward the self.

The self, then, is an enacted processes, not a static object or set of traits that exists within you. We’re constantly drafting and re-drafting who we are.

You can’t “find yourself” because you don’t discover yourself in order to act—you act in order to discover what actions best align with your emerging self-narrative.

Self-cultivation begins when we shift from predicting meaning to practicing it—using our actions as a filter for what resonates and shaping ourselves through lived experience.

A Case for Self-Cultivation

At it’s core, self-cultivation is a refusal to outsource meaning.

Self-Cultivation: the ongoing process by which individuals refine their thoughts, behaviors, habits, and values in pursuit of greater alignment with their chosen ideals—rather than externally imposed goals.

Self-cultivation is action-oriented. It’s not theoretical.

It’s also not a chisel, it’s a filter for deciding which of our actions produce meaning.

As we enact the self, we ask “Does this action cultivate a more meaningful lived experience for me?”

We then find ways to take that action more frequently (see: proportional time investment).

The key benefits are extremely important:

• Self-cultivation leaves you open to integrate many interests. You can create a unique mosaic out of your diverse curiosities.

• You begin and aim to stay where you want to be, rather than ending up in a place you hope you’d like to be.

• You can iterate in smaller steps. If you find you don’t like where you’ve ended up, you’re usually able to take one step back.

• You double down on what’s working, and grow the focus until that area becomes a bigger part of your life.

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Self-cultivation isn’t an easy approach though. It comes with real tradeoffs:

• It requires you to find what you want outside of milestones and goals

• It doesn’t benefit from quick-fixes or life hacks because it’s an ongoing process, not an outcome

• It requires deep introspection, which can be uncomfortable for some because it’s inefficient

• It’s non-instrumental. The value it produces isn’t necessarily in the form of wealth or status—it’s in the quality of being. The value is in a more personally-tailored meaning.

This is the reframe that has been most impactful to me over the past 10 years: self-cultivation is about cultivating more of the actions that create meaning in our lives. It’s not about the future, it’s about the now.

This is merely a case for self-cultivation. In future articles, I’ll provide more tactical ideas for “how”.

Instead, in the up-coming series on self-cultivation, I’ll discuss:

• High-agency frameworks that I’ve found helpful

• Lessons I’ve learned during my own efforts

• Principles I’ve found useful

If there’s anything specific you’d like to hear in future articles, let me know in the comments below.

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I like the phrase Eat the fish, spit the bones. Take what you like, leave the rest. Many seem to be taking sides on whether AI is all fish or all bones. I’m here to advocate for a middle path with humanity at its center.

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Many of us want to think. We want to write because we see it as a tool for shaping our own minds. We care about the simple pleasure of learning for its own sake. We do it unprompted in our free time. It’s a part of how we operate. We enjoy wading through felt ideas.

Since we see the value in the actions themselves and not just the outcomes, many of us don’t want to outsource our thinking and writing to robots. We don’t want AI to summarize entire books for us, to parrot feelingless versions of thoughts like a soulless puppet, or to reduce entire schools of thought to bullet points.

We want to wander—to saunter intellectual vistas ourselves.

AI doesn’t have to replace that. It can help us do it better.

Using Human’s Razor and Kaleidoscoping

To maximize the good and minimize the bad from LLMs for lifelong learners, I propose a simple razor that I call Human’s Razor.

Human’s Razor: Take the shortest path through AI to a human-made artifact.

The Human’s Razor pushes us to leverage what AI is best at—making connections between ideas—and limits the downsides. By taking the shortest path, we get right back to connecting with other humans, with their ideas, and with the artifacts they produce.

Essentially, kaleidoscoping is just a loop of applying human’s razor over and over. You bounce from poem to film to painting to song to inspiring person.

It’s an intuition-led way to explore deeper, less-traditional, and more satisfying connections between ideas.

Kaleidoscoping: Using an LLM to connect ideas, books, articles, poems, paintings, films—any human-crafted product of the mind—to other human-made artifacts based on shared themes, feelings, aesthetic emotions, values, direct or indirect inspiration, or any other type of relationship.

Now that we’ve explained the terminology, let’s run through how you can leverage kaleidoscoping for fun, self-directed learning.

I’ll give some examples of prompts that leverage Human’s Razor:

What are 5 poems in the public domain and 5 books of poetry from living poets that deal with the same aesthetic emotions as A Noiseless Patient Spider by Walt Whitman?

Name 5 living authors who stated that their writing was inspired by Tolstoy.

I loved the movie 2001: A Space Odyssey. Help me pick out the themes, the emotions, the values, and the underlying philosophies. For each emotion, value, and underlying philosophy identified, point me to a few poems, paintings, books, and other films that explore those same themes.

All we’re doing is asking for the conceptual connection.

Then, it’s our responsibility to go deeper and actually engage with that artifact to create a personal connection. Buy the book. Read the poem. Look at the painting.

Pay attention to what resonates while you’re looking, and record it.

Each human-made artifact that the AI points to is like an anchor point when rock-climbing. If we climb too far without anchoring, we risk bad outcomes.

When we choose to engage with human-made content, we can feel the difference. AI output is the processed food of information diets.

Kaleidoscopers in the Wild

Phil Tippett is one of the greatest stop-motion animators in the world. He shaped the visual language for iconic films like Star Wars, Jurassic Park, and RoboCop.

He has a fascinating system of using an analog version of kaleidoscoping in his creative process.

Over time, he’s filled a room with trinkets.

The trinkets are not random—they’re items with which he felt some sort of connection.

He photographs these items, puts the photos in a random order inside of a photo album, and flips through them when he’s experiencing creative block.

By flashing images of artifacts he felt connected to, his mind makes connections and he finds inspiration.

That’s the whole goal of kaleidoscoping: assembling an arsenal of diverse ideas, concepts, and all kinds of artifacts made by other humans that we feel strongly connected to.

If we catalog what we find while doing this intuition-led learning, it’s a gift for our future selves.

I have a personal system that I use to capture these kinds of ideas. It’s essentially a modified version of Zettelkasten. I use what I call an Idea Spine to relate ideas together based on feelings, types of intelligence, vibes—really anything that can help me connect them and spark new paths of inquiry or creation. I’ll write more about it if people are interested.

Conclusion

We don’t need to convince AI to go away to have more human connections.

With the right perspective, AI can help us do more of what we love.

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The bigger the question, the bigger the gravitational field. A big enough question can pull ideas from nearly every domain of human knowledge into the same conversation.

This gravitational property is what gives an inspiring question the power to reshape our perception over time. A big enough question pulls new parts of the world into your perception. Your perception shapes you.

Anchor Question: A question large enough to pull unrelated ideas toward it like a gravitational field. A question big enough to unite both people and ideas.

It’s not one answer that changes us, it’s the way the presence of the question itself in our mind calls out a million answers throughout our lives in everything we see.

Rilke talks about this idea in his famous Letters to a Young Poet:

“[B]e patient toward all that is unsolved in your heart and to try to love the questions themselves like locked rooms and like books that are written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

For those of us who are generalists, lifelong learners, and multi-passionates, having an anchor question in the mind serves as a natural stabilizer for broad curiosity.

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In this article, I want to

• share how I found my anchor questions

• show how anchor questions can improve your life and learning

The Questions are Obvious in Retrospect

If you want to find your anchor question, look for it in the shower.

What do you think about when there’s no pressure and nobody is looking? Can you find an anchor question associated with it?

If there’s a recipe for finding the questions that drive you, it might look like:

• Move consciously through the world.

• Pay attention to your own thoughts.

• Find patterns in your thinking over time.

• Attach those patterns consciously to an anchor question in retrospect.

Here are three of my personal anchor questions as examples:

• My Anchor Question: How does one fill, invigorate, and rightly apply the mind?

• My Work-Related Question: What is the true role of knowledge in decision making?

• My Writing-Related Question: How can self-directed curiosity help us live a good life?

The way I came across the core question that drives me was unceremonious. I didn’t even realize it until many years later, in retrospect.

When I was 15, I picked up Descartés’ Discourse on the Method off of the shelf out of sheer boredom. This isn’t a humble brag. I had no business reading it, and I didn’t even finish it at the time.

I found a thought in the first few pages that I’ve carried with me ever since:

“For to be possessed of a vigorous mind is not enough; the prime requisite is rightly to apply it.”

The exact words have left my mind many times, but the general idea remained.

The meaning behind these words wasn’t concrete to 15-year-old me when I read it.

That’s not the point.

The point is that, despite having no business grappling with the ideas, I have vivid memories of reading this passage to adults in my life. I remember holding the book in my hand while talking emphatically about it. I walked around with the idea held loosely it in my mind like a rock tumbler.

This question has wandered with me for over 15 years. It shaped me. It’s changed my perception on countless parts of my lived experience.

I didn’t choose it based on an aptitude test, a strategy, a trend, or an obligation.

I share this as an example because there’s likely already a question sitting in you. It probably got there through a similarly innocuous event. There’s value identifying it and consciously holding it in your mind.

What You Hold In Your Mind Is What You See

If you want a controlled way to practice holding an idea in your mind and watching the world reconfigure around it, watch the movie Paterson with Adam Driver.

It’s a quiet movie about a bus driver who writes poetry in a little notebook as he goes about his day.

What’s fascinating about this movie is that the subject of whatever poem he happens to be quietly writing shows up in subtle and unrelated ways in the background of the movie. Everywhere. They’re so subtle that you might not even notice them if you aren’t holding the poem he’s writing in your mind as you’re watching it.

The subjects of the poems always seem random at first, like when he chooses to write about Ohio Blue Tip Matches after seeing the box during his breakfast. Throughout his day he begins seeing literal “matches”—like twins, or matching home decor. He hears a poem from a young girl called Water Falls and later sits by a waterfall and remembers the poem.

The point of the movie, if there is one, is that holding an idea in your mind highlights connections to that idea in the world around you.

Holding details or questions in your mind makes the world come alive around you.

Another example is found in the book On Looking by cognitive scientist Alexandra Horowitz. In the book, she takes 11 laps around the same city block with different people ranging from a physicist to a child.

She points out that we miss probably 80% of what’s going on around us, simply because we aren’t paying attention to something that would flag it as important to our brain.

Holding a question in your mind as you move through the world is a walking meditation. It brings certain aspects of the environment into focus.

A new question invites otherwise trivial details in our world into a tapestry of meaning.

Stop Planning. Let It Emerge.

The modern world is obsessed with syllabi. We’re told what to know, what not to know, which sections to read, and which books to skip.

The assembly-line of formal education makes wandering intellectually feel wrong at first.

Pull my string and I’ll talk for two hours about how this is ruining the joy of learning for the world.

But here’s the twist: you can put down that thinking without anyone’s permission.

Tear up the syllabus and let a path emerge beneath your feet.

Most won’t. There’s an abundance of pre-laid paths that are much less fuss (and much less fun).

If the anchor question is what draws ideas to your core, the next step is to walk with it in mind.

Here’s how I navigate:

• Identify interests and tie them to parts of myself.

• Use proportional time investment to lay the path: an hour to test if it’s worth a day, a day to test if it’s worth a week.

• Set constraints to steer the direction

• Focus on a mode of operating rather than a fixed destination

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Conclusion

We’re used to looking in prescribed places for answers.

Throw out the right places. Search quietly, lightly, softly, everywhere you go.

Be loyal to the question. Know that holding the big question will change you more than finding an answer.

What’s your anchor question? I’ll attempt to share a personal connection to a film, poem, book, or other resource for everyone who comments below.

Umwelt is a German word without a direct English translation. It describes the unique ‘bubble world’ of any creature’s subjective perception and meaning.

A bee’s umwelt is characterized by it’s ability to see ultraviolet light and to sense certain pheromones.

A person’s is characterized by culture, language, and personal experience.

Every individual’s brain leaves cognitive fingerprints on the information it takes in based on its umwelt.

Think for a moment: how could you reduce an umwelt to data? Is it even possible?

We’ll come back to this question.

On Looking

Even when we’re trying to take in as much information as possible, our perspectives are biased based on what we know.

I’m reading a wonderful book called On Looking: A Walker’s Guide to the Art of Observation. In it, the author—a cognitive scientist named Alexandra Horowitz—walks around her neighborhood eleven times with different characters, ranging in perspective from a physicist to a child.

Each walk and corresponding talk conjures different mental and emotional specters in the author, despite seeing the same sensory inputs each time.

While reading, it reminded me of something a colleague had recently said about how a category-defining leader he’s working with is different from the other mere mortals we’ve worked with.

“I can’t explain it. She is able to look at the same data as everyone else and know exactly what to do—often subverting the expectations of other experts along the way. She’s not just right, she’s more right and in more nuanced ways than those around her.”

Deep, hard-won experience generalizes in ways that seem to defy our best attempts at turning them into systems.

On Trying to Scale Perception

Gary Klein, an organizational behavior expert, points out an interesting paradox: businesses want to hire people who have struggled and succeeded, but it’s against their best interests to create an environment of struggle.

They become concerned with simulating growth. Not in real, gritty, ugly, inefficient actual growth.

Struggle is, after all, the antithesis to efficiency. It must be rooted out to maximize profit.

As a result, many organizations are filled with people living off the table scraps of great leaders who have struggled and succeeded themselves.

Klein argues that they share these learnings by passing along mental models. It could be as complicated as a process or as simple as a rule of thumb.

This is where we start to go off the rails.

On Looking Too Hard

As soon as we start trying to make concentrate from people’s struggles by turning them into systems and frameworks, we run into a universal truth:

Meaning seems to actively resist being quantified.

John Keats’ famous poem Lamia about the Greek figure of the same name captures this idea better than any other.

In the full poem, Lamia is a mysterious being who “melts into a shade” when Apollonius, a philosopher, applies cold rational scrutiny.

Here’s a relevant excerpt.

Lamia

By John Keats (1795-1821)

Do not all charms fly
At the mere touch of cold philosophy?
There was an awful rainbow once in heaven:
We know her woof, her texture; she is given
In the dull catalogue of common things.
Philosophy will clip an Angel's wings,
Conquer all mysteries by rule and line,
Empty the haunted air, and gnomed mine --
Unweave a rainbow, as it erstwhile made
The tender-person'd Lamia melt into a shade.
[229-238]
The bald-headed philosopher
Had fix'd his eye, without a twinkle or stir
Full on the alarmed beauty of the bride,
Brow-beating her fair form, and troubling her sweet pride.
[245-248]

Keats describes the awe-inspiring sight of a rainbow and notes how it loses its luster “in the dull catalogue of common things.”

It’s a beautiful lament on how dissecting can stunt imagination and wonder.

We Live in a Retrospective, Dissected World

We live in an era that worships what can be quantified.

AI is a massive oracle to consult all of human retrospect.

We’ve lost sight of the profound value of the fundamentally unique perception of each person. We treat these idiosyncrasies as speed bumps. We assume every blind spot can be filled in with a corresponding manicured piece of information.

Horowitz points out that “You are missing at least eighty percent of what is happening […] You are missing what is happening in your body, in the distance, and right in front of you.”

We’ve replaced original thought with an insatiable desire to standardize perception in nearly all areas of our lives. We take the same classes. Watch the same shows. Read the same books. Cite all the same great thinkers.

Our near-constant diet of idealogical concentrate has divorced us from original experience.

If a right answer could possibly exist, we live in a time where there’s a near moral-imperative to find it. In parenting, in business, in life.

Original experience is, after all, a painfully inconvenient inefficiency in both education and business.

In Conclusion

The antidote to watching meaning “melt into a shade” under the microscope of reason isn’t to try to change the world.

It’s to try to change your world—your perception.

Nobody will prioritize your original experience if you don’t.

I’ll offer three suggestions that have helped me:

• Limit consumption of concentrated, heavily distilled ideas in the same way you’d limit processed foods in your diet

• Maximize time spent having inefficient, original experiences with ideas by thinking through ‘solved’ problems on your own

• Prioritize non-propositional sources of meaning like art, poetry, narrative, beauty, story, and shared struggle

In doing so, accept the key tradeoff: exploring the world first-hand is less efficient.

Efficiency is a small price to pay for meaning.

"For to be possessed of a vigorous mind is not enough; the prime requisite is rightly to apply it."
René Descartes

Here's how to integrate your seemingly unrelated interests to create a higher quality of life without trying to overhaul your entire existence.

I’m a generalist. I’ve also worked as a specialist at top tech companies and have built a successful agency around that specialty. All the chatter on the internet seems to be about how you must choose between one or the other.

I’m living proof that you can be a specialist at work and a generalist in life. It’s not just possible, it’s ideal.

This is called being a master generalist.

Master Generalist: A person with a broad base of knowledge and experience across multiple fields, combined with a high degree of skill and proficiency in ~1-3 areas.

Today I’ll share some key unlocks that have helped me to shift my focus from arriving as a specialist to thriving in a process built around my interests.

Foundations: You Are Greater Than the Sum of Your Parts

I have a vivid memory of sitting in a bathtub as a Sophomore in college with a fever of 102. I was agonizing over a spreadsheet with every major sorted by my subjective aptitude and career outcomes.

The semester was starting and I felt like I was on a deadline to find my identity. Choosing between diverse interests like literature, philosophy, business, and writing felt like choosing which child to save.

At that moment, I was missing crucial information.

This decision (it’s relevant that the etymology of the word decision is from the Latin to cut off, as in to cut off alternatives) felt impossible for two reasons:

1. Each interest was connected to a different part of myself.

2. I had framed the decision to myself as a permanent choice between those interests. One interest would prevail, the rest would be indefinitely cut off to make room for a focus.

Have you ever seen the movie Inside Out? It's based on real psychology. We all have different sides—or parts (Disclaimer: I'm not a licensed expert in this area, but I've found the idea is foundational to understanding what it means to be a generalist).

There aren’t good parts and bad parts. They’re just parts. They all need a seat at the table.

In fact, each part of yourself can "have its own attitudes, ideas, desires, and even hobbies or creative outlets". It follows that having many interests can be a sign that you're successfully integrating more of your personality. Generalists—those of us who have many interests and often master more than one—aren't chaotic and flighty. We're actually well-integrated and have more of our full selves on display.

In retrospect, the agony made sense. It wasn’t about interests at that moment. It was about which parts of myself would survive.

In that light, it makes sense that they would fight for their existence: I had internally framed the decision as a lifelong commitment to honor one part and snuff out the rest.

I could have also framed specialization as a collaboration between those parts to build a specialist skillset. In that moment, I didn’t have the tools to do that.

At its core, that’s what it means to be a master generalist. You don’t just pick a speciality, you harness the power of all of your different parts and their interests to help create a speciality with a broad base.

Realizing that many of us are actually wired to have varied interests completely rewrote my internal monologue.

I began looking for ways to compromise intentionally. To pull chairs up to the table in my mind. To find ways of integrating parts of myself through pursuing interests and self-directed learning.

But it was just the start. I had to learn (often the hard way) how to actually make a career and a life as a generalist.

Parts form a helpful backdrop for the rest of this article, where we’ll talk about:

• Making a path from parts-anchored interests.

• Walking the path by trying everything and doubling down using proportional time investment.

• Steering gently by picking strategic constraints rather than setting huge long-term goals.

• And managing your drive as a generalist by finding modes of operating that allow you to both fill your bucket and find states of flow.

I hope it helps you on your way.

The Path: Parts-Anchored Interests

Prioritizing your own interests doesn’t need to ladder up to promotions or career shifts to be valuable. It can easily be done without reorienting your whole life toward a new identity or career. In fact, it’s often best conducted as a leisure activity.

Having no pressure to monetize the things you love means you can explore without restraint.

Though it’s not strictly necessary, I recommend trying to connect interests to parts of yourself. I find it helps me to rotate my interests with more intention, to find new interests, and to more intentionally integrate parts of my mind.

If you want a full framework for identifying and understanding parts, I’d recommend Jay Earley’s book on the subject. Rather than try to recreate that resource here, I’ll just share what I’ve personally done.

I’ve learned that I have two dominant parts which I named:

• The Analyst - the part that thinks about things from every angle. It wants to understand root causes, and to predict future outcomes. It wants to keep me safe and stable.

• The Artist - the part that resents structure, craves open blocks on the schedule, wants to make things intuitively, and appreciates all kinds of aesthetic beauty.

I used to be unable to explain why I both wanted and resented structure. Why I wanted to create systems but didn't want to live within the systems I'd created. Why I wanted to walk through the MoMA but I also wanted to write code.

You may have a similar contradiction that exists in your mind. It may point to two parts of yourself.

As soon as I had clearly identified these two parts of myself, a lot of things began to make sense. 'Conflicting interests' suddenly seemed more like interests that resonated with different parts of myself for different reasons. 'Focusing on one thing for my whole career' suddenly began to look more like shutting out parts of myself than being industrious.

If you want to try picking parts, don’t overthink it. Just pick the two most obvious parts that seem to be in dialogue with each other in your head all day and give them names.

I try to understand what these parts want by writing dialogue between the parts. I ask them questions about themselves like you would a new friend. I ask them what they like, what they dislike, and why. I ask them what they want to do in life. I ask them to talk to each other.

The answers form a basis for self-exploration in leisure research and skill development.

Pursuing these interests will help you to integrate those parts of yourself.

Parts-Anchored Interests: Simply interests that you can connect to a specific part of your mind.

I'll call these interests that you can connect to a part of yourself 'parts-anchored interests'. It’s not a term found in the literature, it's just a term I've made up to reference this idea.

Walking the Path: Trying Everything

Parts-anchored interests form the basis of an emergent curriculum for leisure research.

It's not top-down, it's bottom up. The syllabus emerges—not from an authoritative source—from our own interests. Don’t surrender that.

When we begin creating an emergent curriculum, we need a way of keeping it organized. A way that doesn’t require us to know everything about what we’ll study up front. We need room to explore.

I use intuition to choose what to research, but I use a simple system I call proportional time investment to choose what to stick with. I spend an hour to see if it's worth spending a day; spend a day to see if it's worth spending a week.

Proportional Time Investment: Spend an hour to see if it’s worth spending a day. Spend a day to see if it’s worth spending a week.

Note: I don’t think that dopamine-laced activities should be evaluated in the same way. These activities aren’t always bad, they just play by different rules than quieter interests.

I listen to myself each step of the way to confirm it's a path I want to keep traveling.

I ask myself whether what I’m learning can be applied analogically to my specialties.

I also try to notice whether I’m truly not drawn to something, or whether it’s just getting harder to progress. Difficulty increases with skill, so this is important to monitor.

If I’m researching, I push myself to take an action based on what I learned.

Proportional time investment allows me to lay the path, brick by brick. I then saunter along the path I’ve paved—all day, every day. That’s not something I choose to do, it just happens whether I like it or not.

Action is a critical part of this system. Creation is what separates things like research from reading or study. Research isn't just consumption—it involves some degree of synthesis into a (usually written) work. Synthesis is a form of creation, creation is a form of action.

I'm a big proponent of embodied learning—of finding ways to use what I learn as quickly as I possibly can.

Many of us know this intellectually. Few of us act accordingly.

Trying everything is how we distinguish between what we enjoy in practice and what we only enjoy in theory.

The sooner you act, the sooner you know whether you enjoy the action itself.

If you take a parts-anchored interest, learn about it earnestly, try what you learn yourself in some small way, and increase your commitment to ideas from the bottom up, it's almost impossible to go wrong.

You'll wind up somewhere you want to be because every step was a step you wanted to take.

The knowledge will stick because you've found ways to use it.

Steering Gently: Swapping Long-Term Goals for Constraints

Long-term goals are risky. Especially when they involve changing something significant about yourself.

They're something like the opposite of the process I just described; long-term goals are usually rooted in assumptions rather than iterative, intuition-led action.

I used to agonize over long-term goals. I would spend days or weeks thinking about grandiose five year plans. I even achieved or exceeded most of these grandiose plans.

I learned the hard way that you can both make sacrifices on the journey and not enjoy the destination.

A goal is a strategy that says: 'Pick where you want to go and act accordingly.'

The action is chosen by the goal.

A constraint is a strategy that says: 'Pick how you want to act and see where it can take you.'

The action is chosen by you.

A goal shrinks the horizon onto a point. A constraint challenges you to turn a point into the horizon.

Constraints, as I'm using the term, have a lot in common with boundaries or principles. I use the term constraint intentionally, though, because I think it's helpful to think in terms of what you will not do.

Ideally, what you will not do should be in service of who you know yourself to be—in service of creating the conditions that you know have helped you to flourish.

Here are a few of the constraints that have defined how I work. All of these are hard-fought. They came from difficult life lessons I'll surely write about in future posts.

• I only optimize what I'm actioning

• I only write about ideas I've felt at least twice (once when I note it down, and again when I review it)

• I only consume content with intention

• I only allow myself to disagree with an idea when I feel I fully understand it

• I only spend a day if I’ve first spent an hour and decided if I want to proceed

You can quickly see how even a few constraints provide structure.

The constraints, taken together, form an identity. ‘I’m the type of person who…’ is a powerful frame.

Immediately, categories of writing are unavailable to me because they aren't felt, and feeling new things becomes an implied avenue to expand my writing. Optimization is something I choose to earn through action because it comes naturally to me. Consumption isn't bad, it is a tool. Pursuit of understanding must precede opinion.

Parts provide your intuitive curriculum.

They also help you decide which types of constraints will work for you.

Proportional time investment paves the path as you walk.

Constraints help you steer the path as you build it.

Finally, in order to really consistently do all of this over a long period of time, you must find your mode of operating.

Maintain Your Drive: Find Your Modes

If a constraint describes how you will not operate, a mode of operating describes how you will.

Don't seek people's permission to operate in the way you want to operate.

Defining a mode of operating challenges you to think less about where you’ll be in five years and more about how you’ll operate at your desk today.

Mode of Operating: An intentionally sustainable rhythm of working that facilitates the constant pursuit of interests while respecting constraints.

It's not a routine, but a good mode of operating is fertile ground from which routine usually springs.

It’s a set of conditions that you’ve learned are necessary for entering a state of flow.

Creating a mode of operating will keep you from the feast-and-famine cycle many generalists find themselves in: finding an interest, researching it obsessively, doing nothing meaningful with it, and then moving onto the next thing.

I've been there. It's important to recognize that this isn't altogether bad. It's simply unharnessed potential.

Some simple examples might include:

• Using the pomodoro technique (25 minutes on, 5 minutes off).

• Setting focus blocks that align with your natural focus windows.

• Limiting prioritization to selecting a single top priority and working on it until it’s done.

There are at least two very important categories of modes for you to define for yourself:

• A Filling Mode. This is a mode of operating that is closely associated with being a generalist. What fills your bucket? Exploring new ideas, reading, walking, meditating, stream-of-consciousness writing, talking with inspiring people, reviewing notes from things you’ve read, and consuming inspiring art are some good places to start.

• A Flowing Mode. This is a mode of operating that pushes you to integrate generalist knowledge with specialist skills. What allows you to drop into a flow state and create things? Under what conditions do you tend to produce your best work?

You may even have a different filling mode and flowing mode for each part of yourself.

Focusing on the mode ensures you’re always where you want to be. You stop trying to arrive.

When I’m in my mode of operating, I feel alive. I feel present and content. I feel peaceful.

Work can feel this way. It can feel peaceful. It can feel intentional.

I'm working the way I want to work every day. I'm focusing on my experience today, not just in retirement. I'm optimizing my experience for my current self, and allowing my future self to emerge naturally.

I'm a gardener, not an architect. I create the conditions and observe what arises, and I attach what I can to my specialties.

The rest of what I can’t attach to a specialty just makes me a better, more integrated, more well-rounded person.

Conclusion

In summary:

• Identify your key parts that drive your diverse interests

• Allow parts-anchored interests to inform your emergent curriculum

• Try everything, and use proportional time investment to decide what sticks

• Be intentional about selecting strategic constraints

• Spend as much time as possible in your mode of operating to avoid burnout

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  Let me know in the comments if there’s anything you’d like me to expand upon in future articles.

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