Shading my Circle

A little context before we begin...

A couple years ago, I was flirting with the pursuit of an entrepreneurial venture. Since my sophomore year of college, I'd put entrepreneurship on a pedestal because of the scale of impact that 1 person could have in the profession. I drank the Silicon Valley Kool-Aid that pitched entrepreneurship as "the 1 true way to change the world." So, an entrepreneurial venture felt like my only hope for achieving my goal of "positively impacting 1 billion people" (more on this below). My skillset was "business" (whatever that means), so entrepreneurship would be my swimlane.

In a way, I felt shackled by this "calling" because I couldn't conceptualize another pursuit that would enable me to hit my lofty expectation. Yet I was plagued by guilt any time I even considered "settling" for anything less than 1 billion, let alone pursuing a career that wasn't entrepreneurship. If I did settle, that would mean that I was ungrateful for my gifts (at least that's how I internalized it).

This piece was an attempt to unpack how my "potential" transitioned from being motivating to paralyzing. 

After starting the first draft in Fall 2022, I came back to work on it in Summer 2023, then again in Fall 2024. Take this as evidence that this internal battle remains relevant. It's an ongoing debate of what to do with my “boundless potential", while feeling like no matter what I do, it will never be enough.

The Circularity

"You have so much potential."

"You have so many opportunities in front of you. I can’t wait to see what you do.”

"You can do anything!”

I've heard this for most of my life

Words of encouragement that are meant to inspire & motivate

Words of encouragement that do inspire & motivate

I didn't know that my gifts were unique

What's so special about a moderately-functioning photographic memory?

Doesn't everyone have one?

It didn't feel "special" when it was the only reality that I knew

I was just me

These comments opened my eyes

To the possibility that I was different

That I could do something special

That I could achieve more

But more than what?

So after internalizing these realizations

Why did I begin to feel stuck?

How did words of encouragement transform into a feeling of “never enough”?

That answer is found in a shape:

A circle

This circle represented my "potential"

My potential to change the world

My potential to make a lot of money

My potential to give back to my family

Whatever form of "potential" I was fixated on at any given time

My circle representing the person I could become

The person I'm meant to become

If only I’d live my life to the fullest

My circle expands as I invest in my future

As I open up new worlds of possibility

As I learn & grow

Circular Silver Platter

Since the day I was born

My circle has been growing

But let's be clear...

I inherited a pretty large circle from the start:

• White

• Male

• American

• Californian (don't know if this helps in the career pursuit, but it does make me wayyyyy cooler than your average bloke)

• Middle-class family living safely in the suburbs

• Loving parents & siblings

• Able-bodied

• Mentally capable

My circle might as well have been a circular silver platter

My parents cared about me

They wanted me to be happy

They wanted me to succeed

So they did everything in their power to help my circle grow

And my circle did grow

My childhood was a stage of endless circle growth

Teachers gave me extra attention (especially after I finished my multiplication tables in record time)

Sports coaches gave me positive reinforcement (and not just the Little League coach who shared my last name)

Boy Scout leaders held me to a higher standard and passed down sage advice (before I even began to formulate my own beliefs)

Words of encouragement flowed in as my circle grew

"You have so much potential"

"You can do anything"

Adults helped me see that the bounds of my circle were far beyond where I currently thought possible

I was riding high

My circle kept expanding

Shading

So what happened?

How could motivation become dissatisfaction?

Well... there's another aspect of this circle

The circle’s bounds (my potential) is only the beginning

The circle also includes shading

The shading shows what I've achieved with that potential

As I "fulfill my potential"

I fill in my circle

So my personal circle always has two marks on display:

1. What's my potential?

2. What have I achieved with that potential?

From Circle-Expanding to Circle-Shading

As a kid, nobody cared about how much I'd shaded

I was in circle-expanding mode

"Just keep learning"

"Just keep growing"

I was good at learning

I had mastered this “school” thing

Bouncing from bio class to math to English

The formula was clear:

Get class schedule, get A’s, get out…

Year-after-year, on repeat

And I was praised for it

Because I was in my circle-expanding stage

And my circle kept expanding

But as I got older, things changed

Expectations were layered on

"You can do anything" became "So what are you gonna do?"

Woah… hold up!

What do you mean, “What am I gonna do?”

What happened to "You can do anything"?!?

Anything that will expand my circle

I show up, I learn, I get A's, I get praise

I don’t choose what to do

Just tell me what to learn and I’ll learn it

Just tell me what to do and I’ll do it

To choose would mean that I might miss out on other options

To specialize in 1 thing means limiting my potential

I have to keep my options open to keep my potential ever-expanding

Again, what happened to “You can do anything”?!?

Despite my protests, it was clear that change was-a-coming

It was time to shift from circle-expanding to circle-shading

I leveled with myself:

"Ok, I can do that... achievement time!"

“This is good,” I tell myself

I spent all these years expanding this circle

All these people invested in me

I’ve been given all of these opportunities

It’s time to cash in on all this potential

My circle could use some shading

Time to achieve!

What I didn't know is that it’s not a clear shift

What I didn’t know was that as I shaded, my circle would keep expanding

As I achieved, my potential to achieve grew too

Opportunity begets opportunity

Fulfilling potential creates potential

"The reward for good work is more work"

As I shade

I feel good about how much I’ve shaded relative to my circle

"I'm getting close to the edges!"

“I’m fulfilling my potential!”

But as I shade, my circle expands

So the shading that looked full today, suddenly looks tiny tomorrow

I worked hard in high school to get into a good college

Then I got into Penn

At the precise moment that I started celebrating my college-acceptance shading

My circle inflated immensely

"You're going to the Ivy League! Now you can really do anything."

So I worked hard in college to get a good job

Then I got a job in Venture Capital

At the exact moment that I started celebrating my job-signing shading

My circle got a dose of HGH

"You're going to a world-class investment firm. Imagine the possibilities now..."

As my borders expanded

My current shading looked smaller

"Oh, you got into Penn?

So did all of your classmates..."

"Oh, you got a job at a world-class firm?

So did all of your colleagues..."

The only question is:

"What are you going to do with this opportunity now?"

Frustration mounts as I become aware of the cycle:

I have big circle

I shade big circle

Circle gets bigger

The cycle becomes exhausting

"Does this treadmill ever end?"

"Will I ever achieve enough?"

"Will I ever be enough?"

Hello Insecurity, my old friend!

Ungrateful Prick

All the while, the encouragement doesn't stop

"I would do anything to trade places with you!”

“Do you know how many people applied to Penn? People would do anything to get your spot!”

I think of my classmate in high school whose dream it was to be a Quaker (the Penn version, not the religion)

I think of her crying when she got her rejection letter

Was I feeling "grateful enough" for the opportunity I'd been given?

“Woah you work in VC?!? You’re living the life. Do you realize how lucky you are?!?”

I think about my College Self who wanted nothing more than to get this job

Was I taking this position for granted now that I was in it?

Now, was I just suffering from Down the Beach syndrome?

Sounding like praise to others

These words are a crippling reminder to me that my internal complaints prove that I’m an ungrateful prick

Complaining about the opportunities I've been given

Complaining about the recognition I’m receiving

Complaining about inheriting my massive silver platter

So I refuse to stop

No time for self-pity

No time for reflection

There’s a circle that needs shading

So I strive

I struggle

I fight back this feeling of "never being enough" by doing more, more, more

I charge head on my circle-shading crusade

Why?

Why do I possess this unrelenting drive to keep shading?

To avoid the shame

The ultimate insult:

"He was a waste of potential”

As others tell me:

"You were blessed with immense potential"

I internalize the unspoken remainder:

"And you better not squander it"

1 Billion People

How do I handle these great expectations?

I set lofty goals

Goals worthy of the size of my (massive) circle

At least if I set lofty goals, I can tell people:

“Don’t worry - my shading might look small today, but I’m playing the long game. My shading is still on the come… And it’s gonna be YUGE!”

As a sophomore at Penn, I commit to the goal:

"Over the course of my career, I will change 1 billion people's lives for the better"

1 billion people…

Sounds about right for the gifts I’ve been given

I’m regularly reminded that I’m the luckiest guy in the world

I should accomplish something proportional to that

Fueled by my own sense of nobility

I get to work

What I didn't consider:

1 billion is a big number

An intoxicating commitment to make today

A paralyzing pursuit to fulfill tomorrow

I have to make every decision through this filter:

"Will this help me impact 1 billion people's lives?"

I reject opportunities that I would’ve probably enjoyed

Saying to myself, "Not big enough"

I bypass my passions

“No time to waste. 1 billion people are waiting. Gotta get to work.”

Yet, my expectation breeds inaction

"1 billion or bust," I tell myself

That doesn't leave a lot of options

A favorite quote from Naval (and inspired by the Tao Te Ching):

Taken literally (which I did), my goal meant that I was committing to being unhappy until I hit the 1 billion mark

A short-term commitment to address my "shading vs bounds" dilemma

A long-term commitment to my unhappiness

Until I achieve the 1 billion mark

The work would not be done

And I would not be enough

The Impact Justifies the Neglect

It’s often said that "the ends justify the means”

I implemented this as "the impact justifies the neglect”

As I’m on my campaign to help the face-less billion,

I’m neglecting the people in my life who are actually present

I ignore my family

I fail to show up for my friends

I deny love to myself

Ain’t nobody got time for that!

After all, I’m working to change the world

Surely they’ll understand

Potential doesn’t last forever

I’ll be present once I hit the mark

I’ll be present once I shade in my circle

Start with Yourself

I’m lost in this trance for years

Ceaselessly striving to change the world

Until 1 parable upends my perspective

The perspective that I need to break the chains of this paralyzing pursuit

Here it is (unattributed because I've been unable find the source beyond “Unknown Monk”):

This knocked me on my a** because I realized I've always been that "young man."

But what to do now?

Start with myself?

What does that even mean?

Just because I can, does it mean I should?

If I "start with myself"

What does that mean for my circle?

I'm grateful for my gifts

But I'm not beholden to them

I'm grateful for others' encouragement

But I'm not burdened by their expectations

I do the work that I’m inspired to do

Because "work is love made visible"

Rather than preparing to help the face-less billion

I work today to impact those around me

Those who I can actually see

Those within my reach

Starting with myself

I used to be fixated on my imaginary company’s manifesto

“Mission, vision, values”

Now I simply focus on my Personal Credo

Who I am, who I want to be, who I can be... today

I used to inhale “management best practices” in hopes of becoming a Fortune 500 CEO

Now I practice mentoring whoever comes to me... the best I can... today

Rather than stockpile ideas for a book “one day”

I give all my writing away... weekly

Rather than burn out in pursuit of impacting a billion

I create a pace to play the long-game

Because I’m a part of that billion too

And the "impact" I intend to have is certainly not "harm"

But, harm becomes the impact I have on myself when I'm convinced I'm never enough

So I chat with the barista

I smile at the stranger

I show up for my family

I’m present with my friends

I take a break, take a run, take care of myself

I’m less concerned about doing in order to shade my circle

I’m more focused on being Whole from the start

I reflect on what I've achieved

Rather than just obsessing over the work left to be done

I ask myself the question:

"Just because I can, does it mean I should?"

Unbothered by others’ opinion

I shade my shape in my own way

I deliberately set my own expectations

Blind to the size of my circle

Indifferent towards its expansion

Content with coloring inside the lines

Realizing my circle's been the same size from the start

That we all have the same size circle

And all of our circles are already full