There is no beauty without the broken.

We're doomed to keep glossing over mental health until we start acknowledging this.

I’ve been thinking a lot about “kintsugi” over the past couple of days. It's the Japanese art of putting together broken shards of pottery -  only instead of using a clear glue, you use a lacquer dusted with gold. More than a form of art though, it's a philosophy - a way of viewing the world. It asks - what happens when we celebrate the piece’s history of imperfection, of brokenness, rather than try to "fix" or disguise or ignore it.

What’s more, it’s a recognition that this beauty and extraordinariness does not exist without the broken. That it is a fundamental part of the piece’s existence that must be celebrated equally as the “good stuff”. 

I wish this was how we thought about humans and particularly how we truly view mental health.

This week, when Naomi Osaka made the decision to pull out of the French Open, what we really saw was exactly how far we are from a kintsugi mindset.

We are a society that lives to idolize our heroes but we can’t stand to examine what forges the steel that lies beneath. We love to marvel at how she’s the highest paid athlete but we have no stomach for her possible fallibility; a people primed for consumption without caring about the price. 

Our heroes’ stories must be wholesome and whole. Cracks are always seen as weakness never as a history to more. A history of persistence and survival and that grit we all love to talk about.

We need to change that.

Because otherwise, we’re relying on empathy to do the heavy lifting in making mental health more widely acceptable and understood.  

But in the same way it's hard to understand physical pain or being drunk or altitude sickness unless you too have experienced it, it’s nearly impossible to really understand what a day trapped in the cold fog of anxiety feels like. Or how terrifying the utter lack of will in depression is like. And while I could wish for everyone to experience just one day of it, the truth is, I wouldn’t wish that on my worst enemy.

I say this as someone who otherwise would be considered all the admirable words –– accomplished, successful and the worst of them all–– happy. 

But I find myself desperate to make people understand: Very rarely is there beauty without the broken.

Almost 3 years ago to this day, I hit publish on a piece I was terrified to put out into the world. Because it made me feel weak and broken and damaged. It was the first time I put words to the Dementor-like fog that would engulf me for days and weeks but that I have learned how to become bigger than. I didn't want to open myself up to doubt and question and worst of all - pity. After all, all my life I've been taught to never appear "weak". 

But the world had just lost Kate Spade and Anthony Bordain and we were all talking in surfacey devastated terms that completely glossed over the devious efficacy of mental illnesses. 

"Oh how could she do this to her daughter?", or, "...but he had the best job in the world!". 

And today, we’re back at it, with Naomi Osaka’s decision to pull out of the French Open because of her mental health. Thankfully it’s not to talk about a death but a life that someone is trying desperately to save for herself. 

When she couldn't be more brave and clear and upfront about the demons she's battling, it seems all we can find ourselves talking about are the sponsorships she willingly took or the rules she understood she needed to abide by before coming. All rational, valid points if that’s actually what mattered. 

But those are matters of obligation and optimization. 

We’re talking about survival. 

Of waking up and constantly feeling threatened and under attack from all directions, and scariest of all, from within. 

And of course I can only speak to the ways that this shows up in my life, which is to say it could be completely different for others. But every morning, I wake up and test the waters of my thoughts. I reach a bit further and bolder to see if they shoot out in bold, colorful jets of confidence and creativity or if they get bounced back off of a dark forbidding wall, ricocheting around my brain, making me feel small and brittle. 

From there, I take stock of what must be done. If it’s a good day, I do everything I can to keep it like that. I limit alcohol, I try to be outside and active, I only surround myself with people that make me feel good about myself.

If it’s some degree of a challenging day then I go into protection mode. I push everything else out - meetings, plans, to-do’s and I go do what needs to be done. Often it's a hard workout. Sometimes it's a cafe and a book (the past year I've had to find other go-tos). Inch by inch - and I'm being quite literal here - it feels as grinding and as grueling to go inch by inch, I work to get myself back into the headspace I need to then do the rest of life - work and parenting and being. 

But other days it’s not enough. And it just gets worse. Every thought, every moment can be a threat, making it all worse until it threatens to consume me completely. 

On those days I can’t do anything but try to survive. I’ll make excuses to my team. I’ll cancel meetings I’ve been looking forward to for days. Not in a self preservation way. In a destructive - "I’m a failure, why would anyone want to talk to me or work with me or even be around me" kind of way. 

And here’s the part I wish others could understand. Here, there is no choice. There are actions I can take but it’s terrifying here. Because it truly seems like you’ll feel like this forever. That this is all there is. 

Just as lucidly as I can tell you today, on a good day, that I'm certain it always passes, at those other times, I’m just as certain it won’t. That actually, that is the true me. The other is just an imposter. A happy facade.

I make destructive choices in those moments because I think that’s what’s best not for me, but for everyone else - why would they want to be around me when I can’t give them what they need and deserve. So in business school I hid in my dorm instead of joining parties and study sessions and new ventures. Today, I'll bail on meetings or I won't hit publish on something I've been working hard on (like this piece).

It doesn’t make me proud or feel strong to admit this. 

But just as I felt compelled to talk openly about what failure was like with Poppy, I feel compelled to bring every ugly, dark reality of this, out into the light. So we can talk about it and render it powerless. 

Even though I don’t know Naomi’s pain or struggle, it connects back to mine. Every time someone says, "it’s just a little press conference", what’s the big deal? I want to rage against the lack of understanding. 

I'm not surprised press conferences are a source of extreme stress.  Her sister has even said: Naomi has insecurities about the French Open and every time the press digs into it, it makes her doubt herself.

Reading that struck me in my heart. Because this is me every time I go out to raise a new round of funding. Full of scrutiny and criticism and poking and prodding to break through to the “real story”.

Imagine a day filled with meeting with really smart, engaging people that you would love to work with - whose POVs you respect on Twitter, who are just really good at what they do, who quite literally make their names on “picking the right bets”. Then imagine meeting with all of them and having them tell you why it won’t work, second guess your decisions, your choices, your view of the world. And ultimately: No. You’re great and all, but this is not a thing we’re excited about getting behind. 

And listen, I get it. It's all a part of what I signed up to build a “venture scale” company that can have the biggest, broadest impact possible. I know that finding the right investors is critical to this ambition and I’ve been so fortunate to work with so many of the best (the ones that immediately get it and it feels like collaboration rather than interrogation). So naturally I completely, rationally understand and accept this part of my job. 

But what’s harder to understand from the outside is that what I actually signed up for was to solve people's problems. To make their lives easier. Not to split my heart open and share my life’s work for others to judge it and find it wanting. Over and over again. 

Knowing that the constant scrutiny and rejection is a painful but necessary part of my mission doesn't make it any easier. I understand we’re all just doing our jobs - that it is theirs to figure out all the ways my venture is and isn’t a good bet. I know I could and should do it differently - care less, be more removed. But I can’t. That’s just not me. 

So all there’s left is to figure out how to do it on my terms that doesn't constantly destroy me and therefore, ironically, my company.

Because on this side of the table, underneath the glib advice of “for every 99 nos you only need 1 yes” is a person hearing all the ways that she’s inadequate and that she’s not enough. That she’s destined to be a failure. 

I say all this not for pity. I say this so you can see another more human and more complete reality of what gets glossed over. Of being more careful the next time you say, "but they signed up for this willingly." or, "It doesn't look like she's having issues on her Instagram on that fancy photo shoot."

These are complex, messy lives being lived every day as we all know how. Every single person trying to figure their shit out as much as the next. 

And as we work to figure it out, we understand our boundaries and our limitations. You see, though it might seem it with what looks like callous action on the outside, I am not trying to be reckless or inconsiderate. Rather the opposite. Each day I’m meticulously trying to figure out what might break me and avoid those things as much as possible. 

On a regular day I've got battles to fight. But on days that I know I'm going to be putting myself out there for particularly intense scrutiny and criticism? Well those days I’m just trying to figure out my armor. The force field I can put up around me before I go in. 

And sometimes the force field holds, and sometimes it doesn't. Like a great scene out of Star Wars, there comes a time when the shield didn't start out strong enough or you end up taking too many hits. And in those times you have to get yourself out before you're destroyed. You're not thinking about anything other than survival. 

For me, it has always been coming back to my users and why I'm doing the thing in the first place. I have a doc that holds out user feedback. And I go back to that to remind me ultimately of how worth is measured. I’ll schedule to pick up my daughters from school so I remember the fierce love that lies within me. I go for a walk with a friend so I remember that life is more than anyone else's estimations. 

I do what I have to to protect myself and my peace and my grace. 

It might look cold from the outside when I decline to do a coffee chat or to respond to the hundreds of LinkedIn or Twitter outreaches. 

But it’s not about you. It’s about survival and me doing what I need to not only get through the day, but thrive in my way. 

So I’ll be damned if I sit idly by and let people judge me for that. 

It’s not pretty. It’s not perfect. 

In fact it’s messy and downright ugly.

But you - you have two choices. You can just leave us be. Leave the judgment, the commentary, the consideration. Just completely ignore our imperfect existence. But then you don't get to marvel at our wins, our achievements, our extraordinary. 

Or you can accept us for our messy selves -  witness and celebrate the brilliance alongside the wreckage. 

So yeah, I'm thinking about kintsugi a lot right now. I’m tired of using the clear crazy glue that does nothing but make me feel broken and, well, crazy. 

It’s nothing but gold for me from here on out - celebrating the broken bits along with the whole. Because every single time that I break a little, I figure out how to build myself back - more beautiful and valuable than ever. 

And that’s worth something more, I think.

🌄 The unevenness of hope.

Finding the ground you can hang onto, even when the world is hellbent on throwing endless curveballs.

🎧 The Soundtrack

Listen to this while reading:

✨The Wonderings

Somehow, I've found myself standing in the dark pantry. Sia is blaring through my AirPods, the lyrics of her Move your Body injected directly into my brain.

I let everything go.

I close my eyes and just start moving. My limbs cut through the air in ways that feel foreign to me now.

"Free the beast from its cage,
Free the rage, like an animal."

I feel everything pouring out of me - the pent up frustration and rage and exhaustion. Trying futilely to squeeze new resolve out of fumes. To keep showing up. For everything. For everyone. When it all just feels…unending. Unyielding.

Against the sunny optimism of the cherry blossoms, our city is has returned to stricter restrictions. Family across the country is under full-out lockdown. A close friend and her family is recovering from COVID, a grim reminder the claws of this virus are never far.

But this is a reality all of us have lived over the past year. What’s new is that we are no longer all “in it together”.

It’s the unevenness of hope that is breaking me down.

Over there, I see Instagram images of vaccinated friends giddy with freedom and sunkissed on beach spring breaks. Over here, I’m Facetiming my niece for Easter, not in school or hockey, the two things this kid needs. There, peers posting vaccination cards proudly. Here, my mom still not eligible to get her first jab.

I am happy for you and wildly impatient for me. It is this duality tearing me up inside.

So here I stand in my pantry, eyes closed, swaying, pretending like I'm on some packed dance floor blaring music, mere inches away from other humans moving, perspiring, breathing. Things that are still deemed Dangerous and Not Allowed.

And for four minutes, I can believe it. I can feel my limbs loosen and lighten and let go.

It doesn’t matter that my hands brush up against the granola bars that need to be packed for lunches. Or that I am squeezed between two walls hardly bigger than a closet. Or that I might get busted by a kid at any moment, face filled with certain horror for having a mother that dances out her fears and anxieties in the pantry.

No. None of that matters. What matters is that I have found joy. And hope. On my terms.

I have found a space and a place that feels solid and safe and mine alone. Ready, without judgement or price, without expectation or envy.

And there, I feel my feet, solidly under me. Ready to field the inevitable next curveball.

🔮 The Curiosities


by Naomi Shihab Nye

Before you know what kindness really is
you must lose things,
feel the future dissolve in a moment
like salt in a weakened broth.
What you held in your hand,
what you counted and carefully saved,
all this must go so you know
how desolate the landscape can be
between the regions of kindness.
How you ride and ride
thinking the bus will never stop,
the passengers eating maize and chicken
will stare out the window forever.

Before you learn the tender gravity of kindness,
you must travel where the Indian in a white poncho
lies dead by the side of the road.
You must see how this could be you,
how he too was someone
who journeyed through the night with plans
and the simple breath that kept him alive.

Before you know kindness as the deepest thing inside,
you must know sorrow as the other deepest thing.
You must wake up with sorrow.
You must speak to it till your voice
catches the thread of all sorrows
and you see the size of the cloth.

Then it is only kindness that makes sense anymore,
only kindness that ties your shoes
and sends you out into the day to mail letters and purchase bread,
only kindness that raises its head
from the crowd of the world to say
It is I you have been looking for,
and then goes with you everywhere
like a shadow or a friend.

🔥 Find the heat

Whether you're a writer or an early stage founder, your job is to "find the heat" - the only bits that readers and users care about - and double down on them.

There's an expression in writing where you want to "find the heat". The parts and passages that convey the strongest ideas or bring the story to life.

As a reader, you know what I’m talking about. They’re the sentences that swept you away, that get your heart pounding faster, that get your mind fully invested into the piece.

The heat is the good bits.

For a writer, it's really hard to make the whole thing "the heat" (though the very best writers have honed this skill or work with talented editors to get them there). It’s a process of writing, refining and sometimes scrapping to piece it all together again from scratch.

But I didn’t come her to tell you about writing. I came to tell you about building a startup.

Early stage founders building new things have the same exact challenge. Their job is to find "the heat" in what they're building.

But it's really to know where it might be by just observing users, in the same way it's really hard to know which writing passages have it, unless you ask the reader to circle them and tell you why.

You need to sit down with users and have them point out exactly what (and why) something is "the heat" for them. What makes them ignore the jankiness of the rest and keeps them coming back for more.

The whole period before you get to product market fit is this journey. I'd say most only ever get to PMF because they did this relentlessly.

Starting off, you probably don't have very much heat. Your hypotheses and your ideas cover a vast terrain and you can’t really know what's going to resonate. But slowly you start to get a sense. You start to feel the emotion and the hook.

You tighten up the surface area - for writers, it's focusing more sharply on the key points. For founders it's narrowing to the 3 things to get to “Great” and not worrying about the rest.

Until you've got something that is nothing but heat. No extra friction.

Seamless so that the letters and words on the page disappear, seamless so that the pixels of the UI melt away. Until all you're left with is the good stuff.

This is the work of every writer, of every early stage founder.

Find the heat.

⛰ The Map is not the Terrain.

The folly of believing that the first will help you conquer the second.

🎧 The Soundtrack

Listen to this while reading:

✨ The Wonderings

When distance is more illuminating than the details:

This is an essay mostly about startups. But also about any difficult endeavour where you’ve been charting a map in your mind for months, maybe even years.

Eventually, you come to a point where you say to yourself: “I have the map. Now I may commence”. It’s also easy to look at the map, marked in milestones: come up with an idea, assemble a team, build a product, tell people about it, get them to pay for it, grow it - and say, “now that I’ve mapped it, I am prepared to go do it.”

That’s probably the single biggest folly of first time founders. The reason people say that startups are impossibly hard to explain unless you've done them is one reason:

The map is not the terrain.

The map shows you space, the markers, the milestones. It knows nothing of friction and grit and perseverance. Of setbacks. Of doubt.

Maps are exercises in intellectual bravado. Encouraging you to say: Look at what I know! Look at my cleverness in figuring this all out. Fooling you into false security.

Maps are business plans. The Terrain is the arena in which things are built.

The Terrain is where everything gets real. Where you decide if this journey is really the one that you want to be on. Where after the first arduous climb and devastating descent you have to dig deep and figure out if you're in it for the long run. There is no shame in turning back or stopping. But nor is there much time to idle and deliberate.

Teams are forged on terrain. Culture matters not because a map looks hard. Or that it’s long and winding. Culture matters because when each of you individually is focused on putting one step in front of the other, trying to get through this impossibly stretch, culture is what binds you. It's what give you assurance that you have a teammate with you without casting a glance behind.

I never understood terrain when I first started thinking about leaving my corporate job. At big companies, there is no terrain to speak of. The jungle has been cleared, the land flattened by bulldozers. That isn't to say there aren't challenges, but they're wars fought on grand battlefields with ample resources, not stealth expeditions on the most meagre of rations.

So how does one prepare for the Terrain?

🗺 First, arm yourself with a sketch of a Map. This is your insight and your mission and your Big Vision. This map will not be step-by-step Google Maps instructions but rather your guide, especially the middle years when you feel most stuck - can’t turn back and afraid to push on. This Map should mark destination not distance. You shouldn’t stall before you set out to try to fill in details you don’t know. You can’t know, won’t know, the details until you come upon them.

✏️ Second - as you do traverse the Terrain, fill in the Map as you go. These are your experiments, your findings, your metrics. What worked, what didn’t to get you to this point. So that if you need to go back a bit and try something new, it doesn’t feel bleak and daunting but rather just another approach to test and try out.

🏃🏻‍♀️ Lastly, if there is training to be done before you set out or in the early miles, then learn to be nimble. On being perceptive. On taking in and responding to the data around you quickly and decisively. On training your team on doing the same. Setting up one week sprints with bold experiments tethered to clear goals and metrics.

Fractions of degrees pointed in the right direction in the early steps will compound to miles and miles saved and will hasten you to your destination.

But a Map won’t help you with that. Because the second you step foot on the Terrain you’ll immediately feel disorientated. The pungent smells, the biting wind, the rocky inclines, the peaty, boggy soil.

The quick sprints will settle you into a rhythm until it becomes second nature. So that by the time the early energy starts to fade, muscle memory kick in. And that’s what ultimately will power your mission in the middle and longer stretch.

The map is not the terrain. I tell myself this every morning when I consult my Map - my mission there to point my ambition towards each day. I take pride and solace in the miles we’ve already covered. In what we have learned. In the team we have recruited along the way.

But my gaze always settled on the Goal. Off in the ever-shifting distance. It’s there that I keep in my mind as my North Star as I set off on the day’s expedition. Will direction, with resolve, with purpose.

🔮 The Curiosities

Ode to Dirt

Written and by Sharon Olds

Dear dirt, I am sorry I slighted you,
I thought that you were only the background
for the leading characters—the plants
and animals and human animals.
It’s as if I had loved only the stars
and not the sky which gave them space
in which to shine.  Subtle, various,
sensitive, you are the skin of our terrain,
you’re our democracy.  When I understood
I had never honored you as a living
equal, I was ashamed of myself,
as if I had not recognized
a character who looked so different from me,
but now I can see us all, made of the
same basic materials—
cousins of that first exploding from nothing—
in our intricate equation together.  O dirt,
help us find ways to serve your life,
you who have brought us forth, and fed us,
and who at the end will take us in
and rotate with us, and wobble, and orbit.

🗺 Point Two Designs Maps

The daughter of parents that for 30 years built and grew a travel company from the ground up, I’ve been surrounded by maps all my life. They hold a fascination for me that few other things do. Put a map in front of me and you’ll have to excuse me from fruitful conversation for some minutes. I came across these gorgeous prints years ago. I love how they sit at the intersection of art and science - accurate geographic markers set to striking colors.

🌳 Forest app

One of the hardest parts of day-to-day building is the constant context switching from dealing with minutiae of a release to the high level strategic work. This app is deceptively simple in its premise - “plant a tree” for a set period of focus time - usually right around the 25min of a “pomodoro”. If you touch your phone or go away from the screen, the tree dies. Successfully focus for that period of time and you’ve planted a tree. Sufficiently motivating for me and a great way to quickly “get into flow”, especially with its background soundtracks.

🌖 Poetry + space

Thoughts on the beautiful, profoundly inextricable circle created by the arts and sciences that make life worth living.

Though I have written and shared thoughts for some time now, I’ve always wanted to try something that went beyond simple words. That did justice to how I want to experience life in all its visual and auditory and sensory splendor. So, an experiment. To start with a thought. But to wrap it in the imagery and music and poetry that might bring the words into the world in a more artful, a more human, way.

🎧 The Soundtrack

Listen to this while reading:

✨ The Wonderings

Imagine this while reading:

Do you ever hear a song that immediately grabs you and submerges you within its melody? That makes you stop in your tracks, close your eyes and lets the notes wash over you?

The first time I heard this song, that’s how I felt. I couldn’t tell you for sure what instruments were being played - a cello? Bass? A violin? It didn’t matter because my mind shut off and I felt the notes in my heart. It made me, makes me, feel.... so much.

Loss. Joy. Hope.

It’s beautiful, to be sure.

But more, it’s the reminder I need every so often that life is more than my to do list. More than my goals and my ambitions. It lies hidden within the notes of a song just begging to be lost in.

When I find a piece like this, the first people I want to share it with are my daughters.

Yes, because they are extensions of my heart and I am compelled to share something so profound with them. But also because I need them to understand that music, that poetry, that dance, is as essential to their souls as math and science and spelling is to their minds.

Without both, life is certainly interesting, but it is so very incomplete.

So much of my life has been filled with that which can be measured. Coming from the sciences, the pursuit of knowledge, through thoughtful measurement, has been the dominant presence in my life.

But in Grade 11, I started a new school to do the IB program. Though I chose the Sciences track over the Arts, it was my science teachers who introduced me to pursuits borne of passion. I can still recall our geography teacher's lectures on moraines and cirques delivered as eloquently and as passionately as sermons. Our chemistry teacher was the school's wresting coach and never failed to explain the matters of molecules and reactions in terms of practicality and poetry.

But physics was the most memorable to me. Our physics teacher introduced us all to opera. It blew my mind. Not only that one could be so ardently committed to the opposing poles of experience - quantum physics on one end, gorgeous, soaring arias on the other. But also, that he had the expectation that 17 year olds should and could appreciate opera as vitally as energy-mass equivalence.

He took us to see Puccini’s Turandot and that's when I realized it wasn't a spectrum, science on one end and the arts on the other, as we’re all lead to believe, but a circle. There is something profoundly poignant in the theory of relativity, something that almost abuts religion. And there is science and structure behind the dance performances that move us to tears.

It's a lucky thing, to be 17 when you first learn that lesson. But like so many things learned in youth, I didn’t really understand the importance of the insight. I just marveled at the joy it brought me. I didn't know that in our society, it’s what we can see and tally that we value most and so it takes deliberation and work to right the scales by intentionally weaving in what we feel and what cannot be seen. So I went about my 20s and 30s, with each living in their silos, their compartments, each sharing space with the other only briefly and only sparsely in the words I would write.

But finally, finally, the past year has taught me the foolishness of that. There is nothing but what we choose to put deliberately into our lives. Once all the motion was cut out from my life, I was forced to examine what was left. Forced to choose and nurture what I needed to keep alive.

It's the arts I miss and mourn. The music. The dance. The art. The poetry. The things that have always fed my soul but on the side and in the dark. Hidden in my personal playlists, my evening journal, my iPad sketchpad.

I don’t want that for our girls. I don’t want them to miss the point of this whole thing. I want them to find the melodies that touch their hearts. The math equations that feel like poems in their simplicity and searing insight. The art that catches and hold their imagination. The lines of code that unlock oceans of possibilities. The dances that come from within them, borne of a place they might not understand but know lives in them.

I want them to know both poetry and space.

🔮 The Curiosities

The Peace of Wild Things

Written by Wendell Berry

When despair for the world grows in me
and I wake in the night at the least sound
in fear of what my life and my children’s lives may be,
I go and lie down where the wood drake
rests in his beauty on the water, and the great heron feeds.
I come into the peace of wild things
who do not tax their lives with forethought
of grief. I come into the presence of still water.
And I feel above me the day-blind stars
waiting with their light. For a time
I rest in the grace of the world, and am free.

How to Pronounce Knife

Kids of immigrants all have shades of a similar story. Cast into the wilds of a foreign land, without the typical protection of parents able to explain and soothe and anticipate the parts of the world that don’t make sense to kids. Language can be the most cruel, especially a language like English, almost like its designed to humiliate and cause a lifetime of second guessing in non-native speakers. Forever uncertain. Forever tentative. Forever self conscious. And so first generation kids become virtual dictionaries. The translators to the outside world.

Souvankham writes a whole book of short stories on the painful yet beautiful bits of immigrant life, none so cutting as the namesake - about one word that shatters a child’s illusions of a parent’s all knowing invincibility and lays bare how unforgiving the journey of learning a language like English can be.

Airpod Case by Rifle Paper

For something lighter and more material, my favorite product pick right now. Writing or deep thinking work requires me to put in my Airpods and listen to music or white noise. But though I go quite literally nowhere these days, it’s shocking how often I will lose my Airpods in one pocket or another. The white, slippery case is no help. I found this case and not only does the design bring me joy, the clip ensures it’s never far.

Did you enjoy this? I’d love if you’d share it with your dearest friend or the person you that loves asking questions and discovering new things.

Share a wild and precious life.

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