The Fruits of Friendship

We don’t talk enough about friendship.

Friendship gives flavor to life. Rather than treating friendship as a nice-to-have luxury, reserved for people who have their lives in perfect order, we should cultivate friendship intentionally and treat it as the necessity it is. We need to be intentional in our pursuit of it, especially as we age.

Like a marriage, the best friendships require investment, compromise, and sacrifice. By creating shared alignment, trust, and companionship, strong friendships nourish the soul and sharpen the mind.

The Loneliness Epidemic

America’s loneliness epidemic is a direct result of the structure of American life. Work is changing and modern life keeps us distanced and disconnected from the people we love.

Loneliness plagues modern life. In big cities like New York, where I live, people lack community. In a city where everybody is chasing their dream with the focus of a hawk swooping down for the kill, it can be hard to forge deep relationships. We should reject the status quo.

Last summer, I moved into an apartment with a close friend. By living together, we could spend more time together. But after going more than 50 days without a meaningful conversation, we decided to schedule time together with a calendar invite. A calendar invite… for my roommate. What is going on?

Turns out, it isn’t just me. In a book called Bowling Alone, sociologist Robert Putnam studied the decline of social interactions in America through the lens of declining participation in labor unions, fraternal organizations, and religious groups. Putnam contrasts the struggles of building friendships in urban communities with “The Sprawl Civil Penalty,” which states that urban sprawl and suburbia lowers community involvement by roughly 20 percent. As a result, American communities have lower trust, reciprocity, information, and cooperation than they once did.

The world Putnam describes is a long way away from the post-World War II American society, where big unions and tight neighborhoods ran the show. The hollowing out of friendship is tragic: and 25% of them have no confidants or close friends. None.


The mobility of modern life doesn’t help. According to one longitudinal study which tracked best friend pairs, people moved 5.8 times on average over a period of 19 years. But people aren’t just moving more. They’re moving farther too. Epidemiologist David Bradley tracked the lifetime movement of four generations in his family. His great-grandfather’s entire life took place in a square of only 40 kilometers, his grandfather’s took place over 400, 4,000 for his father, and his own extended to every corner of the globe across 40,000 square kilometers. The geographic circle of life has expanded, so friendship strategies that depend on constant proximity are no longer effective. In the modern world, you cannot cultivate a strong, multi-decade circle of friends unless you are intentional about it.

I refuse to accept that weak friendships are the price of ambition and career success. In response, I’ve developed a philosophy of friendship.

Deep Bonds Take Time

I’m not talking about the temporary, friction-free relationships that social technologies make so easy. No. I’m talking about friendships where two identities merge. The kinds that stretch across decades, the kinds that blossom into extended family, and the kinds of friends who your kids call “Auntie” and “Uncle.”

Friendship is vital to your whole spirit — your being, your character, your mind, and your health. And yet, all too often, humans don’t realize what’s essential until they are in trouble, so they dismiss the power of friendship when things are going well.

I take extra care to prioritize extended time with friends. If you want a deep conversation, you need time. Instead of spending two or three hours with somebody, I prefer to spend two or three days with them. More, if possible.

After 24 hours, the small talk disappears, and after 48 hours, philosophizing is inevitable. The benefits are exponential.

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In his book on friendship, John O’Donahue asks:

“When was the last time you had a great conversation? A conversation that wasn’t just two intersecting monologues, but when you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that found places within you that you thought you had lost, and the sense of an “eventive” conversation that brought the two of you into a different plane and then forthly, a conversation that continued to sing afterwards for weeks in your mind? Conversations like that are food and drink for the soul.

Like a massage, time softens the human heart. With each tick of the clock, the soul awakens to the layers of trust and tender vulnerability required for a deep conversation. Nurtured by the trusted cradle of companionship, time steers conversations in rich and unexpected directions.

A good conversation exists at the outer edge of consciousness. Luckily, there are proven ways to spark transcendent dialogue. Laugh. Have fun. Don’t gossip. Find a quiet place. Then, shake things up and go somewhere else. By changing your environment, you change the energy of conversation, and when you switch up the energy and move to a new place, people blossom into a kaleidoscope of personalities.

The benefits of friendship compound. Friends who act with grace and sincerity over a series of repeated interactions will be gifted with selfless generosity and loving kindness.

A Model for Friendship

Before his sudden death in 2008, John O’Donahue wrote a beautiful book on friendship called Anam Cara. Anam is the Gaelic word for soul; Cara is the word for friend, so Anam Cara means soul friend.

In the early Celtic church, an Anam Cara was a teacher, companion, and spiritual guide with whom you revealed the hidden intimacies of your life: your dreams, your fears, your hopes, your struggles, and your insecurities. With them, you can open your heart, stretch your mind, and freed from the Orwellian cage of judgment, you can take off your mask and be seen as you are.

Rather than homogenizing or imitating each other, soul friends sprout in different directions. They praise the other’s unique and unusual nature, and as they do, their friendship warms the soul. As John O’Donahue wrote:

“In this love, you are understood as you are without mask or pretension. The superficial and functional lies and half-truths of social acquaintance fall away… When you really feel understood, you feel free to release yourself into the trust and shelter of the other person’s soul… Love is the only light that can truly read the secret signature of the other person’s individuality and soul.”

By freeing you to speak with honesty and communicate with love, your Anam Cara frees you to explore the wildest possibilities within you. No matter who you are, what you do, or how much money you make, this kind of companionship will foster alignment, safety, and growth.

The Fruits of Friendship: Alignment, Safety, and Trust

1. Career Alignment

A strong network is fuel for career success. Unfortunately, most networking advice is garbage. It leads to transactional relationships, robotic interactions, and long nights at loud, head-shaking networking events where you count the seconds before it’s okay to put down your drink and storm out the door.

Thank u, next.

Early in your career, the most important aspect of networking is building relationships with up-and-coming people who have similar interests. Scooter Braun, a talent manager who represents Justin Beiber, Kanye West, and Martin Garrix, had this to say about networking:

“The mistake of youth is thinking that the mentors you need are older than you. That you should work on getting in a room with some powerful person because that’s going to change your life. It’s not true. What changes your life is your peers… The people you rise up with. They’re your power base. Not the person who’s already done it.”

Most people see a strong divide between “work friends” and “life friends,” but that will never work for me. My life and my work are one-in-the-same.

Peers are the engine of career success. Together, the ones you’re closest to comprise your “10 Club.”

The 10 Club is a group of 10 people you want to work with later in life, and every member should be kind, ambitious, and generous. Travel together, meet their families, and attend their weddings. Get to know them. Then, team up and support each other.

Or as Shakespeare said: “grapple them to your soul with hoops of steel.”

2. Safety

Beyond the 9-to-5, friends provide safety.

Trusted friends magnify the shine of life. In turbulent times, they smoothen the ride. And in moments of joy and ecstasy, they make the world a richer, more saturated place. In that way, friends are like a trampoline. They soften the fall so we jump like a Marvel superhero: the 360-backflip, the swirling mid-air corkscrew, and the WWE wrestling moves that would otherwise make your mom’s hair grey. If the landing wasn’t so cushy, you wouldn’t even attempt the jump.

Choose your friends carefully. You will rise and fall to the level of the company you keep. As a general rule, you should spend time with people who energize you, inspire you, and make you proud to call them a friend.

The mark of a great friend is somebody who believes in you, looks out for you, and has your best interests in mind. Those who give you honest feedback, even when the truth is hard to share and even harder to hear are worth their weight in gold. When you acknowledge their feedback, friends become like bumpers at a bowling alley. They let you bounce around, but not too much. By protecting you from stupid decisions, they free you to go all out and bowl for strikes.

The Buddhists have a name for this: Kalyana-Mitra — a “noble friend.” Since nobody can see their life totally, they confront people when they misstep even when doing so is awkward and uncomfortable. Like mirrors, even when we’re blind to our own actions, the words of a Kalyana-Mitra reflect your true self.

Once you find a Kalyana-Mitra, invest in their friendship. Accelerating feedback loops is the fastest way to accelerate your learning or improve your behavior, and when you give excellent people a clear window into your life, their feedback will be invaluable. Unfortunately, most friends can’t really help each other. Since they don’t communicate with depth, honesty, or frequency, they gloss over their true challenges, many of which are taboo to discuss. But the shine on top will never fix the cracks beneath the surface.

When you speak with somebody at length, you realize that everybody — yes, everybody — faces a waterfall of challenges. In difficult moments, friends serve as guides. Through dialogue and feedback, they help us navigate the unknown, alleviate suffering, and dodge the bullets of everyday life.  

The algebra of a well-lived life puts friendship in the center of the equation.

Shared experiences — especially novel, challenging, and unfamiliar ones — are the best way to foster tight bonds. Host a retreat. Travel with friends. Rent a car, start driving, and see where you end up. One close friend says that relationships, from friends to lovers, are only built once bodily fluids start flowing: tears, blood, sweat, and you know… whatever else.

Struggle and shared experiences are like fuel for friendship. My closest childhood friend was born out of hours on the golf course and the ruthless pursuit of a spot on a college golf team.

Together, my friend Zander (an outstanding writer) and I traveled across the state of California, where we played in ultra-competitive golf tournaments and crashed in two-star motels. Rituals emerged. Starbucks sandwiches for breakfast, In-N-Out Burgers for dinner, and Krispy Kreme Doughnuts for dessert. During our senior year, we hosted a charity golf tournament for the Bonnie J. Addario Lung Cancer Foundation, which is the most I’ve ever enjoyed working on a project.

(Quick story: On the day of the tournament, we arrived to the course early. We snagged the keys to the golf cart and sped out onto the course. Literally. Five minutes into the ride, we looked at each other, smiled, nodded heads, and turned the drive into a go-kart race. Game on, Zander: first person to get to the fourth hole wins. In the thick of the moment, we made a sharp 90 degree turn onto a narrow, wood chipped path. Then, the maintenance guy found us, stopped us, and like a cop, pulled out his walkie-talkie and snitched to the Director of Golf. Golf cart privileges: REVOKED).


In short, Zander and I have years of shared context. As John Lilly wrote:

“The special thing about having that much context, and people around who know & believe in you is how much they can frame the year that’s past, and the year ahead. Your tribe has the context about you & your life — and can remind you, when you need it, of who you are, and who you can be. And beyond all that, it just feels good (and restorative, and challenging) to come home once a year, and see friends & allies, and tell all the old jokes, and just listen about where you’ve each been, and plan about what’s to come.”

That decade of travel, conversation, and hitting golf balls under the moonlight in his backyard bound us like superglue. From the inside jokes about Family Guy to our endless impersonations of our high school physics teacher and the girl in our American history class who fell asleep every… single… day, John Lilly’s words perfectly describe my friendship with Zander. 

Most importantly, it’s friends like Zander, who, through direct and earnest feedback, illuminate my blind spots. 

3. Growth

Conversation unshackles the mind from its usual constraints. When we keep our thoughts inside, our minds look like dark, murky water. But like a river, clarity requires flow. 

Speaking is thinking. When we share our ideas, we discover unexpected insights and unlock the hidden realms of suppressed thought and forgotten ideas. Through the unexpected randomness of conversation, we maximize intellectual serendipity and explore the contours of our own minds.

So often, time with friends is seen as unproductive or an inefficient distraction from the main task of being productive and achieving our goals. Paradoxically, even though city life fuels ambition by aggregating millions of people into a dense metropolis, it makes it hard to build friendships.

But when you find the right friends, the opposite is true. Intelligence is enriched by kindness. If people don’t trust you, they won’t open up to you. As Visakan Veerasamy wrote:

“If you care about having an interesting life, you have to care about winning over other people – so that you can access that information. If you really want to be smart, you’re going to have to tap into people’s perspectives, insights, questions and so on. You can’t learn it all from books and essays – because there’s a lot of “living knowledge” that never makes it into those things.”

These words came to life during weekly sessions with my friend Chris Sparks. Chris’ work is one-of-a-kind. He coaches high performance knowledge workers and wanted to accelerate the growth of his coaching business. He built his skills the hard way: through hundreds of hours consulting entrepreneurs and thousands of hours playing poker (at one point, Chris was ranked as one of the top 20 online poker players in the world). 

Fortunately, due to my marketing background, I was the right person to help him build his business. In exchange, he helped me tweak my daily habits and develop my online course.  

We met weekly. Within five months, I had successfully launched an online course. Ultimately, without kindness and generosity, I wouldn’t have been able to absorb Chris’ living knowledge and use it to launch Write of Passage

The Utility of Friendship

As the world changes faster and faster, the utility of friendship will increase. The people in your “10 Club” will help you navigate the future and point your career in a productive direction. Like cartographers, friends who help each other and map out the future together have an advantage.

Cultivating these life-long, work-centric friendships can come with tradeoffs. Building friendships doesn’t scale. On one hand, you want to build relationships with enough people, so that when you’re ready to start a company or recruit for an executive position, at least one person in your friend group will be able to join you. But on the other hand, deep time is the best way to build friendships, and there’s only so much time in the day.

Instead of growing your Rolodex, double down on your best friendships, and find your 10 Club.


Note: This was originally a letter to myself. Then, I sent it to a couple friends, and now I’m sharing it publicly. In it, I outline my philosophy of friendship and the kinds of people I want to surround myself with in my 20s.

Acknowledgements: Special thanks to Vinay Debrou, Ryan Blake, Sid Jha, Derek Urben, and Nicolas Marescaux for editing drafts of this essay. And thank you to Kevin Kwok for sparking these ideas in the podcast we recorded together.