You could get it for less

If you’re pricing right for your outstanding work, it will sound expensive to others.

After all, they’re not used to buying outstanding work.

This means that the moment you tell them the price, it will probably feel uncomfortable, both to you and to them.

It helps to remember that yes, it’s true, they could find another way to do this.

Maybe they could get some graduate students to do it for free.

Or find someone who’s just starting who is desperate for the work.

Someone on a website, somewhere, who does piece work at a seemingly-cheap hourly rate.

Or someone who can do just enough to make the problem go away, but who won’t fundamentally move things forward.

All those options are possible.

But for this work, at this standard, delivered in this way, it will cost this.

And it will be a bargain.

The Empathy Challenge

The challenge of empathy is that it requires us to overcome our own convenient mental shortcuts.

“He’s just disorganized.”

“She is so rigid.”

“They are biased.”

“They don’t care about disadvantaged people.”

These shortcuts are the opposite of empathy, which is defined as “vicariously experiencing the feelings, thoughts, and experience of another.” Surely someone else doesn’t feel they are disorganized, rigid, biased, or uncaring.

Our first step towards finding empathy is to see our mental shortcuts for what they are: they save us the trouble of seeing the world from someone else’s perspective, helping us box in and simplify another complex human being.

Our next step is to work to see and hear the story they tell themselves about themselves.

This story is, of course, a positive one.

“I am flexible, nimble and creative.”

“I am structured and diligent.”

“I’ve been around the block, and I’m not naïve.”

“I value hard work above all.”

What are the truly good, worthwhile things they are in favor of? What are the values they cherish?

Our empathy breakthroughs ultimately come when we understand the values someone else is fighting for.

We are all protagonists in our own story.

Mariano Rivera on Luck vs Skill

At the end of every How I Built This podcast, host Guy Raz asks his guests whether they’d attribute their success in building their business to luck or to skill.

Hearing that question, it’s hard not to think: how would I answer?

Listening to episode after episode, I looked forward to this question. Both answers seemed valid to me. Then, last week, I attended a benefit for Family Services of Westchester, a not-for-profit that supports the community in Westchester County, where I live.

FSW is a wonderful organization that does important work. However, like most non-profits, their benefit followed a familiar script: drinks, a seated dinner at 10-tops, a silent auction, and a litany of speakers all saying how humbled they were to be honored… It’s not fully FSW’s fault. This is what is expected, and meeting people’s expectations is an accepted way to grab attention to raise money and awareness for good causes.

Mariano Rivera Hall of Fame
Mariano Rivera in 2011. Photo credit: Richard Perry / NYTimes

Near the end of the event, it’s time for the guest of honor: Yankee relief pitcher and Hall of Famer Mariano Rivera. I’m not a baseball fan, so I don’t know that Rivera was the first baseball player to be inducted unanimously into the Baseball Hall of Fame. I don’t have any expectations.

But when Rivera starts speaking, the mood shifts. He has a natural charisma that holds the room, an easy smile and a quick wit. Sports marketer Brandon Steiner, who is set to interview Rivera, walks up to the dais and spontaneously asked him if he’d auction off his watch and his tie for the cause. Without missing a beat, Rivera flashes a big smile, says yes, and runs the impromptu auction himself. The room is jovial, relaxed and engaged.

For all his confidence, charm, and sense of humor, Rivera shifts gears when he’s asked about what got him here. In response to how he stayed calm in big situations, where his famous 90+ mile-per-hour cut fastball came from, how he became one of the all-time greats, Rivera’s answer is the same. He is a religious man, and time and again he says, clearly and simply: he had been blessed by G-d, he is just the vehicle for this blessing.

There is something about the clarity and genuineness with which he says this. He isn’t boasting, grandstanding, or prostrating himself. He is speaking his simple truth. As noticeable, he does so in ways that don’t diminish his own struggles, hard work and perseverance. Yet the ultimate message is that he isn’t the hero of his story, he is a vessel for a bigger story.

Whether or not you’re a person of faith, I’d offer that there’s an old lesson to be re-learned here.

The successes that really matter are ones of good health, a loving family, the talents we’ve been given and the opportunities we’re lucky enough to come across. Whatever other successes we might pursue, and achieve, are built upon this foundation of good fortune.

Yet increasingly I worry that we’re living, in the United States at least, through the logical endgame of our national narrative of an individualistic, “meritocratic” society. As religious practice fades, as our communal ties weaken, and as technology feeds us stories that reinforce our worldview, more and more of “successful” people believe, deep down, that we’ve earned our good fortune.

What I saw in Mariano Rivera was the power of faith of any kind, and the truth that if we’re successful by any conventional measure, we probably have been outstandingly, undeservedly lucky. I also saw in the way Rivera told his story that there is no necessary trade-off between gratitude and agency, no need to diminish ourselves as we acknowledge that we are small players in our own story.

The best part is this: the moment we let go of our story of deserving what we have, we find greater ease in connecting with others, in giving thanks, and in doing what we can to rebalance the scales.


We’ve all had powerful moments when the right person says the right thing to us in the right way at the right time.

Often, these moments will fade for them…just another day and another conversation.

But they stay with us for ages.

It’s because of who they are, the relationship we’ve built with them, the fact that it’s them saying the one thing we need to hear right now, allowing us to believe that we can take our next big step.

We carry these moments in our back pockets where, like photographs, they get worn and a bit faded. In times of doubt and uncertainty, we pull them out, gaze at them, and take comfort.

“This person, who really and truly knows me, said this thing. Maybe it’s true.”

There are many reasons we keep showing up for our colleagues and friends, reasons we continue to be present and why we endeavor, each day, to fully see one another. One reason is for the privilege of saying those right words at a Polaroid moment, to give the gift of hard-earned belief and trust to someone who can do great things.

If you’re carrying around one of these snapshots, today might be a good day to thank the person who gave it to you.

Reflections from Hamilton Fish Park

Squash at Hamilton Fish Park
A picture I took while leaving the park. The white box is the public squash court.

Last summer, I joined a group of about 75 people to watch an exhibition squash match at the first outdoor public squash court in New York City. Former World #1 and squash legend Nick Matthew was playing American up-and-comer Andrew Douglas. If this were tennis, this would be pretty close to the Federer-Isner match, except that since it’s squash, 75 people showed up instead of 1,000.

The exhibition was to bring attention to the first free, outdoor public squash court in New York City, in Manhattan’s Hamilton Fish Park, a beaux-arts jewel in the chain of public parks built in New York City in the early 20th century. The park is surrounded by hi-rise public housing, squat, hulking and indifferent.

As a native New Yorker, I love finding new neighborhoods and I’m always struck by how different worlds coexist next to each other, marked by invisible borders of class, race and unspoken signals. While I’d never been to the Park, I spent two years going to a yoga class six blocks away on Clinton Street, and would eat an Italian lunch after each class. I’m more than an observer of separation, I’m a participant.

The afternoon was a coming together of different worlds, creating as many questions as answers for me.

The public court is, of course, privately funded. It is innovative and technologically advanced – it plays like a wood-floored squash court but is impervious to snow, rain and heat. The privately-raised funds were to demonstrate that squash could be a public game. It’s an effort by squash lovers to democratize access to an historically elite, blue-blood sport. Since squash is one of the few niche sports left that can get you a ticket to an ivy league college, it’s a laudable endeavor.

And yet the court is miniscule in the context of the park, dwarfed by the public space and the 50×25 yard swimming pool built by Robert Moses, one of the most powerful men of his era (who, of course, worked in the public sector). The pool itself was funded by the Works Project Administration, one of 10 $1 million pool projects started in 1936 ($18 million today) for the city parks. This pool, over the decades, has vacillated between the pristine state it is in today and, in the 1970s, a dangerous place to buy and sell drugs. There are no simple answers.

Back to the squash match on that hot summer afternoon. For an hour or two, worlds come together: a group of Squash fans from the 1%, kids from CitySquash, a not for profit that is bringing squash to urban schools, and the park regulars going about their business, playing basketball and splashing in the pool.

We were all quietly other occupying the same space, not quite connecting or interacting but at least in physical proximity.

It reminded me of an unspoken truth of modern social change work: that the “exciting,” “innovative,” and privately funded now idea is often nice but small relative to the greater forces of public spending, public spaces, social fabric, and community. It felt metaphorical to witness this positive, new-style, small charity project in a revived, old-style public park that itself is nestled on the Lower East Side, the corner of Manhattan where wave after wave of immigrants arrived, struggled and, often, eventually thrived.

I left that afternoon seeing the strengths and limitations of both the old and the new approaches, and wondering what it will take for us to do more than comfortably and habitually occupy our own spaces: how do we actively and deliberately make the best of these spaces come together?

Most days, even if we’re in social change work, we are like the two neighborhoods right next to each other: the fancy yoga studio five blocks away from public housing. We frequent our respective places, are generally positive and well-intentioned people, but we don’t talk to each other.

Sometimes we do a bit better, like we did that afternoon: two worlds occupied the same space and peacefully, albeit inoffensively, coexisted.

Rarely, though, do we really stop to interact with each other.

Rarely do we take the time to intentionally learn from each other.

Rarely do we notice how much those who came before us have to offer.

Hamilton Fish Park
New York Times article on Hamilton Fish Park from June 21, 1936.


Why New Strategies Come Up Short

Someone had the idea to install a high-end Dyson hand drier in this bathroom. It’s more efficient, cleaner, and will decrease paper waste. It is, quite simply, a better mousetrap.


Except that the paper towels dispenser wasn’t removed. Maybe there was a good reason to do this, and maybe there wasn’t, but either way, it’s before noon and the  paper towel waste bin is overflowing. The new device, the new approach, is being undermined because no one had the guts to say “and we’re going to stop doing the old thing too.”

Strategy is about making choices.

Most of the time, our new strategies come up short not because we don’t have enough good new ideas, but because we’re scared to let go of the old ones. We are unwilling to stop doing the things that are comfortable that got us here–they feel like they form our identity, there are people who are accustomed to doing those old jobs, so let’s have our strategy be “in addition to” everything else rather than “instead of.”

That all sounds plausible enough, but the truth is we’ll never get to the other side of the pool if we keep clinging to the edge over here.

Maybe You Should Focus on This

I notice this all the time with my kids.

I can’t solve problems for them.

Often, as they get older, they don’t even want my help any more.

But sometimes, just sometimes, I can say, “I think focusing on this part will make a big difference.”

And it does.

Because they have the skills. That’s not the problem.

Some of the time I can help them with diagnosis: how to apply their skills to this problem.

But most of the time it’s not even that. They have all the tools, it’s just that it feels uncomfortable–to them, to to anyone–to stick with and prioritize the hard bits.

As bosses and colleagues, as coaches and spouses and friends, we don’t need to have all the answers. Even if we had them, that wouldn’t matter, because they’d be our answers, not someone else’s.

What we do need to do is to listen attentively, to pay close attention, and, occasionally, by reflecting on our own experience, context and perspective, suggest a slightly different focus: a new lens through which to see a situation, a rejiggering of what could be at the very top of the list.

We shouldn’t be in the solutions-giving business. The answers we can provide are rarely just right, and, even if they were, it’s disempowering when an answer comes from someone other than the person facing the challenge.

But helping people channel their energy in the right way—that’s a great way to partner.

The Difference Between Discomfort and Injury

Every athlete knows that aches and pains are part of the process. Especially as we get older, something always hurts a bit.

The challenge is distinguishing between aches and injuries.

For an ache, the best approach is to continue to work the area to promote healing. Usually a slightly different activity is best, but, counter-intuitively, healing happens faster through more use of the affected area. This increases blood flow and stretches and strengthens the supporting muscles and tendons.

Injuries, on the other hand, require rest. We suspend activity, ice the area, maybe immobilize it until it stabilizes and is ready to be built up again.

These truths apply to our mind and hearts, not just to our bodies.

When we are challenged emotionally, when we take what feels like a professional risk and fall short, we often misdiagnose the difference between discomfort and injury. Any blow – in the form of embarrassment, a critique, a sale we didn’t close, a displeased client – hurts our ego.

It can feel like an injury, but it’s usually just discomfort.

If we allow ourselves the mistake of bandaging up and immobilizing that new muscle that we’ve just used the first time, healing will take forever.

What this new muscle really needs is more work and more effort, so it can be strengthened.

The Purpose of Capital by Jed Emerson

Late last year, I was having breakfast with Jed Emerson in a noisy restaurant on the East Side of Manhattan.

I asked him what he had been up to lately and he smiled, paused meaningfully, and plunged under the table. He pulled out a massive manuscript and thudded it in front of him, nudging aside a small collection of plates, coffee and cutlery.

“This,” he said. “This is what I’ve been working on for the last three years.”

It was a few weeks before Jed’s new book, The Purpose of Capital, was published. When I read the book I realized that it is not just the product of three years of work, it is a life’s work.

For those of you who don’t know Jed, he has for decades been a leading thinker in impact investing (he coined the term Social Return on Investing, or SROI), and he advises many individual and institutional impact investors about their strategies. The decades he’s spent discussing how to deploy hundreds of millions of dollars  to create social impact have given Jed a rare view into the strengths and limits of our current paradigms of deploying capital for impact.

Ultimately, this experience has led Jed to ask some fundamental questions about what it is that we are trying to do here.

Even if you’re not familiar with the phrase “impact investing,” what Jed has to say might interest you. He is asking where the assumptions of our current financial system came from, and why we take them as a given.

Unfortunately, such broad and deep questions defy a pithy summary—so I won’t attempt one. The good news is that questions this big shouldn’t be addressed in just a few paragraphs since, borrowing from Jed’s quote of Peter Orner’s, part of the problem of modernity is that we are living through “an epidemic of glib conclusions” about the answers to the most basic and important questions.

The biggest problem, according to Jed, is that we think we’ve answered the big questions underlying our work. In Jed’s words:

A central issue for many of us in impact investing is that we are operating within an assumption we’ve answered the question, Why?…

The question of why we are investing….is rapidly answered with an interchangeable set of seemingly self-evident answers:

  • To minimize negative impacts while creating positive impacts;
  • To do well and good;
  • To align money and mission;
  • To respond to climate change;
  • To advance a positive response to social/environmental challenges

These are not, in and of themselves, wrong answers. But they are light responses to what are fundamentally deep and profound questions of personal meaning and purpose. They are responses to the “why question” offered with a lower-case “w.” They are the easy responses one would expect from a first round level of conversation on the topic at a cocktail party…

[They are responses that let us] off the hook of accountability, slightly modifying our investment practices and capital allocation assumptions so we may think all the better of our selves and sleep more soundly….[knowing our capital] is proudly parading in the light of day, bringing good things to good people—including bringing good, clean profits to our own good selves.

The Purpose of Capital is the opposite of a cocktail party answer to this question, taking seriously the question of accountability for our actions.

The book digs deep into history and philosophy, touching on topics as varied as: where and why our society came up with the separation of Self and Other (in the Axial Age from 800-200BCE); the distinction between sacred and profane; the roles that Locke and Descartes had in laying the foundation for modern thinking; and the near-religious nature of our faith in modern capitalism (one of countless gems in the book, “That economists can’t measure any of their quantities even to their own satisfaction, can explain neither prices nor the rate of interest and cannot even agree what money is, reminds us that we deal here with belief not science.”)

While I admit that the depths of Jed’s inquiry led me occasionally to lose my bearings—if economics, the social contract, the pillars of capitalism, and dualism itself are called into question, you’re not left with much to stand on—I found deep wisdom in his pulling back the curtain on an important, unstated truth: there are some elements of capitalism that cannot be questioned lest one be called a heretic, and yet, if the system is fundamentally failing us, we have no choice but to leave no stone unturned.

Here’s Jed quoting historian John Reiger:

There is a firm belief in the moral benevolence of the free-market system and private property, combined with a common acceptance among liberal, neoliberal and neoclassical theorists that this is the only system that works. This system takes on quasi-divine and transcendent qualities when it begins to block any and all alternatives and challenges.

If we all, collectively and irrespective of where we stand on the political spectrum, have quasi-divine faith in market economics as morally benevolent (and I think that we do), then Jed is an intentional heretic. He calls upon “those who call themselves impact investors and social entrepreneurs [to]… recognize ourselves as members of a new Reformation. We are members of a happy heretical tribe advancing fundamental aspects of our central faith and creating new metrics to explore its implications.”


Like most important works, The Purpose of Capital tells us that we have been asking the wrong questions. It argues that impact investing is not simply a tweak or even a slow evolution of an existing system. It is, potentially, a full reboot of our current system and the orthodoxies that underpin it.

Yet that is not how impact investing is traditionally viewed. Indeed, in practice impact investing presents itself as a mere (and mild) extension of traditional investing, with the assumption that most of what “we” learned in business school and at investment banks applies.

As Jed states:

As impact investing continues to go mainstream, we now see a plethora of traditional investment strategies, tools and practices applied with even greater complexity in the name of impact, and a decreasing amount of innovation in how capital is structured to transfer the actual power of money to the objects of our influence.

Over generations we have come to embrace a notion that…the expert at navigating financial analysis and handling an investment tool knows best what the purpose of that tool is. In truth, tools are merely means to an end and nothing more.

Acumen, where I’ve worked for the last 12 years, wrote a manifesto six years ago, and one of its core tenets is to see “investing as a means, not an end.” This simply-stated inversion of means and end is a truly radical act, and I can say with confidence that it is no small feat to take a well-honed, sacred tool and say, “this is just a tool.”

Operationalizing this shift this is far beyond the scope of even this long blog post, but Jed at least gives us guideposts about what our underlying purpose might be:

Impact investing is, first and foremost, an exploration of the purpose of capital…[one that] seeks to lay the foundation for the emergence of new 21st Century forms of economics and capitalism…

Impact investing is also about mindful money that integrates the power of presence with considered intentionality within capital flows throughout the world. It places resources within new structures, pumping life-affirming blood into new organizations and corporate forms. Impact investing is about pursuing an array of related strategies that promise to optimize total performance of financial returns with the generation of social and environmental impacts. It is integrated impact, not disconnected from life, but life promotion, life affirming and life creating capital.

When understood at this level of purpose and meaning, those who continually question whether or how one may achieve ‘competitive’ or ‘market rate’ returns on impact capital are skating on the surface as opposed to delving into the greater possibilities of how we might optimize the total performance of capital in the fullest sense of the term.

Hopefully these excerpts have whetted your appetite for Jed’s book, which is available as a free ebook for download or as a hardcover on Amazon. It’s not a light read, but if you’re intrigued by some of the bigger questions, Jed’s book should be on your list. (Bonus: Jed just let me know that the book is being translated into Mandarin and he’ll be doing a book tour in mainland China this fall.)

Before wrapping up, I’ll share a few reflections on Jed’s core thesis.

First, I fully agree with Jed that we, the impact investing community, have let ourselves off the hook. We act like we know (and are living) the ‘why’ of impact investing. We don’t know the why, and we’re certainly not living it. Not yet.

I do believe we have the potential, as a community, for revolutionary change—if we have the stomach for it. Our job is to be willing to fundamentally question all the norms and rules given to us by traditional investing. While many of them might still be useful, none of them should be taken as a given. The criterion we must apply in examining each of these rules are: does this rule serve the change we hope to make in the world? That is, in most cases and for most investing ‘rules,’ a tricky question to answer.

In order to do this properly, I believe we, as impact investors, must understand much more than how to deploy capital and build companies: we must be from and deeply connected to the communities in which we deploy capital; we must be students of the history of social change; we must be willing to engage in conversations about what makes a good society; and we must be interested in looking in the mirror about our own privilege, biases and blind spots, and begin to engage in the slow, meaningful work of self-transformation. These are all new muscles, but necessary ones if we endeavor to make lasting positive change.

Second, while I firmly believe in the potential that Jed describes as the purpose of capital, I am left wondering about the seemingly-individual transformational focus of the book: my relation to my capital and my (and our) sense-making and meaning. That’s the right place to start, but what happens to these individuals, and their lone voice(s), as they move out of sync with a broader system?

Meaning: I agree that the first step is for each individual impact investor to have more fundamental conversations about the purpose of their capital. However, when they act alone and against the tide of the larger system (including the larger impact investing system), will they have the leverage to make meaningful change? If the locus of the changes they make are primarily: 1. Personal (their values and worldview); and 2. Strategic (how they deploy capital), does that run the risk of omitting the larger levers like norms, story, the rules of the game, what’s considered “standard” impact investing products, the metrics for social performance, and, ultimately, expectations for how the system operates as a whole? Jed’s book itself starts to bridge the gap between the individual and the system, by reframing the broader narrative about what we’re all doing here in the first place.

Finally, to take things a step further, I did find myself a bit surprised that impact investing seemed to be both the question and the answer in the book. For a book willing to be so radical, I was waiting for the moment that Jed would to look at the whole thing and say, “and even if we do all of this, it alone won’t be enough.”

If our fundamental problem is that we misunderstand our relationship to money, can a sufficient solution be recasting our relationship to money in the context of higher (personal and societal) meaning?

Perhaps I’ve been coming across Anand Giridharas’ Winners Take All: The Elite Charade of Changing the World too often, but it does echo in the in the background of this conversation. Anand’s thesis is that our current system of philanthropy and impact investing only exist to reinforce existing power dynamics. This makes them a generosity charade that undermines social justice. Anand challenges us to be willing to look at the fundamental power dynamics that created inequality of wealth and power in the first place: Jeff Bezos pledging $2 billion to fight homelessness is well-intended, but wouldn’t it make much more sense for Jeff to stop using Amazon’s clout to avoid local taxation and to fight zoning laws that make housing unaffordable in Seattle?

Knowing Jed, who has a much longer and deeper background in social justice than I do, I expected him to conclude that that better deployment of capital by the few is but a small part in the much bigger reboot of capitalism that we need to create a more just and inclusive world. That, at least, is where I’d like to see the conversation go from here.

Flexing Just One Muscle

Weight lifter straining and Coralie Camilli
Images courtesy of and

You’ve probably seen weight lifters (or folks at the gym), and what their face looks like on that last repetition: veins popping out of their foreheads, everything shaking and straining, as if the muscles in the face are somehow exerting force on the bar they’re trying to lift.

The face of a martial artist, on the other hand, is calm. The muscles she uses, the momentum she creates, are limited to what is needed to produce the desired force. There’s no spillover, nothing is wasted.

The same thing happens to us emotionally.

When we find ourselves under pressure, or provoked, or in a period when the stakes are high, we act as if we need to flex all our emotional muscles: we bark orders at the people around us, we replay conversations in our head, we cannot sleep.

This overflow of emotion, and the resulting unproductive behaviors, is repetitive and exhausting. It’s not just that it doesn’t help us, it actively wears us down.

It can feel impossible to stop acting like a weight-lifter with our emotions: that first wave of emotions triggers more emotions which trigger more… soon enough, metaphorical veins are popping out of our heads, and the anxiety, frustration, and fear all feel so real.

But, once we’ve felt all of these feelings, we do have the option of letting them go.

It’s not easy, but perhaps it helps to remember: my job at this moment is to do less.

Practicing when the stakes are lower is another good place to start.