Is this imposter syndrome? Faking it in philanthropy

Last month, I defended private foundations from their critics and argued that, when done right, philanthropy can move us away from plutocracy by deepening democracy. I still feel that way today. But every coin has two sides, and at least once every few months I experience the sinking feeling that I am faking it — that philanthropy perpetuates elite capture and status hierarchies more than it dismantles them.

I know that I’m not alone in feeling this way, though we rarely discuss it openly. And so I’d like to share a piece — dare I call it creative writing? — that aims to give a glimpse of what it feels like (at least for me) to be a program officer at a private foundation. The text intentionally has a dream-like, drifting quality to it; for that’s how I largely experience the world with the jet lag from an 11-hour time difference.

After three flights and a few delays, it was 1 am by the time I arrived at my hotel in Nairobi, but only 2 pm according to my body, which was stuck 11 hours in the past. I popped a melatonin and began counting sheep.

Four hours later, I was wide awake but looked like a haggard mess. It was 5:30 am, pre-dawn, and in three more hours, my colleague and I would convene more than 25 Kenyan grantee organizations for a four-hour workshop. It was going to be a long day.

In a beautiful reflection about when and why we pay attention to small details, LM Sacasas described how he struggled as a teacher to distinguish between some of his students:

When I taught five or six periods, it would usually take me two to three weeks to learn the names of most of my students. Invariably, there would be a handful of students who I would go on to have some trouble telling apart. Maybe they all were of a certain height or hair color or whatever. Long after I could confidently call on most students by name, these few students would remain indistinguishable to me. But, naturally, a few weeks later on their uniqueness would gradually become more fully apparent to me. And by the end of the semester, I always marveled at the fact that I had ever had any difficulty telling them apart.

I relate. There would be at least 50 people at our workshop. I had met most of them several times. I was the only white man in the room — easy to identify — and I was terrified that I would not recognize someone’s face or that I’d forget their name. I scrolled through the participant list and searched social media for their latest photos, populating my brain’s feeble facial detection system.

Despite my preparation, I was stumped twice. They were both gracious, fully accustomed to the dumbfounded, struggling gringos unable to distinguish among a sea of black faces.

As the workshop went on and the participants positioned their agendas, it occurred to me that after more than a decade of attending grantee meetings in Kenya, this was likely my last. I became distracted for a moment while thinking of Sam Harris’ profound guided meditation, “The Last Time.” We never know when we might be doing something for the last time. And even those things that frustrate us — the meeting that should have been an email, the self-promotional monologue — they somehow become sweeter, almost charming, when you realize it might be the last time you experience it.

The next week I was at the inaugural Africa Media Festival. At Hewlett Foundation, where I work, we “only” have about $1.5 million per year to support free and independent media in Kenya, but the challenges are endless: the public increased their distrust of mainstream media after they skewed poll results to favor their preferred candidate in last year’s election; publishers block stories they deem politically sensitive, newsrooms suffered mass layoffs, and nonprofit online investigative outlets struggle to compete for attention with TikTok influencers. At the conference, there was much “admiring the problem” and few concrete ideas about what to do about it. Despite a lack of concrete ideas, during each session break, I was surrounded by hungry fundraisers pitching me their projects. This is the worst part of my job. I’m the jet-lagged white guy who knows comparatively little about Kenyan politics and society, and here I am with my stupid American smile politely explaining to extremely smart Kenyan journalists why we won’t fund their passion project. My justifications feel arbitrary and rehearsed, and I want someone to call me on my bullshit. Instead, they smile back and say, “well let’s keep the conversation going. So, when are you going to be in Kenya again?”

A few weeks ago, while I was doing some research about culture and status, YouTube suggested the video “How to Impress Someone Who’s Higher Status,” which has been viewed more than 4.5 million times. I can’t get used to the fact that during these dozens of funding pitches, I play the part of the “higher status” person who rejects the request for money from the person playing the part of supplicant. You can phrase it in more self-effacing terms, but that’s the nature of the thing. And I hate it. Those of us who are the gatekeepers of funding decisions at private foundations delude ourselves that we are empowering others while we often perpetuate the same status hierarchies we claim to disrupt.

That evening I popped another melatonin and rolled around in bed for 20 minutes until I gave up and flipped on my bedside lamp to read. I chose an essay by Leslie Jamison, who looks like a model, is not yet 40 years old, has published four books, and recently wrote a piece for the New Yorker to explore her feelings of inadequacy and imposter syndrome. It’s often the highest achievers, I find, who suffer most from low self-esteem.

Before I had read Jamison’s essay, “Why Everyone Feels Like They’re Faking It,” I thought that I suffered from pervasive imposter syndrome. After all, I constantly question why I am the one arbitrarily responsible for making these funding decisions when almost anyone else could do so just as well. But I came to realize that I don’t really suffer from imposter syndrome, at least not as it was originally conceptualized in the 1970s. I think I have an accurate sense of my abilities and shortcomings. In professional circles, lacking any Ivy League degrees or prep school pedigree, I feel underestimated more often than under-prepared. My sense as an imposter has little to do with my own psyche or capabilities, and more to do with the randomness of how we take up the roles we each play on the stage of life.

Eventually, I drifted to sleep. The next morning I woke up looking like I hadn’t slept in days. I checked my phone and saw an email from our director of communications that the president of the foundation was revealed in the media to be one of the co-signers of Sam Bankman-Fried’s record $250 million bail. We were told that he was acting in a personal capacity and not as a representative of the foundation. As I walked from my hotel to a nearby restaurant for breakfast, my brain was filled with thoughts in the form of a ranting Twitter thread. I imagined how Bankman-Fried would be treated if he were Nigerian or Puerto Rican. (He certainly wouldn’t be watching the super bowl in the comfort of his parents’ house.) I thought of all the young Africans who were swindled by social media influencers into losing their savings. I thought about the Bay Area’s elite triangle that binds together Stanford University, VC firms, and private foundations while the rest of the region struggles to pay rent. But why were these thoughts entering my head in the form of tweets? And did my brain think like this in 2005 before Twitter existed?

While sipping my morning coffee, I typed out my Twitter rant with my thumbs, saved it as a draft, slipped my phone into my pocket, and made my way to a meeting with other funders at “Kenya’s most exclusive business club.” We went around a u-shaped table and each offered our diagnosis of the challenges facing Kenyan media without committing to coordinate more closely in our attempts to address them. Once again, my brain was filled with Tweet-sized complaints — this time about the unnecessary meetings and consultancies simply because some foundations still don’t publish their strategies or grants.

There were about 15 of us in the room. Just a decade ago, when I started working at Gates Foundation, a room like this would have been 70% middle-aged, white Americans and Europeans. This time there were just two of us, a shift that took far too long, and then happened all at once. Those middle-aged white folks have largely been replaced by younger, feminist, African women. They are the proud, outspoken daughters of politicians and diplomats. Many of them went to liberal arts colleges in the U.S. and then did a master’s degree in development somewhere like LSE or the New School. They speak in academic jargon, referencing French post-modern theory while starting most sentences with the obvious: “as an African woman.”

“This is the next chapter,” I think to myself. It is a wonderful thing that the white American has been displaced by the young African feminist in shaping Africa’s development agenda. But it still feels far from true representation. It still feels like trading one form of elite capture for another. Will elite African feminists eventually let go of the power they have accumulated so that others — who never left their country nor attended private school abroad — can join their ranks? We shall see.

I wasn’t in the mood for conversation on the drive back to my hotel. I pulled out Twitter to distract myself and came across this from a former journalist:

I relate to that teenage self. Is it still somewhere inside me? Have I used my time in philanthropy to disrupt status inequities, or have I merely advanced my and my friends’ status?

I felt annoyed and a little sad, but was I actually annoyed, or did I just need to sleep? Back at my hotel, I slipped in my earbuds, closed my eyes, and listened to a guided meditation by Andy Hobson titled “Breath, Body, Sounds and Thoughts.” I paid attention to my breathing, which slowed and deepened until I felt a sense of calm. I scanned my body, relaxing the muscles of my forehead and shoulders. I paid attention to my emotions, annoyed and unsettled, until they felt like temporary visitors who would soon be on their way. And finally, I observed the thoughts as they entered my mind like twigs floating down a river. Where did these thoughts come from? What was their purpose? I watched my thoughts go by until they disappeared and my mind was empty.

After 30 minutes, a chime signaled the end of the meditation. I opened my eyes and saw the golden light of Nairobi’s afternoon sunlight reflect off so many glass buildings that didn’t exist when I first visited Kenya in 2007. The chime was a reminder that this may be the last time I look out at the skyline for another decade or longer. I was tempted to pull out my phone to snap a photo. Instead, I just stared out over the hustle and bustle of the Westlands neighborhood.

I thought of another line from Jamison’s essay about impostor syndrome:

Capitalism needs us all to feel like impostors, because feeling like an impostor ensures we’ll strive for endless progress: work harder, make more money, try to be better than our former selves and the people around us.

All week, I caught up with former colleagues from Gates Foundation and Luminate. They were eager to know what I would be doing next after my time concludes at Hewlett Foundation later this year. “I still don’t know,” I told them, and then thought to myself: but I know I will need a break from this.

I still think that we are better off with philanthropy than without it. I feel extraordinarily privileged to have had the opportunity to work as a grantmaker. But the contradictions and hypocrisies are real, and anxiety and self-doubt are the price of admission.