2020 Chairman's Letter

Hello again! I am incredibly happy to be writing what is now the second annual Chairman’s Letter for the American Leadership Foundation.

One way to look at the success or failure of an organization — business, non-profit, whatever — is to say that it meets some need (or fails to) and then it finds efficiencies that help it get better at meeting that need over time (or fails to) which will let it grow and thrive over time (or not).

Another way to look at that same narrative is to see an inherently improbable idea become a reality or disprove itself. What starts as, say, a 5% chance of success will either become 100% real or fall to 0. After the fact, when we know the ultimate outcome and look back on the path things took to get there, it’s easy to feel like things were predetermined. But when that path is still unfolding in front of us, there are a lot of external factors guiding the course of events that can’t ever be predicted, and it’s a lot of hard work to keep up with those twists and turns that can’t ever be properly accounted for.

With that in mind, I want to first express some gratitude going into this second year.

First I'd like to say thank you to the other members of the A.L.F. 's board of directors: Aviva, Claire, Tyrone, and Peter. When we had our first board meeting in the fall of last year, none of us had any way of knowing everything that was going to unfold in the months to come. But we were still able to come together, collect and review dozens of applications, interview candidates, and find so much promise in the students graduating (while studying remotely in the midst of a pandemic!) that we ended up expanding the program to include secondary grants to an additional three emerging leaders when we had originally only planned to award one. I’m really happy with our operational success in year one and it wouldn’t have been possible without the team coming together in what’s been an unprecedented and challenging year for all of us.

I also want to thank our early partners at Montgomery Blair High School who have been really key in helping us get the A.L.F. off the ground as the home of our inaugural scholarship program. A special thank you here is definitely owed to Kevin Shindel, who has been important as a contact within the school and also important as one of the first people to hear some of my ideas for the A.L.F. and believe in what we’re trying to do here.

Ultimately, though, everything we do circles back to the students we’re trying to support. I’m proud of what we’ve been able to accomplish this first year, but I’m honestly more impressed by the graduating students I got to talk to, who are pushing forward in a world no one could have prepared for and finding ways to keep going.

I think there are different kinds of work that we engage in over the course of our lives. There is a kind that we might actually just call “toil” — work that is necessary but draining, the kind of work that saps us of strength. There’s another kind of work, though, that nourishes us as we labor; it gives us energy rather than draining us, it’s the kind of work that reminds us that we’re alive. It might seem kind of odd, but when I got to talk to each of the grant recipients — Natnael, Faith, Amanda, Emma — during the interview portion of the selection process, I really felt inspired by the determination and drive each of them showed. There’s a circular property to the foundation’s work that I think is a source of strength for us: even as we work to support these emerging leaders, that work gives us a reason to keep pushing forward in everything else we do.


It’s odd (and maybe disappointing) that this kind of work we could call nourishing seems to be so much more rare than just regular toil. I think there’s a lot to be said for being mindful and diligent in our day-to-day routines, and I think there’s a lot of virtue in finding meaning in the lives we already have rather than thinking it only exists in theoretical lives we might imagine living. But I also think the need we sometimes feel to find some higher purpose is a a real one; I think that if there’s some part of you that’s always looking to find something more engaging, something more meaningful, something more, then a world where you have some shot at finding it is a better world than one where you don’t.

These thoughts were running through my head the other day when I was talking to a friend about how she got started in her PhD program. She had actually gotten rejected by some universities, but she wasn’t too disheartened by that — it was just a bad fit. She explained that the real challenge wasn’t to become a perfect prospective graduate student, but instead to find the perfect advisor for her, specifically.

To say it in her words, “it’s not an optimization problem, it’s a matching problem.”

In some ways it reminded me of my experience applying to college as an undergrad; I think I must have messed up my applications somehow, because despite graduating high school with perfect SAT scores and a GPA somewhere around 3.5, I got rejected by every college I applied to, save for one. I ended up taking a gap year anyway, working, gaining some great experience, and then when I did go back to school at the University of Maryland, everything ended up working out as well as I could have possibly hoped.

Looking back, I don’t think my path was “optimal” in any conventional sense of the word, but it might well have been a perfect match for exactly who I was and am still today. UMD led me to a lot of great opportunities that I never would have guessed at when I was still in high school, and by the time I was an upperclassmen I had a breadth and depth of experience that really helped me stand out. I ended up following a somewhat odd and winding road to things that other people tend to assume you have to optimize your whole life for — things like working for Google, which opened up all kinds of possibilities for me.

When I was at Google, incidentally, I ended up being an interviewer for potential new hires. I was impressed by how seriously the company took its interview process and how hard they were always trying to make it better.

The biggest thing I appreciated was that everyone was very much aware how imperfect the system inherently was.

It’s just plain hard to tell if someone would be good at a job after talking to them for 40 minutes, and while the company had come up with all kinds of ways to do a better job with these things, we also encouraged people to just reapply and re-interview a few months down the line. There were people working at the company and doing quite well there who’d been rejected two or three different times from that initial interview process! Trying to get a job there clearly couldn’t be an “optimization problem”, then; there was room for error on both sides.


Having had all these experiences, I find it hard to understand why our undergraduate applications processes work the way they do. There are test scores and some essays people are asked to write and even letters of recommendation, but in the end it just seems like rather little information, and the institutions themselves don’t seem to be all that intensely bothered by any deficiencies that might be lurking there. People seem to largely just accept “this is how it is, maybe we can make it a bit better but not much”. That implicit attitude just seems wasteful to me, more than anything. Wasteful of applicants’ time, wasteful of reviewing resources, but also, in the end, wasteful as a way to open or close opportunities to people.

I suspect that most things we pursue in life — especially the most meaningful things, the work and challenges that truly nourish us — end up being gated by these “matching problems”, with opportunities and people on opposite sides of some big room and a lot of confusion trying to connect one group to the other.

I also suspect that there’s one side of any given “matching problem” that is less actively invested in making those matches happen.

It doesn’t make sense to me.

Truthfully, it bothers me, deeply. It bothers me on some moral level, but that’s somehow hard to talk about.

I’m reminded of Michael Lewis writing about the lead up to the global financial crisis in The Big Short:

Here was a strange but true fact: The closer you were to the market, the harder it was to perceive its folly.

People who become successful end up embedded in these large, complex systems underpinning our society. Somehow, once there, they lose perspective on how dysfunctional the whole thing is, no matter how obvious those issues were from the outside. They find it easier to imagine changes stemming from a series of orderly, incremental steps — a walk being led by people who are able to function well within the system as it is. But what does it mean to function well within a fundamentally dysfunctional system?

There is a tension between affecting change and averting chaos that is not wholly resolvable; we tend to do one more than the other at any given point in time, and just kind of hope we’re able to balance the two in the long run.

I think the reason that The Big Short comes to mind, however, is that the 2008 Global Financial Crisis could really be seen as a forced semi-resolution to an enormous Nash equilibrium. There were many independent agents, each acting in their own self-interest, and the system that emerged was dramatically worse for everyone involved than if there had been even slightly more cooperation.

Even in all of the turmoil that followed, we never quite learned the deeper lessons about these emergent systems that we might have. The U.S. still struggles with a dearth of local institutions and lack of informal support structures, and the pandemic has undoubtedly made these problems even worse. That big, ultimate issue, the fundamental reluctance to cooperate for mutual benefit, also seems to be in danger of getting worse, as we turn our backs on our neighbors instead of trying to build community in a time of crisis.


There is an inescapable drama to the moment we find ourselves in. The problems we’re facing are real, and the stakes are high no matter how we play these cards we’ve been dealt.

This election will inevitably serve a historic cornerstone no matter what happens, but the underlying realities of our situation today are not going to be decided by the electoral college or change in any given office.

I started the American Leadership Foundation because I believe in that idea of leadership, and I believe we need leaders to bring people together in times of strife. But I don’t see that need as a short term lack; it's a profound and lasting truth. We will always need leaders, we will always need to dig deeper within ourselves to find that strength to support others, to look beyond short term goals and self-interest, to help others live their best lives, and in so doing, to make our communities — even our society — stronger.

Doing that is a lot of work, honestly, and the payoffs can feel vague, unclear, and indecisive. But it really is work that nourishes us.

Ultimately, it’s the kind of work we’re all alive to do.


Thank you,
R Phillip Castagna
Chairman, American Leadership Foundation