Why I have an open calendar policy
One of the most meaningful parts of my professional journey has been the open conversations I’ve had with people navigating their own career paths. These moments of connection have shaped who I am as a professional, a leader, and a person—and I want to share why I believe they’re important.
For years, I’ve maintained an open calendar policy: anyone—college students, recent graduates, early-career professionals, or seasoned leaders at a crossroads—can book time with me to talk. Sometimes this is just a 30-min 1-time interaction. Sometimes it turns into a longer relationship.
- This practice has roots in my own story. I wouldn’t be where I am today without the generosity of mentors and peers who gave their time to help me think through big decisions, get unstuck, and see new possibilities. Some of the most pivotal conversations in my life came from people who had no obligation to help me but did anyway—offering encouragement, asking thoughtful questions, or simply believing in me when I wasn’t sure I believed in myself. There are still moments in my day to day when I’m stuck or unsure and I think back to something one of these mentors said when I was 18, or 25, or 30. That’s a lot of value and impact packed into an interaction from so many years ago!
- Now, these conversations have come full circle. Every person I meet teaches me something—about the challenges they face, the creative ways they solve problems, and the courage it takes to take the next step. Practicing listening, active problem-solving, and helping someone (including myself!) get unstuck has made me a better coach and collaborator in my own life. It’s sharpened my ability to approach complex challenges with empathy and creativity, both at work and in my personal relationships. And if I can deliver something encouraging or useful in that moment, maybe it will stick with them for years and that’s pretty remarkable.
- Not every conversation is as impactful but I think the cost of losing 30-minutes of time to a conversation where this kind of connection doesn’t happen is worth it. More often than not, if both participants can get to an open, vulnerable, generous place, something meaningful comes out of these interactions. Even if it’s as simple as feeling energized by a new idea for the rest of the day.
- More broadly, fostering a generous, open professional community isn’t just good for individuals—it’s good for the world. When we share time, insights, and encouragement, we make the spaces we’re part of more human. This ripple effect—helping one person who then helps someone else—has the power to create lasting positive change. Even if this is not ultimately true, I like to think that the marginal effect of this choice has a positive impact on the world I’m co-creating with my peers.
For me, these moments of connection are about more than giving or receiving advice—they’re about creating a culture of generosity and growth. They remind me why I’m so passionate about education and collaboration, and they challenge me to keep learning and evolving alongside the people I meet. These interactions are some of my most cherished moments every year.
Until I can’t anymore, my calendar will remain open. I believe in the power of connection and shared growth. And if you’re someone who’s already benefited from or offered this kind of openness, I’d love to hear your “why”. And if this made you want to connect or re-connect over a call, I’d love that too!
Navigating and “illiquid” career path
Brynne Hobart’s always-excellent newsletter recently mentioned a post by Vaishnav Sunil about the difference between “liquid and illiquid careers.” Here’s Brynne’s summary that caught my attention:
There are some job paths that make someone's value to a prospective employer incredibly legible (if you went to HYPS and then spent two years at MBB, employers know roughly what you can do and almost exactly what you can accomplish). And if you taught yourself TypeScript while pursuing a career in jazz performance before getting into longevity research, there's a wider range. Compressing away that career volatility is convenient, and it's a defensible choice, but one of the upsides to an illiquid career is that you get a lot more input into the rubric used to evaluate your own abilities. The analogy immediately made sense to me, given my own career path. The post is worth your time in full but below are some quotes that stuck with me as I nodded my way through it all.
Overall: I agreed with much of Sunil’s evaluation of the positives and negatives of this kind of career development. For me, the breadth of impact across industries (presidential elections, small business marketplaces, journalism, population health and now education technology) has been very satisfying. And the setbacks along the way have been, thankfully, quickly followed by steps forward. There may be some selection biases at work (immigrating across the world at 10 years old is perhaps the most risky event of my life and probably shaped my risk profile in ways that I’ll never fully appreciate) I’m glad I’ve ended up on an illiquid trajectory. When I talk to peers or folks now deciding on their own trajectories, I often sing the praises of this approach.
On higher uncertainty in illiquid careers:
Illiquid career paths typically yield a wider distribution of outcomes. For those aiming at the extreme positive tail, leveraging unique strengths and actively managing one's career become crucial. This approach can potentially lead to outsized returns in terms of impact, personal satisfaction, and financial rewards. However, these paths aren't suitable for everyone. They demand higher tolerance for uncertainty, proactive career management, and often rely more heavily on social capital and personal initiative. So if you’re looking for a nice job that pays the bills and can fund your lifestyle, you should probably chase liquidity at the expense of expected return.
On talent-stacking:
More generally, avoiding linear paths means the ability to choose roles based on the skills that you want to work on and develop at any given point in time. This flexibility aligns well with Scott Adams' concept of a talent stack. In non-traditional paths, you can strategically select roles and experiences that allow you to build a unique skill set based on your situation or their future value when stacked together, which might be larger than the sum of the parts. On the importance of organization and attention to detail, or, generally, shoring up weak spots:
Communication skills and strategic instincts are probably both incredibly important to a business leader’s success. However, a young person who clearly outperforms his or her peers on these abilities probably won’t make it up the corporate hierarchy to become CEO if as an entry level executives, they fail to excel in a role that tests their attention to detail and ability to process high volumes of routine tasks to perfection . As someone who struggled with this early on, I’m convinced that cultivating a minimum amount of organization and attention to detail is important no matter what one wants to do, but the degree to which this can be emphasized to the exclusion of almost everything else may not predict future success. Be that as it may, your boss probably won’t care that he’s failing to see the flashes of brilliance in you that could transform the company 15 years from now.
On the characteristics of illiquid careers:
- Industry growth and activity: Skills that can be deployed in high-growth industries or sectors with high levels of activity tend to be more liquid. The increased "trading volume" of human capital in these areas enhances liquidity. 2. Skill specificity: Counterintuitively, more specific skills often enjoy higher liquidity. A carpenter's abilities are well-defined and easily understood, whereas "project management" can vary widely based on context. This clarity makes it easier for a carpenter to market their skills, even in a new location. 3. Testability: Skills that can be easily and quickly assessed tend to be more liquid. For instance, a software developer's competence can often be gauged through a brief coding test. In contrast, evaluating leadership or managerial skills typically requires more time and varied assessment methods, resulting in lower liquidity. 4. Context dependency: If your value primarily stems from familiarity with a specific organization or geographically limited social capital, your skills may be less liquid. However, this can sometimes correlate with skill specificity, so the net effect on liquidity isn't always straightforward. 5.Institutional brand: Larger, more established brands often provide greater liquidity to their employees' human capital. This is due to their well-known screening processes and the larger sample size of previous employees, allowing potential employers to better estimate the value typically generated by individuals from these institutions.
Scaling yourself up and down
A few months into my latest professional home, transitioning industries (healthcare to ed-tech) and organization lifecycle (Series A and D startups to post-IPO medium tech org) the topic of coaching and team leadership has been on my mind. This framework of scaling yourself up and down, based on organizational needs, has stuck with me and I’ve been experiencing it first hand over the last few years and across different company cultures.
Startups require a combination of “I do X and I build teams that do X,” while more mature orgs require leaders to transition from, “I do X to I build teams that do X.” Scaling impact in a more mature org happens mostly through vision, mission and inspiration. As a coach, the most impactful thing I can provide is a clear vision, aligning the strengths and values of my teams with our mission, and inspiration to unblock them when we inevitably run into obstacles.
Among other things, this requires deeply understanding where the team is and where we need to go. And then managing their “energy” to grow smoothly without burning out or getting bored. Especially in high talent density teams, like Duolingo , this is where good leadership can truly make a difference. Good coaches can also dive into the details when necessary. You have to use good judgment and intuition to know which layer of abstraction your team needs and when. Sometimes diving into the details is the right thing to do.
As I move into (wince) my mid-career years, this transition to coaching and leadership is helping me find pleasure and excitement about work in a different way. Instead of individual accomplishment, I’m motivated by unlocking the potential in the teams and colleagues I work with. It is not hands-on-keyboard work. But it is a good antidote to the general burnout and malaise I see settling in for many of my mid-career peers.
My next adventure: Duolingo!
Last week, I started a new role at Duolingo as Group Content Program Manager. I will be working with a group of program managers, learning scientists, linguists, technologists, strategists and all around impressive group of Duos on scaling Duolingo’s content to serve hundreds of millions of learners. I’m grateful to join this warm, welcoming, very smart group of folks who are committed to Duolingo’s mission: to develop the best education in the world and make it universally accessible. And the timing couldn't be more urgent, given the widespread operationalization of AI technology.
As Noah Smith noted in a recent newsletter on the topic, AI is poised to generate instability, require much adjustment and magnify differences in comparative advantage in our economy. Unlike recent tech innovations, this innovation feels truly exceptional in it’s possible level of disruption and impact. As I get to know more about Duolingo’s strategic use of AI, my excitement is growing about working on these questions here, with these colleagues, for content creators and learners around the world.
Reflecting on the past decade, I have followed my instinct to join mission-focused, innovative, organizations to make progress in sectors like electoral politics, small business e-commerce, journalism and healthcare. Joining Duolingo feels like coming full circle. Pittsburgh has been our home for almost two years and joining Duolingo has already been a wonderful way to meet and work with Pittsburghers. And as an immigrant and lifelong language learner, supporting language learners around the world has brought me back closer to home, too.
Hindi, English, Punjabi, French, Arabic and Spanish have played important roles in my life since childhood. Duolingo’s mission strikes a chord with me on a personal level. Language acquisition, as the founders of Duolingo understand firsthand, holds immense potential to mitigate inequality. And the company's expansion into new subjects such as math and music signals just the beginning of its impact.
I also have my life partner, Elise Hawthorne, to thank for showing me the power of education technology and for keeping education and student service front and center in our lives.
I’m grateful for the opportunity to continue working on an innovative, urgent, personally compelling mission. To do it with fun, supportive, and smart colleagues. And (almost to the day) after 4 years of building teams and companies remotely from my house, to get back to doing this work in person. Yeehaw, let’s go!
What I learned in my first 3-hour marathon attempt
On November 19, 2023, I ran the Philadelphia Marathon with about 15,000 other runners. It was a beautiful sunny day and the route was chock full of spectators, family and friends. For me, this was a culmination of about 10 months of training and my first attempt at breaking the 3-hour mark in the marathon. I learned a lot of valuable lessons over the course of this training block, many of which, only slightly abstracted, apply to other endeavors like team and company leadership. So I thought I’d share them here.
Goal setting is an essential skill: picking a 3-hour goal was somewhat arbitrary. But once I picked it, it was extremely clarifying and a powerful motivator. I started in early January with a fitness level of about a 4-hour marathon. After almost 2000 miles of training, milestone PRs along the way, and seeing progress week after week, I showed up on race day in shape to truly attempt to break 3-hours. Setting clear, ambitious, goals as a team can be clarifying and create cohesion and motivation.
Understanding the journey through narrative: as I trained, ran tune-up 5Ks, 10Ks and half-marathons, and kept my eye on the 3-hour goal, it was helpful to know where in the journey I stood. Especially during setbacks, knowing that I was on a journey, where each mile would build on the last and set me up to attempt my goal was critical. It gave me the faith to keep showing up for every training run and race. This applies to work teams too. Understanding where you are in a project, and that every step builds towards the end goal, can be motivating.
Mental fitness is a critical part of leveling up in any skill: in this case it was running, but in a professional context it might be a new technical skill, a bigger project, a new area of ownership; wherever there’s up-skilling happening, building confidence and resilience will be necessary. And this fitness compounds. The more you show up and try the more you’ll want to. Under valuing mental fitness (confidence, tenacity, mindfulness, etc) can be a misstep when you’re aiming high.
No big goal is achieved alone: from my running coach, to my local neighborhood run club, to YouTubers / TikTokers / Redditors who have provided guidance online, to the strangers on the course on race days, I’m indebted to dozens of people who helped me this year. The same is true in professional contexts. Very few big goals happen without input, guidance and advice from the community you build along the way. Thoughtfully building your community is critical to achieving big goals.
After starting on pace for 20-miles and feeling great, I experienced heavy cramping in my legs for the last 6 miles. I think I just didn’t have enough salt in my system. I hobbled through the finish in 3 hours and 20 minutes, well short of my goal. All the confidence I built in the first 20 miles, the lessons I learned over this training block, and the clarifying discipline of setting and working on a big goal are more than enough to make up for this first miss. And the pride I feel for making it through those last 6 miles will be an important reminder to myself, too, about my own mental fitness.
After some rest and recovery, I look forward to putting another race on the calendar, remembering these lessons about ambition, resilience and community. And to putting in the miles before arriving at the next starting line.
What I highlighted the weeks of July 10, 2023
Articles
The Long Annoying Tradition of Anti-Patriotism
Anti-populism, along with its cousin anti-patriotism, is an elite response to demands from below to change a social hierarchy, which is why it’s so pervasive today, at a moment when the public is angry. I saw it all the time when researching corporate power - which is the bedrock of our social hierarchy. It was particularly pronounced during the New Deal. In 1933, upon the ascendance of Franklin Delano Roosevelt, for instance, Columbia University Nicholas Murray Butler told incoming freshmen that Totalitarian dictatorships are putting forward “men of far greater intelligence, far stronger character, and far more courage than the system of elections.”
Mark F-king Zuckerberg Is Not Your Friend
We all know how this works. Bots, farms, artificial boosting, algorithms, astroturfing, paying influencers, brands, and celebrities to migrate without saying they were paid. We are not new here. Asking Facebook to not fake engagement and steal data is like asking Canadian goose not to rip anyone’s face off. That is, fundamentally, what it does and what it’s for.
Who Employs Your Doctor? Increasingly, a Private Equity Firm.
“Private equity is like the system on steroids,” said Sherry Glied, the dean of the Wagner School of Public Service at New York University. “Every time there’s an opportunity for making money, P.E. is going to move faster than everyone else. And consolidation is the way to do that.”
New to me was this Job Decision Matrix and some other linked resources about career development which resonated with how I've thought about career development recently. Relatedly, this life and parenting philosophy about doing hard things resonated for me, especially for career development.
The key thing is to really try to decide which bucket is MOST important and which is LEAST important I’m regularly surprised when a mentee hasn’t thought about what kind of people he/she wants to work with.
The barely believable after-work activities of young people in 2002 was a fun read to remember some parts of my early career professional life. My version was a bit later, like 2010, and more as an intern and junior analyst rather than NYC media professional who are mostly discussed in this piece. But I remember lots of coffee and bagel runs, long meandering conversations in the company cafeteria over lunch and post-work city outings in DC and Chicago like concerts in the park and happy hours around town.
Gokul's S.P.A.D.E. Toolkit was a useful re-discovery as I'm spending more time in a new role as a Series A exec. Working with founders, new incoming execs, adapting to a new culture requires lots of meshing of decision making styles. And this is a good tool toward consensus building.
Music
Anthony Fantano released his Best Albums of 2023 So Far and I've been loving many of his picks, especially:
Caroline Polachek's "Desire, I Want To Turn Into You"
The Lemon Twigs Everything Harmony
McKinley Dixon's Beloved! Paradise! Jazz?!
I also discovered two older albums this week that I've been loving:
King Sunny Ade's Juju Music
And !!!'s Thr!!!er
Movies
Biosphere was a pretty good Duplass Bros movie, kind of like "The One I Love" with a relatively simple SciFi-lite setup and a 2nd and 3rd act that escalates the stakes hanging mostly on excellent central performances. The choice of acapella music made it feel closer to "Swiss Army Man" than I imagine the filmmakers intended. Still, something affecting about this, for me, a man with many close male-male friendships.
Joy Ride was a riot and a blast to watch in the theater. And when I whispered, "that's Baron Davis, he used to date Laura Dern" to my wife in the theater, that felt like our own personal "that's Chappy" moment to me.
Beau Is Afraid was a tough hang. I found the project (Jewish neuroses, guilt and paranoia magnified and explored) admirable but the execution...did not work for me.
TV Shows
The Other Two S1 and S2 were very funny, breezy and had multiple laugh-out-loud lines per episode.
Books
I re-read parts of Fortune Smiles by Adam Johnson, still among my favorite short story books ever. The first story, "Nirvana," felt once again very relavant as LLMs have come into the zeitgeist more.
Podcasts
This A24 pod with Julia Louis-Dreyfus & J. Smith-Cameron was a delight. Full of hilarious stories from the sets of Veep and Succession. And an amazing interlude where Kenneth Lonergan shows up and JLD tries to convince him to see the new "Spidyverse" movie and Lonergan talks about Spider-Man as a tragic figure. Great stuff.
What I highlighted the weeks of June 26 and July 1, 2023
Articles
Maximum Canada is happening by Noah Smith
I wish Americans could tell themselves a positive narrative like Canada’s — of immigration as the way to build a multicultural nation. Many of us have tried to tell that narrative, and have foundered on the rocks of America’s age of division. As John Higham wrote, when America is underconfident — when we start to doubt who we are as a people and a nation — we instinctively think about closing the door. Right now, America definitely doesn’t know who we are, as a people and as a nation. Maybe next decade we’ll remember.
A great Noah Smith essay on pro immigration frameworks in Canada that the US could learn from. I've been working on a smaller version of this in our new home city, Pittsburgh, with a group of leaders in the city committed to turning around the population decline this city and region have faced for decades. One of our main focus areas is in-bound immigration, of all kinds.
The True Threat of Artificial Intelligence
But this ideology — call it A.G.I.-ism — is mistaken. The real risks of A.G.I. are political and won’t be fixed by taming rebellious robots. The safest of A.G.I.s would not deliver the progressive panacea promised by its lobby. And in presenting its emergence as all but inevitable, A.G.I.-ism distracts from finding better ways to augment intelligence.
With A.G.I., this reliance will only deepen, not least because A.G.I. is unbounded in its scope and ambition. No administrative or government services would be immune to its promise of disruption.
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Grohl has dug himself, and his band, out of a trough, but absence, to borrow from W. S. Merwin, goes through him like a thread through a needle, stitching everything with its color.
An amazing longread on Gini and Clarence Thomas
I wish I lived in a world where I had to know less about the personal lives of Supreme Court justices to understand where my country was headed. But this is not that world. So learning about the histories and psychologies of these people remains fascinating.
Movies
Past Lives was extremely emotionally affecting. But less impressive cinematically.
Asteroid City was a blast. And more people should be talking about its meta-modern themes like we did with Everything Everywhere All At Once
Showing Up was an excellent Kelly Reichardt film, I think tied with First Cow as my favorite of her films.
TV Shows
I watched the first half of The Bear S2 and it was excellent. The music, as in S1, has been a real highlight. And unlike many prestige shows from the last few years, this show has the distinct advantage of all the main characters being eminently hang-out-able. I don't know if I can say that I'd particularly want to hang out with Kendal Roy, Walter White, or Don Draper. But Carmy, Richy and the gang, absolutely.
Not exactly a TV show (but also yes a TV show), I enjoyed John Mulaney's Hot Ones episode.
Podcasts
This Jungian Life on bipolar disorder
One of the best episodes from this podcast, which I generally love. I've found myself thinking about some of the frameworks they presented around mania, hypomania, the American culture, especially corporate culture, as bipolar. I feel like I'm going to come back to this one a few times over the years.
What I highlighted the week of June 19, 2023
Articles
"Why Do Movies Feel So Different now"
This video essay by Thomas Fligth was a great description and discussion of modernity, postmodernity, hyper- and metamodernity in film over the last 50 years. It captured a lot of what made "Top Gun: Maverick" feel like a breath of fresh air and what made "Everything Everywhere All At Once" so successful.
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We live in an anemic period of capitalism in which excessive returns are hard to come by unless you engage in exploitative labor practices, self-dealing among friends, frenzied lobbying aimed at shredding regulations, political projects aiming to privatize what’s left of the commons, or geopolitical strategies that aim to protect a dying empire’s dominance from ascendant powers.
The Nation, under Bhaskar Sunkara, has been publishing some interesting things. This piece had a long section on the relationship between venture capital and American hegemony on the global stage which I found less compelling, but otherwise is chock full of interesting data and commentary about the failures of venture capital and the lack of rigor on the part of the defenders of the Silicon Valley model of innovation and investment.
"The Godfathers of AI are at war"
Other experts echo Hinton’s disquiet. One of them is Yoshua Bengio, with whom Geoffrey Hinton shared the 2018 Turing Award. On 31 May, Bengio told the BBC that he feels “lost” over his life’s work. “It is challenging, emotionally speaking,” he said, as researchers are increasingly unsure how to “stop these systems or to prevent damage”.
I found the amount of emotional language quoted in this piece about Hinton, Bengio, LeCun and other AI leaders to be notable. More emotional language than I'm used to in coverage about AGI, existential risk and such topics.
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You might miss this if you believe AI is a brilliant, thinking machine. But if you pull back the curtain even a little, it looks more familiar, the latest iteration of a particularly Silicon Valley division of labor, in which the futuristic gleam of new technologies hides a sprawling manufacturing apparatus and the people who make it run. Duhaime reached back farther for a comparison, a digital version of the transition from craftsmen to industrial manufacturing: coherent processes broken into tasks and arrayed along assembly lines with some steps done by machines and some by humans but none resembling what came before.
When AI comes for your job, you may not lose it, but it might become more alien, more isolating, more tedious.
An excellent piece in NYMag about how much human labor is behind most current AI models and the development of the next generation of models. This piece had some of the most believable descriptions of AI led job disruption that I've come across in recent coverage, which tends to be too doomy or boostery for my taste. This piece felt more grimey and tactile, which tends to match the lived experience of work for most human beings.
"Everyone Says Social Media Is Bad for Teens. Proving It Is Another Thing.""
It’s not about monitoring certain apps, said Caleb T. Carr, a professor of communication at Illinois State: “Instead, parents should engage with their kids. Just like parents did pre-social media, talk about being good humans and citizens, talk about respect for others and themselves, and talk about how their day was.
Helpful compendium of the kinds of research happening in psych and sociology about the effects of social media on kids that paints a much more complicated picture of the relationship between social media and kids' mental health and the kind of picture Haidt and Twenge tend to paint.
Movies
- I laughed a lot and very hard at "John Early: Now More Than Ever", the latest special from John Early. Early, Kate Berland and Jacqueline Novak are maybe the best comedians working these days.
TV Shows
- We started a rewatch of "High Maintenance" and it's just such a good show. So much to reminisce and wince about 2010s Brooklyn. S2E1 about election night in 2016 was as excellent as I remembered.
Books
- Thanks to this NYT piece about the recurring popularity of Norman Rush's 1990s novel Mating I picked up the novel earlier this week and have been really enjoying it.