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One of the exercises in CLP is about identifying and clarifying our personal values. In Cohort 10, we each identified our top five values, writing one each on five index cards. Then we set one aside, and another… until we were left holding the card with our number one, top value. What is your current One right now and why?
I always struggle with what really is “a value,” because I think of them as broad adjectives. But, I think the one that resonates with me the most right now is thoughtfulness.
It surrounds so much of what I do. I don’t know anything about astrology other than Virgos are over-thinkers, and, to the extent that the cosmos had any predictive capability, they got that right with me. [laughing] I painstakingly pour over decisions. And it’s not to say that I’m perfect at it, but thoughtfulness is always on my mind. I think that thoughtful people are the ones that make a difference.
So I try to be thoughtful enough, right? Like, got the I’s crossed and the T’s dotted – publishing joke there. But I try to think about what I’m not thinking about and what my blind spots are, and how I can add value by bringing deep thought to a table.
I hear you. I wonder what your other top core values are, that would steer thought-fullness towards the positive impact you have? Because I feel like someone could be thoughtful as in thinking a whole lot, but also still harming.
Yeah. I’d say it melds humanity, integrity, and respect. A lot of the work that I do is community-involved and thinking about how to make the world a better place. What I’ve realized in thoughtfulness is you can’t be everything to everybody. And the more you try to be everything to everybody, the more disappointed people become. I also hate and fear disappointing people.
But I think humanity and integrity are really important, in the sense that no one’s really in this alone, and in being thoughtful you do have to not only take into account your own experience, but also what other people are experiencing. And what they’re experiencing because of you. So those are really big to me too.
And I think respect’s a big thing. Love is very interesting, because it’s the one that we talk so much about how we can’t define it, but we know how it feels. And I think it’s both in how we receive, but also perceive love. Sometimes I think it’s easier to discern that someone respects you, than it is to discern that they love you.
Respect a lot of times is a lot more clear. So we can try to love everybody, but I think if we respect everybody, our intentions will be a little bit easier to discern.
I appreciate that context. Would you say those have consistently been true for you over the course of your life, or have they changed in ways that stand out to you in this moment?
That’s a good question. I feel like so much of what we tell ourselves about the past is like a story that we craft. Because there are things that I can remember clearly about who I wanted to be, but I don’t know that I was really thinking about my core values in third grade — or at 23.
But I think the one consistent thing was community involvement, in wanting to give back. Some of it was pre-programmed in the way that I grew up — my family, going to church, and doing community service in the summers.
I think I started putting together the fabric of who I am when I got to college. I majored in economics and minored in community development. I did a lot of writing and researching about the wealth gap, and the idea that African-Americans needed to close that. What practical things could we do to make people have better futures than their previous generations? I interned at social justice nonprofits during my summers, and eventually turned that into a lot of the work that I’ve been able to help and assist with at ConnCORP, and now at ConnCAT.
Another thing that’s really important to me is intellectual curiosity – to really think through the tough problems and how to solve them. I’m a little bit less interested in the debate of all of these things as opposed to creating solutions, things that we can do so that we’re not just thinking deep thoughts while people are suffering.
Amen. Are you from New Haven?
Yes — I was born and raised in New Haven. I went to undergrad at Howard University — of course, a historically black university. And I went to law school at Wake Forest, which is sort of the opposite. Then I moved back to New Haven once I finished law school.
You know, they say Connecticut’s largest export is college students; so I guess I defied that when I moved back 10 years ago. I’ve lived in different places around the city. When I was born, we lived in Westville, then we moved to Beaver Hill. After my dad passed away, we moved to Fair Haven, Oyster Cove, by the Waucoma Yacht Club. Then from there, my mom moved us back to Beaver Hill, and that’s where she lives now. When I bought my house, I moved back to Westville.
What is one big, burning leadership question you are wrestling with these days?
How can I be more patient.
If I’m thinking about being a board chair, I’m usually thinking about what it’s going to take to get things done, and what is my role in that. As a board chair, sometimes you’re kind of calling balls and strikes… other times, you’re listening… and at certain times you’re a motivator, or you’re driving things. And I often have to try to take a step back and ask myself how I’m showing up in this moment, and where does that position me to what needs to get done?
I think we all have our frustrations and things that bother us, but you eventually have to kind of mute that in favor of what it takes to get things done. I might not think it’s happening in the best way… Or that people are thinking about the critical issues… but rather than getting frustrated about that, the idea is I can raise what those things are, and start to influence and empower people to consider these positions. It’s a very strategic way of thinking.
Whereas, when you’re just a board member, you can pound the table, be a single-issue person and get frustrated. But as a board chair, there’s a certain amount of patience that you have to have about the bigger picture and about the mission.
From a leadership position at work, my goal is to get a businessperson to consider all of the relevant issues that come up in the law as it relates to their business decision — get them to yes, and also protect the company. So, a lot of that is building enough of a relationship and rapport with a businessperson for them to trust not only what you’re saying, but also that you’re not a blocker to what they want to do. So that listening to you will… pay dividends, no pun intended.
So, a lot of it is the “soft” factors. Communication, being willing to answer emails when you’re on vacation, thinking thoughtfully about how you may have to say no, but still getting someone to really believe that you’re on the ride with them and not just the person waiting to kill their idea.
What inspires you, gives you hope these days?
I’m like the hopeless optimist; there’s things that trigger joy in that, right? Because sometimes when you’re optimistic, you’re like, ‘here I go, being a fool.’ I gave an award at the Neighborhood Music School award ceremony recently — the Board of Directors Award. It’s reserved for a student that’s active in the NMS community, active in their own community, and really exudes all of the values of the school.
And in a place that looks to transform lives and nourish the soul through arts, what really makes those words real are the students and the amazing things that they’re doing. I joke around whenever we give scholarships out, that I would hate to be competing with some of these young students. As much as we talk about their lack of social skills or other things, just seeing young people so involved and so optimistic about the world, really makes me optimistic.
I think you get kind of jaded in the day-to-day of growing up and having adult issues, but there’s another generation of people who are coming behind, who are going to have similar, if not the same issues, but they’re going to bring their new perspectives and new ways of going about them.
Knowing that these students think about the world in such a positive way, when you can start to look at it so negatively? It’s like, okay, there’s someone else to help carry forward this commitment to try to make the world a better place.
When you say you’re a hopeless optimist, do you mean a play on hopeless romantic?
[laughing] Yes, exactly. Like, you’re just so in love with the idea of love that you do actually show up. You’re going to show up on every single date because this next one is going to be the love of your life.
My view on being a hopeless optimist is… that there is something that can be done about all of these problems and plugging the hole in the boat. There’s another good group to support another generation of young people that need the support, the mentorship, the sponsorship.
So I’m on this constant loop of — things can be terrible, things can be bad, young people are being murdered, all of those things. And you’ve got to sit in those feelings. And I don’t feel like, with all of the bad things going on in the world, that I can take a day off from hoping that things can be better, or involving myself — my life’s work is to try to make the world better.
I believe that people are one life-changing opportunity away. Not from the “American dream” — the deck is stacked against a lot of people in that way. Also, I don’t think that your life being transformed should be contingent on you turning into the next Elon Musk or entrepreneur, right? People should be able to have a comfortable life where they can afford to take care of their obligations and just be happy.
When you look at how transformative going to a place like ConnCAT is, and learning life skills that will allow you to have gainful employment, or start a business, right? I’m not so much invested in what the end result narrative has to be for a person. I don’t think you have to be a particular thing.
But I do think that you should be able to have hope and optimism and opportunities for better in your life. And what you make of that is really a function of time, space and opportunity.
But when we talk about things like privilege and access and proximity? Like, if you go to Hopkins, you’ve got a life changing opportunity that probably happens every day, right? There’s something that you’re going to learn or someone that you’re going to meet or someone in your network who has the ability to help move mountains for you. Whereas if you grow up in certain communities, no matter what the color of your skin is — Newhallville to Appalachia — things can look and feel different. And closing that gap is what’s really important to me.
Had it not been for people in my life that invested in me or really just had conversations about what to do; I don’t know where I’d be. So, knowing that that was helpful for me, I’d like to make sure that other people have those opportunities. I recognize well that I don’t necessarily have the answers, but I don’t think that there’s a way that you can go wrong with providing people opportunity.
This work of transformational change, over time, can be draining — physically, intellectually, emotionally, psychically, spiritually. How do you recharge, restore, take care of yourself, rekindle your fire?
I don’t know that I’m the best person to answer this because I don’t know that I do the best job at it, to be honest. I work too hard. I take too little time off. My bosses always encourage me to take time off.
One thing that prompted me to have more self-care, is that my brother passed away in October 2025.
I’m so sorry for your loss.
Thank you. He was involved in a car accident in 2005, and was paralyzed from the neck down. With his injuries, he always encouraged me to get out and see the world and do all the things that he couldn’t do.
I felt this sort of renewed sense of wanting to make good on that promise, because I… candidly didn’t do that well in the 20 years that he was alive after his accident. So, I told myself I was going to travel more this year. I’ve gone to Houston a lot; I just went to Barbados. I’ll probably get down to Puerto Rico.
So I think now it’s making time to do other things. The tough part about that, though, is when you take off time, you come back to 300 emails. I was recently in Dallas for 4 days, and I didn’t really have time to check email. And I had like 300 emails when I got back. So it’s a delicate thing.
Also, one way to recharge is to spend time with good people. Things like CLP or just hanging out with my guy friends every Thursday, have been really, really helpful. I’ve also been more intentional about the types of conversations I’m having.
And thinking through what I want to get out of life, and how I want to move things forward, things that I haven’t done. I ask myself, what do I need in life to be a complete person? That’s a question that I’ve been tackling over the past couple of years. What things have I been sacrificing, in favor of building a successful career? I missed my nephew’s performance in his recorder recital but made it there nonetheless. Just spending that quality time with him and giving him a high five reminded me of how important the little moments are in life. I want to make more time for that stuff.
I was on a really accelerated path in the first half of my career, and there’s now a feeling of — not necessarily, ‘I made it’ fully, but I feel like I’ve arrived enough to take time to smell the roses. So, I’m trying to do a lot more of those things.
Thank you for sharing. I wonder what other things show up for you in smelling the roses, whether food or exercise or nature or something else?
I’ve been focusing a lot more on health. I like to walk, I like to exercise, I like to lift weights. I saw a bear in my neighborhood when I was running recently. So, I’m not quite going to give you the generic “nature” response, there’s an asterisk there. [laughing] Yeah, nature’s real cool until a bear shows up.
[laughing] That’s fair.
I waffle and waver on it so much; like, self-care is so important and so critical… but then, so is the work. And that’s where it’s tough, right? Something’s always got to take the “L,” and it can’t always be you. But, then it’s this prioritization of the work.
And I don’t think that the two things have to be at war, but back to that idea of thoughtfulness… there’s this idea that you need it — not that we don’t need it, but… it comes with a cost. So, I just — I struggle with it.
You mentioned prioritizing connection, friends and family and intentional conversations. In that vein, would you introduce us to someone you are or were close with, who shaped (or shapes) you and how you view leadership and possibility for a better world?
I’m an amalgamation of so many people.
My mom; she’s the hardest working person I’ve ever met. She worked hard so that I could sleep in and dream, and I’m forever grateful for that.
My Aunt Carol championed me so much and believed in me so much. My Uncle Jim, her husband, he’s been such an example of what hard work and integrity mean. He’s the kindest person I’ve ever met, and shows respect to all people. I borrow so much from him, in terms of how I carry myself as a lawyer. He had been a federal judge for 30 or so years.
My Uncle Bill. He’s very loving, and also very clear and definitive on things. I remember driving down Whalley Avenue and telling him that I was going to major in business management when I got to college. And he’s like, well, what is business management? He’s born in 1942, and he’s like, “We didn’t have that as a major when I was growing up. What are you going to do with that degree?” I was like, ‘I don’t know, manage a business.’
He said, “Alan, you’re going to major in economics because it’s a classically-trained education that’ll send a message to employers that you can think.” I had done really well in an economics course in high school. It was actually perfect for me; economics is the study of what people do with limited resources. And I was like, ‘oh, this is a nice way to say like the study of being Black.’ (I’m kidding.)
So many of my family members have poured love and kindness and their time into me. As I’ve had these different phases of things that I’ve considered or wanted to do, they’ve always met me with both good advice and the belief that I could do it.
So, I think sometimes when I have these unrealistic beliefs about what can be done? If people care, they get together and they think shit happens, good shit happens. That’s been the story for me.
Thank you for taking the time. What do you recommend to us, in each of these categories:
- Reading — Fiction. I like nonfiction and people’s stories, especially stories of people that I can relate to. So, I was encouraged to read more fiction, and I started reading fiction by Black women, and then Black men authors, and then really any fictional things that I found to be interesting. I really enjoyed it, and I think it’s really important right now that we have an escape. And it’s cheaper to read a fiction book than it is to go to Barbados. So, like, in between 100 videos, there’s this other way to escape to different worlds, whether it’s reading about outer space or period pieces, giving your mind something different to think about. The House of Eve, Sky Full of Elephants, Head of Household, so many more.
- Listening — A lot of jazz. I think it’s really hard for people not to like Coltrane or Miles Davis — so that’s always a good start.
- Eating — I just got back from Barbados, where I went to a fish fry. I’d say eat some good seafood.
- Watching — A good documentary, those boring nonfiction titles. It’s where I always plug into.
- Laughing — Laugh at yourself. I think it’s important to respect and be respected, on a human level, but being able to not take yourself too seriously unlocks the deep and self-critical, gets away from being self-loathing or not liking yourself. Laughing at yourself is important.
- Wildcard — your choice — A breakfast sandwich with wheat toast, guava spread, thinly sliced cheese of your choice, bacon and an over-medium egg. Thank me later.
Interview with The Circle’s Creative Director & Editor, Lara Herscovitch (Cohort 10). To reach Lara directly: thecircle@clpnewhaven.org or Lara@LaraHerscovitch.com
Learn more about Alan via LinkedIn
Get in touch with Alan directly: Alan.Bowie@simonandschuster.com