Leap Academy with Ilana Golan - Former Obama Foundation President: How to Lead Through the Toughest Moments | David Simas

Episode Date: March 25, 2025

David Simas grew up in a Portuguese immigrant family in Massachusetts. His mother, who lost two fingers in a factory accident, instilled in him the power of resilience and the importance of community. These lessons shaped his career, from practicing law to advising President Obama on key national issues and eventually leading the Obama Foundation, where he worked with global leaders to promote democracy and address critical global challenges. In this episode, David joins Ilana to share valuable insights on navigating political crises, leading with empathy, and maintaining personal balance during high-stress moments in public service.  David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government. In this episode, Ilana and David will discuss: (00:00) Introduction  (00:44) Growing Up in a Portuguese Immigrant Family (04:01) Family Struggles and Community Support (07:54) How Legal Training Shaped His Perspective (15:48) Transitioning from Law to Politics (18:35) The Call That Led Him to the White House (22:10) Why Obama’s Team Chose David (26:21) Giving the People a Voice in the Oval Office (31:02) How Great Leaders Handle Crisis (35:29) Balancing Humility and Authority in Leadership (39:19) Navigating Political Pressure and Public Scrutiny (50:03) The Power of Personal Responsibility David Simas is a lawyer, political strategist, and former CEO and president of the Obama Foundation. He served as White House Director of Political Strategy and Outreach during the Obama administration and has held key roles in state and federal government, advising on political engagement and policy strategy. He is currently the Managing Director of Research and Impact at Emerson Collective, where he focuses on democracy, immigration, education, and climate initiatives. Connect with David: David’s LinkedIn: linkedin.com/in/david-simas/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Well, I am so excited about the show today, and I'm sure you're going to have an amazing time listening. But I have a favor to ask. See, I'm on a mission to help millions leap their careers, elevate their careers, land their dream rules, fast-track to leadership, jump to entrepreneurship, create portfolio careers. And this podcast is about giving you the map of how some of the biggest leaders of our time reach success.

So subscribe, download to never miss it. Plus it really, really helps us continue to bring amazing guests your way. So let's dive in. My parents are two Portuguese immigrants who grew up in a fascist dictatorship. I am sitting in the west wing of the White House with the opportunity to serve the president

of the United States and the American people. Why wouldn't I want that opportunity? David Simas, former president of the Obama Foundation, from serving in local government in Massachusetts to advising President Obama. When you show up somewhere and people know who you work for, you are representing them.

There's no downtime, There's no off time. It is a reflection on them. Democracy is a process. It's not an end goal. It requires an openness to others who are not like me, who don't agree with me. Do you need a thick skin to go into any kind of politics? The culture in Washington is a constant fight.

You need to... David Simas, former president of the Obama Foundation from serving in local government in Massachusetts to advising President Obama. Oh my God, I'm so excited about this conversation because David dedicated his career to strengthening democracy, creating impact. Oh my God, so amazing to see this, David. Thank you for joining us. Ilana, I am so glad to be here with you today.

It's always a little weird and nerve wracking to talk about yourself, but I am sure that, given how good you are at this, it'll be a good chat. It will be an incredible show. I mean, you have such an incredible story. But let me take you back in time. So you grew up in Massachusetts, It will be an incredible show. I mean, you have such an incredible story. But let me take you back in time. So you grew up in Massachusetts, small Portuguese immigrant family.

How did that upbringing shape you? Take us back in time, David. So my parents, who are still alive and still live in Taunton, Massachusetts, are two Portuguese immigrants. My mom grew up in rural southern part of Portugal. My dad grew up in the middle of the North Atlantic Ocean in the Azores archipelago in an island called Saumigal, Saint Michael. His village was probably 300 people literally in the middle of nowhere. The furthest that they went in school, their formal education ended at the age of 10.

Hard workers, folks who left everything behind to start something new in a country that they had never been in. It's just, it is the American story, which is so amazing. And so the piece of Taunton, my hometown that stays with me, is I have a very vivid recollection of living in two cultures, always. When I went to school, it was as if I was going to America. When I came back home, at the end of the school day, I was going back America. When I came back home at the end of the school day, I was going back to Portugal. And when I went back home, the food was Portuguese.

The radio was Portuguese music. My aunts, my uncles, my mom, my dad, my grandparents, my cousins, everyone was talking in Portuguese with an English mixed in. But then you would leave and I'd be with my parents and we'd go to McDonald's or we'd go to someplace else. And it was this, I have a vivid memory of trying to like reconcile, wanting to be American,

but also being anchored and tethered to the very different way of being of my parents. And so that bicultural tension, that bicultural, how do I fit in? What do I retain? And I guess as many young people that have had that experience, I wanted so desperately to be American that I bristled. I didn't like the Portuguese aspect and wanted to leave it all behind until I was in my 20s and then now in my mid-50s. And oh my goodness, Ilana, that part of me.

That's a big part of you. And I adore it now. It's something that's so... But that biculturalism and that desire to fit in was always something that I think to this day I carry with me a little bit. And I love that. I have the same from Israel and I always wonder if I ever gonna feel home in each one of them because I love both, but I have both, right? And it's like this mix, which is beautiful.

And by the way, my mom's parents all talk Portuguese. They came from Spain and Portugal. So we have a lot to talk about, but kind of funny. But knowing a little bit about this culture and you'll share more. I think there's something about this culture of everybody helping one another and lifting one another. And I think you also have a really interesting story

around that. Would you share a little bit? They immigrate from Portugal and because they really don't have a formal education, they're working in factories. And my mother worked in a silver factory, making forks and spoons and knives and silverware. And it was mostly women on her floor. And one day the machine malfunctioned.

And just the way the machine was set up, she couldn't, even though she noticed that it malfunctioned, you had a split second to remove your hands from the press. And the way the forks and spoons and knives are made is literally it would press down. And unfortunately for her, something impeded her ability to remove her left hand entirely. And in the blink of an eye,

this young 20-some year old woman loses two fingers on her hands. And for them, all you have are your arms and your hands and your back and your legs and the physical labor that you're using to build this new life. And everything was thrown at that moment. And I thank you for asking, because what I remember so vividly was, even though she was suffering, and my dad was suffering, even though I was little, the memories of my family

and my neighbors, and to me, a little boy, this entire community, at that moment in time, coming to lift up my mom, to lift up my dad, gave you that sense of, at that moment of peril, at that moment when you fall, a sense of both family, but also that sense of a broader community. And these other-

We'll be there for you. Yes, these other immigrants who are going through the same thing and for them, because it's also was a very deeply religious, deeply Catholic community, there was always this, not a fatalism necessarily, Ilana, but like, okay, this has happened. Now what do we have? If this was what happened, we

now have to lift each other up and that sense of community, even as I fast forward through different parts of my career, it would come up in my mind over and over and over again. And the other thing about that, let me just say about them, which is why they are not just my parents, but I'm lucky enough that I can say that they are heroes and inspirational. They never once complained. I never heard them or my mom specifically complain about what had befallen them. If they did, they would close the door or never show their child, their son, or then their daughter, my sister, who was born. And so it was always this, OK, this terrible thing has happened. What am I going to do? What am I going to adapt?

I remember her doing physical therapy with a tennis ball, where just for hours she would be squeezing the ball. Why? Because she needed to and wanted to get back to work. Ah, so beautiful. I hope they hear this. And I think you bring that with you and we'll talk about it.

There's a pattern there that keeps on that compassion, but not going into victim mentality, but staying victor. There's like a pattern that I see throughout your career that I'm sure that has a little bit definitely came from there. But let's fast forward for a second. So you finished school and you studied law. What are some of those lessons from law school?

Because one of the things, David, that I want our audience to hear is that even if you're not staying in law, there's so much transferable skills. There's so much transferable experiences that shape you to where you are going, right? So tell us a little bit and maybe a specific story that shaped you.

So the law for me, actually it flowed from, I remember the person who represented my mother. And it was from that young age I said, that's what I want to be. That's who I want to be. And I mean, he was physically like this very short man, but to me he was this unbelievable giant. So from a young age, I wanted to be

a lawyer. But the biggest takeaway for me once I got to law school was the practice and the discipline of legal training requires the following. It requires a broad understanding of the basic rules and the structures, the system. It requires the regulation not to memorize them, but to have the ability in that moment when you need to to go find it. Once you have that understanding then of the rules, because you're dealing with different fact patterns that always arise, how then do I take a series of different facts that are always up for grabs, that it requires you to have a broad and open perspective about memory, about recall, about perception of the people you're dealing with and then take the ever-changing facts and apply them to the rules, to the law, to the structure.

And then, most importantly, either in writing or verbally, to make the case, to argue the proposition, to tell the story. And so there are these three components that then I just saw after law school and after the practice of law that this thinking, this approach is applicable everywhere because what do you do in any environment? What are the basic rules? What is the circumstance that I find myself in? How do I apply that set of circumstances against the rule?

And then how do I add value and tell the story or to engage in a persuasive way for myself and for others? That is applicable everywhere. And the beauty of the legal training, there's this, Alana, many folks who are listening to this will know, the Socratic method of teaching. And so you show up in your class, you've had to read the specific case, and all of a sudden the professor goes through the list of 100 students and says, Mr. Seamus, are you here? And all of a sudden you want to like hide. Totally. And the first question or two will be very basic based upon what you read, and then the

professor will do this. Okay, even though the case had these facts, how do you think about what you read if you change this fact or that fact? All of a sudden, this isn't a rote and superficial memorization of it, but it is a critical analysis and a deep understanding of the philosophy of the underlying currents of the notion that things in general

are both conditional and provisional. You're reacting to the conditions that you find, but you also understand that they are provisional in terms of the only constant is change. And that's the beauty of both the legal practice but also the legal training that I just, to this day, even though I haven't practiced law in forever, I apply it every day.

I think we apply it every day because what you just said is almost like the basic emotional intelligence, understanding of what's around you, or understanding people. It's all of this and it's happening in every conversation. is almost like the basic emotional intelligence, understanding of what's around you, or understanding people. It's all of this and it's happening in every conversation. Was there a specific story as a law student that just crystallized the importance of it?

Less as a law student, but I remember when I was practicing very early, I was practicing law, and I thought I was 100% right. And you know, I was young, cocky, show up at the local court, and I'm cross-examining a police officer who had pulled over my client. And just based upon what the police officer had said in his police report, likely if the judge, in my opinion, followed the law,

that report and the testimony would be thrown out and my client would be fined. So the police officer, I walked him through on the stand. He basically repeated what he said in the police report. And then again, in a fairly obnoxious kind of self-righteous way, I cited a United States Supreme Court precedent and told the judge that he was required to suppress the testimony. Alana, the look on the judge's face turned, this look of anger came across his face, called me and the assistant district attorney to the bench,

and he basically said to me, I'm going to deny your motion because you didn't understand this precedent and that precedent. And frankly, I don't like your attitude. As I was leaving, the assistant district attorney who was probably 30 years older than I was at the time, soon his mid-50s and had been doing this a long time, put his arm around me and he's like, look, kid, you're going to learn that when you're in front of this judge, when you make the arguments that you are making, nothing is ever 100% right or 100% wrong. You need to understand Him.

Pricelifts. Right? That was just an amazing lesson that in very few things, very few things in life, can you say with certainty that what I am saying to you is definitively right, incorrect, or fact. It's one of the things even in politics, in the practice of politics, the discernment between fact and opinion and fact and information is important. That there are very few things that you can actually treat as settled fact. The rest you're in persuasion mode and if you're in persuasion mode it brings a very different way of being and engaging that's important. Oh my god I love love that David. And first of all, I love that you shared this

because I do believe that we learn better from failures or from things that we've done wrong versus the things that we've done right. I have my, a pretty famous story that I talked to a commander in my F-16. We were teaching them and training them. He was like 30 years more veteran than I am and he basically stood, honey, do you know who I am?

And I'm like, oh God, the truth is beyond his name, I didn't know who he is. And it's a long story, but I will just say, knowing your audience is still probably the most important lesson that I learned from that day. I'm like, oh darn it, because I said the right thing, I should have said it differently. I love this story and how it ties into everything. You then eventually go to politics. And I want to understand why do you leave law and, you know, I mean, for

everybody in the political, you know, they're trying to get into anything politics, like White House is like a dream. So share a little bit about that story. My parents, Portugal when they were being brought up was a dictatorship. Antonio Salazar was the dictator, had been the dictator for decades. There's secret police all over the place. And so they didn't have an understanding and earn appreciation for liberty or basic ideas of freedom or democracy. And so when they immigrated, especially my dad,

oh my goodness, we would watch the news every single day. I remember reading the newspaper with him as a little boy. And he would always be the mindset of a citizen as someone who had a voice and had a responsibility to be informed and to participate. And when he would talk about it, there was a reverence And when he would talk about it, there was a reverence to it that was informed by the experience that both he and my mother had come from. And so for me, politics was always this ultimate expression of the sovereignty of the people. And oh, I just followed all of it. I remember being a young man.

My father was a very conservative Republican. And so Ronald Reagan was the epitome for him. But I remember one day where he was saying wonderful things about the governor of New York, a man named Mario Cuomo, a liberal Democrat, during the era of Reagan. And I said to him, I'm like, Dad, they could not be more different.

And he's like, well, that's kind of where you're wrong. Have you ever listened to the way they talk about this country? Have you ever listened to the way they talk about the promise of this country? And that when you listen to the poetry of a Mario Cuomo and the poetry of a Ronald Reagan, the means to get there were different. And so I just fell in love with that.

So I ran for office when I was a young man, and it just began the political career of engaging that all of a sudden ended up in a crazy way with it was the inauguration of Barack Obama. I had not worked on the campaign. I had been working for the governor of Massachusetts, a man named Deval Patrick. My wife and I were in Washington. All of a sudden my flip phone rang. I answered it, and there was a man who was purporting to be David Axelrod, the chief advisor to the president of the United States. And I thought it was a joke.

He's like, this is David Axelrod. I said, yeah, right, I'm Barack Obama. And he said, no, you're not. I was just with him. I said, oh, blank. And I said, how can I help you? Aren't you busy? And he said, your boss, Governor Patrick of Massachusetts

says that you're interested in a job. I said, well, yeah, but why are you calling me? And he said, I need an assistant. And are you available for an interview tomorrow? Ilana, I had never been in the White House. And so the next day, after a completely sleepless night of not even knowing what I'm interviewing for, so you can't prepare, I walk by, and this never got old, you go through the North Gate onto the North Lawn and the White House is there in front of you.

You then approach the West Wing and if the president is in the Oval Office or in the West Wing, there is a United States Marine at the door. And you know this with your background as a military, he or she is in complete dress, not making eye contact, but as soon as you get to the point, they open up the door and then you're in the West Wing of the White House. David called me. Finally, I went into his office, which was the office adjacent to the Oval. He asked me how much I was making for salary. I told him he's like, well, this job only pays 50 percent of that.

Like, OK. He asked me how many hours I work per week. I said probably around 60. He's like, well, this will be much more than that. He asked me how much time I spent with my family and my daughters. I told him, he's like, well, maybe Sundays. And after he went through this litany of terrible things,

he said, so why do you want this job? I said, Mr. Axelrod, my parents are two Portuguese immigrants who grew up in a fascist dictatorship. I am sitting in the west wing of the White House with the opportunity to serve the president of the United States and the American people. Why wouldn't I want that opportunity? And as he was walking me out, he didn't say, he said, let me call you in 72 hours, Ilana, we went into the hallway, the president had left, he walks me into the Oval.

And I was standing there looking at the resolute desk, looking at the bust of Dr. King, looking at the eagle on the floor, and those images that I've always, I remember seeing that place and thinking to myself, this is either the most wonderful thing that's ever happened to me or one of the cruelest things after he tells me I'm not getting the job. And I got the job and it began a 14 year relationship with the president, which is amazing. Hey, I'm pausing here for a second. I hope you're enjoying this amazing conversation.

Don't forget to subscribe and download. Now, if you're looking to leap your own career, figure out what's next for you, fast track your own growth and create portfolio career. Check out my free 30 minute training at leapacademy.com slash training. That's leapacademy.com slash training. Now back to the show. David, I want to go there for a second because that's one of the most incredible stories. Do you know why they reached out to you? How did you build that credibility, that authority, that reputation for yourself? And I want to make sure that our audience gets it. These kind of jobs are not on the hiring boards.

Everybody gets that, right? It gets all in the hidden market. It's who knows you, and it's according to what you want to be known for. So how do you think you were able to build that kind of reputation to be the person that somebody like this calls? It only happened, obviously, because my boss, the governor, who had known David for a while, vouched for me and vouched for his assessment of my capacity to work, but also his assessment of who I work, but also his assessment of who I was as a person. A few months after, when I finally asked Axelrod, hey, man, I didn't work on the campaign.

I didn't go to an Ivy League school. I went to Stonehill College, a commuting school. I'm a lawyer. I've been in politics. I've never been at work in Washington. Why me? And essentially his answer, I'm paraphrasing, was that's exactly why.

Because what he wanted, what he needed at that moment was someone he trusted implicitly vouched for from a character in a work ethic perspective, who had never been tainted as the wrong word, but too immersed in the culture of Washington, right? Still had that outsider's perspective. And because of my background in politics, and I think the thing that was most interesting to David,

when I ran for office when I was in my early 20s, and in running for office, what I did was I knocked on thousands of doors and had hundreds of conversations, mostly listening to people. And then you take what you're listening to and you engage with them both in a conversation, but then to inform how you're going to approach, if you win, the process of governing. And so what I found out was he wanted someone with a fresh set of eyes who understood politics at the most basic neighborhood at the most basic neighborhood, interpersonal level, because, and this is one thing that I learned in love, to this day, the overwhelming majority of people do not approach democracy, the American Republic,

governing or politics via an ideology or a set perspective. Some do, those are the partisans. But most people are living their lives. They will check in periodically, and they want to make sure that the people that they put in charge are listening to them and connected with them. Right? And that's what I heard on the doors when I was knocking. I was running for my school board. So I had my policy, my 15-point plan, and I was prepared to talk about the plan. No one ever wanted to talk about my 15-point plan for education in my hometown. What they wanted to know was who my parents were, what school did I go to, what church

did I attend. They wanted to get a little bit about who I was. Why? Because what they're doing is they are entrusting in you, their agency, to say, okay, I don't know you, but you are going to act on my behalf. You are going to be my voice. That's not a political or a substantive issue. At its core, there's something much deeper than that. So on the one hand, it was the lack of Washington experience. And on the other hand, it was a depth of local interpersonal political experience

that just made me lucky at that moment in time to be there. Amazing. And it's probably a combination of really hard work that they're seeing your loyalty, but also I think even you talk about it, even when you were in the Obama administration, you probably had hundreds, if not more, of occasions where you were listening to other American stories and conveying them to the president, which is just so incredible. But can you share a moment that touched you or maybe a story or two? Yeah.

So you just alluded to it, Alana. It was the best job ever. I was the luckiest person on the planet because I would leave Washington. I would fly to someplace in the planet. Because I would leave Washington, I would fly to some place in the country, I'll just say Des Moines, Iowa. On a Tuesday night, I'd be in a bar or at a restaurant. No one knows who I am. I'm not talking about politics, but I'm just listening and talking to everybody around me. Politics generally would come up. And I'm just receiving. The next night, I'm behind a two-way mirror and a focus group, listening to people, talking about their lives, their communities, their assessment of Washington.

And one thing stuck with me, there are many that stuck with me, but the one I'll mention now was there was a question about immigration. And obviously, that's something happening now, not only in the United States, but globally. And we had some work to do around immigration. And the purpose of the listening session was to get at the core of the emotion around the issue. And so I remember this one woman was saying, look, I don't blame folks for coming here.

I don't blame folks even when they cut the line. I get it. I don't condone it, but I get it. But what bothers me is that the school rooms are now filled with kids. The emergency rooms are now filled with folks, many of whom I don't think are paying their taxes because they're all working under the table. And so they cut the line and now I think that they're getting benefits that other

people aren't getting. I've got two jobs. I'm struggling to make ends meet and it just burns me that this is happening. It's not right. It's not fair. Right? You know what didn't come up? Race, nation of origin, or any other kind of identitarian factor. It was this perception of both line cutting, unfair, and a lack of reciprocity. Unfair. And so my then job was to take these conversations, fly back to Washington.

In the morning, on a Thursday morning, I'd come back and I'd brief the senior team, here's what I heard. And then I would go into the Oval Office, sit across from the president, and he would say, hey, what'd you hear? And I would tell him this story of how voters were perceiving this, and every single time,

there was this, for me at least, I can't speak for him nor will I, but there was this transference where I was in this position where my job was to in a non-editorial, non-judgmental way, to tell him precisely what I heard, the words I heard, and my assessment of the emotion I heard, Ilana in the light most favorable to the individuals that had conveyed that at that moment in time, right? Because one of the insights that he gave in passing that just stuck with me, and this happens with leadership of any kind, he said, look, as soon as I became the president, the

ability to have anyone talk to me in the way they used to, past. You're his eyes and ears basically on the ground. That was the job. And the responsibility to do that without, and look, it's impossible, because I have my own baggage, right? But to present to him without judgment, some ugly stuff, some beautiful things, but as much

in an unfiltered way as possible was extraordinary. What a gift. Thank you for reminding me of that because, God, that was a gift. That's such a gift. It's pinching me moments, probably again, again. It's pinching me moments probably again, again. And again, you've had 14 years around these various roles. Share a little bit some maybe moments that stuck with you that you learned about leadership or you've seen something that you think will be beneficial. There was a, what we learned was a terrorist attack in San Bernardino, California

while the president Obama was still the president and I remember vividly where he said something like at moments like this our job and he pointed to all of us essentially was to Make sure that these are my words, that we don't inflame the emotions that arise in that moment. Because the emotions naturally of people when there's been a tragedy like that are raw in the sense that we need to do things about it is immediate.

At that moment, the president serves as a way to not cool things down, but to just take that collective deep breath before we act. You have your emotion, you understand it, you create the space then to act in a way that is meaningful. The other wonderful example of it is if you think about, I think one of the most amazing acts of presidential leadership in my lifetime was after the September 11th attacks. George W. Bush went to a mosque, right? The image and the importance in that moment for this deeply Christian man to go into a mosque because he knew where the emotions were going and could go. That's one example, both with Obama and Bush, that I saw that. Another very quick example of presidential leadership, early

in the first term, when the auto industry was collapsing in the United States. The great recession and the financial collapse was intense. And I remember, essentially, the President Obama was weighing whether or not to do a bailout of the auto industry. Elana, the polling and the focus groups were terrible on this. People's reaction was, you know what? They made their bed to hell with them. No bailouts for anybody. My job, I came back, I gave the information to David Axelrod.

David and I went into the president. We briefed the president, David briefed the president, and he gave him the numbers, and the president said, I understand the politics. I get those numbers, but here are the numbers that I need to deal with, that if I don't do this, hundreds of thousands of additional Americans are gonna lose their lives, their jobs, their livelihoods in the communities

that are gonna be devastated. And then he concluded by saying, look, the politics will take care of themselves. I need to do what I believe is right and work backwards from that. It's the importance of the immediate versus the important, or even the understanding, especially in politics, that you win, and if your obsession

becomes reelection right away, you're doing a disservice. You can never take politics out of it. It is the business, but those are some examples. And David, I love that because you can translate that to any kind of leadership in any kind of company, right? Because when the emotions are not necessarily aligned, our instincts may be wrong. So it's important to listen to the emotions, but it's also important to not act without thinking for a second and not taking that deep breath for a second. Right. And for me, this is just such a great reminder. without thinking for a second and not taking that deep breath for a second, right?

And for me, this is just such a great reminder. I remember as an Israeli, sometimes it would be too fast on my emails. You know, I'm just like, okay, send it to me. You know, and everybody's like, did you just fire me? What happened? I'm like, no, no, no. I just don't want the whole politeness.

Hi, how are you doing? You know? But sometimes your instincts are not what is needed at that time. And I know I'm dumbing this down to the basics, but I think it's just so, so, so important. So talk to me for a second, David, again, you've seen so much and you somehow got into being part of the Obama Foundation. Why you again? Which is amazing.

Good question. And obviously you proved yourself in a little bit about how did you see leadership there? The why me I think is cause no one else wanted to do it probably. I don't buy that. There's probably a little bit of it, but I think the way that when I left,

one of the kindest I think the way that when I left, one of the kindest things that the former president said was that in every instant, I represented him in the way that he would want to be represented. And it was something, especially for that type of organization. And even when you're working for a president, a governor, a mayor, or someone else, when you show up somewhere, when you show up anywhere, and people know who you work for, you are representing them. There's no downtime, there's no off time. It is a reflection on them.

And that's something that I just always took very, very seriously and personally. In terms of what it told me about leadership is the entire idea of the organization from the beginning to this day, even though I've been gone now for a couple of years, is what happens if we spend the next 10, 15, 20, 30, 50 years, identifying, training, and connecting a generation of leaders who are informed not by the same ideology or the same worldview, but a certain set of core democratic values. And to me, the most important piece of democratic, small-D leadership is the radical nature of the American Constitution, which said that the people are sovereign. They are in charge at its core.

That is a crazy, radical idea that the founders had now close to 250 years ago. And so what does that require then someone who aspires to any kind of leadership? As yes, you need to lead, you need to point the direction to say here's where we're going, but you have to do it in a way that is consistent with the mandate and the permission that you have been given by the people. It's this mixture of both humility and authority that's in constant balance intention. You don't want to be so humble that you're not pointing in the direction that you believe people should go, but you also don't want to be so authoritative in your belief

that clearly this is the way we should go when the overwhelming majority of people are saying, stop. This constant calibration, it goes back to what I said about conditional and provisional. So that's a mindset that we were looking for with young people, because the idea that then if you brought them together and they create this culture of leadership and leaders, then I don't know what they're gonna do, but I have a pretty good sense of how they're going to do it, which at the end of the day was always the most important piece of it.

And that's the ethos of that type of leadership. And I love that because when you can lead from community and love and trust versus hate, we won't go into politics. But when you can do that, that makes a big, big, big difference, I think in leadership and in any kind of culture. But talk to me for a second, David, I'm really, really curious.

As somebody that represented a specific individual or a specific party, do you need the thick skin to go into any kind of politics? Do you feel like you constantly battle or do you feel like in peace with that? How does that catch you? The culture in Washington, it was similar when I was serving in Boston for the state government,

is a constant fight. It's a constant us versus them dynamic. It becomes the way of being, the language that you use, the worry about the sharing of information, the assumption about motives and intention. It creates this dynamic where there's a constant stress and attention, which can be very, very good if you know that there's always another side and always a different perspective to keep you in check.

But it does do something to you. And I found this with myself, which was for me, the beauty of leaving Washington every couple of weeks. If I went a period of time where I wasn't connecting with people, those were the moments where cynicism would creep up. Those were the moments where the fight became most important and was in some ways detached from the purpose of the fight.

Right? So, yes, you need a thick skin. Never ever ever read the comments. Ever. Ever. Ever. Oh, that can be so daunting though, David. How do you- Have someone else read them and synthesize. AI is a beautiful tool for that now.

And then for me, it was leaving Washington was a way, but then whether it was my family or my contemplative practice, a way to get out of that mindset of opposition, of constant opposition, we'd be at dinner, I remember, in Washington, and you would always wonder who was around you listening, right? Is there a reporter? Is there someone from the other party? So what does that create in terms of a mindset? And so if you want an insight into the culture

of a place like Washington, that's the way that I try to describe to folks is, imagine going out to dinner and your default is you have to look around all the time. So how do you emotionally go through that, especially for such a long time? Do you need to train yourself? Do you wake up and I can't do this anymore? Interfernership is like that. My husband hears me a lot like I can't do this anymore.

And then you push it back and you continue. Right. What is it like for you, David? Yeah. and you continue, right? What is it like for you, David? Yeah, what was it like was my habits became my fuel. Exercise, daily, no matter what, whatever that time was, meditation, no matter what, and then how it infused throughout the day. What was that moment of pause, taking the deep breath, and

assessing whether or not the emotion was overwhelming, whatever strategic objective or reason that was appropriate at that moment in time. Reading, making sure that I was engaging with things that weren't politics, right? And most importantly, my wife and two daughters, that at the end of the day, they could care less about whatever drama or perceived drama usually that I was engaged in. And so it's what even with the young leaders at the Obama Foundation, when I was there, we would say to them, look, you're going to be thrown into things that you today cannot even anticipate or imagine.

You need to find for yourself on a daily basis some safe harbors that you can go to that get you out of that moment of emotion, that moment of almost being taken by the momentum of the situation to get out of the river, out of the current, and just kind of sit on the bank for a little bit, even if it's five minutes. It's why we always begin with leadership of self. Because if you can't lead yourself, and it's not perfect, how can you presume

to lead anyone else? And so for me, again, it wasn't perfect. God knows I failed more often than not and got caught in the current in ways that I should not have. But when I had some refuge, it was because I remembered to get out of the river for a little bit, just get on the bank and watch. I love that Safe Harbor idea. It does get overwhelming. It does get too much. I think for our audience, a lot of times, they're not taking action on certain things because of what will people say.

What if people will hate them? And what if it's not perceived? Or what if they fail? Right? And like you said, the comments, it what if people will hate them, and what if it's not perceived, or what if they fail, right? And like you said, the comments, it's so easy to hate in a comment, right? I mean, it's just, it became so easy. It's just mind blowing. But there's leadership from within.

There's a reason why on planes, we need to put our own oxygen mask on first before we help others, right? Like you can't help others if you're struggling. So I love all of this. When you're looking at all of this, and again, I talked to Dan Ariely about hate and all of this, do you feel like this is a muscle that you're building

to just get back to the habits, get back to your oxygen mask? Is it a habit that you get better at? Yes, it is a default mode, it's a training. It's a, in the moment when I'm feeling frustration, or anger, or envy, or pride, or jealousy, or any of them, if I can build the habit, the discipline of, look, it's going to come, I'm going to feel that at different moments in time. But if I can recognize that I'm in that moment and then say, okay, I'm going to pause, I'm

going to try to view this in the light most favorable to the person who is, that I'm dealing with, the group of people that I'm dealing with. I'm gonna get out of that flow. And again, it's just the habit. And it's never conquered. It's never, ever, ever perfect, ever. I'm sure there will be multiple times today where I will not be my best self. But when it happens, I mean, how

many times have you, God knows this happens to me all the time, you're about to go into a meeting, you're prepared. There's one person that's going to be in the meeting that makes you nuts. Oh yeah, of course. And you know, as soon as they open their mouth, it's almost like when you're driving to Thanksgiving Day dinner or Christmas dinner or whatever, and you're like, oh, God, so and so is going to be there. Not them again.

Right. And you convince yourself that this time it's going to be different. And as soon as you see them, the blood rushes to your... And then you lose control. You have literally ceded your agency to them or to some variant of you, right? And so again, I'm not pontificating. This is like a constant struggle. It's a constant muscle that you're building. But I will say, David, you're one of the few, and we've interviewed a lot of people, but you're one of the few that the very first sentence that

you said when you came on is like, I have a great day. And I think that positivity is also part of who you are. And the reason why, because I think there's certain lenses that you put on, no matter what you hear, you need to look at it in a certain lens and that lens will dictate a lot of the amplifying of how you hear these things, right? And I think that's just so beautiful because you are in general just looking at the world

in a positive, beautiful, community-trusting way. And that's what I hear. I am lucky. You are lucky. All of us are lucky. I can still walk. I can see.

I've got a wife whom I've been married to for 28 years who's my best friend. I've got two daughters who are amazing. My parents are still alive. Now this isn't to ignore personal tragedy, interpersonal tragedy, global tragedy. It occurs. It's part of who I am. But it's not all of who I am. And you're putting that gratitude lens on so it makes other things be seen in a different

perspective. And I think that's the big thing of it. Yeah. That's the hope. That's the aspiration. That's what you try to do. I love that. So David, based on everything that you've experienced and seen and all of that, if you look back in time,

what would you say to David, the kid or the teen? What are the things that you know today that you wish somebody told you or that you would have listened? And that the only thing I truly control are my thoughts, my words and my actions. Beyond that, I can influence, I can have some kind of effect, but the centrality of my behavior and my agency over my behavior, it's back in the courtroom.

Like, don't be obnoxious. Don't be self-righteous. Because you have a little bit of knowledge and there's an asymmetry of that, how do you handle that? How do you present it? That's on you. That for me, just to go back to, but probably I wouldn't have listened.

I'm like, yeah, yeah, yeah, yeah, yeah. Exactly. Yeah, yeah, yeah, yeah, right. It's like you have to go through all of the bad stuff to say, okay, that's actually on me. I did that. You know, when I get angry during the course of the day, it's the, okay, yes, perhaps I am justified.

Perhaps that person acted in a way that is inappropriate and wrong and I am justified in my anger. All right, now what? Is that getting me closer to my goals or not? What am I gonna do with that, right? What is my response? What is my behavior? How do I act in a way that doesn't do harm to myself

or to others? And it's not in a kind of safety-ism or like none of this is safe space stuff. The world is messy. But my relationship to it and how I behave and act, that is the thing that I wish that I could go back and train young David a little bit earlier because perhaps the muscle memory would have been a little bit stronger than it is today at 55 years of age. Oh my God. I love this, David, and I could probably talk to you for hours, but I want to thank you

for showing up, coming, telling that all these like amazing stories that you had, and just seriously a dream, I probably need to come and visit you and we probably gonna like geek out on some democracy stuff. Especially on Alana, what a wonderful way to end. I am a proud American. I love this country and everything that it has given to me, this American Republic and the democracy that we have.

Democracy is a process. It's not an end goal. And the process requires a sense of reciprocity. It requires an openness to others who are not like me, who don't agree with me. It doesn't mean I cede my beliefs. I keep those things that are core to me and my principles. But my fellow citizens, the grace and the openness and the understanding and the respect as a fellow citizen that I give to my compatriot on this process of democracy

as sovereigns. It's especially in moments where it's tested that the power of the idea really becomes central. So thank you for creating this space and for the conversation. and I can't wait to see you in person at some time so we can geek out. Love this David, thank you. My pleasure, thank you. Hey, I hope you enjoyed this as much as I did. If you did, please leave a 5-star review below. This really helps us continue to bring amazing guests. Also, if you're feeling stuck or simply want more from your own career, watch this 30-minute

free training at leapacademy.com slash training. That's leapacademy.com slash training. Now I will see you in the next episode of the Leap Academy with Zilana Golancho.