Career Curves

Seeing What's in Front of You with Jason Elliott

February 13, 2020 Host, Beth Davies Season 2 Episode 3
Career Curves
Seeing What's in Front of You with Jason Elliott
Show Notes Transcript

What if you’re on one path – it’s a path you always thought you should be on – when an experience excites you about something totally different. Do you make the leap? Our guest, Jason Elliott, did just that.

Since graduating college in 2008, Jason has worked in government and politics, currently serving as Senior Counselor to California Governor Gavin Newsom for Housing & Homelessness. This isn’t what he thought he’d be doing when he was getting started in his career. He grew up thinking he'd be a journalist and set off to study this in college.

During our conversation, Jason explains why he left journalism for government, the difference between politics and government, and how he discovered which one plays best to his strengths. His candor and advice are relevant whether you're interested in government or an entirely different field.

Meet the Guest
Jason Elliott currently serves as Senior Counselor to California Governor Gavin Newsom for Housing & Homelessness. 

Prior to serving in the Administration, Jason served as a Senior Advisor to Governor-elect Newsom’s transition and Newsom’s campaign for Governor of California.

Prior to that, he served as Chief of Staff to the Mayor of San Francisco. Jason was first named to the position by Mayor Edwin M. Lee. Upon Mayor Lee’s untimely passing in December 2017, Jason remained as Chief of Staff to three subsequent mayors in quick succession, providing stability to a grieving City in turmoil. 

Mayor London N. Breed, elected in June 2018, retained Jason as Chief of Staff to lead her transition into her new Administration. Jason then departed City Hall in September 2018 when he was named a senior advisor to Gavin Newsom’s gubernatorial campaign. 

Prior to serving as the San Francisco Mayor’s Chief of Staff, Jason was Deputy Chief of Staff and Legislative Director for Mayor Lee, beginning in 2011 when Mayor Lee first took office. Jason’s city service also included two years in Gavin Newsom’s administration as Mayor’s Policy Advisor from 2008 to 2010. 

During his tenure in City Hall, Jason has provided leadership on a wide variety of key policy initiatives, including efforts to raise the City’s minimum wage to $15 an hour, building 30,000 new homes including 50% affordable, launching the Department of Homelessness and Supportive Housing, opening Navigation Centers, seismically retrofitting tens of thousands of buildings, and creating neighborhood Fix-It teams. 

Jason is a graduate of Columbia University and the Harvard Kennedy School of Government. He grew up in Palo Alto, CA and lives with his wife, Nicole and their baby daughter, Lucy.

Beth Davies, host: What if you're on one path, and it's a path that you always thought you were going to be on, and then an experience excites you about something totally different. Do you make the leap? Our guest today did just that.

 Welcome to Career Curves where we talk to people who have interesting careers and explore how they got where they are. I'm your host, Beth Davies.

Today we’re joined by Jason Elliott, who currently serves as Senior Counselor to California Governor Gavin Newsom for Housing & Homelessness. Since graduating with a master of public policy and social policy in 2008, Jason has worked in politics and government, including as chief of staff for three San Francisco mayors, but this isn't what he thought he was going to be doing when he got started in his career.

 During our conversation, Jason explains how he got into government, the difference between politics and government, and how he discovered which one plays best to his strengths.

 I started by asking Jason what he does in his current role in the governor's office.

Jason Elliott, guest: The first thing to understand is that California is a really big place, not just the population (we're 40 million), but the size of the government. We have about 265 agencies and departments, and a little over 300,000 employees that work for us across a budget that's just north of $200 billion.

 So our responsibility in the cabinet department of the governor's office is to ensure that, to the greatest extent possible, the government is moving according to the policy direction of Governor Newsom, the values of Governor Newsom. If he could be everywhere all at once, how would he direct the government to move?

 Beth: So now if I were actually following you around for a day or for a week, what would I actually see you doing?

 Jason: What I do on a day-to-day basis can probably be bucketed out into sort of three big categories. A big category, number 1, is managing the bureaucracy. Finding out what's happening in an agency or a department, working with the secretary of a given agency on getting through a thorny problem, finding out what's happening, giving some direction from the governor's office and managing the bureaucracy in a sort of very traditional, hierarchical sort of system. So that's one group of tasks.

 Another group of tasks is thinking internally with my partners and peers in the governor's office about how we want to move the agenda forward. So it may not be something that we're reacting to, it may be an issue that we want to be proactive about.

 And then I think the third important thing we do is we keep the Governor apprised of what's happening inside the government, receive feedback from him, and disseminate that feedback from him, which is important because ultimately he was the one that was elected. And we often remind ourselves, "I didn't put my name on a ballot and you didn't put your name on a ballot. He did and ultimately he's accountable for the decisions that we make at a staff level." So making sure that we're not stepping outside the bounds of our authority or imprimatur is important too and making sure we're reflecting Governor Newsom's values as opposed to trying to put our own values into…

 Beth: Which is like you said before, that there's a piece of you going into this that says, "If he were here instead of me, what would he be…?

 Jason: Right, and the way I've described this in previous jobs I've had especially as a chief of staff to a mayor is, "I get the luxury of reading more than the mayor gets to read, having more conversations than the mayor gets to have, and thinking longer about this issue than the mayor gets to think about it," because he or she is pulled in 500 directions doing public appearances, fundraising, all that. "If the mayor could have read the whole white paper, what would the mayor do? How would the mayor process this information," and trying to sort of let your boss inhabit your head and you try to make decisions as if you were your principal. That's good decision making as a political staffer.

 Beth: Interesting. How does this role play to your strengths?

 Jason: Oh, well that's a hard one because that requires me to be reflective about what my strengths are. It's a hard thing to do.

 I'd say what I enjoy doing, and the reason that this job brings me joy, and this career and this industry bring me joy is that I get an opportunity to interrogate some of the smartest people on a given issue on a daily basis. Earlier today, I had a chance to sit in a conference room for about an hour and a half with everybody around state government who leads on issues of housing and affordability. They work for us in an org chart, but that's not the way you enter a meeting like that, right? You enter a meeting like that understanding that you've got around the table several centuries of collective experience and we get the opportunity as governor's policy staffers to try to push the envelope, to ask the question, to interrogate in a collaborative sense to get to a policy outcome.

 So that means you have to be willing to admit that you don't know as much as the person sitting across the table from you. You have to be willing to ask the question even when you're intimidated. And I enjoy that. I enjoy the back and forth in a way that it can be banter or it can be collegial, but ultimately you're having a really substantive conversation.

 Beth: Because you don't mean "interrogate" like, "Up against the wall!"

 Jason: No, not at all. I mean it in the way of the Academy, which is going back and forth on an issue. "What do you mean by that? I don't understand."

 Beth: Yeah, you're trying to pull out their best ideas, their best thinking.

 Jason: Right. "It's funny because a week ago you told me this other thing. How does that square with this thing that you just mentioned? Oh, interesting. Great idea." And trying to put together almost like a Socratic dialogue in a way, but not for the purpose of just having a conversation but actually seeking an outcome.

 That's a lot of fun for me. I've been at this a long time now and I'll walk into a conference room or I'll have folks come into my office and you do sort of have to pinch yourself sometimes that you get to have these conversations at this really high intellectual level with people who are truly expert in their field. It feels like a luxury and I really enjoy that part of the job. Yeah.

 Beth: Thinking about yourself as a boy, is this the kind of work you thought you wanted to do?

 Jason: That's a good question. After I got over the fantasy about playing professional sports, I had an intention of being a journalist. Writing was, and still is, a passion for me. From middle school through high school and through college and even into graduate school, I had designs on becoming a journalist and I've taken a few steps in my career that indicated towards journalism.

 I had a moment when I was working for ABC News. I was at a presidential debate I was working for…

 Beth: When were you…?

 Jason: This was in 2004.

 Beth: And were you in school at the time or was this after school?

 Jason: It was a transition period. I was finishing up senior year and I didn't have much to do academically. So I actually started working full time and I was working for Charlie Gibson. The 2004 election, so it was Bush versus Kerry. And we were down in, I think it was St. Louis maybe, for a presidential debate that Charlie was moderating and I was a production assistant or something for him like that. And I remember watching the candidates' staffs backstage prepare for the debate and I thought to myself, "I want to be doing what they're doing. I don't want to be telling the story of what they're doing. I want to be doing what they're doing."

 So that was a hinge moment for me in my career. I think journalists play an extremely important role in holding democracy accountable, especially in this day and age. That said, I think journalists tell a story. I wanted to be part of making the story. And it just felt to me like that was the place I wanted to go.

 I think there's a skill that planning to be a journalist left me with that is extremely useful in the career I have now which is interrogating. Now, I actually do mean this in more in the interrogatory sense, which is you need to be able to call bullsh*t on somebody when you feel like you're not getting the whole story. You pry around the corner for what the real deal is. You don't feel ashamed about asking a question two or three or four times until you get an answer.

 But probably more than all that, I think the thing that journalists do really well, and I respect and appreciate about that profession, is forming a story as you're having a conversation. So being what I call an "aggressive listener," not just an active listener. An active listener is good. We can engage in dialogue. I respond to what you're saying. But an aggressive listener is I'm pushing you to give me more. I'm formulating a story in my head as I'm learning from you. It's more than linear, it's dynamic. It's as I learn something, the narrative in my head changes and now I'm prosecuting this line of reasoning.

 So I think that's something that's a skill that I learned in what was, at that point, a budding journalism career. Now a dead journalism career. But it really does prove helpful in working in an executive office and for elected official.

 Beth: So you just called that a "dead journalism career."

 Jason: Yeah.

 Beth: Do you see this pivot then as some sort of a failure? You sound to be a very goal oriented person, a very driven person. So when you decided to make this pivot, did this feel like failure to you?

 Jason: Yeah, I sort of regret not pursuing that professionally. I think it's really meaningful to be able to highlight what's going well and to call attention to what's not. I think there's a powerful position that journalists occupy and the kind of journalism I would be interested in is in covering government. So I kind of wish I had done that to be honest with you, but here I am anyway.

 Beth: Do you see that door as closed to you?

 Jason: Well, I suppose that no door is ever closed, but I've dove in to this industry.

 Beth: It's not the path you're on right now.

 Jason: It's not the path I'm on now. And I feel like I just made, within the industry, a pretty abrupt career change from working in local government to working in state government, and to some extent, I feel like I'm starting over. Even though it's still government and even though it's still California, it feels all brand new and it gets really overwhelming.

 It's a new city and it's new mores and it's new rules of engagement and it's really overwhelming. And this was just from working in a mayor's office to a governor's office in the same state. And this is like mindblowingly overwhelming. I can't really imagine what it would be like to just hard abandon government and move to journalism or any other career for that matter. It's a frightening proposition to be honest with you.

 Beth: As you make these changes like you were just talking about – and thank you for being so candid about how scary and how hard it is – how do you, as you're making this transition, manage this feeling of turmoil and scary and overwhelming.

 Jason: My coping mechanism on that kind of thing, and it's just my personality, is I'm just really honest with people about it. When I'm feeling overwhelmed or when I'm feeling like I don't understand something, I just say, "I don't get it." Or, "This is all very confusing to me. I'm sorry. I don't understand." There's something really powerful about making that admission and you can sort of watch people's defenses melt away.

 I was in a big meeting earlier today with probably 20 or so people, all way above my caliber on this particular issue. It was about pharmaceuticals. I don't know anything about pharmaceuticals, except here are all the people that know everything about pharmaceuticals. And there was an acronym that got used and I just said, "I'm sorry, I don't know that acronym," and everybody started laughing because it turns out nobody actually did either.

 When you just reveal your own humanity, it's like a magic trick. All that facade just sort of starts to crumble away. And by the way, if it doesn't and you reveal yourself to someone and say, "This is all really frightening to me and I feel like I'm over my head, and help," and the person doesn't respond to you, I think that's the character judgment that you need to know what kind of person that really is.

 So that's just my strategy. I'm sort of like an oversharer, I guess, which is probably good for podcasts.

 Beth: It's perfect for me. Are you kidding?

 Jason: But that's my strategy because you keep it bottled up and then you don't learn. If you pretend like you know what's going on all the time, nobody actually knows what's going on all the time.

 That's the big secret! When I talk to high schoolers or whatever, I have like a little shtick I do about the fact, "Okay, you're 17 or 16 and you're looking at me and I'm 36. I'm very old. I remember what 36 year olds looked like when I was 16. Very old. I'm very grown up. Well, let me tell you something. I have no clue what's happening. I'm completely overwhelmed on a day-to-day basis at work. When are people going to figure out that I do not belong here? And that's a feeling I come into work with every single day. So guess what? Go do something and scare the hell out of yourself. You should always feel completely overwhelmed because human nature is to then learn and adapt. And you know, humans are real adaptable."

 Beth: Rise to the occasion.

 Jason: Rise to the occasion, or don't, by the way, and then you'll learn. So long as you're not actually working on life or death issues, failure is all right.

 Beth: So going back. So here you are, you're with ABC News, you're at this debate…

 Jason: Oh, we're going all the way back.

 Beth: Right, I'm going all the way back. You realize that's what you want to be doing and you're finishing up your undergrad. Did you go straight from undergrad into grad school?

 Jason: No, I went and worked for a great guy who was running for mayor of New York City named Fernando Ferrer. He ran against Mike Bloomberg for his second term.

 Beth: So at this point you really decided, "That's it. I'm leaving media, I'm going for politics and I'm going right into a campaign?"

 Jason: I didn't want to do politics, I wanted to do government, but I was 20-whatever, 22, and I didn't know any other way to get into government.

 Beth: What's the difference between government and politics?

 Jason: Good question. Really good question. So the clearest line is the difference between working for a campaign and working for a government. So I think that's the clearest line.

 Politics and policy, there's a much more blurred line between those two. Certainly when you're on a campaign, you are doing much more politics than you are policy. And when you're in government, ideally you are doing more policy than you are politics, but those two things definitely bleed into each other.

 One of the frustrating things for a policy guy like me about a campaign is you can have an idea… If there's sort of 10 steps of policy-making: have an idea, brainstorm the idea, refine the idea, talk to stakeholders, develop a budget for implementation, write the law. Or whatever the 10 steps are. You can go 9 of those 10 steps on a campaign, but you can't take the 10th step, which is implementation. I think that can feel can leave you feeling pretty empty if how you find fulfillment – how I find fulfillment – is in implementation. In the running of government. It sounds Pollyannish, but getting it done. Changing people's lives.

 It's a trite thing to say, but it isn't because it's what I wake up and do every day or try to do everyday, I should say. But if you don't get to take that last step, it can leave you feeling really empty.

 As a consequence, I've found that I enjoy much more working on government staffs than I do on campaign staffs, but the best kind of staff is one where the government folks understand how the work they're doing impacts the political imperative and the political staff or the campaign staff understand that the things they commit the candidate to, or say on the campaign trail, have real world implications.

 Beth: Because they become the work of that government staff.

 Jason: So, I think when everyone can move as a team, that's how you get the best outcomes, I think, for elected officials.

 Beth: So you originally thought you wanted to get into the campaign side, the political side. How did you discover that it really was the government side that was your passion?

 Jason: After I finished working on the campaign – we obviously were not successful in that 2005 mayor's race because Mike Bloomberg went on to serve that second term and then the third term – I went back to graduate school because I had an inkling that public service was what I wanted to do.

 Beth: At this point, graduate school, off the journalism track…

 Jason: Yeah, I went to the Kennedy School of Government and pursued a master's in public policy with an emphasis on social policy, workforce, homelessness and that kind of social services, social policy space. Honestly, grad school for me, confirmed something that I had inside me, which is that public service felt like the right place for me.

 I talk to a lot of younger people who are considering going to grad school and say, "Should I go to law school or business school or maybe I'll do a joint degree with a master's?" And the answer to that question is always, "What are you looking for?" Not career. Not what do you want to do? But what are you looking for? Are you lost and you want to find direction? Do you have a sense inside you and you want to test it? Are you on a default path that your mom or your dad told you got to go down? What are you looking for?

 Asking people to ask themselves that question, "What are you looking for?" And then, "What are you going to do," comes later. But what are you looking for?

 Now, I did not have this much insight into myself when I went to grad school, but I had a sense, but I could not really explain it. I think in retrospect, what I was looking for was a validation that a life of public service and policy and white papers and regression analysis was something that was going to be fulfilling to me. And, I found that in grad school.

 I feel like I was lucky to be able to have the space, have the financial resources, and have the freedom and flexibility to pursue that, which is a luxury that not a lot of people have. I did not have to support my parents. I did not have to support a family. I had the ability to run down a passion, which is a luxury. So I acknowledge kind of sheepishly that that was a luxury.

 But that was two really great years at the Kennedy School. I met some of the most interesting and dynamic and publicly-driven people that I've ever met at school. So it was a really meaningful experience.

 Beth: As you finished up that degree, was it at that point that you did pivot into government and what did you do coming out of grad school?

 Jason: I wrote a thesis – or maybe it wasn't my thesis, but I wrote a paper – that unbeknownst to me, I had sort of replicated a program that this guy named Gavin Newsom had put together called Care, Not Cash out in San Francisco. Now I'm in Boston at the time, mind you. So I write this paper and, I'll spare you the details, but it's this kind of welfare reforming, homeless funding, housing kind of thing. Think of it in the social policy, homelessness and housing space.

 Beth: Got it.

 Jason: And one of my advisors, one of my professors, said, "Are you – I'm not saying you plagiarized here – but are you familiar with this Care, Not Cash thing?"

 And I said, "No, I'm actually not."

 "Well you may want to Google that one."

 Then, I start reading about what then Mayor Newson was up to. And I say, "Wow, not only is this back home where I'm from," because I'm from Palo Alto and so in the Bay Area, but also then being able to work for this guy who, from what I can see, he's been mayor for a handful of years and gosh, he's doing some really interesting things. I kind of wanted to see about working for him.

 So, I sent some emails and I tried to work the network and talk to some people…

 Beth: I'm totally curious how you cracked that nut and got into his office.

 Jason: Yeah, well, persistence is one thing, but I was also, again, really fortunate and I mean that in the truest sense of the word. I was able to do an unpaid internship. I know there's greater awareness now then there was 10 or 12 years ago that unpaid internships are a luxury and that most people who are pursuing careers don't have that opportunity. It's not that they're not offered an opportunity to take an unpaid internship, but it's that, "I can't work for four months without earning money. That's insane." I was able to do that.

 Beth: While you were able to take advantage of, and having the luxury to take advantage of, this unpaid internship, once you got into the role did you set out to prove yourself in any way?

 Jason: Oh, hell yeah.

 Beth: So tell me…

 Jason: I was 20-something years old. I was cocky. I was all those things and, you know, you come out of grad school and you just think you know everything.

 Beth: So how did you prove that you were competent rather than just cocky?

 Jason: Oh, that's a good question. I would say that if you asked my colleagues, I still have not yet proven that. So I don't know that I've actually accomplished that.

 I think some of the mistakes I made when I started in City Hall for then Mayor Newsom, I'm trying very hard not to repeat now working for now governor Newsom. One of the things we talked about earlier was the luxury of being able to walk into a conference room and have the 15 smartest people on an issue sitting around that room. Okay, well, don't try to prove that you're smarter than them because, guess what, you're not.

 Beth: Right. They will see right through it.

 Jason: They'll see right through you and it will devalue your ability to participate on that team. Everybody brings something different. What I bring to a team is very different than subject matter expertise because, with a few very narrow exceptions, I am not the subject matter expert on things in our office. So instead of trying to muscle up and show that you belong, take that proverbial step back. Say, "This is all very confusing to me. I'm eager to learn from you. Let me ask some questions."

 The #1 career advice, secret to life, key to success is other people love to talk. So give them that opportunity and you just may very well learn something along the way that you can then put to practical use in writing some piece of policy or doing a briefing, but let other people talk.

 Which I know is a silly thing to say as I'm sitting here filibustering 95% of the time, but in an interview format, I don't feel guilty about this.

 Beth: Nor should you. That's exactly the intent here.

 Jason: So, I would say reflecting back on my early career in the mayor's office, I don't know that I did a very good job of that.

 Beth: But did that internship convert into a role?

 Jason: Yeah, I got to know folks. I was asked to take a leave, which is weird from City Hall because I had just basically started there, to go work on the mayor's campaign for governor. That was the election of Jerry Brown.

 Beth: So here you were just getting started in government and somebody said, "Will you get back into politics?" Why did you decide to do that?

 Jason: I never actually realized how much of a weird turn that was until you just asked me that. I've never actually thought about that before. Why did I do that? Why on earth did I do that?

 I really don't know. I guess that it felt at the time like I was being told, "This is what we need you to do," and it felt like one big team. And so that's what I went and did. But, that's a really good question. I don't know, actually, I have to reflect on that a little bit, but I did.

 What I ended up doing on the campaign was many things, because when you're on a campaign everybody does everything, from dialing donors and staffing events and stuffing envelopes to writing policy and planning campaign events and all kinds of things. But what I really found my niche doing on that campaign was developing policy agenda. But again, you're on a campaign, so all the things you say you want to do…

 Beth: You can go through 9 steps, but you can't take the 10 steps.

 Jason: That lasted for about a year and change. During that campaign I was the deputy campaign manager and I met a young woman who was an intern at City Hall working for Mayor Newsom as an intern in the budget office. We got to know each other a little bit and now we're married and now we're expecting a child. And that was 10 or something years ago. So I would say the greatest gift of all gifts of doing that job was I got a chance to meet my wife.

 Beth: That's why you took the job! You said the universe has a message for me. I don't know what it is.

 Jason: I knew it. I knew it.

 We obviously weren't successful in that campaign. I returned to City Hall as a staff person. My title at that point was policy director, I think.

 Beth: So at the mayor's office. Gavin Newsom's the mayor, his term is ending, but you stayed in the mayor's office in San Francisco and had a really interesting run there. Tell me about that stretch of your career.

 Jason: Sure. it was a beautiful time to be working in San Francisco because we had a mayor, Ed Lee, who was the kindest, gentlest, most public service oriented person I have ever met in terms of elected officials in all of my years working in government. So he was the mayor. For most of his term, there was a guy named Steve Kawa who was our Chief of Staff, who was a mentor and a friend to us and who taught us. (When I say "us", because it was me and it was my wife and it was so many of us that worked in that administration.) He taught us what it meant to serve the public. So Ed Lee, Steve, the 20 or 30 or 40 other people that we were. We were a family.

 And working in local government, there's something about being in the place that you are serving that you are connected to that community whether you like it or not. In San Francisco, I commuted from the Inner Sunset to City Hall, which is in the Tenderloin district of San Francisco, which is one of the hardest to serve neighborhoods in terms of the concentration of poverty and homelessness. You're faced with it. It is inescapable in the sense of you cannot pretend that it's not a defining part of your day. Look, I did not love stepping over broken hypodermic needles and people passed out on the sidewalk, but I'll tell you what, you can never forget what you're supposed to be working on that day. So there's something about being in the city that you're serving that is so challenging and rewarding.

 Beth: There's going to be plenty of people listening who don't know the San Francisco story, but I as somebody else in the Bay Area know that there was this news. Unexpected.

 Jason: Yeah.

 Beth: I think you may have woken up to it one day. You may have gotten notified in the middle of the night?

 Jason: I was on my way back from a Warriors game. I was in my car, almost home, and I got a call from the head of the mayor's security detail. Guy I've known, Sergeant, great guy, I've known a long time. And there was something in his voice. So I got down to SF General, the hospital, as quickly as I could.

 The doctors and the nurses and the paramedics and everybody, they did everything they could and more, but his heart was not going to cooperate. He ended up passing away, maybe about three hours after I got to the hospital. His wife had traveled with him there, and by that point I had called a few of our other colleagues to come down to the hospital because I needed help.

 We all needed to be together. This was part of the Ed Lee family – staff, family, that is, not literally his family. They were the ones that actually suffered a tragedy, not us. We also knew that we had to grieve, which we did, sort of, but we also had a city we had to run.

 When the mayor passed away, by operation of our charter which was like our constitution, the President of the Board of Supervisors, who at the time was London Breed, who now is elected in her own right, she became mayor. And we had a grieving, confused city that we had to shepherd through with stability.

 Beth: And on a personal level, you're grieving as well.

 Jason: Yeah, and you push a lot of that stuff down, to be honest with you.

 I had a staff of probably 60 or 70 or 80 people who were also similarly confused and grieving and shocked and angry and sad and all those things that you feel. And then on top of all that, we were immediately thrust into special election for mayor. So we had this personal grief, this professional change, the chaos. Anytime you have a big change like that, you wonder, "Am I supposed to still be working on this project?"

 At that point I was the Chief of Staff to the mayor and so people are looking to you for guidance. "Should I leave my job?" Permission? "Hey, I was just about to initiate this new project. Should I do it?"

 Beth: Do I still do it?

 Jason: "Am I still wanted here?" And you don't know what to say.

 Beth: Did you think at any point in this, that same kind of question of should I leave my job?

 Jason: I didn't actually. I had lots of other questions that went through my head and are still going through my head about those days. But, I had to stay and I don't regret it and I don't begrudge. There was no choice of what I was going to do. I was going to stay and I was going to do everything I could to support the department heads, and the mayor's staff that were working to try to keep the city moving forward. That was just very clearly what I wanted to do, what I had to do, all those things. And so that's what we did.

 The mayor's race was contentious in San Francisco and it was in part a referendum on Ed Lee's legacy, which was a really hard. That's a natural thing to do in when it's an open seat. That was a really hard thing to watch when your grieving desperately for your friend and boss. And part of the discussion in the political context is things that we had screwed up.

 Beth: That's right.

 Jason: Now, by the way, some of the criticism was fair and we didn't do a perfect job,

 Beth: But the timing just feels so wrong.

 Jason: The timing feels wrong and it's one of those things where you go back and forth about what was the level of appropriateness. And I had some really hard conversations with some people that I really respect, who were working on some of those campaigns, and they said to me, "Tough sh*t. You guys ran a city. We think you didn't do a good job on these particular things. It's fair game for us to call it out."

 I sort of understand that. What I said back to this one particular friend and colleague was, "I get it, but I can still be angry about it."

 Beth: Intellectually I can get, but I don't feel good about it.

 Jason: Right. And, I would probably do the same thing if roles were reversed. I can hate it and I can be angry and I can be sad about it, and it can make me want to cry, but I can also understand why you're doing it.

 Anyway, so the mayor's race went. It happened a particular candidate won. It Happened to be London Breed. I really like her personally. I support her politically. And, I think she's doing a great job now.

 Beth: Ultimately though, you ended up leaving that role and stopped working for her. Tell me about the decision to, after I think you said 9 years, leave the mayor's office.

 Jason: It was one of those moments in life when you have to just see what's in front of you. And what was in front of me was a pretty profound change in the politics of the city. Mayor Breed, who was beginning what I hope will be nine years of term for her, and she needs to have her own people and set her own agenda. Although she was very kind to me, she deserved to have her own team in place.

 Beth: That becomes for you, "Okay, time for me to move on."

 Jason: Yeah, and by the way, in no stretch of the imagination, did she make it uncomfortable for me. She was nothing but gracious, but it was more like I was saying, "You got to have your own. You have an agenda. I'm not going to be here for nine years and you should have someone that you could plausibly really partner up with and really put your team together and do your your thing."

 Beth: Fair enough.

 Jason: By the way, I also knew that I probably wasn't going to be left out in the cold because there's this other guy named Gavin Newsom who's five months away from being elected Governor of California.

 So, you just sort of look and you say, "Okay, timeout. Where are we at?"

 I was having lunch with somebody today and I said, "I'm not supposed to be here. I'm still supposed to be in San Francisco. Ed Lee would still be mayor right now if he weren't gone and I'm not supposed to be here. I'm not supposed to be in Sacramento. I'm not supposed to be sitting here at lunch with you. Now, I am and things are working out and I'm a happy person, but this is not where I was supposed to be."

 Beth: Right. This was not the plan.

 Jason: This was not the plan. To reflect on it that way can knock you for a loop and you realize that you're not really in control of your own destiny. You gotta take things as they come.

 Beth: You can make the right next move, but beyond that, you don't have the control.

 You're working again for Gavin Newsom.

 Jason: I am.

 Beth: One of the things I've heard people say is that sometimes it's hard to work for somebody twice because their perception of you is still locked into the first time they worked with you when you were younger and had a whole different set of experience. Did you experience that with Governor Newsom? Did you have to do anything to shift his perception of you to mature it to who you are today?

 Jason: Really, really good question. I think that it is only natural and I know I'm guilty of that with people that I have worked with for a long time. You always see people the way you knew them when you first met them. It's natural.

 I don't know the answer to the question of whether he sees me differently or treats me differently. I think the best I can do is not to worry about how others perceive me, but to not commit that same mistake on other people.

 Beth: Great. A few more questions for you.

 Jason: Sure.

 Beth: And thank you for sharing your story.

 Jason: My pleasure.

 Beth: What would you say is the smartest career move you made, whether accidentally or intentionally?

 Jason: This is going to sound like a goofy answer to pander to my wife, but it's not. Working with my wife was the best thing ever, and we work still sort of together. She has a somewhat different job than I do, so we're not literally two doors down from each other. But working with your spouse or partner, if you can manage it, is the greatest thing because you have someone who intrinsically understands what you're dealing with. When you come home stressed, you don't have to explain why. When you're happy you can just raise a glass and toast to it. In a world that can sometimes be, as I've described previously, hostile – I mean, it's politics and politics can be hostile – knowing that you have someone who unequivocally has your back is like having bumpers on a bowling lane. It's just, it's the best thing.

 So I would say marry someone at work. That's my advice.

 Beth: The flip side of it: if you had one do-over, what would it be? What would you do?

 Jason: I lied once. This was when I was in City Hall working for Mayor Newsom, actually. I didn't want to seem like I didn't know what I was talking about. And that lie… "Lie" is a strong word; I overrepresented and the overrepresentation turned into an even bigger over-representation and it turned into an even bigger problem. Then, at some point, it became a lie. The issue was not an issue of consequence, but it costs me credibility with people that I cared about.

 Going back to an answer I gave earlier in the interview, I was not comfortable with myself in the workplace and I made the mistake of thinking that if I could just muscle up and puff out my chest, that things would go better. It didn't go better. It went worse and I spent a long time – and perhaps I didn't even really successfully – but I spent a long time trying to re-earn the trust of the people that I had misled.

 And by the way, this was on an issue that was not that consequential. So I can't imagine how I would have tried to reconcile if it had been something that had been really significant. I still think about that. When you get that instinct of wanting to kind of push your way in and give an answer, think about that because people will listen and when you lead yourself down the path, it's very hard to turn around and walk back.

 Beth: And the last question. How do you define success?

 Jason: How do I find success? If I can sleep at night, I know I'm doing okay. I actually literally mean that. When I'm worked up about something, when I think I've screwed something up, when I'm stressed out about not having achieved the outcome I want, I can't sleep. I lose sleep. And when I lose sleep, then it becomes a downward spiral. I then am tired at work and I'm frustrated and I lose focus.

 When I can sleep, that means that I know I'm happy with what I've sort of done that day or that week. So, I think defining success is not about saying "once I get that title" or "once I passed that law" or "once I get that raise," because you're just going to always leave yourself wanting. You're still hungry after that.

 So I think success for me is if I got a good night's sleep. I got a good night's sleep last night, so I feel like, right at this moment, I'm successful because that means that I did a good job. I'm not worried that I screwed something up. I think that's how I define success.

 Beth: Wonderful. Thank you so much.

 Jason: My pleasure.

 Beth: I really enjoyed our time together.

 Jason: Like I said, people love to talk, so you're asking me to talk.

 Beth: Perfect. Thank you so much.

 Beth: A quick epilogue. Jason and his wife, Nikki, welcomed Lucy into the world in December. Congratulations to the entire family and Jason, it might be a while before you get that sleep that you value.

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