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When Alyssa Mastromonaco was Deputy Chief of Staff in the Obama Administration, there was a point in time when she was averaging two hours of sleep per night. After a doctor’s visit confirmed she was exceedingly sleep deprived, she decided it was time to leave the White House after working for President Obama for nearly 10 years. Sam asks Alyssa what it was like to go from that high-stakes environment to watching HGTV all day, what made her decide that she’s never wearing Spanx again, and how she got deep into the world of jam making.

Follow Alyssa Mastromonaco @AlyssaMastro44 on Twitter and @mastro175 on Instagram.

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Transcript

SPEAKERS

Alyssa Mastromonaco, Samantha Bee

Samantha Bee  00:16

The average American worker is going to have about 12 jobs in their life. My expert opinion leads me to believe they’re going to like about half of thumb, get health insurance from some of them and suffer through, you know, clip art filled PowerPoints at all of them. So far, I’ve had so many jobs in my life, and they’ve each shaped me in various ways I was I was a T sample giver outer at grocery stores, a teen bank teller, like I couldn’t even really see over the marble teller pod. What do you call that? It’s a counter, Oh God, I was a phone operator at an erectile dysfunction clinic, which was yes, a real job for money, not just for comedy. And my longest job to date was as a correspondent on The Daily Show with Jon Stewart, from 2003 to 2015. Frankly, people in the industry like to say that I’m the longest serving correspondent in the show’s history, which is nice, because it makes me feel both accomplished. And old, great. Leaving the Daily Show was such a complicated career decision. It obviously had been my dream job, it paved the way for me to relocate to New York where I was raised in a family with my husband who also happen to work with me at The Daily Show. But you know, part of having a job, even a job that you love means at some point, you’re probably going to have to leave that job. Things are different now. And we both started getting that feeling after we’d hit the decade mark at The Daily Show like nothing about the job had particularly changed. But we had changed. We had been there a long time we were very experienced. We were busy doing other stuff. And we felt organically that we needed to make a change. So when it was announced there was going to be a regime change at the show, we knew that it was our time to move on, no matter what it was just we were going to move on. But just because the timing was exactly right didn’t mean it was an easy decision. Because even when you love something, you can outgrow it. And it was our time to be challenged. I guess by something new. My something new was my own show full frontal on TBS, which really was a startup compared to the show that I was leaving. I knew that it wouldn’t have as many viewers or social media followers or Emmys in its back pocket, but at least it would be mine for however long it lasted. It’ll be full of my decisions, some very good decisions and some very bad decisions. But it was all mine. And after 47 years, I was ready to be in charge. And like, as soon as that show began, I knew that at some point, I would leave that show as well. I mean, that is just how the cookie crumbles. Like in my next job, I’m definitely going to be a baker. And because the average worker is let go from some of those 12 jobs. My decision to leave full frontal was actually made for me. It turns out sometimes the biggest decisions like that are made by someone else. Unlike my decision to leave the erectile dysfunction clinic that choice like our patients was not hard. I’m sorry. This is Choice Words. I’m Samantha Bee my guest today knows firsthand how important it can be to leave a job you love when it is time to go. Alyssa master Monaco is a former Deputy Chief of Staff to President Obama and current co hosts of hysteria on cricket media. She’s also the author of two books, who thought this was a good idea and other questions you should have answers to when you work in the White House. And so here’s the thing notes on growing up getting older and trusting your gut. Most importantly, she makes delicious jam. So take a listen and make good choices.

Samantha Bee  05:24

Hello, how are you today?

Alyssa Mastromonaco  05:28

It is a great day because I am with you.

Samantha Bee  05:30

I feel the exact same way. I don’t even know where to start with you. There’s so much. There’s so much that we need to talk about. But primarily, there is one thing that we do need to talk about and that is cats.

Alyssa Mastromonaco  05:45

All the cats the furry cats the rescue cats the messed up cat. Yeah, the cats with no teeth.

Samantha Bee  05:51

Do you want to just do a cat related podcast?

Alyssa Mastromonaco  05:53

Listen, I did a whole Instagram story about my cat Winkies adopt aversary today, and I made her case, you knew I had to.

Samantha Bee  06:02

That is true. Well, okay, we got to the cat during the pandemic, we named her Susan Collins, because we always wanted to laugh. Yeah, because we always want her to laugh every time we set her name. And we do. That’s hilarious every time but she was born without a tail. So she’s large and fluffy. But uncle was terribly uncoordinated. And she hangs from the screens. Okay, choice words is now it’s just a cat podcast. It’s

Alyssa Mastromonaco  06:28

Ita cat podcast, and people will still love it.

Samantha Bee  06:31

Everybody wants that.

Alyssa Mastromonaco  06:33

They do.

Samantha Bee  06:34

Okay. Okay, we are going to now we’re going to talk about choice, because we know that this podcast is about choices, or that’s our entry point. You know what I mean? We have so many we have so there are so so many. And you have specific ones that I’ve heard you speak about that I want to talk about get into it and get into it. But like first I want to ask you just very generally, okay, what is your Are you good at? Are you good at making decisions for yourself? Are you gonna make good choices? What is your path?

Alyssa Mastromonaco  07:01

I’m very good at making choices for myself.

Samantha Bee  07:03

You’ve worked in high pressure situations.

Alyssa Mastromonaco  07:06

I have I’m not gonna say I haven’t made some bad choices. I have. Yeah, I mean, we’ve all made some bad choices. But in general, I think I am blessed with and I don’t know if it’s the fact that I was born with IBS or what but like, I have a real gut. You know what I might not talk to me and tells me it’s like, Alisa, you know this is right or wrong. And the only time my gut has wavered isn’t even when my gut wavered. It’s when my brain tried to intercede.

Samantha Bee  07:34

Really? Well. Can you give me an example of when that yeah, of course.

Alyssa Mastromonaco  07:39

So I was not even 35 years old. I was just about to turn 35. And President Barack Obama wanted to make me White House Deputy Chief of Staff. Yeah, right. I mean, come on, Sam. Like mon What the fuck I it was it’s like, it was a put the thing is, it was a huge job. Yes. And I was like, I can’t do this. I can’t do this. And so I actually went to the President and was like, I have some other people for you to consider. And he’s like, What on earth are you talking about? And I then went to the senior counselor in the White House at the time Pete Rouse, who had been my mentor for years and years. I said, Pete, look, I just told POTUS, I told him, I think you know, that this person would be better than me. And he said, God, dammit, Alyssa, you are the only person who thinks you can’t do this job. And you know, what, if I’m being honest, I was I was great at the job. But at the time, I was just like, there was a certain amount of ageism. You know, people always ask me was the White House sexist? And it’s like, no, it actually to me felt more ageist. Oh, I was so worried. Like, here was our first black president. Did you want to be the one who function up like, did you want to be the person who he had faith in and then you let him down. And so that was one time I was like, I in my in my gut. I think I knew I would do a good job. But in my head, I was like, you’re too young.

Samantha Bee  09:03

So you were trying to convince yourself I was that you couldn’t do it. You shouldn’t do it. That I shouldn’t do it. But you woke up and were you waking up in the night going? I really should. This isn’t I can’t pass the stick. Like what did that turmoil feel like?

Alyssa Mastromonaco  09:19

It felt very So luckily, I had some good friends like Dan Pfeiffer who were like, buddy, yeah, what do you do in here? Like, what are you even thinking about? Right, who? And actually, I think he’s the one who put it to me best. He’s like, whoever you’re putting forward for this job is just going to ultimately come back to you and ask questions. Like, you’re the one who knows how all this stuff works. And so you’re being ridiculous, right? And ultimately, I was like, You know what, I just had to go into my deep my dark place where I was like, You know what, I would be really fucking mad if someone came and was like, asking me questions for a job that I could have had and then I turned down, but it was it was also the stuff that I kind of had known. about myself that I’m actually a very creative person, which is what makes me good at operational things because I think I can think creatively about solutions. Right? And so I was like, Alyssa, what are you going to do? But that was the one time I almost derailed myself.

Samantha Bee  10:13

You almost derailed yourself think I’m so glad that you didn’t.

Alyssa Mastromonaco  10:18

I’m glad I didn’t too.

Samantha Bee  10:19

How long did you wrestle with this?

Alyssa Mastromonaco  10:26

In my brain. It felt like months. In reality. I mean, things in the White House move so quickly. In reality, it was probably two or three weeks, maybe two weeks, or maybe two weeks.

Samantha Bee  10:37

How did you decide to join, like a young Barack Obama Senatorial Campaign? What made you take a gamble on a candidate like Barack Obama?

Alyssa Mastromonaco  10:48

It’s funny, Sam, is that when I was in college, I was at the University of Vermont, and this, you know, college back then I don’t know what it’s like. Now, I just know what I see on Bama rush. Tiktok. And I’m like, this is very removed from my experience.

Samantha Bee  11:03

But you didn’t have the Bama rush experience at the University of Vermont?

Alyssa Mastromonaco  11:07

I did not I did not what I did have was a socialist, who, by the way, I think was roughly the same age, I am now coming to my dorm to talk about voting, and his name was Bernie Sanders. And I was not in the I was not in the let’s do politics thing. Yeah. But I could not get enough of him in a state like Vermont, which I think a lot of people don’t understand is actually quite a poor state, or at least, it is now but it really was back then. I couldn’t believe what he could get done for people in a week. I ended up being an intern. He’s he I was an intern in Vermont. I was an intern in DC. Yeah. And the funny thing is, when I saw Barack Obama, when I met him for the first time, which was in like December of 2004, it was the first time I felt like there was someone as in tune to what people needed, as Bernie Sanders was. And so I said, You know what, and I had just come off the Kerry campaign, the John Kerry for President campaign. I was devastated. We lost and yeah, Sam, I was like, listen, junior senator from Illinois, Barack Hussein Obama Never gonna run for president, I’ll never be disappointed, and brokenhearted again. And that’s actually why I felt like this would be such an I thought it would be such an adventure to work with someone who would rather unlike so many politicians in Washington, DC, who will pull test and focus group everything that they’re going to say, he didn’t care. I mean, he’s like, I’d rather lose being me than when being pulled tested and being fed words to speak.

Samantha Bee  12:41

I feel I have to close my eyes and do a meditation, as you say those words because they feel that that is so rare. That is I know, so increasingly rare.

Alyssa Mastromonaco  12:51

Listen, when we decided when he when we there was a small group of us who helped him decide whether to run for president. And it was the reason I picked up and moved to Chicago because I’m like, first of all, we were all like, we’ll be here for six months, right? We’re like, come on, he’s running against Hillary, like, we’re gonna be fine. We’ll be home in our DC apartments in no time. But it really was that like, you know, leave it all on the field type vibes, like, we’re just going to be ourselves. And he accepted us entirely as we were and and, you know, we just gave them 100%.

Samantha Bee  13:21

There’s something about the human brain that just can sniff out in authenticity so quickly, and when you know, yeah, like when you know that someone is speaking just from the heart or extemporaneously or that these are just their true values, and they can just pour out so effortlessly. It’s so relaxing to the brain.

Alyssa Mastromonaco  13:41

You know, who is like that? You just had her on your podcast, big Gretch over in Michigan.

Samantha Bee  13:48

I love the Gretch, bYeah, she does that too. She unspooled having a conversation with her. I felt unspooled my brain.

Alyssa Mastromonaco  13:58

Yeah, she gets it. She totally gets it.

Samantha Bee  14:55

Now okay, well, let’s talk about your decision to leave the White House. Sure. That’s interesting, too, because it’s really hard to leave a job that oh my god, incredibly prestigious. Oh, yeah. Assume unbelievably rewarding, but sometimes you literally have to, I mean, what was that like?

Alyssa Mastromonaco  18:02

So going into the 2012 election, our reelect was unbelievably stressful. We had one we had, you know, we had a real race against Mitt Romney. And Hurricane Sandy happened. And that was my I was in charge of response and recovery to natural disasters, I coordinated the inner agency. You remember how bad that was?

Samantha Bee  18:26

Oh, it was so bad.

Alyssa Mastromonaco  18:28

I was, I was sleeping two hours a night. I was I mean, Sam, the president said to me, you’re either going to be a hero, or I’m gonna have to fire you because there was going to be no in between. either. I was going to I mean, like, and there are people from the campaign because I was obviously in the White House. People from the campaign who would be like, Alyssa, like, you know, like, you can’t fuck this up. And like, you can die. Like, like, thank you so much for that information.

Samantha Bee  18:53

Oh, I didn’t know that. I didn’t realize the stakes were high. Thank you.

Alyssa Mastromonaco  18:57

But like, you realize that you have really sort of garnered people’s attention when like the treasury secretary and DHS are all sitting in the office, and they’re like, Okay, Alyssa, tell us what to do. Um, I was 10 o’clock at night, disbanding treaties from the 1800s. So that like ships could get into New York Harbor and bring us gasoline. Like I could go on and on. By the time we got to the inauguration in January of 13, which I also sort of oversaw, I had no gas in the tank, I was totally done. And I said to the President, I said, Look, I am no good if I’m not giving you 150% Like, that’s what you need. I think it’s time for me to go and he was like, listen, take a vacation. You need to recharge. And I was like, okay, and Sam, the vacation never happened. Yeah, but when you’re in the White House, it’s like you end up in the middle of like the biggest things and you’re like, I can’t leave now like you. Like there are people. I’m not going to name names. There are people who have occupied the way had house who I don’t think we’re really waking up every morning being like things depend on me. You know?

Samantha Bee  20:07

Like I’m having a trauma response right now.

Alyssa Mastromonaco  20:10

Yes, yes. And I, we all deeply felt that right. And so finally, there came a point when I was I was in my office, I was having a conversation with David Plouffe, who had been our campaign manager at this point, he was senior advisor. And he looks at my computer and he’s like, you’re not typing because I was a real multitasker. I could type and talk to someone at the same time, right? He’s like, you’re not typing any words. And I looked at the computer, and I was like, Oh, my God, and I had been like, forgetting my keys and all this kind of stuff. And I just burst, he left my office, I burst into tears. The way my office was set up my my wall, one of my walls didn’t go all the way to the top. So my assistant could hear everything that was happening, okay. And he comes in, and he’s like a list, I called you, I’ve got you an appointment down at the medical unit, like it’s okay. And so they did a couple of tests on me. And it turned out that I was exceedingly sleep deprived. Okay, exceedingly. And so ultimately, I just decided that I was not. I given all I had to give, you know, it had been almost 10 years. And it was, it was time I helped. You know, I think that if you’re in an organization, and you’re managing something, we always kind of operated in the like, get hit by a bus theory, right? You know, if you got hit by a bus, everything should go on without you. You’re not a hero. If everything falls apart, it doesn’t mean that you were very special, it means you were very bad manager. And so I decided to leave in May of 2014. And Sam, if I thought the the idea of getting ready to leave, like when you leave, there’s this whole process, right? You get read out in air quotes, read out of your security clearance. So the the Office of Security comes in and they read me out, they go to take your badge, right? I just burst into tears. And I’m like, I go I bet this happens all the time. And they were like, actually, no, I was like.

Samantha Bee  22:07

Really? Like, we don’t know what to do with a crane person.

Alyssa Mastromonaco  22:11

They did not know what to do with me. And I like busied myself, you know, my, my friend, Dan Pfeiffer was taking my office and I like set it up for him, because I’m like, This is gonna make me feel okay. And when I went out to drive, I mean, Sam, it was like my last trip with the President. The all the Secret Service guys sort of reported to me and you know, in on TV shows, you always hear them talking over the radios. And I was like, Can I can I do that for my last car ride? And they were like, Yeah, of course. And so the President’s code name was Renegade. And when you’d arrive at the White House, they’d say, renegade arrives, renegade arrives and they let me say, renegade arrives. And then in like the most cinematic I get in my red Ford Escape, covered in stickers. Yeah. And I drive out onto Pennsylvania Avenue through the iron gates, right. Like an all the tourists and all the Secret Service agents are clapping. It was like some Rudy level shit, you know. And then I just sobbed for days. I mean, I really did. And then on Tuesday, I started my career of watching HGTV all day.

Samantha Bee  23:13

I can’t believe that that so if that must be because I can’t like remember, when you’re in a flurry of activity, and then everything goes quiet. It’s like being on a beach and listening to a seashell. Yeah, but it is very hard to make that transition from high adrenaline. And like that’s it cortisol spikes all the time to like.

Alyssa Mastromonaco  23:35

They actually think the one of the doctors told me they think by the time I left, I had something. I don’t know if it’s real or something they made up to make me feel good that I had like adrenaline toxicity that I’ve been running on it for so long. Yeah, I just kind of went off a cliff. And, you know, David Axelrod, who I know, you know, after I wrote about this in my book, he was like a list. I wish we had talked about this, like, I wish we because the same thing kind of happened to him. They just really, because you think Sam you think when you leave that the next day, they’re gonna call you and be like, Girl, we miss you so much. Can you tell us X, Y and Z, but the phone doesn’t ring? Your job right, the phone does not ring. So it was it was a really tough time.

Samantha Bee  24:19

How in the world? And, you know, the former President accepted that he does not belong in this category. How does any president literally endure the experience of being President like you have to be a bit of a psycho right, like you have to.

Alyssa Mastromonaco  24:36

I think you either have to have really incredible perspective which I think President Obama did have that he understood you take everything piece by piece there are the fights are gonna fight there are the fights that are not worth fighting, right. Um, but I mean, it is. I mean, it is like nonstop like you come in. Yeah, I’m one morning I wake up and as Deputy Chief I had This like apparatus in my very tiny bedroom that was a secure phone, a secure computer, it made my bedroom so hot and I run hot. So it was like very hard for me. And it’s like, you wake up in the middle of the night, and the Situation Room is on the phone. And they’re like, man, there’s a nuclear meltdown and Fukushima and I was like, what? Like, what? You just there is not and just when you think something else is happening, something else is going to happen? Because it’s America, it’s the world. So everything is happening all the time.

Samantha Bee  25:33

How long did it take for you before you were ready to do more work? Like, at what point? Did you start writing your book? Like, how long did it take before you were able to get the gears going again?

Alyssa Mastromonaco  25:46

You know, I had, as I was leaving the White House, I did an hour long interview on Charlie Rose. And Hachette actually reached out to me and it the story is I remember was the niece of the woman who was the president of 12, the imprint under her shed at the time, she said to her and this is I want to hear more people like her. And they reached out to me, and I think that I had my book deal by like, June, you know, and I started writing it. Yeah. And of course, because again, type a sure I start writing it. And it was bad. It was so bad, because you know what I was trying to sound in. Not important, but I was trying to sound serious, right? And you can be you can be like a, like I had a good, you know, important job. It doesn’t mean I have to sound any different than the way I sound. But I’m talking to you right now. And that’s what it took me, I’d say almost a year to really understand that if anybody was ever going to read my book, they were only going to read it if I sounded like me. So that took a long time.

Samantha Bee  26:50

Right, right. And how long did it take you to write the book?

Alyssa Mastromonaco  26:52

Up to two years?

Samantha Bee  26:56

How many versions of it? Did you throw out?

Alyssa Mastromonaco  26:58

Two full versions where I was like, Oh, my God, who is this? You know what, Sam? It’s like what we were just talking about? The first version sounded utterly inauthentic. Right? Right. It just, it was I was like, Who is this person? I was like, No. And so luckily, Hachette was into sort of this, like young ish at the time woman who had done big things, but was kind of a hot mess from a small town, you kno?

Samantha Bee  27:20

Right, right, right. Everybody just wants to hear the real goods. Everybody just wants to hear the real good say, doo, doo. I have read that you say that every component of a good decision is contingent on your ability to take care of yourself. But how doesn’t sound like you’re super taking care of yourself, or?

Alyssa Mastromonaco  27:40

Well, at the time, I thought I was, you know, now I do much more. So since I have left at the time, I thought that going to Pilates at 730 in the morning on Saturday, Sunday was ideal. Now, the truth is, I had had back problems at the time. And so it did help me. Um, you know, I always made sure I was home to watch him like girls on Sunday night. And, you know, those were, there were certain things that I looked forward to throughout the week that I was like, I’m going to do this.

Samantha Bee  28:12

That is true. You have to draw lines for yourself, and you can night you cannot cross those things. No, that’s in a way. You know, I do think that we kind of like overused the concept of self care. Yeah, you know, I mean, it’s important, but also, it’s not the most important thing, but maybe maybe drawing lines for yourself is the most important thing.

Alyssa Mastromonaco  28:31

I think there’s like real self care. And then there’s Instagram, self care and Instagram. self care is not my cup of tea, but a very different understanding when I am exhausted, or overtaxed and don’t have the bandwidth to be around other people, to me is the best thing I can do for myself.

Samantha Bee  28:47

I like that you mentioned girls, because I just love girls so fucking much. And I feel like it’s really worth a rewatch. I rewatched the whole thing during the pandemic, because it’s like, I gotta read, I gotta get back into this show. It’s so it’s beautiful.

Alyssa Mastromonaco  29:06

I think and I think back when we were in the White House girls was on and then Veep was on right after, and we would come in the next morning. It’d be hilarious. We’d see Joe Biden, who at that point was vice president and be like, are you on the phone with JLD? Were you talking to Julie Louis because that episode hit close to home. You know, it was those were the things I think that we all kind of looked forward to they were our appointment viewing and we would all talk about it on Monday morning.

Samantha Bee  29:32

There’s more with Alyssa Mastromonaco in just a moment. I’m sure everybody asks you this, but how are you feeling in the current political climate? And do you tired of telling people to vote? I do.

Alyssa Mastromonaco  32:12

Well, you know what it’s you know, what’s so hard is that like when something bad happens, for example, when Roe was overturned last summer, and people get on, you know, podcasts and cable news and they’re like, everyone has to vote and it feels so fucking hollow. You know, like, yeah, of course, man. But voting isn’t going to change. That is not going to change things immediately. Right now, that is I think the hard part. But yes, I really just wish people would vote.

Samantha Bee  32:42

I really wish they would. And I wish that it was not the end stop for a lot of people. I know. It’s like, Oh, I’m gonna do I did it.

Alyssa Mastromonaco  32:53

Well, and let me say I really feel that way about like, you know, people who like I always think of when we did GOTV and even back, you know, when I had left the White House and I did more GOTV look, if some person who is working a nine to five job or to nine to five jobs, and they make time to vote, that is great, people who have more flexibility, those are the people I feel like shame on you should be doing, you know, there are some people who only have the bandwidth to get out and vote, you know, once a year. And to that I say thank you so much, especially if you live in Georgia. Um, but but it’s the other people who just like are very performative on Instagram, and I just, I’m like, okay, but like, Did you did you vote? Did you not just vote in the presidential? Did you vote in the midterms? Did you vote for your school board? Because Sam, that’s the big problem. Republicans have been grassroots elections for a long time. And they have the state legislatures and they have the school boards. And so those are, those are the elections that we really got to make time to get out for.

Samantha Bee  33:57

A really, really long time like school board takeover. I mean, it’s, there’s there’s a playbook. Like there’s like 10 steps. It’s like, it’s very clear.

Alyssa Mastromonaco  34:09

And successful because they are successful damage in the last 5-10 years.

Samantha Bee  34:14

Extremely high amounts of damage, unlike our cats who are sweet and cuddly, and I want to.

Alyssa Mastromonaco  34:20

Except they do do damage, but it’s usually fixable.

Samantha Bee  34:25

Do you ever get sick of the feeling that every election is the most important election? I feel like every Yes, like from a from a complete outsider, like just from someone working in a comedy show for 20 years in the world of politics and like every election had.

Alyssa Mastromonaco  34:41

Every election is the most important and the and the truth is I painfully I do think as the years go on, it’s like not not true. Yeah, like, like 2020 was vitally important and then Swanee 22 was vitally important, so Sam, this is the most important election. The production company is George Stephanopoulos, Ali Wentworth and myself. Yeah. And honestly, George is on GMA. So he’s 100% in bed by 8%. If I am being honest, I am not far behind.

Samantha Bee  35:52

I love there’s nothing I love more than being horizontal. Within the eighth.

Alyssa Mastromonaco  35:57

I agree. Feet, my mom has the same ganks up, it means your feet are up and you’re relaxing in the eight o’clock hour.

Samantha Bee  36:03

Ratings have to be up? Making sense to be up? I know. And I feel that you. You are a person who gives no fucks you give? No. Yes. Pretty much after that begin for you. How did you how did you find that in yourself?

Alyssa Mastromonaco  36:19

You know, honestly, as I got older, that’s just the truth. You know, I think that it’s funny because we talked about a little bit before about Hurricane Sandy. And during this whole thing. I mean, Sam, I was in the same puffer vest and corduroy pants walking into the White House every single day. Right? And I was like, I’ve got this like, I mean, not like I never rested on my laurels. But I was like, you can do that you are doing this, you know. And from that point on, I think I was like, You know what? I’m gonna say what I think and if people don’t agree with me, that’s fine. That’s fine. But I am never going to wear Spanx again. I am going to grow out my hair as I want to grow it out. I’m going to let it go gray, I am going to be myself. And the truth is that like after, because, you know, when we were in the White House, there was a blog, a blog back in the early days, that would attack how myself and the other Deputy Chief at the time, Nancy Ann would dress really and I was like, oh my god, like again, the whole idea like I cannot bring shame upon this president you know, and so began, you know, some form not always but some pantyhose, some Spanx. I wore more skirts than I normally ever would have. I put makeup on Sam, I do not wear makeup, not my thing. And I try to play a part at least aesthetically. Right? And now I just am never gonna do anything where the way I am is not okay to walk in the room. That’s just how I feel. Right? I love there are enough people who are down with that, that you don’t have to be with people who are like, could you do that like a little differently?

Samantha Bee  38:09

No, I would love it if you just kind of like polish it. Polish it a little bit.

Alyssa Mastromonaco  38:16

Do you have pumps? It’s like no, I have Birkenstocks and clogs, loads of clubs. So many clogs.

Samantha Bee  38:21

I vote although I will say that I have a young teen daughter and she keeps looking at me and just going like just analyzing my I feel her analyzing my face sometimes. Just for flaws, just things that could be improved.

Alyssa Mastromonaco  38:36

You know what, you know how I feel? I look at like what it was the it was maybe two years ago last year whenever that movie Nomad land came out with McDormand. Yeah. I was like, You know what, that’s my vibe. I want Francis McDormand accepted. It was either in me or no, it was like a Golden Globe or an Oscar. And she had no makeup on. Yeah. And I’m like, That’s it. That’s no one respects her any less. There are people who love it. And you know what, go with God, enjoy yourself. But I just, you know, when I am made up, you know, like, the day I got married, my hairdresser was like, Don’t you want to do something special? And I was like, No. And he talked me into like putting my hair up. I just I went home and I cried, I just redid my hair. Because we were we got married. blessedly at the Supreme Court, Elena Kagan married us, Oh, we did not have a wedding. It was just me and him. And I wore a blue dress. And it was like, you know, totally simple. But like, even that was just like a lesson. It’s like, why didn’t you listen to your gut, like you know how you like to look you like to look like yourself? Even if that means you’re not very glamorous on your wedding day.

Samantha Bee  39:40

I feel like at the age of I’m 53. I’m turning 54 in the fall. And I feel like it maybe took 52 years to understand that no one’s ever going to tell me to put my hair up in a tight button again. ever in my life. It can’t it should not be done. No, it will never be done again. Oh, it hurts. It looks I look like I don’t have hair. I look. It’s terrible.

Alyssa Mastromonaco  40:06

I look silly.

Samantha Bee  40:07

I look silly. I feel embarrassed. You feel like shame. The whole like you’re in a costume. Like I’m in a costume. Like I’m wearing a woman suit begging for people to love me. I actually just donate it because I had a lot of there was a time at doing television where I obviously worse banks because you were like, I have to wear spank. You wear Spanx. And then at some point during the show, I stopped wearing them and I was like, I will never I cannot I just don’t know. I don’t give a shit. I don’t care no. And also no one cares.

Alyssa Mastromonaco  40:39

No one cares. And it doesn’t feel good. Like you’re conscious of it the whole time. And the people who care.

Samantha Bee  40:45

aren’t gonna like me anyway, so it doesn’t matter I’m like not gonna win.

Alyssa Mastromonaco  40:49

That was the other thing I realized Yeah, there was no group of people I was like what bringing to my social media feed if I acted any different than knowing.

Samantha Bee  40:57

Exactly, and I just donated them all. I had like a huge box of it in my garage but you did I did. I mean huge box of shapewear with tag like tags on and I just donated it. I was like, please go with God. If you love shapewear, please enjoy this.

Alyssa Mastromonaco  41:11

Have a enjoy and have a second life someplace else.

Samantha Bee  41:14

Have a second life. turn into something useful. Like maybe you know like a like a hairnets for cats. I don’t know fishing equipment.

Alyssa Mastromonaco  41:23

Oh my, it’s all fishing equipment.

Samantha Bee  41:26

A gill net on the show alone. I don’t know. For you to decide. I want to not only is this podcast about cats it’s also about jam. Yeah, it’s really a food and cat based podcast disguised as like other interesting topics. But I fucking love jam. I make jam. But you sell jam.

Alyssa Mastromonaco  41:51

What kind do you make? What’s your favorite? I do sell jam.

Samantha Bee  41:54

I make a sarah cherry jam. I have a pitter I have a bone. Usually I just do it by hand like a big pet note sound like a FISA it’s just a single. I mean I’m small. I’m not I don’t sell my jam. I just give it away but like so you know I just have like a single header and then usually I just go oh fuck it like I just do with my fingers that my fingers get all stained but sour cherry. Yeah. is my favorite. Apricot. Close.

Alyssa Mastromonaco  42:20

I love making jam.

Samantha Bee  42:22

How did you cook everything you love to cook or you specifically love the meditation?

Alyssa Mastromonaco  42:28

I specifically I love the meditation. It was so years and years ago, I would get really stressed about the end of summer. And what’s the end of summer peaches? Right? And so there’s this woman who by the way, I made it my life’s mission to make her my friend. Oh, she was like the most real deal. Serious farmstand farmer, her name is Nancy. Okay, she I would go and I’d get the peaches. And I would like kind of tell her my life story. And she was like, fucking Pull yourself together. She was like, I was like, I get so sad at the end of the summer.

Samantha Bee  43:04

Like we just live this way. Just fucking preserve it. It’s fine. We’ve been doing it.

Alyssa Mastromonaco  43:08

Have you ever thought about preserving it? And I was like, no. and of course being me. I then do ages of research about how to preserve and I find this like pioneer inspired recipe because of sugar was really expensive for the pioneers. And I don’t like jam, that’s too sweet. You tell. So I followed this recipe where you probably use like half as much sugar, but you bring it to a boil and then you let the jam cool to room temperature and the water evaporates. The natural pectin comes out and like you don’t have to use nearly as much sugar nor do you have to use pectin. And so I started just making jam and then but like just like jam that was like in the basement. You know, I just made it. I canned it. I put it in the basement. Yeah. And then my friend Mona Talbott, who is a chef, she has our big shop in town. She’s like, um, this is excellent. You want to be our jam maker. And I was like, what? And Sam. I am like, listen, it is like I am. I feel like the mafia, the fruit mafia. I’m like, Alright, I’m going to Nancy, when we went to my husband, I went on our first vacation and forever. I was so stressed about missing black raspberries season that Nancy was like, Listen, I’m gonna freeze them if we have them because we had a terrible fruit shortage up here this year because of an early thaw in February and then a late freeze in May. We lost all of our stone fruit and like loads of other things. She’s like, I’ll freeze it. I was like, Oh my god. Thank you so much. And at one point last summer, so this summer, I have not made nearly that much jam. But last summer I think I made over 2000 jars. And it was at Eli’s at bars on Third Avenue. It was at Talbot and arting it was it Max MorningStar Farms. It was like I had it everywhere. And I loved it, Sam. I felt so accomplished. I love this so much. I felt so accomplished. Just only podcasts on no television while I’m making jam. Yeah, I buy it I get the fruit all local or I pick some sometimes I pick it myself. Okay, I get out there I’m like let’s get those concord grapes. concord grapes are the only thing my husband will come out in the vineyard. Whatever it is, yeah orchard for because he’s like, Okay, this is adorable. Like she’s the same size as the vines you know, just like under they’re getting the concord grapes. And I can it myself I label it myself I do the whole thing it is it is the best thing I could do for my mental health Truly, it helps me focus because I have anxiety you know, which I didn’t realize when I was in the White House, I just channeled my anxiety into being great at my job. And then when you leave you’re like oh my god, what am I going to do? And so I make jam. I’m gonna have to send you some you have to tell me your favorite fruits.

Samantha Bee  45:53

You know what I’m going to send? Okay, you’ve if you send me junk. Are we going to do a jam exchange? No, I’m going to send you a jar of honey from my honey bees that are in my back yard.

Alyssa Mastromonaco  46:03

Oh my god. This is you know what’s happening right now. We’re living my dream which is baby boom. I am JC Wyatt, your JC Wyatt. Okay, we’re in Vermont. There’s a wagoneer involved and we it country baby is happening.

Samantha Bee  46:16

I just got flushed again. for good reasons. I got turned to all red and got excited. This is it. I don’t have any more questions for you. Because all I really wanted to talk about was Jama cats.

Alyssa Mastromonaco  46:29

Me too. This was a great.

Samantha Bee  46:31

I’ve enjoyed this so thoroughly. I feel rejuvenated. I’m sweaty.

Alyssa Mastromonaco  46:37

Me too. I’m a little like little schmaltzy and you know what? It’s not a Peri menopausal no hot flash. This is no legitimate like, like, I don’t even know how to say I’m like, Oh my god. Should we date like that’s how.

Samantha Bee  46:51

Well, I feel like I just met my my fruit and honey and sugar match. In life. That’s like soulmates.

Alyssa Mastromonaco  46:59

We’re sugar in all its forms soulmates. Yeah, that’s that.

Samantha Bee  47:09

Okay, thank you so much. This was incredible.

Alyssa Mastromonaco  47:12

Thank you. This was so much fun.

Samantha Bee  47:20

That was Alyssa Mastromonaco. And I had no choice but to look up one thing. She said back in pioneer days, there wasn’t a lot of jam making this sugar was so expensive. I love jam. So I had to check that out. And yes, it’s true. Sugar was prohibitively expensive, and people often used sorghum in its place. Samantha Bee not a fan of sorghum. I have to admit that to you today. Anyway, thank you so much to Alyssa for joining me. And good news, there’s more choice words with Lemonada Premium. Subscribers get exclusive access to bonus content like a rapid fire round of trivia questions based off my recent interview with Judy Blume. Subscribe now in Apple podcasts.

CREDITS  48:17

Thank you for listening to Choice Words which was created by and is hosted by me. We’re a production of Lemonada Media, Kathyrn Barnes, […] and Kryssy Pease produce our show. Our mix is by James Barber. Steve Nelson is the vice president of weekly content. Jessica Cordova Kramer, Stephanie Wittles Wachs and I are executive producers. Our theme was composed by […] with help from Johnny Vince Evans . Special thanks to Kristen Everman, Claire Jones, Ivan Kuraev and Rachel Neil. You can find me at @Iamsambee on Twitter and at @realsambee on Instagram. Follow Choice Words wherever you get your podcasts or listen ad free on Amazon music with your Prime membership.