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May 24, 2022 34 mins

Designer and podcaster Debbie Millman on creativity, vanity projects, and how to inspire people to change. Also, she is Roxane’s wife, and Roxane tells us how they met and fell in love.

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Episode Transcript

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Speaker 1 (00:01):
I have two book recommendations this week. They come out
later this summer, so really I'm just putting them on
your radar for now. In Marcy Domanski's Hurricane Girl, Allison
has just bought a home on a beach in North Carolina.
She is in many ways running away from her previous
relationship to a high powered studio executive in Los Angeles

(00:23):
who had really bad habits behind closed doors. And she's
enjoying that home in North Carolina when a hurricane blows
it all the way. She's featured on the news, and
later she encounters the cameraman at a bar and from there, well,
things take a turn. I don't want to give away
the novel, but she suffers a traumatic brain injury and

(00:44):
returns to her hometown in New Jersey to recuperate, and
it's just one hell of a novel. Jermanski is one
of my favorite writers. I first encountered her work with
her novel Bad Marie, and in this her fifth, she
continues to write some of the sharpest, most irreverent women
on the page. They make terrible decisions but look so

(01:04):
very good while doing it. I also recently read The
Crane Wife by C. J. Houser. The title of this
memoir and essays went viral a few years ago, and
you can read it online at the Paris Review. I'll
definitely be including a link in the show notes so
you can read the essay for yourself. C. Jiant Houser
has a very appealing narrative voice. It's right, but it's

(01:27):
also warm and generous. The essays often end in really
elegant and unexpected places, and rarely do they give you
the finitude that you crave. There's not much certainty to
be found in those pages, but there is a lot
of reflection. In an essay about a home of her own,
there is this incredible description of a perfect house in

(01:48):
Tallahassee where a young woman can live happily and alone.
There's a lot of intellectual wandering in these essays and
also self examination as a whole. This is a book
about a woman and affirming her place in the world
and the complicated journey she's on to get there. There
are some repetitive themes, like girl, we get it you

(02:08):
who have broken up with some men, But still the
writing is so beautiful that it is very easy to
forgive a minor obsession. You will not regret either of
these books, which in many ways are two sides of
a similar coin. They are out in June and July,
and I hope you enjoy them. From Luminary. This is

(02:29):
the Roxanne Gay Agenda, the Bad Feminist podcast of your Dreams.
I'm Roxanne Gay, your favorite bad feminist. On the Roxanne
Gay Agenda, I talked about something that's on my mind,
and then I talked with someone interesting to find out
what's on theirs. On this week's agenda, How I met
my wife. It started with her podcast Design Matters. She

(02:52):
tried for quite some time to get me on her show.
At first I sent her to a publicist, and then
I demurred because honestly I was just in her peued out.
Then she sent me a lovely and detailed email about
how much she was moved by Hunger. And then much
later she did an event with my dear friend and mentee,
Ashley Ford. After that event, Debbie, Ashley, and some other

(03:15):
folks from the event were in what is now our
backyard having drinks enjoying a warm summer night. When Ashley
mentioned me, and Debbie blurted out that she had a
crush on me. Now she knew I was in a relationship,
so she asked Ashley, you know, like, what's the deal there?
And Ashley told Debbie, go ahead, shoot your shot. Listener
she did. She emailed me again and asked me out,

(03:38):
in her words, on a proper date. So I wrote
back and I said yeah, and I literally just wrote
back that one word, did not offer any other details,
did not elaborate, and did not try to make a plan.
It's a much longer story, but eventually we did go
on that proper date in New York. After I launched
Best American Short Stories. I didn't google her. I had

(04:00):
no idea who she was, what she did, or what
she looked like. And so when each person came up
to the table from the signing line, I wondered, like,
is this her? Is that her? With varying degrees of interest,
and then finally it was her, and she was really hot,
and so we went out for dinner and on the
street afterwards she asked if she could kiss me. We

(04:21):
have been together ever since, and in some ways it's
kind of strange. I'm happy, and it's actually hard for
me to say those words. I don't trust them. I'm
always waiting for some shoe to fall, and of course
we're living in a pandemic, and Rovie Wade is on
the verge of being overturned in the supply chain, and
it's another election year. How on earth do I embrace

(04:41):
or claim happiness or some version of it while the
world is falling apart? My guest today will hopefully give
me some insight into that question, But first let me
tell you a little bit about her. Debbie Millman is
a designer, an artist, and educator, and an author. Most
recent book available now is Why Design Matters Conversations with

(05:04):
the World's Most Creative People, which is in many ways
a retrospective of seventeen years of her award winning podcast,
Design Matters. She started Design Matters back in two thousand four,
when almost no one really knew what a podcast was. Now,
eighteen years later and hundreds of interviews under her belt,
she's still doing the damn thing with long form interviews

(05:26):
of not only designers, but writers, actors, playwrights, artists, entrepreneurs,
really anyone who is out there leading a creative and
often wildly successful professional life. Debbie has also written six
other books, mostly about design and branding, and she's a
great dresser. Deborah Millman, Welcome to the Roxanne Gay Agenda.

(05:48):
Thank you, Roxanne Gay. It's great to see you today.
It's been so long now. Debbie, you are a co
owner of Print Magazine. Your very first magazine, though, was
an incredible publication called Debutante that you created with your
best friend, also named Debbie. The year was nineteen seventy three,
you were twelve. Tell us a little bit about Debutante. Um. Well,

(06:15):
my friend Debbie, Debbie carp she lived a few houses
around the corner from me, and we both loved magazines,
and one summer we decided we were going to make
our own magazine. We wrote all the articles, we drew,
all the illustrations, made pretend photographs. Just a magazine named Debutante.

(06:37):
A plus on that name. Thank you, and I think
we both know Debbie and I both regret neither of
us having kept it. I didn't have it. I didn't
know if she had it, and she was like, no,
I don't have it either. So you have been making
your podcast design Matters for quite some time. I would
love for you, though, to tell me about the television

(06:58):
pilot that you shot onto some or seventh two thousand nine.
I see you're picking up some of my research techniques.
I am. Indeed, we did two episodes. We did one
with Milton Glazer and one with Stefan Sagmeister, and UM,
I hated it. Really, what did you hate about it?
I felt like somehow I had sucked the oxygen out

(07:20):
of the room in doing this live interview. I was
very nervous um and so I decided that I liked
audio much more, mostly so I didn't have to think
about how I looked when I was doing my interviews.
I could really just concentrate fully, totally obsessively on my
guests and not myself in any way, shape or form.

(07:43):
Has your opinion on that change. Do you ever aspire
to television and maybe trying again with design matters especially,
I think in the vein of like a Charlie Rose
or James Lipton on inside the actor's studio, I think
if I had a really good director that could navigate
that space for me and help me find a television voice,

(08:06):
I'd be open to it. In that I'm kind of
open to almost anything at this point in my life.
And why are you open to almost anything at this
point in your life? Like, what is it about this
moment in your life that has you thinking, you know what,
let me try something different. I don't know if it's
being well into my middle age or or just a

(08:27):
sense of freedom that I'm experiencing now being happily married. UM,
let's say it's the ladder just for ships and giggles. Um.
I think that. Um. Certainly, the last three or four
years have have shown me that the most unexpected things
could happen in ways that you never anticipated and fundamentally

(08:51):
change everything that you think about the trajectory of your life.
And I think when that happens in the best possible
way that it has, it makes you feel ever so
slightly more are hopeful that other things might do that too. Interesting. Yeah,
you know, I had never previously thought of marriage as
a sort of gateway to adventure, and yet I have
found myself where we are on all kinds of adventures

(09:11):
over the past four years. And I blame you. Well, Yeah,
I think anybody that dregs you to Antarctica to try
to see the solar eclipse of the Sun, you know,
can have that that title pointed at them quite emphatically. Indeed,
now many of my listeners will also be familiar with
your podcast, Design Matters, which you started in two thousand four,

(09:32):
and at the time you exclusively interviewed designers. So why
was that and really what what is the origin story
of Design Matters? Well, Design Matters happened because I was
forwarded a cold call in my office from somebody that
was interested in inviting me to work on a show

(09:53):
for a then fledgling online internet radio network called Voice America,
just different than Voice of America. And this lovely man
called me up. I thought he was offering me a job.
I was sort of fancying myself, sort of Charlotte ronson
type DJ, you know, with the headphones and the groovy turntable.

(10:16):
Um thought they were offering me a paid position, when
in fact that was not the case at all. They
were actually offering me an opportunity to pay them to
produce a radio show. But at the time, I was
experiencing a real sort of barren period in my in

(10:36):
my creative life, everything I was doing was corporate. It
was all about shelf presence and marketplace and shareholder value.
And so when this opportunity came up to do something creative,
I sort of convinced myself that it could still sort
of help my business because I could interview designers and

(10:57):
clients that AM affiliated with, and it would also be
something that could be ever so slightly experimental and different
and unique and challenge me in a creative way that
I hadn't been challenged before. And so I signed on
to do thirteen episodes. I had to pay Voice Amrick
about five thousand dollars and and that was a lot
of money. But I also, you know, I wasn't married

(11:19):
and didn't have kids, and so I had some disposable
income and thought, well, why not invested in myself and
do this silly thing, totally vanity project paying someone to
produce a radio show for me. But I decided to
do it, and in February of two thousand and five,
the show aired for the first time, and I've been

(11:42):
doing it ever since. When you first started, did you
ever imagine that you would still be doing it now? No? No,
I did not. I thought I would do thirteen episodes
and and maybe another thirteen. I fell in love with podcasting.
I fell in love with re connecting with my creativity

(12:03):
in a way that I never experienced in this brand
new discipline, and so it's evolved from a show primarily
about design and designers to really show about any kind
of creative persons. As you said in the intro, the
reason it was designers at the beginning was because that
was really my circle of friends, and nobody had heard

(12:25):
of podcasting before, and an internet radio show wasn't all
that glamorous. So it wasn't like I was reaching out
to celebrities and well known artists beyond the design business,
because they no one else would have known who I was,
and certainly wouldn't have agreed to do something that they've
never heard of before. One of the things I've noticed

(12:48):
about episodes of Design Matters is that there's this narrative arc,
and in many ways you really trace the arc of
a creative life. And every interview begins much in the
same way I began this interview, where you share some
factoid or interesting piece of information about someone that lets
them know I know what I'm doing here, I've done

(13:09):
my research, and now let's go what are some of
the things that keep you so interested in that arc
of someone's life instead of, for example, just focusing on
whatever their latest project is. Well, chances are if it's
somebody that has accomplished great things, A lot of people
know what that most recent project is. That's why they're

(13:31):
in the news as much as they are. I'm much
more interested in what led them to this moment in time,
What propels someone on a path, How do they overcome obstacles,
self doubt, insecurity, trauma, rejection. Those are the questions that

(13:53):
I am fundamentally interested in understanding and and helping other
people that are listening understand that this is just a
very human way that we all live. We just don't
always talk about those conditions that lead to us having

(14:15):
this Award winning novel or Tony winning play or Grammy
winning album or whatever it is. What are the conditions
that have led you to where you are in your
career right now? Well, I wish that they were more intentional.
I tend to stay in things a very long time.
I'm very scared of change. As a result, I've probably

(14:38):
stayed in a lot of things too long, jobs, past relationships,
all sorts of things, apartments, um. But because I'm older
and am now really afraid that I'm running out of time,
I'm being more intentional with what I'm doing, only because

(15:01):
I like doing so many things, and I don't want
to leave this earth regretting what I didn't do. Is
there anything you haven't done that is on sort of
I don't like the word bucket list. The phrase bucket list, Oh,
I hate it, so just makes you feel like gross, like, oh,
you're going to pick something out of a bucket? No,

(15:22):
thank you. But is there anything sort of on your
list of ambitions that you have not yet done that
you would like to accomplish and the many years you
have left well, I definitely would like to work on
a memoir. I would definitely like to make more art.
I'd like to write a one woman show, not that

(15:42):
I'm in, but for somebody else to perform in. Wouldn't
mind singing in a little cabaret band, a pub maybe.
I think you'd be great in I think intimate, in
a slinky dress with a jazz trio. I know which
stress you would wear. I don't, so we'll have to discuss.

(16:03):
I would have to talk a little bit about your
career because you're one of the most creative people I know,
and you have astounding output. Why did you first know
you were creative and what did creativity look like? For
you as a child other than debutante, I can't ever
remember a time in my life where I wasn't making something.
Now I'm I'm a bit lucky in that I was

(16:24):
always encouraged to make things. My mother was very artistic.
She was a seamstress, and so I learned how to
sew from a very young age. I was always making
my own clothes and doing kinds of embroidery, and making
pillows and curtains. And I remember the summer after college
when I was staying back home, I moved into the

(16:46):
basement and wallpapered the basement with blue astronomy sheets so
that I felt like I was living in outer space.
You were an English major, So what were you thinking
you were going to do with that English degree. Well,
I thought that I might go into journalism. I had

(17:06):
a degree in English with a minor in Russian literature.
So now I joke that I have a degree in reading.
And so when I graduated, I I ended up getting
a job at a magazine doing the only thing I
had a marketable skill four, which was old school layout
and paste up of the magazine. I learned how to
do that working at the student newspaper. You know, one

(17:28):
of the things that always amazes me when you talk
about your job history is the varied number of jobs
and just across different genres fields. It's just amazing. For example,
this and this was one of the first things you
ever told me that shocked the shift out of me.
You became the creative director of Hot ninety seven as

(17:50):
they were transitioning into a hip hop station, and so listeners,
once in a while, we'll be listening to hip hop,
especially from the eighties and nineties, and she knows every
single word. She knows the cadences. She you know, like,
she just knows these songs. And I'm like, hell the
hell do you know these songs? You're like a Jewish
lady from Long Island, And she reminds me, excuse me.

(18:12):
I was a creative director of Hot ninety seven and
I designed their logo. What was that experience like working
at Hot ninety seven during those days? It was amazing.
It was one of the great great experiences of my life,
you know, it was. It was an extraordinary time in

(18:33):
hip hop. It was first getting the recognition it deserved. Um,
it was a viable market for the first time. People
understood that and began to craft and reposition Hot ninety
seven from the dance music radio station that it was
to the world's first hip hop radio station, and that

(18:56):
I was able to be part of that very first
attempt at doing this is was really and it remains
one of the greatest experiences of my career. One of
the things that you do in your career is working
brand strategy. And what's always interesting is that you are able,
you know, with the incredible team of people that you

(19:19):
work with, two convince people that something is viable. How
do you start to think about the ways in which
we position, you know, whether it's a radio station or
a brand, like, how do you get people to believe
in these things that we probably inherently distrust. Well, it's

(19:40):
not about persuasion as much as it is about inspiration.
You have to give people a way of seeing the
future in a different way that feels viable and rich
and satisfying. And you're able to help ignite a potential
future that they can see and feel can be manifested.

(20:04):
And if it's something that's good for them, and it's
something that's good for society and you can show how,
then it becomes almost a no brainer. I mean, there's
no brand repositioning project I've worked on or redesign I've
ever worked on that's been easy, not one. Some have
been way more inspired than others. Certainly Hot ninety seven
was one, But they're all difficult because people don't like change.

(20:28):
So it's it's about being able to envision a future
where the circumstances are better than the current and if
you can do that, then you can create consensus among
the group of people that you're working with that then
propels change forward. That was a sexy sentence. You know what,

(20:52):
when Barack Obama was talking about Hope, he was trying
to reposition how we saw the future with him at
the Helm, Martin Luther King did the same thing. And
I have a dream. I have a dream about the future,
and if people can believe in that future, if we
can see how that future is better than today, then

(21:14):
that we create that consensus, that buy in that propels
us to be able to create that future. You have
me thinking about the current political climate and like the
world feels like, you know, as I said at the
top of the show, like in many ways, like things
are falling apart. Do you have the ability, given the
way things are right now, to envision that future that

(21:35):
is better than the present. Well, I can envision it,
and I can articulate why I think it's better. The
problem is, at least from where I'm sitting, I don't
see domestic or national consensus. That's the big problem right now. Now.
If it's true that of the population of the United

(21:58):
States believes in in report active freedom, then the thirty
percent that seemed to be winning that argument have a
better way of eliciting consensus than the majority. I can't
think of another time in our society where the majority
have so little say in consensus building, And so right

(22:23):
now I feel rather hopeless about where things seem to
be going and don't fully understand how we can thwart that.
That's what I'm struggling with as well. I just don't
know sort of how do we begin to get something
like consensus when you know there's an entire population that
doesn't believe, for example, that women are people or that

(22:46):
black lives matter, Like, are those people that with whom
consensus is even possible? And right now my answer is
now absolutely not. Well, you know, I wonder is it
because we've somehow always felt that the arc is going
to bend towards justice. Do we depend on that too much?
Do we somehow think that if it is that somehow,

(23:10):
because it is a majority, that will eke it out
at the end. I think people rely on that. I mean,
what I can tell you is that from my own
experiences in market research, people expect that other people are
going to show up even when they don't. Yeah, you know,
you've touched on something that I've been thinking about quite

(23:33):
a lot lately, and it it's that idea that if
Americans believe in reproductive freedom, like, are we really all
sitting around waiting for like one of or you know,
a thousand of those like do something like or that
surely the majority will prevail when the past several elections

(23:53):
have shown us that the majority doesn't prevail, especially in
a system in an electoral college system. I think a
lot of us are trying to balance that sort of
hope and belief that perhaps we all can do something
with the overwhelming sense that it doesn't matter what we do,
the system is rigged against us. Yeah. And I think

(24:14):
that the way in which these conditions are reported has
a lot to do with how people show up in
the election when it was it seemed all but certain
that Hillary Clinton was going to win. I mean, I
remember that morning, you know, doing like a little fun
checklist like white pant suit check, campaign, buttons check, and

(24:36):
you know, I was I had ordered Chinese food that night.
I was going to my friend Susan Milligan was at
the convention center where she was going to come home.
We were going to celebrate, and then the sort of
world changed right in front of us. I think that
humans respond better to showing up when they feel like
there's a chance they're gonna lose. So if it had
been a squeaker till the end, if it was like

(24:58):
everybody has to show up, is if we don't show up,
we're gonna lose, more people would have shown up. So
I think from now on, we have to position every
election as a squeaker. Yes, especially this forthcoming election. The
next two elections in fact, are desperate squeakers, and so like,
let us all get on it. Yeah, I mean you're
already seeing it. Yeah. In two thousand nine, with Stephen Heller,

(25:22):
you started a graduate program in branding at the School
of Visual Arts. You're still doing this, You're still running
the program thirteen years later. What is the most interesting
thing you have learned about teaching over the years. You know,
one of the things that I've really learned during COVID,
when I had to pivot and start teaching online was

(25:44):
how much space people take up in a classroom correlates
with how vocal they are. Interesting. I mean, this is
not kind of that feel good answer that I think
maybe listeners would want. Although I think that there's something
really interesting about the democratization of space online where everyone

(26:07):
is the same exact size, And I think that democratization
of space is really interesting for the introverts, for the
shy people, for the insecure people, and it changes the
dynamic in a really, really profound way. So that's something

(26:28):
I've been thinking about a lot, as as I'm teaching
now in this hybrid scenario. But I think the most
interesting thing that I learned from watching the great teachers
in my life teach me was how extraordinary it is
to imbuse someone with the sense that they're smart. When

(26:52):
you give the sense to someone that they're smart, it
gives them so much hope about what they're capable. I
absolutely agree, and that to me is the great miracle
of teaching is seeing how feeling smart or feeling proud

(27:12):
of an idea could impact the course of someone's life.
I have found that in teaching writing, and for me,
what I try to teach every student from day one
in my classroom is that you're a good writer, because
so many students come into the creative writing classroom and
frankly any writing classroom believing that they're bad writers because

(27:34):
someone has told them that and someone or they're comparing
themselves to us. Yes, but in this case, it's a
lot of the time it's that faculty have told them this,
and I find that so depressing because that's not our job.
That should be against the law. The way that their
approach to the class just lightens and lifts when you

(27:55):
tell them, I believe you're a good writer already, and
this class is just going to help you to become
better on your own terms, not in comparison to anyone
else in class or to the books that we're reading,
but in comparison to you. It seems to just empower
them in ways that are so gratifying to watch, especially
over the course of a semester. I always wonder, like,

(28:18):
why doesn't everyone teach this way, this sort of idea
that you have to break someone down to build something
back up. I don't find that it's terribly um useful,
And in any educational experience where a teacher has done
that biology freshman year college, I have found it to
be an entirely dispiriting and defeating experience that did not

(28:38):
serve me in the long run. But I want to
switch tracks just a little bit, well not just a
little bit, a lot. I know that you're fascinated by
type and texts, like you love words, and that one
of your superpowers is the ability to write mirror backwards.
And I'm not sure you know this about me, but
I spent an entire year in high school speaking bad words,

(29:00):
and people just seemed to go with it, maybe because
it was a private school. Like so I would mean
like Missy Elliott and working more like I. You know,
I'm like, literally that's that's that's what she has, Just
like say everything backwards and I would write everything backwards.
But I'm curious, how do you even do? I was

(29:22):
not well, but I also had a lot of free
time and a big imagination, and so like one day
I was just like, I'm going to talk backwards. Wow,
that is like the coolest thing, isn't it. Yes, I
felt very cool, and I still frankly feel cool about
it now many years later. But I was curious, how
did you develop that skill? Oh, this is not a

(29:43):
happy story. So my parents got divorced when I was
about eight years old, and my mom got remarried a
year later, and she married a man who was very strict,
very severe, disciplinarian, and as one of his punishments, aside
from being physical, really abusive, he would force me to
write like five times I will not do whatever it

(30:07):
was that I was being punished for. And so I
get bored doing this, and so I just started to
improvise and started to figure out new ways to entertain myself.
As as I was doing this and started writing backwards.
You know, it's amazing what the mind will do to

(30:28):
cope with just about anything. Because I know, I started
talking backwards because I was in a bad place, not
because I was in a good place. Well, yeah, you
were talking backwards because you couldn't speak about the things
that had happened to you. Yes, And it was like
a coping mechanism. And I just thought if I can't
tell anyone, then I'm going to just be incomprehensible correct
at all times, which you gotta wonder, like, girl, what well,

(30:51):
I had a speech impediment as well. If this was
I think in fifth grade. Um, I think that my
world had collapsed so fundamentally that I really lost track
of what was real and what wasn't. And as a result,
I felt incapable of stating anything definitively because at any

(31:16):
moment it might change or shift. So even something like hey, Dad,
you know what the weather is going to be like today,
I'd be like, well, maybe I do, but maybe I don't.
And so everything I said, even are you hungry, Well
maybe I am, but maybe I'm not. And everybody thought
that I was nuts, like completely bonkers. And the only

(31:39):
reason I think I ever stopped doing it was one
of the other things that my stuff mother did. Every
night we had what was called inspection. He went around
the house and looked in our rooms and inspected our
bedrooms to make sure that they were pristinely clean, you know,
hospital corners on our beds and so forth. And one

(32:00):
night he looked into my closet and I guess a
skirt had fallen off a hangar and was in a
heap on the floor, And so of course I got
in trouble for that, and I insisted that I didn't
know that that had happened. I didn't leave it like that,
I didn't throw it like that. It must have fallen
off the hangar. I remember my mother screaming at me, saying,

(32:20):
how could you be so sure that the that the
skirt fell by itself when you can't even tell us
what the weather's like outside. That's how adamant was about
the fact that the skirt must have fallen by itself.
And after that I stopped with my my double talk
as my parents called it. Wow, you contain multitudes every moment.
You really do. Well. My last question for you is

(32:46):
what brings you joy right now in your life? Oh? Roxy,
And you know what brings me joy? You do our
dog Maximus, Touretto, Blueberry Milman, Gay are kiddies, THEO and
lou Just being with you that gives me joy. Oh well,
that's not what I thought you were going to say,
but that makes me very happy. Do you see our dog?
I do? I wish that our listeners could ye little

(33:09):
fluffy muffin for our listeners. My dog came in, so
I'm in my office upstairs and he came up about
half an hour ago and he's just very cuddly and
he had a hot dog for lunch. He's laying in
Roxanne's arm and he's just here and he's very cute.
But Debbie Melman, I want to thank you so much

(33:29):
for joining me on the Roxanne Gay Agenda. Every time
I talked to you, I learned something a little new
about you, and so I hope our listeners enjoy this too.
Thank you, Roxanne. It's been an honor in a privilege.
You can keep up with me and the podcast on
social media on Twitter at our Gay and Instagram at
Roxanne Gay seven four. Our email is Roxane Gay Agenda

(33:50):
at gmail dot com from Luminary, The Rock Sande Gay
Agenda is produced by Curtis fots our researchers Yes More.
Production support is provided by Caitlin Adams and Meg Pillart.
I am Roxanne Gay, your favorite bad feminliest. Thank you
for listening, and Max says him
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