114: Illuminating Invisible Privilege with Karen Pittelman (and Why She Gave Away Her $3 Million Trust At 24)
8 Dec 2025 · 59 min
Podcast interview (Pivot Podcast host Jenny Blake with guest Karen Pittelman) exploring the concept of class and invisible privilege, how privilege shapes everyday decisions and opportunities, and Karen Pittelman’s personal choices to redistribute inherited wealth. Key moments: explanation of privilege (X-ray declassifier metaphor), Karen’s decision to dissolve a $3 million trust (1999) and her ongoing commitment to activist-led giving (e.g., co-founding the Shahara Foundation and supporting the Trans Justice Funding Project), plus practical suggestions for listeners to notice institutional traces of privilege in daily life.
Questions this episode answers
August 26, 2018.
$3 million (dissolved in 1999).
"I'm up to, I think... 13 million."
About $500,000 ("like a half a million dollars").
Aiming for a ~90% lifetime average of redistributing wealth.
Chapters
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I am super duper thrilled to be here today with Karen Pittleman. Karen is the author of Resource Generations.
How to Stop Hiding your Privilege and Use it for Social Change. She's also the co author of Creating Change Through Family Philanthropy. I was lucky enough to find out about Karen and her work through a mutual friend, Dev, who's been on the Pivot podcast. And at that fateful coffee with Dev, where he also told me that Union Theological Seminary existed here in New York City, I remember saying to him that I keep hearing the words privilege and invisible privilege thrown around and I don't really know what they mean. And he said, well then you have to read classified. It's by Karen Pittleman. Pivot Podcast listeners. I am telling you, this book turned on 100 a thousand light bulbs that needed to be turned on. It was so enlightening, it really shocked shifted my thinking in such a profound way. In combination with many of the other books that I had been reading about criminal justice and the nature of addiction and childhood trauma. And it's it's been a year. I've even been reading about angels and souls and past lives. So it's been a fun reading rabbit hole of 2018. But the more I got into Karen's work, I was just so blown away by her. In 1999, Karen dissolved her $3 million trust to co found the Shahara Foundation, a fund that' by and for low income women activists in Boston. And she's been organizing people with class privilege ever since. She currently lives in Brooklyn where she works as a writer and a writing coach and sings with her country band, Karen and the Sorrows. Karen, welcome to the show.
Oh, thank you so much. I'm so happy to be here.
I am thrilled. I've been looking forward to this conversation for a long time, ever since we got it on the books. And I'm just so excited because I'm guessing that there are many people listening to this who might have heard a term like class privilege or invisible privilege thrown around, but don't really know what it means. Or just like this recent Atlantic article about the top 9.9% that a lot of people think, well, that doesn't apply to me. I'm not the 1%. I'm not the super wealthy. So could you just kick us off by sharing what class privilege means? Or even invisible privilege?
Sure. I mean, I do think it's one of those words that right now is getting thrown around a lot, but it's hard to nail down.
And, you know, I think one of the illustrations that's in classified that people talk to me about the most from all class backgrounds is the X ray declassifier. And it's just this illustration of somebody who's going into a job interview. And so you just see all of the fabulous things about them that they're presenting, you know, from like their education to their firm handshake and their great smile and their interesting hobbies. And then we put it through the X ray declassifier and you see how so much of those skills. And even, like, even just your smile, your teeth, like, have a history that comes from what kind of privilege you've had in your life. Like, did you have access to dental care or medical care as a child? How was your school paid for? What kind of neighborhood did you live in? What was your house like? Where did you study? Did you have a quiet room all to yourself? Or were there always lots of siblings around? Did you have to work a job?
Did you learn how to play tennis or golf? Or things that.
Somebody'S looking at on a resume that if they're in a position of power, they connect with all of that. It's, you know, I define it in that way because it's hazy, it's cloud, like, almost. It isn't just one thing. It's this constellation of access that.
That you have in varying degrees depending on who you are and where you're situated. It doesn't mean that you haven't also had experiences of oppression. It doesn't mean that your identity is, you know, the man.
But it just means there are all these little ways that who you are have been supported by systemic injustices, really, that never get addressed. And so instead, you're just seen as the person who accomplished all that on your own. And so, so much of, I think understanding what privilege is is just breaking that down and understanding the systems that create us and create our opportunities so we can be more honest with each other about that.
I love that you brought up this image and you gave so many great examples. It really is something for listeners. The book has all of these great illustrations and on the left hand page, yeah, it's somebody who just looks well dressed going to an interview and then it breaks down exactly as you said. They're well rounded, they have an impressive degree, a high gpa. Well, maybe they were told in school you can do anything in the, in the, in the X ray graphic it says taught perfect standard English. And you are saying everything from straight teeth to a firm handshake are affected by how we're raised. And on that note, another very profound image was the usual story versus what gets left out. And this really was so eye opening for me because you're right, it's. And you say in the book, it's, it's not that we don't work hard, but what often gets left out of the bootstrap story or the building myself from zero are so many invisible privileges along the way, or at least invisible from the outside looking in. It's not just for people who are heterosexual or caucasian or things that we typically associate with privilege. It's actually that the whole story. And so I've really become more careful about how I talk about. I used to say, oh, I bootstrapped my business from zero. Like I didn't take any loans, I built it on the side and then I quit my job and then I bootstrapped. But what kind of boots was I wearing? You know.
And I think that's one piece that often gets elided is like.
Maybe you didn't take any loans, but did you have debt? And what kind of debt did you have? And did you have a safety net if you had that debt? And if you look at for example, just like the racial wealth gap, what kind of wealth families have, depending on where their identity and their history in this country.
Makes a huge difference on what kind of risks you can take in your life and also who you're, who you're responsible for. Like, are you sending money back to your family in another country? Are you the only caretaker for like an elderly relative? Do you have small children that might not even be yours, but you know, maybe a siblings or a cousin's, like depending on your access to resources, the, the number of people who are relying on you really varies, you know. So even if you are, you know, quote unquote, bootstrapping yourself up, who you're carrying with you is also a big part of where that goes. Like, versus for me, where I grew up in a wealthy family, like, I had the freedom to choose whatever path I wanted. Basically nobody was relying on me to eat, you know, and to get by. And I wasn't coming from like a first generation immigrant family either, where I had, you know, where everybody had made these huge sacrifices just to get me to college. Like, I'm fourth generation in this country. So, like, the pressure of that is off. And my family paid for school. So when I graduated and then got to go to an Ivy League school in part, and then that's what to say. Like, sure, I'm smart, I'm amazing. Like, it doesn't take away from that. But the way that the system is stacked in my favor, I mean, I had a $3 million trust fund just for being born. I didn't have to do anything for that. And that changes everything. And even if I never tell anybody, even if I keep it a secret, and even though I gave that money away, it still changes everything in my life, down to what the. What freedom I have to make choices and who's relying on me.
There's so much powerful stuff in there. And I can't wait to ask you about that trust fund, which is coming soon.
But I just want to kind of close out on this. The luck of birth. I mean, even having a family who says they love you or you can do anything you want is not everybody has that, let alone whatever money or finances status. And then it was so powerful, what you said in the book and just now, even the ability to take risks, this affects. People may not realize that having any amount of privilege affects the decisions we make. Where we go to school, if we go to school, and even the risk in my case of moving to New York and starting my own business. I knew deep down I wasn't going to be homeless if it failed. Exactly as you said, I wasn't. I didn't have anyone else that I had to provide for. And although I didn't want to go back and live in my proverbial mom's basement, I knew I very well could have. I knew that my family wasn't going to let me starve and that that wasn't even on the table. So how did that affect a thousand tiny choices? And I'll contrast that to, I do volunteer work with a program called Defy which vivid podcast listeners, you probably know what it is by now, but teaching business skills to formerly and currently incarcerated men and women to transform their hustle. And one of the guys shared his story and he said that at 12 years old, his mom became addicted to crack. And this was during the crack epidemic of the 80s in New York. And so at 12, he had to figure out how to provide for himself and his two younger sisters at 12. So of course, what job do you get when you're 12? Who can hire you? No one can even hire you legally. So how many micro decisions and moments of his life were changed because of that? Which he didn't choose. He didn't choose. So I think it's so important how you highlight the problem with invisible privilege and not recognizing it is that we sometimes think someone didn't work hard or, oh, he went to prison, it's his fault. And that's not the whole story.
And it's just like, I think that shows a lot of the fallacies in the way we think about the American dream. And this idea of like, if you work hard, if you're smart, if you hustle, like, then you will.
Make more money than the generation before you and succeed. And that's what America is about. When it's like, yeah, I work hard, but do I work harder than somebody who has three jobs and it's like working the night shift at Walmart, or do I work harder than a 12 year old who had to figure out how to hustle to support their family?
That's not like, when you take it apart, it doesn't actually make sense. The people who have the most money and the most power in this country, I forget the statistic, but it's a huge percentage of them are inheritors, including Trump himself. Right. Like, isn't that money came from his dad? So.
The best way to have the proverbial American dream is not included in the story at all. It's to be like me and just be born rich.
But you worked so hard as a. In the womb, Karen.
I really, really worked it in the womb.
Yeah.
Clearly hard work has really nothing to do with it because I don't think there's anything harder than trying to survive and take care of your family when you're poor or working class, honestly. So, you know, I think there's just so much we need to take apart. And my hope is that by telling the truth about my own privilege, I can help give, provide a tool to deconstruct some of that.
You've done such an Amazing job of that, really please everybody. You have to read Karen's book. I'll just say that many times before this is over. So, okay, I'm dying to know. How on earth did you have the wherewithal at 24 years old to give away the trust fund? Not only were you born with it, and yes, you got lucky, you inherited this money. None of this would have been on my mind at 24. I probably would have thought, oh, phew, I'm set for life, and wiped my brow. And I can just say right now, I don't think I would have had that thought at 24 to give it all away. So take us to that time. What was going through your mind? And I would also imagine you got quite a lot of pushback from your family. I mean, I don't want to assume, but I just. I can't imagine they were like. They must have been so surprised.
I mean, I think a couple of things. One, like, a caveat is, like, everything we've been talking about, you know, for me to, like, give that money away, like, I could. I wasn't giving away my class privilege. And even if I had never gotten another cent again from my family, which is absolutely untrue, and if you come from, you know, a family with a lot of wealth, like, you're never done, you know, that was one piece of the puzzle. I didn't understand this as much then, but. And I can talk about that in a minute, but like, all the opportunity I have and everything we were talking about on, like, that illustration of the declassifier, you know, my. The fact that I didn't have loans, the fact that I had an Ivy League education and all of these connections and like all the past healthcare and opportunity had already defined the trajectory of my life. And that's something I can't give away. It's in my body. Even. So, I think a lot of times when I tell people, know what I did or I'm talking about it, it feels so overwhelming because it's like people are imagining, like, oh, my God, if I had a couple million dollars right now, I need that, or here's what I would do with it. And. And.
My life was already.
So. So defined by the privilege I came from that money or not, you know, I still had all this opportunity. So I think that's part one of the things that made it easier to think about. But I guess for me, I just felt like knowing that money was there in my name, was holding me back from living according to my values and becoming the person I wanted to be. And I felt like if I really believe in the redistribution of wealth, if I really believed in fighting for a more just world, there's no version of that where this small group of people control most of the resources. And so I guess for me, it was just about, like, am I going to be complicit with the system that created me, or am I going to find a way to.
To align myself, you know, align my life with my values? But it definitely wasn't easy, and.
It was very hard for my family.
And there was a lot of struggle there. And it was hard for, like, a lot of people I grew up with in the world I came from. I think people thought I was bananas. People thought I was being judgmental. People thought I would regret it. Even people who shared a lot of my social justice values were worried that I should wait and maybe I would know better what I was gonna do later.
And have you ever regretted it?
Never.
For one second, I figured that was the answer. I figured probably not even for one second, but of course people would say that.
And maybe there's a future version of me where I'm an asshole, you know, oh, am I allowed to curse?
Yeah, it's okay.
But, like, why would I want to make decisions in line with that future asshole who's like, I wish I hadn't given away that money. I think, like, if you're moved to do something, do it now. That doesn't mean, like, you know, don't be informed and just like, go around, like, just doing, you know, whatever you want. But, you know, I was working together with a group of activists, and there was a process, but I never regret it for a minute. I never regretted any of the money I've given away. I think it's one of the most joyous things I've ever done. And also, it's really easy as far as things in life go that are hard on the scale of hard versus easy. Writing checks is not that hard. Really comes down to it. Like, the redistribution of wealth can be quite simple.
Yeah, it's really incredible. And I can imagine how it's shaped. It's just shaped so much. It actually set the foundation for the work you're doing and you've been doing ever since. And it gave you such a voice. And I just love the way you said how that aligned your life with your values.
And you make a really important point also in the book, that the more privilege we have, the less our lives depend on change. So, for example, some of your peers who had Money or all of these privileges, and myself included. You don't always. I didn't grow up with, like, a lot of inheritance or I didn't have a trust fund, nothing like that. I went to public schools, but still.
I remember in fourth grade in San Francisco, they started to teach us about racism. And I remember thinking, I didn't even know that was a thing. It just didn't occur to me. San Francisco is very diverse. I went to school with people of all ethnic backgrounds. Of course, even homosexuality is, like. You just see that everywhere. It just was no big deal. I couldn't fathom, even as a kid, why gay people couldn't get married. It's, like, didn't make sense. And I remember feeling perplexed. Why are they teaching us this in school? And it was only after reading your book that I realized I had the privilege of not having to think about racism. I didn't have to necessarily consider it because I maybe hadn't been affected by it in that way. And then, of course, I mean, my next school I went to in San Francisco, I got made fun of for being white. So, okay, good that they taught us in fourth grade. But it just only occurred to me later that it's a privilege when you don't have to think about this stuff. And therefore, we kind of have to do a little extra work to raise the awareness.
Yeah, well, I think that's such a good gauge, you know, if you're trying to make sense of what this concept of privilege even is, you know, and it isn't something that you've been thinking a lot about in your life just to try to zoom in, even on one day, and what you have to think about, like, what does it look like when you leave your door? You know, who do you encounter? What. How are people seeing you? What. How are they reacting to you when you go into the store to just, like, buy a cup of coffee? Like, how are you seen? How many times during the day is somebody, like, looking at you suspect suspiciously? Is somebody following you or harassing you on the street? Is somebody, like, reacting to your, like, good faith, like, communication with.
With some kind of, like.
Like, suspicion or distrust or a stereotype? Like. And I think because a lot of times, like, when people are trying to think about stuff that you haven't had to think about before, it feels bad, and it feels like people are making you do it even, you know, and it's like, why are you ma. You know, like, why are you making things so hard? Like, when everything was fine before, but it Was like, it was fine before for me.
Right.
I didn't have to think about that because I, like, went and bought my cup of coffee and they didn't call the cops, you know, like, because I, like, walked down the street and nobody bothered me, or I went into a store and nobody assumed I was shoplifting, or I went to the bank and had to, like, you know, ask for a mortgage. And they treated me with respect versus suspicion or, you know, or giving me some kind of predatory loan. Like, everything from, like the smallest actions to the biggest actions that really define your life and your opportunities, like privileges and, you know, the systems of oppression are determining each of those interactions, you know, the smallest to the largest. But the more privilege you have, the less you have to be aware of that.
You mentioned the resistance that some people feel when they're asked to even consider these things. Or we have more and more nuanced language that we're in society is being asked to use on all types of things. You talk about the Justifier archetype.
Can you explain that for listeners? Yeah.
We'Ve really tried. I was working on this book just to have a sense of humor because.
Not just because it's fun to laugh, but also because it's hard to get in and underneath the stuff you've been taught from before you even remember being taught it. And a lot of times laughing and being a little silly is a good way to actually get into those places in yourself and find out what's in there. And one thing that is a big part of a lot of people's training when you're growing up with class privilege is.
The justifiers. Basically, he's this judge who flies around with a magic scale and hypnotizes people into saying that things that clearly are not fair are fair. And that's really, I think, what entitlement looks like. Because if you weren't trained to think that, you know, like, for example, in my family story, we're talking about, like, the family stories and what gets left out, right, if the story is, my grandfather worked really hard, he pulled himself up by his bootstraps, he was really smart, and he likes grimped and saved, and he was able to build an empire.
So in that version of the story, right, it makes sense and it's even fair. Like, according to the Justifier and his hypnotizing scales, at least that, like, I should have more than other people. But once you see that, that's actually a construction, you know, and that goes back to what we were just talking about before that like, did my grandfather really work harder than everybody else? Like, that just can't be objectively true. You know, you've seen people working their ass off from all class backgrounds, like, is he smarter than everybody? El like, once you start to take that apart, like, there's no way that can be objectively true. Like, but were there other factors that played in, from luck to institutional access to all kinds of things that the, like, that the government provided? Because, like, he was in real estate there, like, when he was building things, or tax abatements, you know, the fact that, like, we are Jewish, but in that time period where he started to build his wealth, we started to have access to all kinds of privileges of whiteness. Because.
Because we're. Because, I mean, we weren't considered white as Jews when we first immigrated, but we are now as white Ashkenazi Jews. So, like, that changes everything.
And so once you see that, like, the justifier kind of, I think, loses his grasp a little. And you have to accept the fact that it isn't actually fair for some people to have everything and everybody else is struggling also. Like, do you really want to live in that world? I mean, unless you are like Charlie sheen in the 80s and Wall street, you know, and learning from Michael Douglas, like, you probably, if you Soul Search, don't want to live in a world that's just based on greed.
I think probably.
Yeah.
Yeah, good point.
One thing I think that was interesting that you mentioned before we hit record, and I hope it's okay to bring it up. But you said after you gave away, dissolved your trust at 24, your family was hesitant to keep giving you money.
Yes.
Say more about that.
Well, and I think that's a really. It feels like a really important part of my story to tell is that, like, unless you won the lottery, like, if you're coming from a wealthy family, like I am, it isn't just about this one trustee. Like, when I was younger, I really wanted to, like, give it all away and be done. And what I learned over time is that, you know, first of all, that I could never give away my class privilege. That that is just baked in. And second of all, it isn't just this, like, one clump of money and then you're done. And there's a lot of wealth I don't have access to. That's my family. And that they, you know, or that they had say over whether or not they were going to give me access to it, and that it was going to be a kind of a lifelong process of dealing with my own access and thinking about how to use that for social justice and also organizing other young people with wealth. Whether or not that was the thing I was most excited about, you know or the people I was most excited about hanging out. Because I think a lot of young people with wealth is like well the last people I want to be hanging out with her where the people I came from, you know. But I think the most powerful organizing does happen when you use the truth of who you are and go back to where you come from and you know, so that has been a big part of my life taking on that, that charge. But then I. So for a while like I wasn't getting money and then I started getting money again and I got have been giving away more money ever since, especially recently. So.
I helped co found the Trans justice funding project. So I have been able to give away a lot of money through that. And my basic lifelong commitment is to always give through activist led funds. Shohara foundation spent down and dissolved themselves so they don't exist anymore. But they were super amazing and badass for nine years. So all that money got given away. But now whenever I have access to wealth, my commitment is to redistribute it through activist like giving. Because it's really important to me to redistribute not just the wealth itself but the power over it and deciding where that money goes. I don't think it needs, I don't think it should be red. Who decides? I think people who are on the front lines who are doing the work.
Know best where that money needs to go. So it's my lifelong commitment to redistribute any the wealth I have access to to activist led funds. And I'm trying to aim for like a 90% lifetime average which obviously if you're getting big money is easier. So it's important to like you know, come up with realistic numbers I think and also take care of yourself.
I was going to ask D does 10% then go toward just your living making sure you have a baseline.
I do. When I was younger I also was very rigid about like well the money from my family I'll never, I never spend and this is the money I earn. And then I was like it's all just the same capitalism. Like I'm not like it's not like you can get off the grid of capitalism. So instead I shifted to just saying like let me do the work I believe in and the work I love. I love being a writing coach. I love helping people bring their work into the world. I have a sliding scale. So I, and I don't have to worry about if I don't bring in enough money because then I can supplement it from the money I get from my family. And then, you know, and I share that with my chosen family and then the rest I give away. And I, I'm up to, I think, wait, I wrote it down somewhere. I'm up to 13 million. Wow. Been moving a lot of cash lately.
I feel good about that. But I also, you know, just to keep it in perspective, like it's so easy. Like my side of it is easy. I just write a check. Like the hard part is the struggle that people are in every day to create a more just world. Like moving money. So easy.
I have so many questions.
What inspired you to co found the trans justice organization? And then you mentioned your commitment is giving to activist led organizations. And I'm curious as opposed to what.
I mean, most philanthropy is still controlled by rich people. And if you look at the history of.
The institution of philanthropy in the United States, it's created as a tax write off and for other benefits for people with wealth, the roots of it are not for any kind of social change. And before 1969, a private foundation didn't even have to make any distributions. And you only have to give away 5% of your principal and you can deduct from that 5% your operating expenses. So.
Philanthropy as an institution in the United States is not created as a mechanism for the redistribution of wealth in the way that say, like the estate tax. One of the things use philanthropy for is a way of avoiding the estate tax. So.
Most of the time giving is controlled by people with wealth or you know, by donors to organizations. Like that's the power. To say where the money goes is just as much or more powerful than having the money.
So for me, when I think about what does it mean to really redistribute wealth? It means redistributing power and it means putting that power.
In the hands of the people who are doing the work.
The other way I think about it too is any other business wouldn't run the way philanthropy runs. Let's say you had a company that made donuts, you certainly wouldn't put in management and upper level positions of that company people who'd never even eaten a donut. That would be stupid, right? Like why would you have people running a donut company who doesn't even know what a donut tastes like, never ate a donut, don't know anything about the history of Donuts haven't even like studied donuts. But that's basically how philanthropy works most of the time. You have a lot of people with wealth and privilege who have no experience.
With the, like, work that they're funding. And they couldn't have that experience that they tried, you know, like, yes, of course their hearts are in the right place and they, you know, let's say like they want to be supporting organizations run by people who are homeless and formerly homeless. Like, and they're doing that out of like their best heart. But if you're a person with a lot of privilege who's never had any of those experiences, why would you know best, where that money needs to go or how it should be spent? Because also, like, social justice is not a business. It is not about.
Great quote. Social justice is not a business.
I want to believe that it is. And there's a lot of venture philanthropy that thinks that it runs the same. But if you spend even 10 minutes studying the history of whatever movement you want in any country, you will see that it does not work like a business. That grassroots struggle is not about like, you know, like good management and like.
Budget, even like redefining failure, which you talk about that it's, it'd be wrong to just say.
That you can't even judge success and failure the same way.
Absolutely. Because also you're up against power. You're fighting the people with all the power as as opposed to trying to get somebody to like buy a product or build a business. Like, it doesn't look, you know, like just sit down and spend 10 minutes studying the history of the civil rights movement even, and ask yourself, does this book the same. Did they, did the wins happen because they followed best business practices? Of course not. You know any of those grassroots tactics, like non violent, like struggle, like that is not, you're not, I mean, I think we all know, like you're not going to sell Pepsi with nothing was learned from that horrible commercial.
That's not how it works. So the whole model is different. And I think if you can let go of that and let go of your power and say, I trust the people who have this lived experience. I trust the people who are spending every day of their life fighting this fight. Let me put the resources in their hands. Because also in the end, I think the other thing that freaks people out is they think it's the money that makes things happen, it's the money that makes it succeed, but it is not the money that makes real change happen.
It's not like that's another thing. Just spend 10 minutes looking at any movement history. Money, it is complicated, and a lot of times it comes with strings attached and compromises movements. So, sure, it helps. And I mean, money is a lubricant. You know, that's a gross word, but.
It'S funny how it became such a.
Gross word, but it really is that it's not what makes the change happen. So just give the money and get out of the way. That.
So many good bumper stickers.
Give the money and get out of the way. Boom.
Okay, I want to come back. I still want to hear about trans justice first, because on the subject of money and wealth, there, as you say in classified, there are also stigmas about talking about money and wealth and even privilege. And. And I can imagine that a lot of people listening to this podcast have the privilege of free time, have the privilege of whatever brought them here. And I even think about this sometimes. I'll be talking to my brother, who's this heterosexual white man. Well, and sometimes I see when people try to jump into these social justice conversations, I watch people get kind of, like, ripped apart. Like, what do you know? Or how can you talk about this? And I know you kind of address the wealth side of this, but it feels like it can be a little complicated for people who are coming from privilege. They might feel hesitant, even. I feel. Feel that where I'm like, I believe in a lot of these things, but I get very nervous to talk about them because.
I'm not. I don't know, I just. And of course, I don't think it helps anyone to have, like, hierarchies of privilege or hierarchies argues of disadvantage.
Absolutely not.
But yet you don't want to deny it at the same time. So that was a long, rambling question, but I would love to hear your thoughts.
Oh, great question.
How to use your voice if you're someone with wealth and privilege, which I also know is why you wrote classified.
I mean, I think one of the first things that just helps with all of that, like, kind of that cluster of everything you're talking about and not wanting to mess up and not wanting to, like, offend other people and not wanting to speak out of turn, like, is to give yourself some time to undo some of. I keep talking about, like, the training we get. Because a big part of training, if you are coming from class, privilege, is to be taught. You always know best. You know, like, you're the creme de la creme. Like, you should be in charge. You should jump in and Those are, like, skills that can really serve you, but they're also skills you want to be conscious of because.
They can make it impossible for you to listen and to also, like, step back and.
Share your power or redistribute your power. So, like, the first thing is, like, giving yourself some time and space, like, and to get in touch, like, with an organization like Resource Generation. This is part of their mission, is to help people with class privilege, like, support each other, to just deconstruct some of these things we've been taught so that, you know, in that, like, proverbial conversation you're imagining, right? Like, being able to just listen to somebody else, being able to hear, like, somebody else's life experiences, or being able to show up, like, you know, as a volunteer and not assume that you should be in charge or that you know best, you know, or that you know what the. What donuts taste like, you know, back to, like, to just kind of get to know yourself and know how to listen. Not in a way that's putting yourself down, not in a way that's saying, I don't know anything, but in a way that saying, like, okay, my life experience has taken me in a certain direction, and I don't know what other people's life experiences are. And I've been taught that I don't have to know. Which is really the big difference between having more privilege versus not having it is what you have to know. Because the less privilege you have, the more you have to understand all the people with power around you just to survive. So learning how to listen and also then, like, learning how to understand the world you came from. You don't. Like, you don't have to throw away everything you know about who you are instead. Like, that's, like, the part and classified about the fancy hood.
That's an exercise of just, like, thinking about, like, look at what's around you. Look at where you grew up, or if wealth is, like, new in your life, where you are now and how all the things that are surrounding you are traced back to institutions. Like, even the simplest thing, like, how is the, like, trash collected on your street? Like, what kind of stores are around you when you walk down the block? Like, what do you, you know, like, what public services do you have access to? What do you think about when you think about the police? Like, are they somebody who's there to protect you or not? You know, and so much that's not just about class privilege, right? That's also about whiteness and about, you know, gender identity. And sexual identity. So all of those things mix together and you may be in a complicated locus of different privilege and oppression. So you don't have to throw that away. You get to be the true of who you are. It's just about trying to understand that you're not just an individual, you are also. We're all were formed by these institutions and we're always subject to them. And so if they're lifting us up and giving us advantages or they're pushing us down or even trying to kill us, like being conscious of that is how I think you can start to then share your own experience and be in that conversation and to just, you know, tell the truth of your own life, that there's always room for telling the truth of your own life. You just need to understand how that truth was shaped by forces that are bigger than us all. Instead of going around saying like, I did this all on my own, because that's not. That's not really contributing to the larger project of us trying to make a more dangerous just world.
How. How did you become passionate about redistribution of wealth? I mean, because if you, you know, if you're born into a family that has a lot of wealth, is this something that you're. I can't. It doesn't sound like it's something your parents necessarily. Kind of sounds like you sprung up as your own unique flower in this environment.
How. What, like, was there a shaping event or just.
I definitely wasn't like a red diaper baby. I mean, I think I did get.
A red diaper baby.
Oh, that means you're like raised by communists.
I'm always jealous of people who come from those kind of families, but I think.
I think part of it is that I, I didn't want to be disconnected from other people in the world. And I think one of the most important.
Strategies for raising the next generation of an upper class is this goes back to like the justifier, right? It's like you can't feel like your fate is bound up with the fate of everybody else and also feel like it's justified that you have more significantly more than everyone else. You know, those two things don't go together.
So I think, you know, there's like a lot of the stereotypes of like poor little rich girl or like justifiabi, you know, like these sad, lonely rich kids, but.
Or super rich kids. Nothing but Fake friends, that Frank Ocean song. But there's a little bit of truth to those stereotypes. And I think that the truth in it is that when you're raising up this next generation of people with wealth and you want them to keep that class system going. You have to make sure that they don't feel connected to everybody else. Because the minute you feel connected to your neighbor, the minute you feel connected to, you know, the person who's struggling, who doesn't have what you have, I think it's pretty intuitive to say, like something's wrong, like, maybe I should share what I have with other people. I think that that's a very normal human reaction. You know, like, I'm not saying everybody would have it, but I think it's pretty normal and I think most people have it. Like if you're just eating a sandwich and the person next to you is starving, it's pretty normal to think, like, maybe I can share my sandwich with them. And that's all this, the redistribution of wealth is just saying everyone should have a sandwich, nobody should be hungry, like, nobody should be homeless. In fact, everybody should have access to these opportunities and to build the life that is full of love and joy and safety. Like the way that I had things, resources to do that, it's just about sharing that. So I think I just tapped into that and the ways that the institutions around me tried to make sure I was isolated from other people. I don't know, I guess it didn't take, you know.
Which we're so lucky. I'm so thankful that it didn't. I know we're coming up on time, but we'd just love to hear what inspired you to co found the Trans justice funding project that we've mentioned.
Oh, thank you. Yes, please again, Transist this funding project, they're saying you should check them out.
And tell us where to check them out and like, please make requests of us. Tell us about it and then where can we go? All of your many websites.
Okay, well, I think just to go back to one other thing you were saying before. If you're listening to me right now and you're like, that person is bullshit. I hate everything she's saying. She's some stupid bleeding heart liberal and it's making me angry.
I'll just say that like of all the people I've ever talked with about this work in my life, the people who, the only people who get angry and think I'm full of it are the people who have the most in common with me. So if you hate me right now, it's probably because we have a lot in common and, you know, whatever that means, you know, post that if you can or come back to it later. Like Classified's meant to be one of those books that like, you see it and you hate it and you put it under your bed, you don't want to look at it. It's the blue Stockings, the bookstore.
Oh, I love blue stockings. In the East, Lower east side.
They told me Classified was the most shoplifted book.
No way. That's so ironic. That's like weirdly ironic.
It's hard to think about this stuff. Everything, not just in the way we're raised tells us, you know, as people with privilege to not think about it, but everything about America tells you to not think about it. We're not a country that is about taking care of each other or thinking about how to share things. We are a country that's about individualism. So it's gonna feel weird, verging on wrong, verging on thinking that I am just gross and you are sorry you ever heard me. But.
So I would say that would be my one request. And second request is transjusticefundingproject.org it's a mouthful. If we had realized how much it was going to take off, I think we would have have at least gotten the acronym that it was not.
TJFP.org was not available. But the reason I did that was there just was no activist led.
Fund that was supporting trans justice work. So I just, I wanted to be giving money to that and so I had to help make it happen. But it's run by and for.
Trans justice activists every year we give away.
Last year was like a half a million dollars to trans justice groups across the United States. And I say we because I helped start it, but I am not, you know, as I was saying, like I'm not involved. Like I just give them money and get out of the way. I helped it get off the ground, but it's.
It'S all led by staffed and all the grant making decisions are made by trans justice activists from around the country who come together once a year and like review all the grant applications and move that money and do their best to get out of the way. Also, you know, just give the money to the groups. There's no requirements, there's no reporting. It's just about trusting and believing in translatorship. So I think that that like, to me that's like the core of what my values are. It's just like give the money, get out of the way. Trust and trust in trans leadership. Trust in social justice leadership. There's so much amazing, amazing work going on right now in this country around the world. It's so easy to just get behind it and support it with whatever you have access to and.
You know, and not. Not trying to control it.
Oh, so beautifully said, Karen. I can't thank you enough. I feel like in addition to all going out for donuts.
Hosting a virtual donut to this conversation.
Dangerous metaphor.
I know we've primed everybody now. Everyone's primed, like you're secretly gonna want to donut, but really, I hope that. I hope that we've primed the pump of curiosity. And I love your homework. I always like to ask for one. What's one thing you'd want listeners to do? And in addition to checking out these resources, I love the idea of just pay attention, look at one day a day in the life and see where privilege has come into play in very subtle ways. And do you have any other. Is there any other small homework you'd want to give or a small experiment?
I think I just add like one other tip to that homework, which is like.
It'S easy to take it to heart and think that this is about you personally. But like, the reason I keep saying the word institutions over and over is because once you can make that shift and understand that you're just, we're just little tiny drops, little cogs, nothing. It's not about anything you as a person did. Maybe you're the best person, maybe you're a jerk, but it doesn't matter. Like, that's not what this is about. What it's actually about is trying to understand these bigger institutions and systems that are around you that are shaping our lives and to see how they've shaped yours so that you can speak truth to power about that. And the clues to it are in your everyday life. The clues to it are as simple as just looking at, like, how many times is your garbage collected? You know, like, what does your street look like? Like, what are the street lamps all in good shape? Like, what are the post office boxes? Like, just go to the post office. What's it like at your post office and office? You know, and are you living in the neighborhood where there are all these kinds of services? Or. And also, like. Or are you trying to live in the cheapest neighborhood you could? Because maybe you have class, privilege, but you don't have access to the cash itself. So you might be living in a neighborhood where people around you are a lot poorer than you are.
Oh my gosh. We're gonna. We might have to do a whole follow up podcast on gentrification.
Because I think it's such a fascinating subject given that we can't really tell people where to move or where not to move, and yet it displaces people anyway. We could really go to town on that.
Conscious is the word. Being conscious about it is, is a first step. Because even knowing, like, let's say you don't have a choice, and you are like, someone who's gentrifying a neighborhood, like, and maybe your neighbors are having a party and you want to call the police because it's loud. Like, just learning about what's the history behind that, the history of behind you in that neighborhood and what your relationship is with the police versus what your neighbor's relationship might be with the police. And the fact that, like, you might be endangering someone's life, but you're not used to thinking about that because you came from a world where the police were there to protect you. So all of that stuff, like, it's in the most minute details of your life. Once you just start to pay attention and you stop taking it personally. That would be the main trick.
I would say it so good. Karen Fittleman, thank you for being you.
Honored to be here.
Everybody.
Classified is the book how to stop hiding your privilege and use it for social change. You can also check out resourcegeneration.org, transjusticefundingproject.org I like TGFP. It's cool.
Yeah.
And then Karen is on the web@writersremedy.com and has a band, which is so cool, we didn't even have time to talk about it. But are you the lead singer?
I am. And I write all the songs.
Go girl.
Karen and Sorrows. It's a clear country band.
Sorrows. What does it mean to be a queer country band?
I'm queer and I make country music. And, you know, so I'm not. I don't change the pronouns around. And I also put on shows for other people who are queer and make country music and just try to create a space for that, because a lot of people who love country music grew up or grew up with it, feel like there would never be a place where they can be their whole selves. And it's really fun to create that space for us all and to have the music that we love together and also get to, you know, just be ourselves. And I always say, like, everybody deserves a honky tonk angel so it doesn't have to be gender specific.
That's so beautiful. And. Okay, let me ask one final dumb question, but what does it mean to you to be queer? Because a lot of us also hear LGBTQ thrown around, but might not necessarily know. So how do you define it for yourself? And then I think it's so beautiful that you're bringing that to kind of country music.
Oh, thank you.
I guess I'm grateful for the word queer as it's evolved because I'm bi and so I've had relationships with men and women and I'm attracted to people all along the gender spectrum. I just kind of fall in love with people, not their gender identity.
And so for me, like, queer is a word that can hold all of that as opposed to saying, you know, like when it was more like, are you lesbian? Are you, you know, are you gay or are you bisexual? Like, I wanted a word that kind of held more sort of more like spectrum, my own experience with my sexuality.
So. So I guess it means that to me and it. But it also means just.
Trying to create a world where there's room for everybody's sexuality and everybody's gender, you know, instead of one where those things have to be rigidly codified. That's what queerness is for me.
Awesome. I know. I guess now we hear it like non binary or just this idea. So thank you for clarifying. And there's your final bumper sticker of the podcast. I fall in love with people, not their gender identity.
Thank you, Karen. Thanks for being here and I hope everybody listening, you got as much out of. I could talk to you all day and just get as much out of your work as I have. And I look forward to continuing the journey. So thank you again, Karen, so much.
Goodbye.
Thanks so much for listening to this episode of the Pivot podcast. Make sure you don't miss an episode or my insider tips and templates by signing up for Pivot List, a curated twice monthly newsletter where I share the inside scoop on what I'm reading, watching, listening to, and the latest tools I'm geeking out on. Sign up@pivotmethod.com pitch pivot list, get show notes from this episode@pivotmethod.com podcast and connect with me on Twitter ennyblake.
Remember, build first, then your courage will follow. Hasn't it always.
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