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This week, we got to chat with the inimitable writer Ashley C. Ford about gaining wealth after growing up without it, growing a following on social media, and the realities of having an incarcerated parent. Ashley gives her super honest thoughts about money, including the unfair realities present in the media industry and how much she really makes as a writer.

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Hello, everyone, and welcome back to another episode of The Financial Confessions.

I am Chelsea Fagan, and I am very, very excited to introduce you guys to our guest today, who is a guest that has been super highly requested by you guys, and someone I've wanted to get into the studio for a long time. But before I introduce you guys to her, I'd like to quickly give a hello to our beloved partners with whom we create every episode of The Financial Confessions.

As you guys probably know by now, we make every episode of The Financial Confessions in partnership with Intuit. And Intuit is basically a brand that helps bring all of the various tools that you will need to manage and optimize your financial life and put them right in your back pocket. So many of the things we have to do in order to get control over our financial lives and understand our money really come down to just having those right tools that make the process so much easier.

Intuit it makes things like Mint, QuickBooks, TurboTax, Turbo. All of those products that you may have heard of and probably used at some point that uncomplicate the financial tasks you have to get done. And it acts as sort of like a second brain to help make sure you're not forgetting things, and that you're doing them right.

I personally use Mint to handle all of my personal budgeting, and QuickBooks every day to manage TFD's finances. So if you cannot wait to learn more about all of the ways Intuit can help you do money better, check out the link in our description, or the show notes. So as I mentioned, our guest today is someone who has been highly requested by you guys, and someone that I've been so excited to get in the studio.

And that is writer, host, and woman about the internet, Ashley C. Ford. Hello, Chelsea.

Hello. Welcome, welcome. Thank you for having me.

Thank you for being here. So in addition to obviously the writing and hosting work that Ashley does that you guys might be familiar with, Ashley is someone that I've really wanted to have on the channel for a long time, because she is so good at talking about money. She's so honest about it, and so compassionate but still clearheaded and thoughtful, and has some righteous anger-- which I think we should all have when it comes to money.

But manages to do it in a way that I find very inspiring. And I know that you're also right now working on a project that is very much about money, that's about to launch. If you want to tell us about that.

I'm actually working on a podcast right now with MasterCard and Pineapple Street Media called Fortune Favors the Bold. I hosted the first season, and then Mona Chalabi hosted the second season, which was amazing. And now I'm coming into the third season as host and producer to essentially continue the conversation about how we identify ourselves with money.

And how identify ourselves or differentiate ourselves with how we spend our money, how we run our businesses, how we buy, what kind of work we decide to do, if that work works for us. Is it possible for everybody to find work that works for them? Questions like that that are things that run through my mind all the time, we're addressing them all on the podcast.

It's going to be a lot of fun. And yeah, it comes out January 16th, 2020. So exciting.

And we will link you guys to that in the description in the show notes. And also, if you are very interested in hearing Ashley talk about money IRL and you live in the upstate New York area, she will be with TFD on February 11th in Buffalo. We're going up there to do a really fun event where we talk about money and planning your decade.

And we're going to have some really great finger foods and wine and sodas and all kinds of stuff. So come hang out with us. Buffalo, February 11th.

That'll be also in the description and the show notes. So many of my favorite things happening. I know.

Pigs in blankets, wine, talking about money. A combo that cannot be beat. What else do you even need?

So as I mentioned, you are someone who talks about money in a very, very compelling way, in my opinion. And part of the reason I feel like you do that and you're comfortable with it and it's such a compelling topic for you, as we were just discussing before we turned the cameras on, you say about yourself that you grew up in poverty. A lot of people are not comfortable with that word.

What makes you comfortable with it? I think what makes me comfortable with the word poverty is I really like to tell the truth, and I really like to put things out the way they are. Because there shouldn't really be shame attached to having grown up in poverty.

It's not anything I could have controlled. You know what I mean? And it's strange I think that we attach shame to things that we have no control over.

And I think that's about not being able to tell the truth and not being able to talk about our feelings. And so I say poverty because that's what it was. I lived in poverty.

There is a spectrum of poverty. There is homelessness, which I've never experienced. There is not being able to eat-- hunger, starvation-- never experienced that.

But I did experience a lot of the things that cause a kind of trauma because you were not able to get what you needed. Not just what you wanted, and not the best version of the thing, but you weren't able to get what you needed when you needed it. I don't want to sugar coat having grown up in poverty, because then I'm not dealing with reality as I deal with the effects of that in my life right now.

If I act like it was something different when I was a kid, how do I deal with the reality of my life where the things that happened when I was a kid are still affecting me? I can't deny them. I have to be honest about them.

What was poverty like for you as a kid? What did it feel like? It took a long time to realize that not everybody lived the way I lived.

I grew up in an area that was already pretty impoverished. In Fort Wayne, Indiana. Fort Wayne, Indiana.

My school system, 75% of my school system was on free or reduced lunch. Which meant we were living in some form of poverty. You get reduced lunch, free lunch, that meant you weren't able to meet that cost.

And that cost was about, I believe, it was $0.90 for breakfast at full cost, and $1.10 a day for lunch at full cost. And we couldn't meet that need. But for the most part, growing up around family.

My mom has four sisters, and they all live in the same neighborhood. And then my grandma was down the street. And you're one of four.

And I'm one of four kids. I'm one of 17 of my grandmother's grandchildren. And we just all grew up around each other.

So it's one of those things where I'm quite often like, was it that we always had enough money to eat, or is it that when we didn't we just went to someone else's house and ate over there? I don't know what the truth is there. But I suspect it's closer to that version of things.

And did you feel like maybe because of that, because you were talking about before-- we started filming about how your experience of poverty was that you just really didn't want for things. That you almost trained yourself to not even think about the new clothes, the toys, the games, all of that. Do you think that part of that was because basically everyone around you was in the same situation?

I think that's part of it. Even though of my mom's sisters, we had aunts and uncles who were more financially stable than we were. And even though their kids lived in the same neighborhood as us and we saw them all the time, we also saw up close that their kids were having a very different life.

They were getting name brand cereal? They were getting name brand cereal, they were getting the toys at Christmas that we couldn't even allow ourselves to imagine. Their home, their backyard, going on vacation.

Vacation. Vacation. We were like, whoa.

And I come from the kind of family where people want to share. And so it's not that I never went on vacation, it's just that I went on vacation with my aunt's family. Do you know what I mean?

Things like that. And that's not a bad way to grow up. That's not a terrible way to grow up doing things with your family.

But I think that what poverty makes you feel is like you don't have options. And when you feel like you don't have options, how can you let yourself want things that are not an option for you? It's interesting, because I feel like with poverty, with people who grow up in poverty, it really goes one of two ways.

You're either that. You're either, it's so not part of my world that I won't even allow myself to think about it. And I feel like often those people end up hoarding money as adults if they have it, because it seems the idea of seeing that money, seeing your net worth or your checking account balance decrease by that much is brutally painful to you.

Because it's about fear, and it's about insecurity. But then on the other hand you have people-- and I definitely would put myself more into this category, having known financial instability-- that I coveted all the time. And I felt angry, and I felt embittered about it.

I felt like, why do I not have and they have? I was desperate for those things. And often, people who had that experience when they become adults, they will then spend very recklessly and just grab everything they can get a hold of.

Which was my experience, which was how I ruined my credit, went into debt, into default all that kind of stuff. Because I had no ability to differentiate between really wanting something and just being able to buy it. And that in and of itself was justification.

Just going to the freaking grocery store and being like, one of this, one of this, one of this. I used to, especially when I first became an adult, I would go to the grocery store and buy Gushers and shit because I was like, I can finally buy Gushers. And it's like, did my 25-year-old self in Williamsburg, Brooklyn really need a closet full of Gushers and name brand cereal?

No, but I could not get over that feeling of, I can have it, it's mine. Finally I can have it. I think the thing that some people have a hard time wrapping their head around is how many things we think of as inherent, or just the ability to make a good decision, that are actually practices.

Being able to discern between a strong desire and a need, and being able to find out that this thing you want might not be as good as you thought it would be when it shows up. Those are feelings that you practice over time. And you cultivate them.

And you cultivate them. And when you grow up in poverty, you don't get the opportunity to practice that feeling. You don't get the opportunity to practice really a whole lot of self-discipline.

Because how do you learn self-discipline when those things aren't for you anyway? I remember growing up and reading books about kids and money and finance. And it would say stuff like, well if you save $2 from your allowance every week, eventually you'll be able to get this thing.

And everybody at my school was like, allowance? Allowance? Yeah.

Like, excuse me? Or they would like, if you saved your birthday money-- birthday money? Am I supposed to get money for my birthday?

When your grandparents send you a card with money in it. And I was like, where does this happen? That idea was so different for me.

People talk, about talk to your kids about money now, help them budget now. How do parents who don't have enough to budget teach their kids how to budget? Well they have to do it completely hypothetically.

But to your point, you don't get that visceral experience of deciding between things. You don't. Which I can totally see how as a child-- I got my first real job-- as in not babysitting neighborhood kids-- when I was 14.

I was working at an ice cream shop. Because that was the time I could legally do it. So from the time I was 14 to the time I was 18-- my 18th birthday-- I was always working.

I worked- full-time during the summer and part time during school year. And my parents made me put 75% of my paychecks into a savings account, and I got to keep 25% and do whatever I wanted to do with it. And obviously I was frivolous about that 25%, because what teenager wouldn't be?

But I'll never forget the day of my 18th birthday when I got control of that checking account-- savings account. I went to the bank, I took all of it out, and I spent all of it within a matter of weeks. And it was probably-- I can't remember exactly how much he was-- but I think I was like $12,000.

Wow. Yeah. It was drained.

It was completely drained. It's funny, because my parents were furious at me, which I would be too if that were my child. They were absolutely furious at me.

They were disgusted with me, and I think rightfully so. Because that money was spent in the most frivolous, stupid, inexcusable ways. But looking back, I have empathy for myself, because I feel like I-- and I'm not saying this was rational.

Because to your earlier point, there are many people who grew up in way worse circumstances than I did. And as you mentioned earlier, I think before we were talking, that poverty is not a competition. And so I never want to make it sound like I was in such a bad situation, because I wasn't.

But I definitely got from my experience growing up, a feeling. An almost frantic sort of furtive relationship around money that was out of my control. And I look back and I say, someone who would have done that on her 18th birthday-- yes, it's immature, yes, impulsive-- but it's also mentally unwell.

That is someone who has a completely unwell relationship to money, and who has no idea what to do with it, and can only experience it as temporary serotonin hits. My parents were totally right to be extremely upset with me. They have every right.

But I also feel, like looking, back I forgive myself for having done that. And I at the very least, even if I still say that was a terrible thing to do, I understand why I did it. And in understanding why I did it, I can start to say as an adult, you now do have those choices to make.

And it's up to you to say, is this thing a meaningful purchase for my life, or am I just thrilled at the ability to purchase it? Which often feel the same on first blush. They absolutely feel the same.

And I think that that's where a certain kind of privilege comes in. And I think that while privilege works in hierarchies-- these people have this much privilege, these people have this much privilege-- but everybody got a little bit. You know what I mean?

The biggest privilege is the privilege of a second chance. Oh absolutely. That is the biggest privilege.

And I think that's something that people who have never dealt with a certain kind of financial instability, that's what they really don't understand. Is that it's not about whether or not people make mistakes, because everybody makes mistakes. Everybody's going to make mistakes, everybody has made mistakes.

The people who are telling you, don't do this. The people who are telling you that when you were five and six and 10 and drilling that into your head before you were out on your own, are usually telling you that because they made their own mistakes. The difference between those people and someone who has to sleep outside, in a lot of cases, is the privilege of a second chance.

Absolutely. The ability to have your mistakes be lessons and not punishments. And being able to learn from a mistake is such a privilege.

And I definitely had that privilege. I was living with my parents when I spent that money. So even though I felt the pain of it in superficial ways, I wasn't on the street because of it.

So I'm very cognizant that a lot of people don't have that privilege. But it's interesting, because we were talking earlier before filming, about how the way we sometimes talk about our upbringings will upset our parents. My mother, even a couple of weeks ago, she was at my house and she was crying.

And she was like, I hear you talking sometimes about how you wanted for this, or you felt insecure or upset about that. And it breaks my heart as I always felt like we had enough . And it's heartbreaking because we did have enough.

I was never hungry, I was never worried about, would we have a place to live tomorrow. And we owned a house in a very not ritzy neighborhood of Charlotte, North Carolina, but we owned a house. And for them, that felt like that was such an achievement, and that was such a thing to be proud of.

And they did raise two daughters, and they did make it, and they have ascended in class strata now. But I always tell her, I'm like, you're right, but so am I. We can both have an experience and a relationship to this.

And to be honest about what that felt like is in no way an attempt to denigrate what you did, because I'm so proud of what you did. But it also is something that I don't think it's fair that you guys had to live the way that you had to live. I want better for you, and I want better for that 30 year ago version of you.

Yes. This is what it's so hard sometimes to get across to my mother. Now my dad is a completely other story.

My dad is pretty much like, yeah, you're right. My dad is very much like, you own your feelings. Yep.

Because my dad messed up in a major, major way. Life defining. How so?

My dad went to prison when I was around six months old. And he did not get out until about a month before I turned 30. I remember reading a lot about your experience with having an incarcerated parent.

And I do want to talk about the financial realities of that. But I am curious what you have a hard time explaining to your mother. I have a really hard time explaining to her that I feel like what she did was miraculous.

My mom raised four kids by herself. No consistent help, never a dual income in our home ever. She raised four kids by herself.

She worked constantly. Like really as much as she could. My mom took all available overtime, everything.

What did she do for work? My mom worked at the sheriff's department in our county. She was essentially like a guard at the jail.

My mom's terrifying. She is. She's the best.

You'd meet her and you'd be like, oh, she's really sweet and charming. Also I would never mess with her in my life. I don't know what it is about my mom, she's just got this terrifying thing.

And she was a perfect-- That's aspirational. --county jail guard. Because everybody loved her and/or was scared of her. But I think what she did was miraculous.

It does not change the fact that she never had enough. And not even that she never had enough in terms of money, but also she never had enough in terms of options. It's not just about what you were able to do, it's about what was available to you.

That's the tragedy. That's the part that's a tragedy. Because there's nothing more she really could have done in terms of work and providing.

Really. There was nothing more she could have done. I can't imagine what my mother's options would have been.

Go back to school? How? That costs money.

That costs money. That costs money. It takes away money, and it takes away time.

Which is money. Exactly. Her options were so few, and so much of that didn't have anything to do with what she chose.

It had so much to do with the circumstances of her life. And I think she wanted to erase that for me, or she wanted it to not be a factor for me by denying it in herself. Which of course doesn't work.

And so now that I'm talking about these things and I'm having this conversation publicly, a big part of my tension with my mom around that is her still holding on to this image, and wanting to have this image more than she wants to heal what happened in reality. And it's hard for me because I'm like, I just want you to be here in reality with me. I want you to come over here to reality with me, not because you're saying these things didn't happen, but because you are really attached to the idea that it doesn't count that we lived in poverty if it never looked to other people outside our home like we were living in poverty.

Absolutely. And also, I feel like our parents' generation is one in which your net worth, your income is completely and inextricably linked with your value, how hard you work, your character, all of these things. Which I think our generation is becoming more lucid about the fact is not true and could not possibly be true.

When we all basically came into the professional world and into our college educations in the middle of the biggest recession since the Great Depression. So for us, that illusion has been shattered since the beginning. That illusion that the number on your paycheck is one to one correlated with how hard you work or how worthy you are.

We know that's bullshit. We know it. And we feel empowered to say it.

We know that if you are drowning in debt for the education that every adult told you was your only ticket to success, that you don't have to be ashamed of that. That that's not your fault. But I feel like our parents, they don't feel entitled to that.

That's not part of their discourse, that's not in their ether. They were raised in that completely opposite world view. And in some ways, the world that they grew up in was more of a meritocracy.

It certainly wasn't perfect, and it still was not a one to one ratio by any means, but it was closer to that. So I do feel like I differ with my parents politically on a lot of things. I'm way further left than they are, and only getting more so every day.

So this whole like as you get older, you get more conservative thing, as we discuss, the clock's ticking, baby. That's not happening. Yeah, that's not happening to me.

It's not. But part of what I want so badly for all of the people of our parents' generation-- like, god, wouldn't the world be a better place if all the boomers felt this way-- was to understand that you should not be ashamed that you didn't have enough. You should be angry that you live in a country where you could work a full-time job-- two people could work full-time jobs-- and still not have enough.

And look at the wealth around us, and look at all that we could have. And so my feeling is always looking back, I never once ever have a feeling of, you guys didn't do enough by me. You didn't do right by me.

All of that. Never. It's quite the opposite.

It's like, this is ludicrous. My mother's a public school teacher. I know what she gets paid and I'm like, that is ludicrous.

You work way harder than me, you deserve way more than I do. Your job is much more important to society. This is all arbitrary.

This is all arbitrary. So I feel like for a lot of our viewers and our listeners, a big issue is crossing that generational divide around issues of money, particularly I think for families who-- we've had other people on the show who support their parents financially, or have to help them. Yeah.

That's me. And I'm lucky to not be in that position, but you never know. A parent can become ill.

I don't know where they are in their retirement yet, but something could happen where they have no choice, and they have to move in with us, or we have to help them, what have you. And that is automatically, I think, a position. And it's kind of inevitable that most of us will be in some form of that position eventually.

And it's not just, I feel for our generations, an issue of the younger taking care of the older, which is in and of itself often an issue of shame and pride. But it's also that understanding of maybe them not believing on some level that we don't think less of them, or that we're not embarrassed of them, or angry at them, or ashamed of them. Listen.

Like a year ago, my mom, I think there was something going on. My mom has retired now, and she has a medical issue as well that has kept her from working for a little while. But she worked at the county for so long that she was able to retire and still get something for that.

She was able to get something from her disability. Great, fine. But every once in a while things happen.

She needs a little bit more than that, she needs something extra that would just help. It's not a big deal with me. I'm totally OK with that.

The only thing I've ever promised my mom is that I will not make myself broke to help you, because two broke people can't help each other. And that's it. But if I can help, I do.

And my mom called me once asking for something that, to be perfectly honest now-- maybe a few years ago, maybe five years ago-- I would have been like, oh, I don't know if I got that. But now is very much like, yeah, that's not a problem. I can do that.

Which changes, and that's another weird thing about class transition. But I was able to help her. And I told her, yeah, mom, no problem.

I'll send that. So look out for it. And then she just started crying.

She just started bawl-- and I was like, I'm sending? What's the problem? I don't know what's going on.

And she just said, I don't want you to be ashamed of me. I don't want you to be embarrassed of me. And she name checked my husband's parents and was like, I know that they don't have to ask for this.

I know that they don't have to do this. I know that you guys don't have to worry about them. Which, to be honest, I love my mother-in-law, but probably some stuff she said to my mom.

My mother-in-law just talks about money a lot. She is a person who loves to talk about money, she loves talking about her 401(k), she wants to talk to everybody about retirement and their accounts and everything. And the stock market do this.

Are you paying attention? That's just kind of person she is. My mom is the kind of person who would never ever talk about money like that with anybody.

But my mother-in-law also just talks about things. So I could see her being like, oh yeah, well we have this in our 401(k), and we're doing this. Ashley said that you're retired.

How's that going? Have you found some passive income? Blah, blah, blah, blah.

And my mom would be like-- She should be a personal finance blogger. She really should. That's the energy.

Not kidding. She has that energy hard. Like, hard.

And my mom I could see just being like-- and I don't know that my mother-in-law actually said something to her. And she wouldn't mind me saying this. But I know that something got in her head, and it became this much bigger thing than it was.

And she worries so much about me talking about having a hard past, or growing up hard, or in poverty, or whatever is part of me saying, I'm not ashamed of this. This is just the way it was, this is how I grew up. But it's always like, you're embarrassed about your childhood.

You are ashamed of me. And I'm like, how could I be ashamed of you? For me that's so outside of my purview, outside of my perception, that I look at her like, are you losing it?

What's going on? But that's how that generation has been taught to perceive all of these things. And it's like, let's be clear mom and dad, you guys are much better and more equipped and more stable human beings than I will ever have to be because I already have infinitely more privilege than you ever had access to.

So clearly my life is going to be like Candy Land, and yours is like Chutes and Ladders basically. So nothing but respect. It's interesting, my husband's family, it's so funny.

The one loophole to all of this, which is that every single member of my father's-- or my husband's family. Yikes. What was that slip?

Yikes. Every single member of my husband's family, they do jobs that existed 2,000 years ago. They're all farmers, hunters, doctors, accountants.

And they're sales people, but traveling door to door sales people. They all have these jobs that are incredibly rooted in the human civilization experience. It's so funny.

So they're middle class. Doctors over there are middle class. They're not super wealthy or anything, but they've always been stable.

They have land, they have their vines, they have their animals, they have their livestock. So they have this sense of, "wealth," quote unquote, that is completely untethered to any of these notions. And in fact, often look at us like, you frivolous little snots with your fake made up jobs and your fake made up towers over there in New York City.

And it's funny, because I feel like unless boomers are literally farmers or have some kind of job that measures value totally outside of your income and has a very deeply rooted community oriented sense of value, they are all raised on that pure uncut capitalist meritocracy myth that I don't know if they'll ever be able to escape. Yeah, it's hard when you don't know any different. I didn't realize until I was in college that you could grow up in places where you just didn't know that these other lives were more ubiquitous than they are in your community.

I didn't grow up around any kind of wealth, so I didn't really know what-- when I was growing up, I thought wealth was-- I had a friend who, whenever I went to her house, they always had fresh fruit in their refrigerator. And to me, that was wealth. Oh yeah.

That shit goes bad fast. Right? So I was like, you can just always have fresh fruit in your house?

What are you talking about? For me that was wealth. The fruit bowl-- The fruit bowl. --that looks like out of a still life from [INAUDIBLE]..

And it's like, but you could eat it? This isn't for decoration? Oh yeah, the plastic fruit.

This is because people are coming over? Yes. The '90s was an era of-- do you ever have the plastic grapes?

Everywhere. What was that? Everywhere.

Me and my brother were so gross. My grandma had this fake vine thing that went up her stairway with fake grapes and stuff on it. Oh my god.

Me and my brother used to take them off because they were so easy to take off. They literally popped off the little thing. And we would just walk around chewing on it in our mouth, just being like, yeah.

And my grandma would be like, what is that? And we'd be like, huh? And she would be look like, what?

These are plastic. And we would be like, they're kind of fun. We had plastic grapes, we had plastic apples.

We also had-- I grew up on Long Island, and I don't know if this is just a Long Island by the beach thing-- bowls of shells that we didn't collect but purchased. You got to go to Michael's-- Bowls of shells-- --and get your-- --that you bought. That you bought.

My grandma was the queen of that. We would go to Value City, and the shells-- Value City. The shells would come in a little plastic bag, and the bowl would be sold separately [INAUDIBLE]..

And so the bowl would be $4.99, but you could get a bag of shells for like $1. And it's like, oh, I'll just get these shells and put this shit in here. I was like, I've never been on a beach-- Yeah, we had conch shells.

And people would always be like, oh my gosh, from Jamaica. And we'd be like, we've never left the state. [LAUGHTER] From the tropical shores of Long Island. Right?

When I was a kid, the vacation spot for us was Gatlinburg, Pigeon Forge, Tennessee, and going to Dollywood. Oh my god. That was our shit, because my aunt could get free tickets for some reason.

And so we get free tickets, and my aunt would rent a cabin and her kids and stuff. And you wake up and there'd be a bear in the backyard. You'd be like [SCREAMING] and go back inside.

And then you go to Dollywood. And you'd go places, because Pigeon Forge, Gatlinburg their tourist stuff is just, lots a hillbilly shit round here, y'all. Come in here and eat alligator.

And we'd be like, yeah. And then we'd do go karts. And you'd go feed some bears with apples.

And then you'd just be out in the fucking country and thinking, this is the best thing I've ever done in my entire life. Eating alligator nuggets was a big thing. It was huge.

I don't know why I was in Charlotte. There were no alligators in Charlotte. Yeah, that's what I was thinking.

I was like, there are no alligators-- There was a place called RJ Gators where my parents would take me, and you can get gator nuggets. They're good. They kind of taste like-- They taste like chicken --like catfish a little bit.

Similar. Chickeny texture, but a little seafood essence. Also, last note, but this is a real heinous '90s fruit decor deep cut, but did any of you guys have-- I just remember it being like a fake pear, but it was covered in this crystal shit.

What was that? It was like the fake sugar crystal classic fruit. Yeah, and it would be covered in it.

And it felt hard like a crystal. And I remember that I would just put it in a sun beam and spin it, and pretend it was like a disco ball or something. I don't know.

But I was always confused by it. I definitely licked it at one point. I had to know if it was sugar.

And the place I worked in high school was the place that sold all that shit. It was called Kirkland's. And all my friends called it the random shit store.

Like a Marshall's? Yes. You could come in and buy a chair or an oil painting or some cookies that had been by the register for months.

My husband still refers to himself as a Maxxinista, because he loves getting discounts. I am a Maxxinista. I buy, I would say, 90% of my clothes are either from a TJ Maxx, Marshalls, or an outlet store.

Because that is something I very much kept from my youth. Also, Macy's. Macy's has the best effing sales, especially at the Herald Square one.

It's crazy. They do. I got my winter coat this year for 80% off through a combination of coupons and sales.

That Macy's at Herald Square is just so good. It's so good. And if you go on the right day, in the middle of the day, there's nobody [INAUDIBLE].

Hot tip I feel for everyone listening. If you have access to a Macy's, Estee Lauder is the best makeup thing I've ever found. Where you buy literally one $20 dollar lip gloss, and they will give you $200 worth of free products every single time.

And when you ask for samples, the lady at the Herald Square one, she literally fills up a proper sized tube. I got like six months worth of foundation off a sample. That is wild.

Old lady makeup is really where it's at. They're really giving all the good deals away. So on a similar note, if you're someone who is always budgeting for a good sale, you're going to need the right tool to do it.

And if you are someone who has been looking to get your budgeting much more on track, I cannot recommend enough more than Mint. Mint is actually the very first app I ever downloaded to get good with my money. And I did that almost a full year before I even started blogging on TFD.

Before TFD even existed, before I registered the domain name. I used Mint and hooked it up to all of my cards and my bank accounts to start to get a picture of my money. Because before that I was extremely avoidant and felt really overwhelmed at the idea even understanding my money.

And what Mint does is basically synthesize all of the different parts of your money life and put them together in a way that's easy to visualize and understand. It helps you track your spending, get to know your habits better, reach your goals, and just generally get a bird's eye view of your finances every single day. I loved Mint so much that I actually wrote about it in the TFD book way before I ever even got in touch with Intuit.

So it certainly wasn't some kind of paid plug or anything. And I still use it and still love it to this day. So if you want to get started with Mint, I highly recommend you check out the link in our description or our show notes.

So we mentioned this earlier, Ashley, but you have written a lot about the fact that your father was incarcerated for most of your life. And I'm sure obviously that's got to have a huge emotional and mental and familial burden. But I'm also interested specifically in hearing about what that's like financially.

Because I know it's got to be among the most exploitative and financially predatory systems out there. And has a huge impact on families and loved ones of incarcerated people. Was that something that you were aware of growing up?

Was that a cost that really factored into your lives? Absolutely. I think the barrier of the cost was very evident in our lives in a number of ways.

Like I said, I was six months old when my dad went to prison. And he and my mom were married. And he went to prison.

And he had been in prison for maybe a couple weeks or something like that when my mom realized she was pregnant with my brother. So very quickly my mom went from being a married woman with one child to having her husband be in prison and being alone with two children. And I don't know if people know this.

I think a lot of people know that you can get a job in prison, but I don't think they know that there is no regulation for wages of a prison worker. So at different points my dad was working and trying to work to send money back to my mom for whatever. But he was making $0.25 an hour working inside of the prison.

And I know that growing up my mom made a conscious effort not to disparage our dad to us. She never said mean things about our dad, and she never was like, your dad's dead. And if he wasn't, blah, blah, blah, whatever.

But my mom at times would get angry. And one of the things she would say was, nobody's helping me. I have no help.

Your dad loves you, but he can't help me. And there was always this idea that if my dad got a present, or if he came home, or if he had been around, our lives would be so much different, just because of whatever income he could bring into our home would have been helpful. On top of that, before my dad got out of prison, I have three memories of seeing him in person.

I don't have any memories of being really around my dad in any way, any consistent or significant way, because we just couldn't afford to go. How far away was it? It depends, because they get moved around.

At any given time, as I remember it, he was anywhere from two and six hours away, depending. But prisons are, as we know, often in the middle of nowhere. There aren't hotels, there aren't things like that.

There isn't much to do with kids or anything around there. If you go to the prison, you have to have the gas to go. You have to be able to wait in a waiting room for quite a bit of time, because you never know how long it's going to take.

And you run the risk that even if you wait in that waiting room for two hours, three hours, four hours, there's still a pretty good chance you're not going to get to see the person just because they're going to say, sorry, ran out of time. So, you can't. And so now you have to drive several hours back from wherever you came without even having the interaction.

So you think, OK, maybe they're younger. You stick to phone calls. Phone calls are not just phone calls from prison.

You have to pay to communicate with the person who's in prison, which means you have to pay for phone calls as well. There's no such thing as a free phone call when it's coming into or out of prison for an inmate. You have to pay for those.

Even now, one of the things that they're starting to do with prisoners that I'm very, very, very much against is they're trying to get rid of in-person visits altogether, and essentially have them communicate via iPads or iPad video. And you have to pay for the minutes to be able to see them and have that conversation with them. You have to pay right now, in most jails, to be able to communicate via email.

It's an account. If you don't write physical letters, or if you can't write physical letters for some reason, you actually have to download an app that you put money on for coins so that you can send each other messages. And that costs quite a bit of money as well.

And so the human connection that is required for healing and for the maintaining of families is not allowed unless it can be profited from by the system at this point. That is horrifying. Out of curiosity-- and please, feel free to not answer-- are your parents still together?

No. Do they see each other? Yeah, they're friends.

Oh, that's good. My mom and dad, it's really weird, because my dad got out of prison, and I went to go see him and I wanted my mom with me. Which I don't usually go to my mom for comfort.

But it must have been so anxiety-- Yeah. But I was like, mom, you have to come with me. And she was like, OK.

And she came with me. And it was their first time seeing each other in 20 years at least. And it was my first time seeing him in about five years.

And he didn't know I was going to be there. And so he definitely didn't know she was going to be there. And he walked into the room at my aunt's house, and he hugged me.

You know black folks. My aunt starts screaming and yelling, thank you, Jesus. Whatever.

And I'm just like, OK. But it's also really lovely, and it's this amazing moment. And then he sees my mom, and they immediately start just joking with each other.

And have this weird rapport where he's like, hey girl, whatever. She's like, oh I see you, blah, blah, blah. And he's like, yeah, well you ain't da, da, da.

And I'm like-- because for me in that moment, that's my first memory of seeing my parents talk to each other. Oh my god. I don't have another memory of my parents speaking directly to each other face to face.

That is unbelievable. That is unbelievable. My mom helped my dad.

As soon as he got out, she helped him get places, get things that he needed. Her ex-husband, my stepdad Donald, he took my dad to his first job interview. You know what I mean?

Like I said, everybody comes together. Everybody is going to help you get up, everybody is going to help lift you. People want to see you rise, they want to see you get your stuff together.

And I think it comes from that understanding of how little we're all dealing with in that situation. Right. And so many formerly incarcerated people don't even have that.

So many don't have that. I don't even know one. My dad said he came out really prepared to start his life over with nothing and no one, because there was just the chance that nobody would want-- Anything to do with him. --anything to do with him.

And instead he was welcomed into his sister's home. His brother came and picked him up. His brother took him to go see his parole officer immediately.

His brother, my Uncle Clarence, brought him to me. You know what I mean? I was there.

I was able to help my dad with a few things. He flipped out because I took him to a store, and I was like, well, you got to get clothes. You don't have any clothes.

Or what you have is fine, but that's not enough clothes. So let's just get you some shirts and some jeans and stuff like that. Makeover.

It was nothing. And he was like-- because he hadn't been in a store in 30 years. My dad didn't know what a cell phone was.

My laptop freaked him out. He didn't know how to pump gas. There was just nothing.

When my dad went to prison, Reagan was president. Like people don't understand. And it is the strangest, most wonderful thing in the world to have him able to be a real part of my life.

But I'm telling you, Chelsea, I will never forget that moment of seeing him and my mom just talking with each other like friends. I will never, ever forget that moment. And it's priceless.

That is a priceless moment. And I just think that that is harder to come by in groups where people have not lived a certain kind of struggle, and they don't know a certain kind of struggle. I think part of why my mom was able to just be like, hey, was because she understood nothing's been easy for either of us.

And when things aren't easy for people, you can sit around being mad about why they weren't easy and whose fault it was, or you can get to work trying to heal, trying to fix something. And I think that's what she chose. Well, first of all, hats off to your mother.

Hats off to that whole-- that's unbelievable. But I'm curious, hearing this story, which is obviously an overwhelming one, someone who follows you on social media and maybe doesn't know a lot about you, you have a very glamorous life in a lot of ways. You write magazine cover stories, and you fly out to interview celebrities, and you have these high paying jobs at prestigious glossy publications.

And you live a life that I think you're on a fucking billboard in your underwear, if I recall correctly. I am, I am an underwear model. Oh my god, that's a whole other story.

But all of that to say you live the life of someone that I think people would consider to be incredibly aspirational and incredibly unrelatable in some ways. And that's true. You do live that life now.

You can't deny that that's your life. But at the same time, I can only imagine that it must cause some enormous dissonance or tension with not only all of these experiences and what you came from, but also the life that so many people around you are still living. And I'm wondering, how does that feel?

How do you deal with it? Therapy. Hell yeah.

Therapy. Well first of all, let me say, being an underwear model was amazing. I'll never forget it.

On a billboard. It's one thing to be an underwear model on the internet, but you're on an effing billboard in Williamsburg, Brooklyn, if I recall. Chelsea, it's always the pretty girls who can't imagine getting up on the billboard.

But y'all might as well do it. I'm just saying. You might as well do it.

It's rough for me. The transition from not enough to enough is already pretty rough, but the transition from not enough to abundance is rough. Because like I said, everything is a skill.

Everything we learn is a skill, including things that we want to think that you could just be good at or you could just decide to be good at. Like long-term planning. Long-term planning is a skill that develops in certain kind of life circumstances.

Which means stability. The ability to plan. The ability to plan.

I have not always had that ability. So many of these things that other people look at and are like, this is a big thing, it's a glossy thing-- and it is-- are things that feel like they happened to me more than I made them happen. Which is not fair to me.

But it's where my mind goes. It is really, really hard to know what it feels like to do tough manual labor, or to do real grudge work. And to know how soul stealing that can be, how physically exhausting that can be, how scary sometimes those situations can be.

And then think about the hours that I spend at a computer being in my brain, drinking some nice tea somebody got me in my apartment in New York with my dog and my husband. And not feel like, why am I getting paid this much money to do this one thing? When this much money 10 years ago wouldn't for me have been like, oh, I'm doing an assignment and I made this much money.

It would have been like, this money just changed my life. This money just shifted everything for me. And now I'm getting those amounts.

And it's not that they don't shift things, honey. They shift. But it's not world changing the way it used to be.

I resist quite often the compulsion to explain to people when they are offering me a certain amount of money that they could have offered me a lot less. Do you know what I mean? There is part of me that goes, you're going to pay me what for what?

No, I'll do it for this much. You almost want to do that because it is so unfamiliar and it feels so weirdly wrong. Yeah.

Also, you realize what people paid you when you had nothing. It was like, when I had no money, squeezing $25 out of a publication for an article was the hardest thing I ever did. And was embarrassing and felt like shit.

And now I'll have publications being like, would you like to write this 500 word essay about women's empowerment for $3,000? And I'm like, no I would not like to do that, because what is wrong with this world? And you feel like you want to just shake things and be like, there's something really wrong here.

And you had mentioned earlier that you had a job at one point where you knew that you were earning like three times more than a lot of the people around you. And you were like, that was the worst feeling. I had to get out of there.

I had to leave. I had to leave. Because I was working at a place that purported to be very invested in women's pay parity, and inequality, and in making sure that women had the financial means to do what they needed to do in this life and to live.

And so I don't know how you purport to have those values and you pay with this kind of disparity. And it's hard for me, because in some of those cases-- look, I know that I'm a good writer. I don't have a problem with that.

I don't have any sort of stuff about that where I'm like, what if I'm a terrible writer? No, I'm good. I can do it.

You know what I mean? I can do it. I'm not the best writer, I'm not the greatest writer.

I love learning, I love working on it. I'm pretty good. I am not so much better than the people I'm working amongst that I should be making three times more than them.

And it's hard for me, because on the one hand, I know that part of the reason why I get paid as much as I do in a lot of these circumstances is because I advocate for myself, because I ask for more. But on the other hand, I am very aware that I have this social following, and that that social following, for some people, makes them feel like I should be paid more in this circumstance. Listen.

If you come to my work via a social following, if you want to work with me because of something that you saw that I posted, great. But if you only want to work with me because of the number that's there, you're probably not going to have a good time. Because I'm not a person who's going to be constantly online being like, hey guys, come to this.

Hey guys, come to this. Hey guys, come to this. And it's not because there's anything wrong with that, it's because that's not my job.

That's just not what I do for work. You're not a brand ambassador. No.

So it's like, yeah, the audience is there. But there's no guarantee that they're going to-- you know? That's not my relationship with my followers and my friends and my family and my fans.

That's not my relationship with people like that. And it's not because I don't want them to support the things that I do, it's just because that's not my job. You're not an influencer.

I'm not. I am not an influencer the way I think most people think of an influencer. Do I have some influence?

Probably. I think there are some people who are really looking at me. And when I say something, they take it a lot more seriously because I said it.

I don't know how I feel about that, but I do think that's the case. That is not work that I do in any consistent or even regular way. And it's because I don't necessarily enjoy it.

And I'm just at a point in my life where if I can afford not to do something that I don't enjoy, then I don't do it. But that's hard to come to. It's rough.

Yeah. One last tiny note on that. It's one of my biggest pet peeves.

I see this all the time on Twitter. People who talk about writing. They're like, how hard writing is.

They're like, the work of writing, the work putting pen to paper. It's so hard. I'm like, really?

Because I feel like the person who prepared your meal at a fast food restaurant probably has a harder job. I feel like if you get to do any job sitting in an air conditioned room sipping a cup of coffee, working on your computer and playing on the internet at the same time-- Listen. Because look, I'm not going to say that writing, that I sit down and it just happens.

But I will say that I worked in a call center-- and that was probably way harder. --for like a month. That job was so draining and so depressing. I used to come home after work and just get into bed with all my clothes on.

And lay there and just try to feel like I'm in my body again or something. Because I just had to black out the whole time I was at work in order to even survive. You know what I mean?

Oh yeah. That is something else. Being a writer, take it seriously, but also understand that you're just telling some stories.

And also, you get treated by society with a certain degree of respect-- You absolutely do. --to which most people are not entitled. You absolutely do, even when you're poor. Even when you're poor.

Even when you're poor as a writer. You might be a poor writer, you might not be able to get enough money. And I feel that especially in this media industry.

But I tell you this, when you tell people you're a writer and you're poor, they at least think you're smart. They at least think you're smart. When you talk about being almost anything else and poor, they think-- You couldn't get it together.

You couldn't get it together. Oh, wait, one last tiny thing before we go to the rapid fire questions. We love on TFC when anyone shares a number.

Are there any numbers, maybe a big job that you got that was a huge thing? Something that you pay in your life? A cost?

Any kind of number? Oh yeah. I can say my number for what I paid for my last interview that's not out yet.

What? $10,000. Oh my god. An interview?

Yeah. An interview on stage? No, a written interview.

Oh, you interviewed someone else. Yeah, I interviewed somebody else. Oh, OK.

For a second I was like, someone paid to interview you $10,000? Jesus. Not that you're not interesting.

But I'm not that interesting. Not yet. I got to do something else first before somebody's paying me $10,000 to interview me.

No, I interviewed someone for a magazine. $10,000. And I bet you that same magazine is paying half their staff unlivable wages. That's the thing.

And that is the stuff that makes me mad. That's the stuff that makes me mad. There are a lot of magazines or places where I haven't written twice because the pay disparity is too great.

And it feels like taking advantage of people in a way that I'm just like, come on, man. This is egregious. I know we all live in a capitalist system, but damn.

But good for you. I'm excited to see that interview. All $10,000.

All $10,000 worth. And the craziest part is I know people get paid way more than that even for magazine interviews. Yes.

Just wild. This industry is insane. It is.

Well actually, on that note, first rapid fire question. What is the big financial secret of your industry? How many people are already rich when they got here.

Man, so many people say that, because this world is rigged. What do you invest in versus what are you cheap about? I invest in anything I cook with.

Got to have good knives, good pots. What brand of knives do you get? I actually don't know.

A friend of mine got me my knives, who's a chef, who was just like, these are the knives you need. And I was like, great. And I got them.

I wonder if they're Wusthof knives. They might be. Do they have a little red-- Yes.

That was my big Christmas gift was knives. And they're Wusthof knives, and everything cuts like butter. It is a joy and a pleasure.

I love it. I put those on my wedding registry, got them. [RINGING] Oh, sorry. No, it's fine.

It's been great. A thing I'm cheap about, probably candles. I have a lot of candles, but I refuse to buy like the good-- I know they smell amazing and they last a long time.

The fucking dyptique candles. And stuff like that. But baby, I go right down to CVS, and I load up on some candles at the CVS.

And those are all the candles at my house, and I love candles. I love lighting a candle. I feel like TJ Maxx slash Marshall's is the candle sweet spot.

Because they're really cheap, but they're nice. They can be. The thing with candles is that they heavy, and I like to buy a lot at the same time.

So I just like to walk down to the corner and get them so I can carry them myself. Those dyptique candles, man, I really am just like, do you guys have nothing else to spend your money on but a fucking $300 candle? Come on.

A candle? Can't imagine. And then they put their makeup things in it.

It's like a status symbol to have your little empty dyptique. Whatever. [RETCHING] No thanks. What has been your best investment, and why?

After I sell my book I told my husband to quit his job and start writing full-time. And he did, and him doing that has been amazing for both of us. And it's not that I fully expect him to get a job, but being able to turn to your partner and give them sort of the same thing they gave you and say, hey, why don't you take some time off from the rat race and focus on yourself creatively.

I feel like the returns on that decision have been the best of anything I've ever done. Also now I just have a live in editor, and he's amazing. That is fucking bold.

I would love to do that with Marc. He's not a writer. But still.

Even if I was like, stay home and play video games all day, baby. I'm there for you. Yeah.

I just want that for you. Also, what about your number one good boy Astro? Oh my god.

We got so many questions about your dog Astro. Oh, the love of my life. Look, my husband is my favorite person, but my dog might be my favorite living thing ever.

I love him so much. I did not want to get a dog until I felt like I could trust myself to be able to take care of them if something came up. And also I think I was just scared of how much I would love him, and that was accurate.

I love him so much. He's the best thing. And I just want to hang out with him all the time.

I wish he was here right now. I'm getting kind of sad. What has been your biggest money mistake, and why?

My biggest money mistake is hiding when I didn't know what to do. There were quite a few situations in my life where if I had gotten ahead of them, would not have caused the kind of havoc that they did for me financially. But I have a tendency with money-- and I think this is part of the reason why I talk about growing up in poverty, I talk about money-- is because shame, man.

You got to get rid of shame. Because when you get rid of shame, you can start talking. And talking helps you figure out what to do.

Hiding exacerbates the problem. Avoidance is such a huge issue with money. People will let the tiniest problems become life ruiners because they don't want to deal with it.

Yes. What is your biggest current money insecurity? That I will never be out of debt.

I worry because of school loans. And really that's it. It's really my school loans.

Everything else I feel very capable of taking care of. And there's plans laid out, and I feel good about it. But student loans fill insurmountable.

It feels like that is a number I will have to deal with for the rest of my life. And I don't know that that's the case. Sometimes I think about, what if I did this?

Or I think about earning potential. I had a conversation with somebody recently who I told them what I thought I could make this year and they were like, you're selling yourself way short. And I was like, damn.

And I have to think about things like that, because when it comes to this student loan number, until that is at a place where it's zero-- Do you mind sharing the number? Oh man. I think right now it's $102,000.

Jesus Christ. Yeah, I think it's 102. And that's for a bachelors degree.

It took me a really long time. Don't get me wrong. I didn't graduate from college until 2018.

What? I didn't know that. I graduated December 2018 is when I finally was able to afford to finish my last class and got my degree.

You are truly an ocean of secrets here. Every question reveals a new layer. Yeah.

But yeah, that's pretty much it. Damn. What has been the financial habit that has helped you the most?

The financial habit that has helped me the most is checking my accounts every day. And not think of it as a scary thing or like, I got to work up my nerve to look at it. And like, I'll look at it tomorrow.

It's like, no, I look at it every morning. And no matter if I'm going to like what I see or not like what I see, I got to see it. I got to face it.

Good for you. And that exposure helps me to just actually be able to plan, instead of hiding and being like, I'll just let life happen to me. It's like I have to be in the driver's seat.

How often do you check your credit. I check my credit probably-- I have on the app as part of my bank app. And I check my credit at least once a month, because it doesn't change.

It's only going to really change once a month if anything happens. Once a month is good though. More than most people.

Final question. When did you first feel successful, and what does that word mean to you? You mean in my adult life, or ever?

Ever. Successful means something different to everyone. I think the first time I felt successful was winning a young authors prize when I was in probably second grade.

I wrote my little story. I wrote my book. That was so [INAUDIBLE].

Yeah. I wrote my book. And I remember the teacher loved my book.

And I mean loved my book so much that she read it to the rest of the kids at story time that day like I was an author. Like I was Maurice Sendak or something. She sat there and read my book.

And I flipped-- I remember going home and showing my mom the book. I wanted everybody to see it. I felt so proud of it because it came out of my head.

And I clearly never got over that. When people connect to things that come out of my head-- I'm looking at all the years behind me where I thought I was alone in a certain way. And I'm like, holy shit, I was never alone.

I was never alone. And that feels really good. It makes me feel really happy and connected to people, and that makes me feel happiest.

What a beautiful and pure note to end on. Oh my goodness. Well thank you so much for being here, Ashley.

Thank you for having me. This was an honest to God pleasure. I feel like we could have five of these conversations and still not get to all the interesting stuff that you have to say.

Where should people go to find more of you? If they want to find more of me they can check out my website It'll send you to my various social corners, different things I've written, talks I've done, interviews.

If that's something that you want to look at. And if you like it, dope. That makes me very happy.

Yay. Well thank you guys so much for being here with us today. And if you want to come back every Monday and listen to more of The Financial Confessions, I'd really like that personally.

Now no matter what your life story may be or your background with money, one thing is going to be inevitable for all of us, and that is doing your taxes. And if you are someone who has felt maybe a little bit intimidated by your taxes, feel like you don't quite know how to do it, TurboTax is the perfect tool to help you understand it, and to ensure that you're getting the maximum possible refund when you do file. Basically TurboTax walks you through the process and helps make sure that every element of filing is being done correctly, and you're not making any mistakes that you otherwise wouldn't catch.

And now the geniuses behind TurboTax have offered TurboTax Live, which is an even more interactive and helpful version of TurboTax. Where basically you have access to various financial experts who are certified and able to help ensure that you are doing your taxes properly. Using a one way video chat, meaning you can look like a mess [INAUDIBLE] can't see you.

You get to ask all the questions that you might have about the process, and ensure that you are getting the maximum amount of money back come refund time. Tax time is just around the corner, and if you're feeling a little bit overwhelmed about how to do your own taxes, check out the link in our description or our show notes. [MUSIC PLAYING]