Afford Anything - The Art of Trusting Your Most Dangerous Ideas, with Ash Ambirge, The Middle Finger Project

Episode Date: February 17, 2020

#242: Ash Ambirge grew up in a trailer park in Pennsylvania. She never met her father. Her disabled mother, who raised her on government assistance, passed away when she was 20. Her childhood goal? To join the middle class. She dreamed of becoming one of those people who eats lemon pepper chicken. What’s more middle-class than that?  She attended college on a full scholarship. When she graduated and accepted her first cushy office job, earning $30,000 per year, she blew her paychecks. She bought a brand-new car, rented a luxury apartment and financed a $5,000 mattress. Yet despite her material luxury, she felt that some important element was lacking. In her quest to find meaningful and creative work, she launched The Middle Finger Project, a company that teaches skills like entrepreneurship, battling perfectionism, and trusting your most dangerous ideas.  She joins us on today’s podcast episode to share her incredible story about struggling to join the middle class, shrugging off a conventional career, and trusting her most dangerous ideas. For more information, visit the show notes at https://affordanything.com/242 Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can afford anything but not everything. Every decision that you make is a trade-off against something else, and that doesn't just apply to your money. That applies to your time, your focus, your energy, your attention. It applies to anything in your life that's a limited resource that you need to manage. Yes to one thing is an implicit no to something else, and that leads to two questions. Number one, what matters most? Not what's captivating your interest at the moment, but what truly matters most in your life. And number two, how do you make a lot?

daily decisions that reflect that. Answering these two questions is a lifetime practice, and that's what this podcast is here to explore. My name is Paula Pant. I'm the host of the Afford Anything podcast, and today, Ash Ambershay joins me to share her story of how she built a life that is entirely her own. Ash grew up in a trailer park in Pennsylvania. She never met her father, and her mother, who raised her on government assistance, passed away when she was 20. Having come from nothing, Ash's goal was to join the middle class. She wanted to be one of those people who ate lemon pepper chicken. When she finally made it, she started blowing her paychecks. She bought a brand new car.

She financed a $5,000 mattress. And yet she still felt that something was lacking. There's a difference, she says, between being grateful and being gratified. And so she set out to find meaningful, creative, gratifying work. She launched a company called the Middle Finger Project, which is all about having a no-holds-barred approach to life, and teaches skills like entrepreneurship, battling perfectionism, negotiating, and trusting your most dangerous ideas.

She recently published a book, also called The Middle Finger Project, in which she shares her story and talks about how to shrug off a conventional career. Ash is a riot. She is funny. She's wise. She's blunt. And we're going to hear her story right now. Hey, Ash. Hi, Paula. There are probably a whole bunch of people listening to this who don't know who you are. Why don't we start?

I want to introduce you because I've known your work for like a million years or at least five. But for the people who don't have that honor yet, tell us about you. And let's start at the beginning. Let's start with Youth Flash. You flatter me, Paula. You flatter me. Five years is like it's like a hundred years and internet years, isn't it? But just an everyday girl from a trailer park in rural Pennsylvania is where I got my start.

I was actually born in Philadelphia. My parents were from Philadelphia. And then my mom, I think there was a couple things going on there. But primarily my mother was a person who suffered from severe social anxiety. This was a woman who didn't have a voice. And I actually think that's why I'm so passionate about giving other. people theirs. But for those reasons, you know, I think she needed to retreat. She needed to get out of the city. The hustle and bustle was wearing her down. And so she moved us to north of Scranton,

about 30 minutes, 40 minutes into Susquehanna County. I graduated with 96 kids, you know, one stoplight in the entire county. So it was a complete about face. And that's where we ended up in this, in this trailer park. My mom doing the best that she could. It was just her, her and I. Before it was just you and your mom, you had a relationship with your dad while he was living. Can you talk about that? I did. You know, it's a real jumble, fuck, Paula. But yes, I never actually met my real dad.

I had someone in my life who was very much like a father to me. And we were buddies every single day. We'd be doing something together. I was his little sidekick. We'd be going to the ice cream stand in the summertime. He would get two medium twists, one with rainbow sprinkles and one without. and we would eat those all the time. And he was kind of my sounding board for everything.

You know, growing up with his mother who had this disability and who really couldn't interact very well socially in the world affected me in many ways, right? Like, you know, I was captain of my volleyball team, but she wasn't able to come to the gym, for example. So he and I were buddies. But unfortunately, when I was in the eighth grade, he took me to the hospital because he thought he had a hernia. And we just bopped along.

It was, you know, going to be summertime. School was ending. We bopped along on this country road over to the Barnes-Caston Hospital. And he was in there for what felt like forever. And I remember just kind of like swinging my legs at the chair like a kid does. And when he finally came out, I was like, gosh, you know, everything all right. And I remember, I remember clear his day. He looked at me and he didn't know what to say.

And he handed me a pamphlet that said, helping your family deal. with terminal cancer. And I didn't know what the word meant. I didn't know what terminal meant. And so, of course, you know, in my very optimistic, youthful sense of innocence, I started rambling on about how everything would be fine and he's a fighter. It'll be great. And needless to say, a few months later, it was not so great.

And he did pass away when I was 14 years old. I'm sorry about that. Yeah. Well, and then there's my mom and I. Yeah. And that's how we ended up. That's actually how we ended up in the trailer park. Yeah.

And so you lived in the trailer park with your mom. And then when you were 20, everything changed again. So time passes. I was able to secure an amazing scholarship to school from the founder ofmonster.com. You know that website? Yeah. Right. So he, Andy McKelvey, chairman of Monster, was a young boy growing up also in rural Pennsylvania.

and decided when he made it big, he wanted to give back. So he found the poorest county in PA, came to my high school and said, I'm going to give someone a full ride to school, whoever demonstrates both financial need and entrepreneurial spirit. That was the second piece of it. And I didn't even know what the word entrepreneurial meant then either. But needless to say, I applied and did all these interviews of Penn State. I remember him sitting in the back corner in the dark. recesses while I was sitting closer to the door being interviewed by a woman named Carol.

And it was so intimidating. And there was so much pressure. By the time the interview was over, I walked out and I burst down into tears. I mean, that was my future writing on that. I didn't know what I would do if I didn't get the scholarship. And I won. I got the scholarship. And that was my savior.

So need to say, I went to school about an hour away. and it was then when I was studying in Wilkeshire, Pennsylvania. You know, I knew my mom couldn't really be all by herself. So I stayed close by. And I got a phone call one day when I was just about to go to my very first internship at a local TV station. The person on the other end of the line said, Hi, come quick, your mom's unresponsive.

And I didn't know what that meant either, Paula. Like unresponsive? What does this mean? I mean, did she fall? Did she hit her head? I knew she was having some problems with her circulation. We had been to a couple of doctors to talk about just, you know, putting like a stent in her leg. I got there.

I drove the hour. Not sure what I was going to find. My college roommate insisted on coming with me. She was a couple years younger than me, so she was only, what, 18 at the time? when we got to the trailer, no one was there. It was very eerie. I was looking for ambulances or maybe the neighbors kind of outside in the street in a huddle, someone whispering, someone looking out a window, and nothing.

It was just dead space. We kind of crept up onto the porch uncertain about what we were going to find. I just didn't know. I thought that maybe they took her and I see a post-it note on the front door. and we pluck it from the screen and it says, call me and a phone number and then signed the coroner. So, yeah, you know, I still held out hope in that moment because I was very young. And I thought, well, maybe he was, maybe they just go in case.

I've kind of rationalized in my head, like, well, maybe once the ambulances get called to someone's home, maybe the coroner has to show up to make sure a person's not dead. I mean, I kind of went through this whole very logical sequence in my mind. Maybe he's just being a good Samaritan and he's staying behind to kind of let me know where they took her, what's going on. So give me a buzz. That was not the case. Yes. Yes.

So that happened when I was 20, approaching 21. Right. And when you did call him, he didn't even realize that you hadn't known yet. So he got right down into business. He did. He said to me, so, you know, I just need to know where you'd like us to send the body, essentially. I don't think he used the word body.

He said, he must have said like the deceased or the, I don't know. Where would you like? Yeah. Where would you like, yeah. I think maybe it was body. Where would you like us to send the body? It sounds so cold when I say it like that. And I remember just on the phone with him going like a lot of that.

like, can you back up a second, sir? Yeah, right? Trying to sound professional with your professional face on. While meanwhile, you're like falling to pieces on the ground. Like, what is happening? And I never saw my mother again. So that was my start in life. It was a little rocky.

And, you know, we've all been through the heart. Every single one of us has their version of that. But for me, I was very stubborn because I never saw, work modeled for me, right? My mom and I were on government assistance the entire time. I never saw her getting up and going to a job. I remember actually saying very hurtful things to her when I was maybe 11 or 12. I know, why can't you just get a job like everyone else's parents? I don't understand. She actually went to court and actually had, she was like clinically declared unable to work. So I became fascinated, maybe a little obsessed with understanding and answering two questions,

which were, you know, what does it mean to live a good life and what does it look like to do work that I'm proud of? Those were the two things that I just, I had burning inside of me that I wanted to understand. I, you know, I knew other people's parents had jobs and they had two-story houses and They had cars. We didn't have a car. I mean, they had, I always laugh about lemon pepper chicken and poppy seed bagels because I feel like those things were very middle class to me. And so I set off for the city of Philadelphia.

I sold our trailer. I had an auctioneer, you know, poor guy, whoever I called at the time and I thought there'd be something worth it. Worth it in there. I called this company. And I said, can you please just come and take everything inside and just give me the money. I was very broken and just in that state of almost denial where you're just operating without thinking, no tears, just move, move, move, go, go, go. Can't afford to break down.

And I left for Philadelphia to start my life new and try to become someone that I never was. You were still in college at this time. You were 20 when this happened. Actually, I was just about to enter my last semester of school. So I graduated. This happened in January and I graduated college in June. So were you 20 or you just turned 21 when you graduated? I think I was turning 21 that June right then. But those kinds of experiences are what really started to propel me forward, not in an angry way, but in a very determined way. I never wanted anyone's pity and I did not want to be looked at as defective. And so what did you do next? So at that point, right, you graduate college and the question always becomes for all of us.

What do you do next? And I think most of us are pretty clear on what happens next. You're going to go. You're going to get a job. You're going to eventually meet someone, get a house, have a baby, the whole thing. But it wasn't that clear for me. I felt very lost and ambiguous about what I should be doing. But the only thing I knew, with all certainty, was that I was going to be middle class, baby. I was going to be middle class. And so effectively, I started the middle class project far before I started the middle finger project. And I went to the city and I got my very first job at a very small company as a marketing assistant. I negotiated up my salary from $28,000 a year to $30,000, baby.

What year was this? This was in 2006, and I worked there for some time, and I actually loved what I was doing. It was a mistake that I was working there. I was actually interviewing at this company for a different position, at a different company, because they were a head hunting team. And the original company I was interviewing for was this giant, media company and the job was going to be something very basic, like data entry, something like this.

Maybe I'm going to go with $12 an hour along those lines. They interviewed me and then the girl said to me at the end, she said, listen, this is going to sound weird, but would you entertain a position with us, working with us here? Because we need someone to help us out with our marketing and we don't have anyone and I just think that you're full of life and energy and I think you could do it. What do you say? And that was when I had to make the decision. Do I want my resume to look good because I worked at this big media company?

Or do I want an opportunity to make an actual impact with my work and be able to have this kind of like leverage? And I decided to do that. And that was my decision. Since my goal was to do work I was proud of, I thought that that made sense. and next thing I know, I'm discovering that the real world is not as cracked up as, you know, I hoped it would be.

And that was very disappointing for me. I really came into this thinking, if I got straight A's, if I did everything right, no one could take that from me. I couldn't mess up. I was going to do everything perfectly and follow every rule there ever was to follow. And I discovered that adults, to my greatest dismay, had no idea what they were doing. was just guessing every single day.

Right, exactly. These grownups who you once thought or competent turns out are just making it all up. Yes, and I really looked to them for guidance. I was very distraught by some. I mean, corporate America just lacked so much wit and imagination and creativity and originality. And it all felt so formulated. and lazy.

And so I decided to try my hand at something else, and I moved to a different position in advertising sales. And this happened after I'd already now worked my way up. Through that original company, it was really great. I started off being a marketing assistant. I ended up taking initiative doing all sorts of things that I wasn't given permission to do, but I thought would be useful for the company. I mean, that I blew it out of the water.

Next thing I know, all of these giant, giant, organizations are calling us to have contracts with us. We didn't have a salesperson on staff. So I volunteered to then go out and meet with these people and sign the deals. And so I just kind of kept, I just kept doing what I thought would be best for the company and taking initiative and it worked. So by the time I had switched to advertising sales, I had already been doing sales. I was very good at it.

I won some national awards for, you know, number of contracts signed on the first meeting, which was not so common because it was a bigger, higher price point. And by then I was making something like $40,000 a year plus commission. And I could go to Target and I could fill up my shopping cart with anything that I wanted. And, you know, I had a roof over my head and all the things. Did that $40,000 per year plus commission, did it feel like a lot? Like, did you feel like you had made it? I'm going to say no, because now I had all sorts of new expenses.

I took on expenses that I absolutely couldn't afford because I didn't have anyone to guide me and tell me that it was a stupid idea to be spending $1,200 a month and rent alone, and you're making $30,000 plus, you know, utilities and all these things that I didn't, I didn't calculate correctly or at all. I went to the Sleepy's mattress store and the guy, gave me a $5,000 mattress on credit. Like what? Why would I ever do that? I would never do that now. I made bad decisions because there was a part of me, I think, psychologically that felt like I deserved it.

I'd slept on a love seat in our trailer in my bedroom for as long as I could remember. I didn't have a bed in there. And then I started sleeping on the floor at one point. I would just pull out all these covers and just sleep on the floor. So for me, it was like I had these weird, you know, weird little hangups. So buying a $5,000 mattress made sense in some ways. But I shouldn't have been doing those things. So, yeah, I mean, I screwed myself in the beginning. I was making some money, but I also took out so much in credit. I bought a brand new car.

Who am I? Yeah, if you're making $30,000, that mattress is a sixth of your annual income. Yes, for a mattress. Right. I know, I know. I know. I was a fool. I was a total fool.

and it wasn't really though. I was kind of going along with it, but some of the research that I've done over the years illustrates, I think, where the root of my dissatisfaction kept coming back from. And that was on the difference between happiness and meaningfulness.

Happiness as the study show is about getting what you want. So, okay, great. I got it. I can make lemon pepper chicken now everybody. I rented an apartment in a place that had steps that I had to walk up just so I had a staircase, right? Like I was doing it. I was happy. But meaningfulness is a little different. Meaningfulness is about getting what you want, things you should be grateful for, and also expressing and defining yourself while you do it. That for me was the piece of the puzzle that was so desperately missing as I

bumbled around doing advertising sales, working, you know, with people I didn't care about, selling products I didn't really care about, going to work, doing work I didn't really care about every single day. So that was when I decided, well, I don't have the luxury to quit right now, but I can at least make my job more creative as it stands today. And that is when I decided it was ridiculous to be cold calling all of these strangers every day from a list and saying, hi, you know, this is Ash from so-and-so company. Can I have a minute of your time? La-la-la-la-la. Can we jump on a call? Oh, like nobody wants to hear that. And that's what the company was encouraging everyone to do. It was a giant waste of time. So I thought to myself, gosh, you know, I wish the people that needed

my help would call me instead. Wouldn't that be great if they called me? And as soon as I thought that I thought, okay, well, maybe I have an idea. And I decided to go to Home Depot one day, and I went into the roofing section of the store. I've spent a lot of time at Home Depot. I know that section well. I went up to this giant roll of shingles. I didn't realize they sold them that way. I thought I could just buy, like, a couple individuals, but no.

Another naive thing. And I bought this giant roll of shingles, and I dragged that giant. roll right back into my office and I dragged it right over to my cubicle and I made a giant scene. All of the asphalt was like asphalt. Can we call it asphalt? Asphalt shingles. Yeah, they're asphalt shingles. Like the little pieces that are that are very loose and they kind of start crumbling off, you know, falling over on the floor and all of my co-workers looking at me like I had 17 heads. One coworker in particular was very, very, very upset that I was doing this. you know, she was demeaning and it was kind of like, you know, oh, what is this? Craft class kind of a thing.

It was messing with her sense of reality too much. You know, we shared a territory, so I think that didn't help. It was threatening her. It was triggering her and threatening her. Of course it was. I mean, listen, I've had to get everything that I have my entire life from being creative. It's the only way forward for me. So it was like, okay, well, here goes nothing.

I cut up those shingles and I placed, you. you know, one inside an envelope, and I had written on the back of the shingle in some kind of like sparkly paint. You plus me equals sales through the roof. It helped that this was a magazine that was targeted for, it was all brand new homes. So it made even more sense in that context. And I sent them out and I sent them so you'd have to sign on delivery just to be an extra big jerk. and the next thing I know, the phone was ringing off the hook.

And I had people calling me, per my instructions in the kit, to set an appointment with me. And that was the best thing that could have happened. Everyone else was pissed that it was happening. But I thought, why am I going to sit here with you guys and read these names off and call these people cold? And so that's what happened. And it was one of the first times that I realized I could do my work more creatively, even in a traditional setting. But other people didn't like it.

You know, my coworkers didn't like it. And I even had one of the regional managers tell me at one point that I needed to tone it down. And I was there to make money and not to make friends. We'll come back to this episode after this word from our sponsors. The holidays are right around the corner. And if you're hosting, you're going to need to get prepared. Maybe you need bedding, sheets, linens. Maybe you need serveware and cookware.

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So there I am working in this job where creativity is not a part of the actual role. And that for me was the point where I started to feel very uncomfortable working in this position because it's like, okay, all of us are going to work every day, feeling good about the fact that we have gone. But what have we done? done. What is the point of all of this? I don't know what would have happened if it wasn't for my next meeting, frankly. My very next and one of my last meetings that I ever took as an advertising executive was with a guy named Terry. And Terry was one of those hard to nail down clients who did not want to meet with me despite my cute shingles. And despite I think I could have

sent this guy. But he was a big fish and I was very hungry. So I kept on Terry and finally one day he said, all right, fine, you got me. You can come have a meeting, but, you know, there's a caveat. It's not going to be at the office. It's going to be at this bar at this address at this time. And I thought, okay, I mean, all right. I'm from Scranton. I can go to the bar and have a meeting. I'm fine with that, totally. But this was like a po-dunk, you're like Bikers Bar.

This wasn't like Applebee's. This was like... I love how Applebee's is your example of something fancy. Right. I know. Well, okay, fair. You know, even like meeting at an Applebee's in that context would have been more appropriate. Right.

Wasn't the matri-D at Applebee's. Yeah, this wasn't the Capitol Grill. This was this podunk, a little bar in the middle of nowhere. I had to drive to get to it. I'm coming from the Philadelphia suburbs. I should have known better for a lot of reasons, but I get there and the guy tells the waitress that we'll have two of the regular. And mind you, this is at like 2 o'clock in the afternoon. She comes back with two Long Island iced teas.

And I'm like, oh, okay. All right, all right. But still, I can hang. I want this contract signed. So we sit down and this guy doesn't let me get a word in. Instead, he starts telling me these tales and that were incredibly inappropriate, including how one of his employees had f***ed his wife. And I'm sitting there young in my early mid-20s going,

how do I transition this? I eventually managed to do so. And I start talking about what we can do for him and how we can do. for him and how we can help. Right. The contracts and the advertising package. Yes. I mean, let's talk about it.

Your competitors are doing X amount of money, you know, just strictly from our magazine. Here are the numbers. Let's check this out. This is awesome. You'd be making Buku bucks just from advertising with us. So as soon as I started talking about that, he took a Polaroid camera out of his satchel. I don't know why this man was walking around with a Polaroid camera, but. What year was this?

Like 2009, 10, somewhere in there? Yep, right around there. Who carries a Polaroid? I don't know why he had this thing. To this day, I do not understand. I mean, maybe, I mean, he was going around taking site pictures, but why would you? I don't think we really had smartphone. 2010, yeah, we just started having smartphones.

Yeah. At a minimum, they had cameras before smartphones. No clue, but he pulls this Polaroid camera out of his satchel. And as I'm talking, he decides to start snapping photographs of me at the table. Without asking you. Of course not. This is very uncomfortable and strange and kind of demeaning. And the waitresses looking at us, like, what the hell?

And I'm like, I don't know. What the hell? And finally, I just decided that I knew how I was going to have to handle this. I got up out of the booth and I slid myself in on his side of the booth and I looked him square in the face and I said, you and I are going to make a little deal.

All right? You're going to give me that camera. I took the camera from him. I'm going to go into the bathroom and I'm going to take a very special picture for you. And while I go do that, I pushed the contracts across the table at him, you're going to sign this. Do we have a deal? And he looked at me kind of just in shock and was like,

you know, well, I know a good deal when I've seen one. Great. Okay. Done. Deal. I think we pinky swore on it, in fact. Yeah. And you had two copies of the contract drawn up, one that was six months and one that was a year. That's true. Always one for the regular that company wanted me to get. And another for double the money because when you're in that scenario, you can kind of feel people out and see where they're at and what would make the most sense. But as an advertising person whose job is to sell, I'm going to go for the most amount I can get. So yes, I definitely gave him the one for double the money. And then I went to the bathroom and I snapped a photo and then I came back out. And this was the moment when I remember just like very ceremoniously holding out

my hand and he placed the contract in it. And I put it in my bag and I put my coat on and I said, thank you so much, Terry. It's been a pleasure doing business with you. And I remember him just being like, what about my picture? You know? And I was like, oh, like, you know, this. And I gave him the picture. And then I walked out and I heard him groan from the parking lot because apparently he had not expected a picture of my middle finger. And that is why. That's the origin story of the middle finger project company as a whole. Because after that, it was just very clear. I couldn't keep doing this and disrespecting myself by keeping doing this. And that was the last straw for me. I love that. Like, talk about saying F you to work. I mean, you quite literally just said F you walked out the door and did so. with an awesome contract to boot.

And years later, I still keep in touch with my boss from the magazine. Him and I are great friends in this day. He loves me. We love each other. And he told me once, he said, you know, Terry still advertises with the magazine. He's like our longest standing client. What? Oh, man.

Isn't that great? Yeah. Yeah, he must have been terrified. So at that point, it was like, okay, well, what happens next? And I will admit to you, Paula, I rebelled a bit. I went in the exact opposite direction of everything that had been the middle class projects. I did what most people do. I did like the worst thing I could have done first.

What most people do when they're dissatisfied with their career. They think about going back to school, don't they? Mm-hmm. And so I took out $80,000 in graduate student loans. And I went back to school for linguistics. Just like living on a prayer, total shot in the dark. I like the creativity pieces of it. I like what I've been doing with advertising and marketing.

I love copywriting. I love language. So how can I study that formally in a way that felt artistic and cool? That was my answer. It was then that I considered that human beings have developed hundreds of different ways to communicate with one another. And so maybe they've also developed hundreds of different ways to find purpose in their lives. That set me on an interesting path where I really did become more like an anthropologist than ever. I think I had already been an anthropologist in many ways looking at the white-collar professional class of people trying to figure out how to mimic them and live amongst them.

Like a participant researcher. Right. Right. How to fit in in this new culture that you weren't raised in? Or I guess I have to learn how to eat lemon pepper chicken now. Oh, yes. There were so many things I didn't know how to do. I remember the first time I ordered a martini because some lady, a work contact, wanted one. And then the bartender looked at me and said, do you want it with vodka or gin? And I remember being like, ah, I didn't know.

Right? So here I am. And I decide to then become an anthropologist. And I decided that while I was here in Philadelphia, I started seeking out subcultures within Philadelphia of different populations of people. I started taking salsa lessons. And I started doing language exchange classes with people from everywhere just so I could meet them and talk to them and find out what they liked about their life. What was going good for you? What was the answer to these questions that I had about what was it to live a good life and do work you're proud of? Maybe these guys know. And that led me to meeting a very handsome man, as you might expect.

He was someone who was the exact opposite of me. He wasn't a high achiever. He was making $10 an hour delivering frozen food supplies to restaurants. He didn't drink any alcohol, so he didn't care about things like $15 glasses of wine or keeping up with the Joneses. He was a very simple man, and he would go to work, and then he would go to gym, and then he'd come home and he'd watch TV, and that was that. And yet, he seemed so content.

He did not have this drive, this insatiable drive that I had that actually was starting to haunt me in many ways. And so I thought, well, maybe that's the answer. Maybe I should lower my expectations of myself. And that's exactly what I did, Paula. I then decided to go. I quit my job. I decided I would become a freelance writer. That money was no longer my priority.

So therefore it kind of gave me the rationale to, go freelance, that I was going to move in with this gentleman and experiment and test out his life, try it on for size, the way you might try on a shoe. Did you finish grad school? Like, what happened with this 80,000 in grad school debt? I was still in grad school. So let me think what the timeline was. I think I was just about to graduate. It was two years. So I was just about to graduate. I had all this debt, but I left my job before I graduated because I knew that I could always fall back on student loans if I really needed them. And I moved in with this guy. And there we were going to Kmart, literally for stuff. Like, I mean, that was a whole different thing. I was living in this

affluent Philadelphia suburbs prior to that. So this to me was like going in reverse a little bit. And I loved it because at the time, it didn't seem to me like I was going in reverse. It seemed to me like I was being whoa. Yeah. Right. Like everyone else cares about getting a partner who has. a perfect golf swing and a 401k and like picket fence and I was like whatever you guys are really living like I remember just being like this is me being woke before that word was even in existence that's funny I never even thought to associate a perfect golf swing with a 401k to me there's such different concepts they're almost the opposite of one another yeah well I bust my friend Sean Ogle all the time because he now owns a golf course and I'm like you're such a

bougie bitty these days. Like, who are you? So I always laugh when I say that because that's, yeah, he's now got a perfect golf thing and a 401 thing. But right, so I experimented with life and I was going down this path just trying so hard to figure it out. That's when I figured out a couple of other things too, including the fact that this man was not who he said he was. He had a complete other identity. This was not a good thing. And that was when I had to decide, okay, well, do I have more integrity, staying with this guy right now, or going to sleep in my car and a Kmart parking lot. Because frankly, by then, I was waiting for some checks to come in. I had $26 to my name at that point. I had no more available credit. I had taken up all the credit with my $5,000 mattress, et cetera.

And the relationship was toxic and not working. Toxic. Yeah. There was one night in particular when it became clear after I found the drawer full of false identifications or maybe 20 of them, same photograph, different names on every single one of them. Terrifying thing, right? When you are, especially a woman on your own, you've just now made this big leap to become a freelancer. You don't have anything to your name. Nothing. I had $26, no credits, no savings, just completely flying by the seat of my pants. And that's what happens when you don't prioritize money in some ways because your discretion goes bankrupt too. And then you open a drawer and you find all these fake IDs and you realize he's not that he was.

Yes. He's a scam artist. I didn't know what he was. Like, what is this? And I confronted him about it because he really walked through the door not minutes later. And it led to an argument. And it was a very violent argument because I had discovered his secret. And the secret was that he wasn't from the country he said he was from, and his first name and his last name weren't actually what they were.

I mean, even the name he had given me was a false name. I got very scared in that moment. That's a scary, very scary position to be, and we don't have anything. And I remember, I mean, I couldn't be in this position. I couldn't stay there. And we fought, and he got angry, and he picked me up by my neck. and he dragged me through that house and he threw me on the pavement

and I remember I was scared but I was relieved at the same time but then I didn't have my wallet and my car keys and everything was still inside so I had to now make this other brave decision what do I mean I need to get in my car I don't have anywhere to go the very least I'm going to sleep in it

I mean, I was young and naive and so, so foolish, but I went back in the house. And that was when he got very angry. And he approached me again in a very similar manner. And I remember looking into his eyes because now he had two hands wrapped around my neck. And I remember thinking, this man is going to kill me. And I also remember my mother giving me advice because, When you are someone who has a severe social anxiety, you find every trick in the book to be brave. And you also know every trick in the book for what happens.

If something horrible happens to you out there. And so she always used to tell me, go for the eyes. And I thought, well, that's morbid. But what else do I do? It was the first thing that came to mind. And I actually tried. I actually remember trying because I was that desperate and thought that this was not ending well. but I couldn't reach because he was a man who had very large arms and I am only five three.

I couldn't even touch him. And that's when I took my car key. That was in my hand. And I somehow managed to wriggle it to the side of his palm where the flesh meets his thumb. And I and I cut. And I remember blood spilled like an avalanche like all over the floor. and it was enough to get him to let me go. And that is when I ran out and got in my car and fled to the nearby Kmart parking lot,

not having anywhere to go and no money left and not a single idea in the world, you know, what to do when you've hit rock bottom. And that's what most people fear, right? Hitting rock bottom. It's interesting. I work with people from all over the world who are making this career change. now. There are a few people who've been there and are a little scared of that, but most of the time, it's the opposite. Most of the time, people are actually living quite average, normal, kind of decent

lives with decent jobs. And maybe they're worried that that could happen at some point. But overall, the bigger threat to them is the advice that everyone keeps telling them over and over and over again. You should be grateful for what you've got, right? Like teachers, especially, suffer from this. You've got summers off. You get out of work at 3 p.m. You have great benefits. What's so hard about it? Enjoy it. People would kill for your job. Be grateful for what you've got. And it is some of the world's most dangerous and worst advice because it convinces us to settle. It convinces us that other people might be right. We get scared. It causes anxiety. And we end up staying small. And we shrink and we live these lives that are beneath us, make no mistake.

Because we are now trapped in that mentality. So sometimes I do think if you have the privilege and the luxury of hitting rock bottom, it is the best thing that will ever happen to you because when you have to sink or swim, you will swim every time and you can't say the same thing about when you're just living a very comfortable existence day by day. We'll return to the show in just a moment. So what do you do, though, when you do hit rock bottom and you're faced with this, and this is when I learned kind of what has formed the basis of my entire company now and the philosophy that we operate under. And it's simply that most people might, you know, have something to sell.

Maybe they've got some family jewels. Maybe they've got their time to sell. Maybe that's what you're selling every single day to an employer. Maybe you've got some bonds you could cash in. a car. I couldn't even turn my car in because they wanted $2,000 to take it off my hands since it was upside down on the loan. But you don't need any of those things if you've got an idea. Your ideas, they are a great equalizer in this world. And none of us trust our own ideas enough. We ask everyone else for their opinions. We listen to the dream zappers. We don't think

we're good enough. We say to ourselves, well, who am I to do this? I don't have enough experience. You know, maybe I'll wait until the timing is better. And we don't trust ourselves in the most crucial moments of our life when we should. Because living this life every day and going to work every day and renting out your weeks to some faceless organization for the rest of your life and feeling like you have no purpose or say in any of it is a very real emergency. And none of us look at it that way. We look at it as we've got time to make these decisions lead or we defer, we put it off. I didn't have time that night in a Kmart parking lot.

It was really the best thing that ever happened. And what the radio announcer said on the radio next changed my life forever. Believe it or not, this radio announcer said to me, well, to me, to all I was listening, he said something very profound, which was, the new Rihanna CD is now available for pre-order. That sounds like nothing on its face, but all of a sudden when I heard that, I realized two things. Number one, art is worth paying for. That's what a CD is. That's what an album is. That's what music is.

Wow, it just occurred to me. Art is worth paying for, number one. And number two, that art doesn't need to be finished yet in order to exchange it for future value. And that was the idea. And I realized if I wanted to be a writer, that was one skill that I did have. You just need one. And you just need to be. able to sell it to one other person. That is it. And that is exactly what I did that night. I made an

offer to the world to write. And in 24 hours time, I had made my first $2,000 and I never looked back within eight months. I had made my first $103,000 freelancing from what later became my apartment in South America in Santiago, Chile, all because I had no choice but to trust an idea that I had. So a lot happened in this eight-month period, right? Let's walk through how that all unfolded, because we're starting with, you've just left this incredibly violent relationship. You have nowhere to go. You have $26 to your name. And you're sleeping in the back of your car in a Kmart parking lot. the radio announcer says that Rihanna CD is available for pre-order. You had a blog at that time.

And so you reached out to your audience and said, hey, I will create something in the future if you pre-order it now. And that's where that first 2000 came from. How then did you get from 2000, which I think is a, I'm sure a lot of people who are listening to this right now can imagine themselves making 2000. But how do you go from 2000 to 103,000 in the span of eight months? That's incredible progress. Thank you. Thank you. There's two parts to this.

Number one, you keep making offers every single day of your life to help people. So many of us are worried about selling ourselves because we don't want to be sales. We don't want to be salesy. We don't want to be salespeople. But I always encourage anyone that I'm working with to think about selling as helping. That's all you're really doing. Hey, here's what I'm really good at. In fact, I'm better than anybody in the world at this thing.

Do you want my help? Could you use this thing? And that for me was the best thing. I just started making offers every single day. I didn't just make one and then let it die. I kept making offers because I was used to selling. So that was great. I had a huge benefit.

But the second thing that really matters is having the courage to lead. And this sounds a little esoteric, but having the courage to take whatever idea you have, whatever skill you have, and putting some money on that and saying, okay, you know what, in my case, I did. I started writing a website. I didn't want to wait for the New Yorker to publish my writing. I realized very clearly that if I wanted to write, all I had to do was actually write. I didn't need someone to publish it for me.

I could do that with modern technology. And the same goes for any single one of us who has a talent or a skill that they like. If you are, you know, are really fascinated by interior design and you're fascinated by wallpaper and all the cool new stuff that's happening with wallpaper right now. And that's what you would love to do. Well, you know what? You better get your a bit out there and just start wallpapering everything you can find, taking pictures of it and putting it in one place where then you can share your ideas

about that. And by doing this consistently over and over again, what you now have is your modern day resume. Whatever you're creating, whatever kind of online form that. takes. This is you standing up and leading. This is you saying, hey, here are my ideas. That's not to be confused with standing up and saying, these are the right ideas. You're simply saying, hey, here are my ideas. Here's what I'm really into. Here's what I think about this. And that is a form of leadership. And when you start doing that, other people see you as a leader.

That is what the difference is between someone who's freelancing for pennies and someone who's freelancing for Buku Bucks. The first person is an order taker. They exist waiting for the next task from a client. The second person, on the other hand, acts as an advisor, and they go into anything they approach and say, hey, here's what I'm really great at. Here's what I think you would, I mean, you would love if we did this. Here are my ideas.

What do you think? Can I help you with this thing? Taking that initiative, being proactive, it's single-handedly the difference. That is what made the difference for me. If anyone came to me saying, hey, you know what, you are a pretty good writer. You want to write this thing for me? You want to write my bio? I wouldn't be like, okay, sure, tell me what to write.

I would turn around and say, okay, great, let's get on the phone. We're going to have an interview. And here are the questions I'm going to ask you. Here's the stuff I need to know. Kind of a thing. It's a complete difference in disposition and posture and the way you show up in the world. The world will reward that for you 10,000 times over because not only does that, person trust you more, they're going to feel comfortable giving you their money, and they're

going to feel comfortable telling you to everyone they know about you. And you can charge more that way, too, because you are more valuable. Did you see how excited I just got about that topic? I was like, woo! Exactly. Well, essentially what you said is, you know, rather than take the position of, I'm going to defer to authority, I'm going to take orders, I'm going to compete, like scrape at the bottom of the barrel for the lowest paying gigs, you took the position of, I'm going to position myself as the authority, and I'm not going to just write an article for you. I'm going to develop your content strategy. Right. Yes. I mean, that's what I had been doing all of those years in my very first jobs, taking that initiative, even though no one asked me to. And I had been rewarded for

that handsomely. It is sort of how I operate, but it was the way that I became so successful in such short amount of time. I didn't wait for people to ask me or give me the job. I went out and I said, hey, you could really use my help. You want it? And it's so simple. It doesn't have to be complicated and complex and all of the mental stuff we put around the act of asking for money and pricing yourself is so difficult in our heads. But it's really not. It's really just an act of helping. It's the most generous thing you could ever do. Tell me more about pricing, especially as someone who started off growing up without much. And then in your first job initially not making very much. How did you readjust mentally to your concept of what is

quote unquote a lot of money? Well, one thing I've had to work on over the years is understanding that my money story is not everyone's money story. It's something that I have to practice daily and remember because especially as you start to change and you move between different socioeconomic classes, everything gets readjusted. And, you know, maybe now, you're someone who a hundred bucks feels like 20 bucks but back then 20 bucks you know felt like a hundred bucks and vice versa so I think for me a lot of that is just about assimilating into a culture so I don't know that I had any like things that I was doing in particular that made me better at this than someone else I do think that my career in advertising helped me quite a bit

because I was selling a product that was not me. And the price was the price was the price. The rate was the rate was the rate. I had no negotiation power on it. And I got used to that mentality. And I got used to understanding ROI. And I got used to understanding that if someone is asking for your help, they're going to get something out of it.

And you're not taking. That is really, I think, where a lot of new freelancers independence really struggle is the feeling that they're taking from some, someone else. But what you have to understand is that person is hiring you because they're going to get something out of it. And most of the time, what they're getting out of it is going to be far greater than what they're spending for it. And if it wasn't, they're not going to buy it from you. Trust. That is their decision. And you have to trust that they know what they're doing. So if they're spending $10,000 for an hour of your time, which is a ridiculous example, but you know

what I mean. That's because it's worth it to them. So you can't decide for them. what their money story is and what they believe about money and what they believe to be valuable or not. How long did you live in your car in that Kmart parking lot? Literally 24 hours. And you got that influx of $2,000. Overnight. Yep. And then you got an apartment the next day?

Oh, Paula, no. No, no, girl. I did not. I did not. I took that money and I got on a plane. You got on a plane the next day? Apparently I am a psychopath. I got on a plane the next day.

Yes. Wow. That's exactly what I did with that. I went to Santiago Chile because I knew that I could leverage a lower cost of living there. And I thought that if I really wanted to give myself a sink or swim environment, well, this is going to be it. I knew I needed to leave Philadelphia. I didn't want to be tempted back into the arms of that man. I had a fear that I might be because I was desperate.

And I didn't want to let myself do that. So I got on a plane the very next day. I didn't tell anyone where I was going. And I flew as far south as I could muster. I had been there once during grad school for a thing with the United Nations as a part of my linguistics degree, so it wasn't completely foreign. I knew that apartments in beautiful high-rise buildings were $300 a month, and I knew that that was a lot less than the $1,200 I was spending in Philadelphia. And it worked. And that eight months, making that first six figures from this tiny little apartment, it was the size of a shoebox, but it was adorable and brand new and cute in the middle of Santiago.

That's the best time in my life. I would never, ever take it back. I can completely imagine that, taking advantage of geo-arbitrage and starting a new life and opening a new chapter. Yes, that's the word. The fancy word. Mentally, how did you have to grow during that eight-month period? We've talked about pricing. We've talked about your money story.

What other mindset shifts did you have to endure during that eight-month, like, all right, I have just hit rock bottom. it's time to go. Where was your headspace? I struggled a lot with being a people pleaser. I think that's something that certainly many people can relate to, especially when now you are taking someone's money. I struggled a lot with boundaries and understanding that I had to set some. Yeah. You know, I didn't know how long things were going to take me back then. I had no concept of time. and if I'm going to tell someone that I can help them write their speech, which, I mean, I started writing anything you can imagine for people. I remember one woman ran the Black Miss America pageant. She wanted me to ghost write her speech for her back then.

I had no idea that was going to take me like weeks. I thought that I could bust it out a day or two. No. And so then you start overlapping on different projects and you have too much to do on your plate all of a sudden. And you don't know how to manage that. And then you don't want to look like a flake to your case. clients. So I struggled a lot with that in the beginning because I didn't know how to not seem irresponsible and still tell them, okay, well, guess what? Here's the timeline. It's going to take

me X amount of weeks or whatever. I didn't know how to set those boundaries for myself, for them. Expectations were really tough. But it's all something that happens with practice. And as long as you're a great communicator and you can say things honestly and with sincerity from a genuine place, you're going to be totally fine. Clients are very understanding as long as you have that communication. And then I learned. I learned about myself and I learned about the process and I learned how to sell my ideas to other people and make a great living doing it. Ash, I know we're coming to the end of our time. So before we sign off, are there any final pieces of a device that you'd like to communicate to the people who are listening to this? Yes. Even though I didn't have a choice

in the matter and I had that rock bottom moment that forced me to figure it out, I will say that in my career now over the last 11 years, I've learned that even when I've thought something was perfect and I had the perfect setup and the perfect plan and the perfect everything, there's no such thing. And the next week, I'm still going to be tweaking and tinkering and iterating everything anyway. So if that's you and you are sitting there going, well, I need to have X amount of dollars saved first or I need to have this whole perfect plan in place and know exactly what I'm doing before I take any leaps, please, please trust yourself more. Trust that you will figure it out as you go. You

will always figure it out. You're figuring out every single day of your life. You are still here and you are still breathing. And I think that's enough evidence. Trust in the evidence that you have about yourself of all of the hard things you have accomplished and the things you know to be true about yourself and the things people thank you for. That's real evidence of your own capability. and I hope you learn to trust that. I love that. Thank you, Ash. Where can people find you if they want to hear more of your wisdom?

Oh, the middle finger project. Go to the website. The website has everything on it. It's the hub. It's got the book. It's got really fun. We're doing a new quiz with our quit your job store called Should You Quit Your Job? We've got all sorts of resources if you're in the process of doing that or thinking through.

Even something as simple as writing a really beautiful resignation letter all the way to learning how to make your first $100,000 by selling your ideas to other people or then scaling a business and going forward and never having to rely on someone else for your livelihood again. I love that. Thank you for sharing your story, spending this time with us and creating something as amazing as the Middle Finger Project. And thank you for taking that badass Polaroid. Thank you, Paula. Thank you so much. It's been my pleasure. Thank you, Ash, for sharing your story. What are some of the key takeaways that we got from this conversation. Here are five. Number one, money is important.

It will bring you security and options, but it will not bring your life meaning. And I realize that's a duh statement, but it's helpful to hear that expressed so poignantly in the form of someone's story. Ash spent the first 20 years of her life striving to join the middle class. And once she got there, she had so many more options and so much more security than she had when she was living. in a trailer park. But she quickly found that more money didn't equal, more meaning, more purpose, or in her case, even a sense of enough. I went to the Sleepy's mattress store and the guy gave me a $5,000 mattress on credit. Like what? Why would I ever do that? I would never do that now. And I made bad decisions because there was a part of me, I think, psychologically, that felt like I

deserved it. And it's completely understandable why she would have felt like that. She'd worked so hard to get to the point where she was. But the career, the money, the $5,000 mattress and the lemon pepper chicken, none of it translated ultimately into meaning. And that led to key takeaway number two. There's a difference between happiness versus meaningfulness. Happiness as the study show is about getting what you want. So, okay, great, I got it. I can make lemon pepper chicken now.

But meaningfulness is a little different. Meaningfulness is about getting what you want, the things you should be grateful for, and also expressing and defining yourself while you do it. Another way to think of the distinction between happiness versus meaningfulness is the distinction between pleasure versus purpose. You may get pleasure from eating a nice meal, but it doesn't infuse you with a sense of purpose. You may get pleasure from renting a luxury apartment with gorgeous hardwood floors and floor-to-ceiling windows. It's nice. It's a nice life, but it doesn't give you a sense of purpose. There must be something beyond that.

And as Ash points out, there is a difference between being grateful for what you have versus being deeply gratified by what you have. And so that is the second key takeaway. The distinction between pleasure and purpose, between being grateful and being gratified. And so Ash was then faced with the question, what next? How does she iterate her life into something even better?

And that leads to the third key takeaway. Your creativity is one of your strongest assets. Listen, I've had to get everything that I have my entire life from being creative. It's the only way forward for me. It's funny because in our interview, Ash said this line almost offhandedly. Listen, I've had to get everything I've had in my entire life from being creative. She said it casually, as though it were the most obvious point in the world.

And yet I found it to be quite profound, creativity was her path forward. Many people think of creativity as something that is at odds with security. In fact, creativity, in Ash's example, was the enabler of security. And so that is the third key takeaway, creativity, and its close cousin flexibility, are sources of security and tools for upward mobility. Now, in Ash's story, as she began her journey upward, it was not one straight, pretty line. It was a volatile ride, and at one point she found herself once again hitting rock bottom, sleeping in a Kmart parking lot. And her story about that leads to key takeaway number four. Don't be afraid of rock bottom.

If you have the privilege and the luxury of hitting rock bottom, it is the best thing that will ever happen to you. Because when you have to sink or swim, you will swim every time. And you can't say the same thing about when you're just living a very comfortable existence day by day. You are smart, you are strong. And if you hit rock bottom, if you find yourself in a sink or swim position, you will swim. And that leads to key takeaway number five. final one of today's episode. Trust yourself. Trust yourself more. Trust that you will figure it out as you go. You will always figure it out. You're figuring out every single day of your life. You are

still here and you are still breathing. And I think that's enough evidence. Trust in the evidence that you have about yourself of all the hard things you have accomplished and the things you know to be true about yourself and the things people thank you for. That's real evidence of your own capability, and I hope you learn to trust that. Creating spreadsheets and contingency plans and plan B and C and D and E, those are great. It's absolutely important to think carefully and critically about any major move that you're going to make because it has a lifetime of consequences. But make sure that you are not using your spreadsheets as an emotional blanket. Planning is fantastic, but make sure that you

are not using the active planning as a substitute for confidence. Because that powerful combination of planning plus confidence will take you further than you can imagine. But the foundation of that has to start with trusting yourself. And leaning into your creativity, embracing flexibility, and following some of your most dangerous or unconventional ideas. Those are five key takeaways that came from this conversation with Ash Amberge. If you want show notes that have a written synopsis of these takeaways and a summary of her story. You can get that at Afford Anything.com slash episode 242, and there will also have links to her website, her social media, and her book, The Middle Finger Project.

Again, all of that is at Affordanything.com slash episode 242. If you want to talk about today's episode with the awesome people in our community, head to Afford Anything.com slash community. We have a super active group that talks about podcast episodes, talks about other issues and topics that catch your interest, whether that's entrepreneurship, side hustles, quitting your job, paying off debt, early retirement, investing in the market, rental properties, any topic that you want to know more about, you can find people in the community to bounce ideas off of and ask questions to. And plenty of people have organized into tribes based on shared qualities like being in your 20s or your 30s or your 40s,

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Thanks so much for tuning in. My name is Paula Pant. This is the Afford Anything podcast. If you enjoy today's episode, please share it with a friend or a family member. That's the single most important thing that you can do to help spread the message of living your best life. Make sure that you hit subscribe or follow in whatever app you're using to listen to this podcast. And while you're there, please leave us a review. Thanks again for tuning in, and I will catch you next week.