Quit Your Job, Become a Writer With Ash Ambirge, Author of The Middle Finger Project and Leader of Mayhem for Good.

ASH, author of THE MIDDLE FINGER PROJECT and founder of www.themiddlefingerproject.org, and my freaking hero, sat down to talk with moi and the Tell Tell audience about how you can create the #smallestsidehustle possible, sell your book without any handouts, and start living in a way you really really want.

[Trigger warning: cuss words occur. Be forewarned.]

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Kallie Falandays: Hey guys, we are here to talk about The Middle Finger Project, the book that reminds us all that we don’t have to ask for permission to trust our most dangerous ideas, and we should ask ourselves to do what feels the most like self-respect. Damn, I feel that. This is written by the one and only Ash Ambirge, hero of women and leader of mayhem for good. I hope I pronounced your last name right. We are so happy to have you on.

Ash Ambirge: I like leader of mayhem. Can I just put that on my bio from now on?

Kallie Falandays: You should add that to your CV.

Ash Ambirge: Adding it. Done, done, done. Thank you. Thanks for having me. Yay, Tell Tell!

Kallie Falandays: So I have been following you forever, and I just want to caveat this with the fact that I did not start taking my business seriously until after reading your 25 to 25 K emails.  And then shit blew up. So I’m eternally grateful for you. Also, I forgot to tell you, check your mail today or tomorrow, a surprise is coming.

Ash Ambirge: Oh my God, I love that. Thank you. Whoo!

Kallie Falandays: Yes. I want to get into this, because we only have 30 minutes, and I know that everyone listening is dying for me to ask this one question, which is, how can I make money writing? And I want to hear what is the single lie that you want to shut down right now about making a living from writing? Is it really as glamorous as people think? Are there jets involved? Do you need a degree? Is there champagne? What’s up?

Ash Ambirge: Oh my God, I want to talk about all of those things. Oh, I love all of those questions. Well first of all, there’s definitely champagne, that is in your future.

Kallie Falandays: Does that come before or after a Penguin book deal?

Ash Ambirge: All of the above. I mean, we’ve been working with Penguin for two years now on this one particular book. So since I signed the contract in March of 2018, it is now almost March of 2020, and I’ve been drinking champagne the entire time, so that’s been great. I do not have a degree in writing, so I think we can shut that one down right away. I did a dual Bachelor’s in Communications and PR, which I will say is kind of close, and Spanish, and then I did a Masters degree in Linguistics, and I haven’t used that on a CV a day in my life. No one has ever asked me if I have the qualifications in that respect. No one’s ever asked me, “Well, about that Masters degree in Linguistics.”

Kallie Falandays: Right. As if you would need that to get a book deal with Penguin, which by the way, how the hell did that happen?

Ash Ambirge: Oh, girl. I mean, there’s so many things. If you’re going to be a writer, I think that all of us have that. If you’re a writer, you have that wet dream of publishing a book. It’s just a thing, right? Have you ever met a writer that doesn’t want to publish a book?

Kallie Falandays: I’ve met non-writers who want to publish books. So I think everybody’s… I think it’s on the bucket list, you know?

Ash Ambirge: It is, there’s something about it that’s so cool. There’s so many things to say about this, but I honestly would say that in the beginning, I thought that I had to have those things that we were just talking about. I thought that I did have to start by pitching different newspapers and magazines, and build my portfolio, and have these different pieces that someone could then reference. And that is the traditional way of doing things, and that’s still what a lot of people are under the impression they have to do in order to start a writing career.

And I’m here to say that I did things a bit differently. The way that I started was by realizing and understanding, one day I had this just giant realization that, geez Louise, the New Yorker is cool and all, but I don’t really need them to tell me that I can write, because all I have to actually do is sit down and write, and I can still publish that publicly online. I can make a little book, I can do whatever I want.

There’s no one stopping me from doing that, and so that’s what I did, and I started writing 11 years ago now on the internet for myself, sharing my own ideas, and that is how my publisher found me, that is how my literary agent found me, which happened first, and that’s how every single client I’ve ever had has found me and how I built a business. I’ve never actually gone out and taken out ads, or pimped my resume out. It’s been all through inbound content marketing, and just having the courage to write about what you think.

Kallie Falandays: Yeah. And while you were doing that, I imagine you were doing loads of other things to make money. So before the money was coming in, I know a lot of people think like, “Okay, fuck it. I’m going to quit my job and I’m going to become a writer,” but I don’t know if it always works like that. Can you talk a little bit about that? What were you doing while… I mean, I know you weren’t just waiting for leads to pour in, so what was that experience like for you?

Ash Ambirge: Yeah, no. I mean, gosh, the way I did it is not the right way to do it. I’m impulsive. I have a hot streak that runs through me. I get very, just spontaneous in the heat of the moment when I want to do something, I just go for it, and I absolutely did that. I did it without thinking through the money piece. I made some really poor financial decisions. In my new book, you can read all about that. It was really, I mean, at some point I found myself sleeping in my car in a Kmart parking lot because of those decisions.

So I did it in a way that I don’t know that I would recommend, but what was great about just doing it without any regard for anything else, is that when you are in a position to sink or swim, you are damn well going to swim, and you’re going to figure it out, and I don’t think that you will figure it out as quickly as you would if you had this other job going on and you had not as much time, but when you are left to your own devices and you’re the only thing you have, you make it work. So for me, that was great, but the internet was the key component to that. I had to stop looking for leads here in Philadelphia, and I had to realize that by writing online, I was attracting people who wanted more of that, and those were the most obvious people to say to them and say, “Hey, here’s how I can help you. Do you want my help?” And you simply make an offer to the world. And you show up and make it.

Kallie Falandays: And you talk about that all the time, and even before this in your blogs, about making an offer to the world, and it sounds like this wasn’t something that you were born with, right? You weren’t like, “Oh, I’m going to offer my skills to the world, and they’re going to love it,” and for those people who are sitting here thinking like, “Yeah, Ash, that would be great, but I have bills to pay, and kids and they’re crying.” I mean, where’s the balance? How do you know when it’s essentially time to quit and do your own thing, and when maybe you need to stick with it?

Ash Ambirge: Right. Well listen, I just made this quiz the other day called, Should you Quit Your Job? And in conclusion, all of the responses that you could possibly get, all the results, they all effectively say right at the beginning, listen, first of all, if you’re taking a quiz called, Should you Quit Your Job, you’re probably not wanting to be with that job anyway. So I really feel very strongly about the fact that if you feel any level of dread right now in your current position and you want to go follow your fucking dream to be a writer, you absolutely need to do that. This is a very real emergency. This is your life. Yeah, this is really, really important. So I think there’s that. But of course, we have practical considerations like children, and mouths to feed, and food. So what I would do if I were starting over again, I would absolutely figure out what is the one thing, what’s my edge? What am I great at? What’s the one piece? I mean, writers come in all different shapes and sizes.

So what are you better than anybody else in the room at when it comes to writing?

And I would double down on that, and I would start my little website, and I would make that one singular thing the focus, and then I would simply find one person that I could sell it to. Just one, that’s it. I would not worry about things like Instagram, and Twitter, and starting this whole business, I would start the smallest side hustle in the world. I would just try to find one person I could sell that to, whether it’s the interior designer who comes over to your house and she’s starting to talk about her website, and realizes that it’s really hard, and you offer to help her, I don’t care who it is.

You make an offer to help somebody do the thing that you’re really good at, and you start there, and that’s it. You sell it to one person and once you do that, you all of a sudden see that it can be done, and it gives you this other level of confidence that you needed to now sell it to two people, and ask somebody else. And next thing you know, you have a legitimate side hustle and you’re spending way more time and having so much more fun with that than you ever would be at your day job, and one thing turns into the next, and then you’re doing it full-time and holy shit, how did that happen?

Kallie Falandays: Yeah, absolutely. Make that one ask. And I love that you said that. You’ve said this before too, in one of your emails series, which is just ask two people. Ask one person to connect you with someone. So it’s these little baby steps, it sounds like, that we can do that actually give us the life that we want. It’s not like, “Oh, tomorrow I’m going to wake up and be a gajillionaire,” which like, “Please universe, if you’re listening, make that happen,” but you actually have to put in the work, and people think like, “Oh, they were lucky or they got a big break.” But time and time again, these big breaks seem to come after a lot of late night edits, and a lot of unglamorous parts of writing. Can we put a mirror to that for a second and talk about those times?

Ash Ambirge: Oh yeah. Listen, I have been waking up and writing for three hours a day, every day, every morning for years, and years, and years, and years, and years, and years, and years. I did that same process throughout the book writing process, I do it now. I did it for an entire year before I sold anything on the internet, before I even tried-

Kallie Falandays: Wait, wait.

Ash Ambirge: I even tried to sell.

Kallie Falandays: Repeat that for everybody. Can you say that again?

Ash Ambirge: Three hours a day, every day, writing every day for an entire year, before I even… I didn’t try to sell myself. I was just talking out loud and sharing my ideas, and at the time, my side hustle was going to a Barnes and Noble and tutoring someone in Spanish and English. I mean, that was what I was training to do was linguistics, right? So it really took a lot of time, and that’s why it’s such a labor of love at first, and if you are doubtful that you really want to do that, then you shouldn’t do it, because it’s really going to take up some time to be successful. And there’s nothing wrong with that, it’s great once you find it, but Jesus. Everyone looks at me like, “How did you get this book deal? How are you-” Jeez, I’ve been doing this for 11 years now, for three hours a day, minimum.

Kallie Falandays: People come out like, oh, overnight sensations, but yeah, you don’t see the times where they were working at shitty bars, or busting their ass writing on their own for years and years before. It’s not just going to happen, and I’m really glad we’re dispelling this myth because it’s one thing where people say, “I just want to make it,” and it’s like, it’s not about making it, I think it’s just about doing the work.

Ash Ambirge: Yeah. On the same token, I don’t want that to discourage anyone either, because you hear 11 years and three hours a day, that sounds ridiculous. That’s how long it took me personally to get to this massively awesome book deal, but terms of me just earning enough money to… I mean, I earned in eight months, my first eight months selling my services on the internet as a writer, I earned $103,000 after just putting in that one year of blogging.

Writers are the best poised in the world right now to run the entire economy. There is no such thing as starving artists anymore. The entire internet runs on words and if there’s nobody there to write them, we’re all in trouble. So writers have no idea how much power they have and how much opportunity there is, in particular when it comes to creating content that gets attention and is fun, and I know that there’s a lot of literary people who look down on things like content and copywriting, but content can be just a wonderful way to have fun and be creative, while still doing something that makes business sense for another person who’s willing to pay you a lot of money for it.

Kallie Falandays: Oh, hell yeah. That’s why I do both. I mean, I think it’s a brilliant way to mix that creativity and pay the bills, and buy a Smart TV or whatever the hell I want.

Ash Ambirge: Yes!

Kallie Falandays: That’s what you do. And I like this idea too of promoting your work, and you talked a lot about, there was a section where you talked about how even Brad Pitt has to promote his work, and I think there was an old blog. But when people are put… once they do the work, let’s say they have this book and they want to put it out into the world, and maybe it’s self-published. What are some things that they can do to get people excited about it?

Ash Ambirge: Oh my God, that’s exactly it. They say that the real work starts once you finish your manuscript, and they were not lying about that, let me tell you what.

Kallie Falandays: You need more champagne, huh?

Ash Ambirge: It’s fascinating, but at the same time, coming from a background in PR, I do understand how this industry works, and I think it’s so great because so often writers in particular, will sit there and think like, “Well, who am I? I have to be picked. I have to be picked out of a crowd of people to all of a sudden, have an interview on CBS, or be picked to be in this magazine, or whatever it is out of all these other writers.” And so, the process of that is so daunting that sometimes, they don’t even try.

But you have to remember from a business standpoint, that these outlets, any outlet in the world, from now we’ve got magazines, you’ve got online media all over the place, we even have an Instagram account. They need content, they need things to write about. And so, that becomes then your number one mission, is how can you take what you’ve written and what you’ve created, and look at it from the perspective of, well, why does this matter for any of us? And I think that’s the important part about writing a book. I think you have to ask yourself that question when you’re writing too.

It’s easy to want to write about your story. It’s a very ego-driven activity, but you have to constantly go back and say, “Well, who cares? Why does this experience that I had matter for anybody else, and what does this say about us as human beings?” Because that’s what people care about, and that’s what you can sell to a magazine or to any kind of outlet who’s looking for that content? It can’t be about you, it has to be about making a greater statement about who we are as people and what we’re doing in this world.

Kallie Falandays: Yeah, I love that. And that’s what you connect with. So you hear all these people say, “Oh, I have to make an Instagram account, and I have to get on Facebook and whatever” but it’s really just about that simple thing, why does this matter and what does this say about us as human beings, and connecting with those people that care about that thing.

Ash Ambirge: Yes. It’s how you elevate your work as well, and you go from just being this like, two cents a word, random freelance writer that no one ever heard of, to taking your ideas and branding them now, and having something that, geez, if… Gosh, Philadelphia Magazine, I’m here in Philadelphia, they just called me yesterday and they want to do an interview, and that’s wonderful. I love Philadelphia Magazine, but that wouldn’t have happened if I was just like, “Hi. So I’m a writer and I wrote a book, and it’s about me.” But-

Kallie Falandays: It’s also true. I mean, that’s not a lie.

Ash Ambirge: I mean, right? But I’m making a bigger statement through the lens of this story, and how I got to where I am today. And so I think that that’s how you have to think about your work from a promotional standpoint, no matter what you’re doing, and use that as your angle, no matter what you’re pitching and what you’re talking about, and all of a sudden, you’ll be the most interesting person in the room because you’ve now given other people some sort of gift, really, about what your experience has meant for you and how it can help them.

Kallie Falandays: Yeah. I think it’s really all about packaging, because like you said, I mean, yeah saying, “Oh this is my book and I wrote it, and it’s about me,” it is true. But when you position it as a gift to the world, as something that people need, which is also true… it’s truer about what it is, because I think people don’t ever write about themselves. I mean, sometimes they do just to stroke their own egos, but usually there’s a larger reason and if we can touch that, I think you become magnetic.

Ash Ambirge: Yeah, yeah. And it’s easy to, when you are starting out as a writer, to want to take orders from people and wait for someone to tell you that you’re good enough to write the article, and tell you that they’ll pay you for this thing and tell you whatever. You’re kind of waiting around for that, but a large part of being a modern writer who is able to successfully monetize, is about personal agency and taking personal responsibility over your own ideas and saying, “Well, here’s what I want to bring to the world, and here’s what I want to explore and discuss, and here’s what matters to me, and here’s what I think will matter to other people who are going through that, or who think similar things,” and having the courage to completely go opposite of what we normally think of when we think about becoming a freelance writer, and trying to bid on these other projects, you start your own project.

Kallie Falandays: Yup. Yeah. I love this, and you write about creating your own version of success. And I’ve been creeping on you on Instagram, I’m checking out you were doing jewelry making stuff in Scotland, right?

Ash Ambirge: Yeah! I love Scotland. Oh my God. Yes, cross-train that brain.

Kallie Falandays: Yeah. Was that amazing?

Ash Ambirge: I would do that a thousand times over again, yes. We’re always looking for new and unique, interesting experiences to go and try.

Kallie Falandays: And when you do that, do you keep your normal schedule? Are you still writing in the morning, or has that shifted now that you have this book with Penguin? What does your kind of daily experience look like now?

Ash Ambirge: Honestly, when we travel, I stick more to that schedule than ever, because I need to get all the writing done first thing in the morning, and I need to be done by noon, so then I can go out and explore wherever we’re traveling all afternoon. And so yeah, yeah, it’s really important to me to get it done, because I don’t want to have to stay inside all day.

Kallie Falandays: Yeah, that’s a great thing to think about, because when you’re creating your version of success, it’s about going on that adventure and doing the things you want, but also doing the things you need to do to get there. So I want to focus in on that idea that again, it doesn’t just happen out of the blue. There’s no fairy godmother. You are your own fairy godmother, and I love it.

Ash Ambirge: Ooh, yes. I love that. It’s so true. Yes. I love that phrasing.

Kallie Falandays: Yeah. And you wrote, “Every good idea is offensive to someone,” and I want to talk about some ideas that offend you. What are some times where you’re just like, No, this idea is not… It doesn’t taste good to me?”

Ash Ambirge:  The idea that I’m supposed to have children really offends me.

Kallie Falandays: Yes.

Ash Ambirge: Greatly. Well, we’ve all been there I think at some point where no matter what side of that, you can’t win with children. If you have them, you’re getting told all sorts of things, if you don’t have them, you’re getting told sorts of things. That’s a really hot topic that offends me greatly. Religion really offends me. Microbladed brows really offend me these days. I’m like, are we sure this is a good idea? I feel like this trend is going to change eventually. But it’s true, every good idea is offensive to someone, and it has to be that way because good ideas change things, and if it’s not changing something, then it’s not really a new idea. So I think we have to think about it that way. And also, my gosh, I found the best example of this the other day, for the writers out there who are really nervous about putting themselves out there and taking a hard line on something, and really branding yourself a certain way, let me tell you, I had a girlfriend staying with me and she was on Bumble, the dating app. And she was reading out loud some of these profiles, and I was dying. I was so excited about it, because some of these men were straight-

Kallie Falandays:  Probably a writer opportunity right there.

Ash Ambirge: Oh my God, it was wonderful, but they were straight up like, no Trump supporters, no… I don’t know what other things they said…some other term that they used that was some kind of an acronym that I was like, “What does that mean?” And she told me, and now I can’t remember, but they were so forthcoming about what they wanted because they have to be, and she was so much more attracted to the people who are straight up like, “Yep. Sorry, no Trump supporters here,” kind of a thing. So immediately she was like, “Oh yes, okay, I’m going to match with them,” whereas if you just got on and you were like, “Hi. Well, I’m a guy and I’m about 5’8″.”

Kallie Falandays: Hi, guy. You’re a guy.

Ash Ambirge:  “I’ve got a penis, and I’ve got a job,” so.

Kallie Falandays: Right.

Ash Ambirge: It’s really hard to tell if you’re going to be a match, and I think the same thing applies to modern day business, especially as writers, because everyone tries so very hard to not be offensive and to keep it vanilla for everybody, so no one’s offended. But as a result, you end up basically being the guy who has a penis and a job, and very-

Kallie Falandays: Right, you’re nobody.

Ash Ambirge: Right, you’re nobody, you’re everybody. I mean, you don’t stand out at all.

Kallie Falandays: Yeah. And I think that also goes back to that idea of trusting in your own ideas and trusting… you write about trusting in your most dangerous ideas, and kind of going to extremes in order to strengthen your self-reliance, and I love it, and I’m wondering how someone can tell if their dangerous idea is just reckless, or if it’s like a great idea. Is there a thermometer we can use to tell the difference?

Ash Ambirge: I love the idea of having a thermometer for a dangerous idea. Unfortunately, I don’t think so. I think we have to engage in trial and error, and I think we have to be willing to be wrong. I think that’s okay. I think a lot of people are worried about wasting time. They’re worried about something not working out and then, “Well, what about all the time I invested?” You got to get really comfortable with spending time and spending energy, because that’s really the part that it becomes meaningful. One of the things I talk about in this book is the difference between happiness and meaningfulness, right? The research shows, happiness is really about getting what you want, but meaningfulness is about getting what you want, and expressing and defining yourself while you do it. So I think that right there is the piece that I would look at for any kind of thermometer. If I had to put one down and I would say, “Okay, well, where am I going to be able to express and define myself the best with any one of these opportunities that I’m potentially pursuing?” Because that’s where the meaning does show up, and starts to feel like you actually have some purpose in this damn big, giant, weird world.

Kallie Falandays: Even if you get what you want, I think so often people chase that, and we see it a lot in business, and you’re chasing this idea, and then you get it and you realize you don’t really want that. So if you search for what you want instead of searching for meaning, I think you’ll end up empty every time.

Ash Ambirge: Mm-hmm (affirmative) mm-hmm (affirmative) I mean, all of us want a salary, right? But there’s a million ways we can go about doing that. And that becomes the question, well, what’s the way that feels the most like you, that you enjoy doing, that does allow you to express and to find yourself? Go after that, do that. That’s the dangerous idea right there. We need you to go do those things.

Kallie Falandays: Yes, I love this. This was amazing, I don’t want to take up any more of your time, but I do want to tell people that they can find The Middle Finger Project wherever books are sold, and you’re in airports now, is that right?

Ash Ambirge: Yeah, it’s in the airports! It’s so exciting. This is a more selective thing than I ever realized.

Kallie Falandays: Oh my god, to be in an airport is, I mean, I think you reached, I don’t know what’s next.

Ash Ambirge: Right? Space station. Yeah, the International Space Station, please. Yeah, that was really exciting. We’ve been hearing from, even Australia confirmed the other day that they’re going to be stocking the book in all of their airports and their train stations, and they’ve made it like their book of the month of March and I’m like “Wow, that’s so cool!”

Kallie Falandays: This is awesome, because you had an idea. I mean, this is literally what you were talking about, and you’re just showing that you did it, and then that’s how you are doing it. You’re so meta right now, you’re just rolling in on yourself, I love it.

Ash Ambirge: Yeah, yeah. The book writing process has been one of the greatest, greatest gifts that I’ve ever experienced. It’s been so awesome. Everyone out there, I mean it is like the stuff of dreams. Once you get to that point, it’s well worth it. It’s worth all that effort and that energy, and I will tell you what, I signed with my literary agency in October of 2015. We did not sign a contract with Penguin Random House until March of 2018. So even when you get to that level, it is still about trial and error. We trial and errored so many different versions of sample chapters before we were happy putting them together into a proposal for the actual final package, and that’s just a part of it. So I was trialing and erroring my writing all of those years before that, but even when you reach that level, it’s still about that. So get really used to being wrong, and get really used to looking at yourself as if you were a chemist and you were running experiments, and if something goes wrong, it’s not your fault, it’s the thing you’re experimenting with, and it’s that that you need to tweak and adjust, and keep changing until you get the right dynamic.

And you will, you will, you’ll get it, you’ll get there, and it’s so exciting when you do! And it makes it so much better, because now you’ve expressed and defined yourself while you did it.

Kallie Falandays: Yes. Oh my God, I need to clap for that.

Ash Ambirge: Whoo!