Sometimes breakups are reduced to something that you feel you need to win to emotionally survive and move on. This reduction can only take place if you are involved with a toxic person. Toxic people are selfish, empathetically bankrupt, and they have a limited relationship with reality but breakups aren’t won by game-playing or vilifying your ex. They’re won by realizing that winning is losing a partner who is proven to be a dead-end. 

In her new book, Win Your Breakup, Natasha Adamo presents the opportunity for a life with relationships that you don’t have to tolerate and eggshell-walk your way through. It’s a life in which your ex regrets the day they ever decided to breach your trust and break your heart, a life in which those who took you for granted wish you could find a way back into theirs. In this life, you can choose to walk away from toxicity. No more trying to be the person someone may want, may commit to, may be honest with, and may treat with respect. This life is about to be your own.

Hey Listeners, my name is Drew Appelbaum and I’m excited to be here today with Natasha Adamo, author of Win Your Breakup: How To Be The One That Got Away. Natasha, thank you for joining, welcome to The Author Hour Podcast.

Natasha Adamo: Hi Drew, thank you for having me.

Drew Appelbaum: Why don’t you kick it off for all the listeners and maybe just give us a brief rundown of your professional background?

Natasha Adamo: My background is anything but professional, you know? I am not licensed or certified in anything. My education does not come from a classroom, it comes from my own life experiences, it is experiential. I went to college but I got a degree in English and Philosophy.

I’ve never taken a psychology class or anything like that and I don’t say that in a braggadocious way whatsoever. I have the utmost respect for the professional community and I’m so honored to coach psychologists, psychotherapists, psychiatrists, certified life coaches, and counselors all around the world who many are clients, many refer me to their patients. But as far as my background goes, I started about half a decade ago — gosh, it’s crazy how fast the time goes — about five years ago. 

I set out to — it wasn’t about making money. It wasn’t about being an entrepreneur and crushing it every morning and hustling and all that. It was just about creating a space that answered every question I ever asked Google at my lowest, most confused, and lonely states that I could not find an answer to in regard to self-help, relationships, breakups, and dating.

I started a blog and there are so many people in the arena who have a lot of money and are able to get their work out there on all the search engines. I, unbeknownst to everyone in my life, was Uber driving at the time, doing my best to make ends meet and make a little extra money to put into this website, to this business and because I didn’t have the extra resources to hire a search engine optimization company and marketing and all of that, I’m pretty much self-taught. 

I did the research on what people were searching for as far as keywords and phrases in regard to self-help, relationship advice, breakups, dating advice and I would just consistently deliver what people were looking for. And when I was extremely low, extremely confused, and very depressed, I would look up things and the title would promise what I needed answered but I wasn’t getting the meat of what I needed. Basically, I set out to give everything that I wish I would have had at my lowest points and that still, I wish I had and it’s served me quite well.

Wanting Revenge After A Break Up Isn’t A Bad Thing. Use it To Your Advantage.

Drew Appelbaum: Why was now the time to share the stories in the book? Did you have some free time on your hand because of COVID? Was there an inspirational moment out there? Did enough people tell you, you need to just write down this wisdom?

Natasha Adamo: The book does not have any stories. It does not have any case studies and that is why I actually ended up going with my incredible publisher, my amazing publishing team at Scribe. I was told by many traditional publishers who rejected me — it’s not like I walked away from some big publishing offer or deal but they said, “You need case studies. This book will never survive without case studies.” 

I thought to myself, I coach telephonically. I coach clients in now 31 countries around the world, I have in-person clientele as well and I’m in the proverbial trenches so to speak every day. I know what people are wanting, I know what they’re needing and if I was having a heart attack, God forbid, and I went to the hospital, I would not want the doctor to show me case studies. I would want immediate defibrillation or whatever was necessary to get my heart back into a rhythm that is conducive to health and living and longevity.

As far as knowing when to write the book, there wasn’t really a time that hit me that I said, “Okay, I need to do this right now. I need to tell my story.” In fact, this book has absolutely nothing to do with me. I made it all about the reader. It is a gift of, again, just how my blog started, everything that I wish I would have had and everything still to this day at times, I wish I had.

I saw a really big hole in the market as far as breakups go and relationships, but really focusing on breakup books, breakups have really been categorized as something running, mascara running down the face, empty ice cream carton, stuff like that, and the advice, it just never resonated with me. We live in a time where – I don’t think there’s necessarily anything wrong with this but — if you’re feeling any kind of feelings of spite, that’s a bad thing, you know? 

We’ve got to mantra it out, we’ve got to meditate it out, we’ve got to kumbaya it out but some of my most incredible accomplishments and work and even psychological steps that I’ve taken, and I am doing my imperfect best, I definitely don’t have it figured out but those things have come from using feelings of spite to my dignified advantage after realizing I invested in a relational Ponzi scheme.

Whether that relationship is romantic, professional, scholastic, in school, familial with family or that relationship be with a bad habit, needing to break up with the cynical audience in my own head, a substance; whatever it may be I wrote this book because when you try to please everyone, you please no one. 

I wrote this book from the perspective of a straight female in a romantic relationship. I wrote it in regard to romantic relationships because the only perspective I can write from is my own and my own sexual orientation and number two, it’s written in the context of romantic relationships. However, it can be applied to as the demographic of my clientele goes. It can be applied to any age, stage in life, orientation, gender. 

It’s not just winning your breakup with a toxic ex in a romantic relationship. It’s winning your breakup with anyone who is toxic or anything that is toxic. That was very important to me and that’s kind of how it came up. My dear friend Greg Behrendt, who wrote, He’s Just Not That Into You, it’s called the breakup because it’s broken.

He was the only straight male script consultant on Sex in the City for multiple seasons. He has sold, I believe, over five million books. He was really integral in this whole process and he kept saying — because I was really taken down by just trying to get this book picked up by a traditional publisher and working with an agent — He said, “You know, Natasha, you don’t need to change your voice. In fact, you don’t even need a developmental editor. I will look this over for you, I’ll step in as an editor but you don’t need it.” 

He said, “But let’s do this, you can do this on your own.” He has not written 20 books but I don’t know many people who have sold as many as he has and he has a way of redirecting a writer when they need to be redirected without disempowering them which was really important because I was very fragile at that time after writing book proposals and not getting calls back and stuff like that.

As far as the book goes, it has nothing to do with me. This is all about the reader and it’s really how to use — how to stop being ashamed of feelings like spiteful feelings, like wanting revenge, all of that, and how to spin it into an advantageous situation for you.

Drew Appelbaum: Now, when you decided you were going to write this book and you had these proposals, in your mind, who were you writing this book for? Is this for folks who are newly single? Is this for folks out there who just can’t get over that ex or is it somebody who doesn’t recognize, or maybe they’re starting to recognize, that they’re actually in a bad or toxic relationship right now?

Natasha Adamo: This book is for anyone who was in a relationship with someone or is in a relationship with someone and sees that it’s ending or is going through a breakup with someone who is toxic. I personally define toxic as anyone who gets validation by exploiting your hunger for theirs.

I didn’t really — I know they always say, have a specific person in mind. I mean, I didn’t really have anyone in mind other than myself as far as when I was there, what I would have needed. Fortunately — and I guess, unfortunately, definitely — this stuff, it doesn’t discriminate against anything. The state of the economy, age, gender orientation as I’ve said.


Till the end of time, people will get screwed over by other people and these people who screw them over are at war with themselves. They’re unhappy with who they are. You can go two ways when you’re living a life of misery and you’re avoiding the proverbial mirror. You can either be a doormat to others and internalize their selfish behavior or you can wipe your dirty emotional boots on the doormat. Like attracts like ultimately. That’s what I would say to that question.

Drew Appelbaum: I want to dig into the title of the book here which is, Win Your Breakup. I want to ask you, why do breakups sometimes or even always just feel like a game, and is it always this way? Are there actually ever clean breaks?

Natasha Adamo: There is of course clean breaks when you’re in a relationship of any kind with someone who is psychologically grounded and emotionally intelligent. The title, Win Your Breakup will only resonate with someone if their breakup has been reduced to something that they feel like they need to win in order to emotionally survive and move on.

That reduction can only take place when you are in a “transactionship” or relationship with a toxic individual. I created basically a way to check all of those superficial, really, sometimes kind of shameful desires that we have: I want to make my ex regret losing me, I want to get revenge, I want to get even. I always get even in life. I always get even but not in the way you would think. 

I always get revenge but absolutely not the way that it sounds and as far as winning goes, I wanted to share what I and so many of my clients that I have helped achieve, and really, they’ve done it on their own. I don’t give anyone the tools, we’re all born with the tools, we just lose access to the tools on our tool belt.

But you know, this book teaches the reader how to win their breakup with a toxic ex without reducing anything to a game, without playing games, without stupid drama, without having to disembark from the dignity and the standards and the self-love that being in a relationship with this person drained you of. 

Drew Appelbaum: Now, you talk about in the book a lot and you definitely guide against it but should you ever get back with an ex, and does it ever have a chance of working out? 

Natasha Adamo: You know, I don’t really discuss it too much however, it all depends. It depends on the situation but generally, if someone has shown you who they are, you have to be okay with the fact that they have the capacity to do something. I mean, I don’t know, if you met someone let’s just say and they were really great but they told you that they had this history of abusing animals and they got into legal trouble for it and they set dogs on fire and kicked cats, that would have to be up to you whether – I am a firm believer in rehabilitation. I am a firm believer in forgiveness and all of that and that people can evolve and they can get better and they can change. I know I am a living example of that and I used to be incredibly toxic. However, it is up to the individual to figure out what their value system is and if they are okay with capacities. I personally am not okay with someone who has the capacity to kick the relational dog, so to speak. Hopefully, that answers your question. 

Drew Appelbaum: Yeah and I also love that you dig into in the book the understanding of how you got into a toxic relationship in order just to avoid another one. There’s two questions here; why does it happen so often that people find themselves in toxic relationships and then why are these relationships so addictive? 

Natasha Adamo: We find ourselves in toxic relationships because we have undealt with trauma from our past, our childhood — thus, we are in a toxic relationship with ourselves. We are more addicted to chaos and we define passion as chaotic, you know, hot, cold, up, down, yes, no, Jekyll-Hyde, which is really what I would define romantic love as, as opposed to linear. We get bored by linear but as Johnny Cash says in his very famous song, “Because you’re mine, I walk the line”. 

Not the quadratic equation or the triangle or the octagon, true love is linear but we get bored when we don’t have to work for something. We are taught that the harder we have to work for something, the more valuable it is. If something is in very limited supply, it’s more coveted. Well, that might be true for cars or designer clothes or whatever it may be a watch, but not things like integrity and loyalty and consistency, definitely not in character and we become addicted to it because we feel as though if we can get the proverbial cat to bark then it will invalidate the pain of our past and the people who caused that pain. 

Boundaries Become Non-Negotiable— And Easier To Uphold — When You Prioritize Yourself.

Drew Appelbaum: What’s the best way to set boundaries with an ex and when you’re trying to set boundaries and, say you have no contact rules going on, can you ever really kind of get them out of your mind with the amount of online activity and social media these days? 

Natasha Adamo: Social media, it’s just — it’s all such a swamp. It’s become, you know, never has it been easier to check up on people and never has it been harder to break up and make a clean break. As far as boundaries go, they’re just non-negotiable. They’re your non-negotiables. It’s like having — it’s like if you’re the CEO of a business, it’s like having your own terms and conditions. It is right there. 

Now, the problem with boundaries is if you don’t feel like what you are protecting has any value, you’re either going to be too passive or too aggressive or when you get it right, you’re going to feel guilty for implementing boundaries. I still have a hard time with the adult that I am. I wish I could look at the mirror and say, “You know, Natasha, you are loved, you are liked, you are beautiful.” 

If I did that today, between you and I and everyone listening, I would feel like a liar. I would feel even worse about myself. Does that mean I’m not qualified to do what I do in life? Absolutely not, it means I’m a human being who is trying her imperfect best. However, I think that it would take, all the years I spent really hating and criticizing and berating the adult that I am, it would take just as many years to undo those neuro-pathways that are very, very deep-seated. 

I have found, and I read about this in my book, that people who are on the brink of suicide, whether it’s physical suicide, emotional suicide — and if anyone who is listening is suicidal, obviously please stop this right now and call the suicide prevention emergency number in your country but — I have found that these people are some of the most compassionate empathetic and sympathetic people I have ever come across. 

It’s very fitting for not only this time of year — I’m not sure when this podcast will be published but for any time of year — one of my favorite movies, It’s a Wonderful Life, when George Bailey, I believe his name, Jimmy Stewart, is about to kill himself, his guardian angel comes down from the sky and pretends to drown in the river in which George is going to kill himself because he knows that if George sees him drowning, he will forget his own suicide carrying that out and save him. 

The one thing for me has been, even when I was at my most suicidal, even when I was at my most depressed, I would stop, drop everything if someone who was voiceless needed saving and advocation. Now, who is voiceless in society? Children, animals, and the elderly in my opinion and so whenever I saw a situation like that, I would get out of my own head and advocate. 

What has helped me is I stopped trying to love the adult that I am, as weird as that sounds and I got out a photo of myself as a child and I look at that photo and I just tell that child, “No one will mess with you today. No one will hurt you.” And I may not be able to look in the mirror and say, you know, “I am X, Y, and Z” but I can look at her and say, “You are more than enough could ever dream of being.” 

Because I see the value in her, I am able to set an example for her because that’s all I can do. I can’t speak with her. I can only lead by example and actions and I got to bed at night feeling pretty great about the adult that I am because I’ve protected her. I’ve gotten out of my own head. So, that is what has helped me the most as far as keeping boundaries non-negotiable. 

Drew Appelbaum: What impact do you hope the book will have on the reader and are there any immediate steps that you hope a reader will take and bring into their own life? 

Natasha Adamo: I hope that this breaks the chains of generational trauma. I hope that this book lets people know that it’s okay to not always have peace-y feelings, so to speak and that you can spin those into gold. You don’t have to let them define your demise. I want it to let people realize that the past can be a very, very strong and influential propellant. It doesn’t need to be a poison anymore. 

Things like fear and spite and heartbreak got a lot of fire-power. They can either be a headwind or they can be a tailwind and I don’t care about bestseller lists. I don’t care about really much of anything in regard to me and accolades. I care about this changing lives and giving back life to people who feel as though they’ve lost it and then their lives had been drained by engaging in negative and limiting self-beliefs and very toxic relationships. 

You know, not put up with bullshit anymore, become un-fuck-with-able. Just say, “All right, enough is enough, life is short.” That’s it. 

Drew Appelbaum: Now, you actually have your own website as well besides the book. Can you tell readers what you could find there and then what kind of resources are on your site? 

Natasha Adamo: Of course. I have I have my blog where I’ve got all kinds of blog posts from the beginning. I also have a few people who have written guests posts. Besides my mother’s guest post, which was incredible, and Greg Behrendt’s, just a few other people who have written guest posts. I’ve actually found them, I’ve discovered them from the help they gave to other readers in the comment section of my blog. 

We live in a time where people don’t comment on blogs anymore. People hardly read blogs and if my business hadn’t taken off in the very unique way that it did, which is another story for another time, I would have had all kinds of things going by now. I’d have a podcast, videos, this, that, but the blog really took off and my coaching business took off. On there, you can find all my blog posts and incredible guest posts. 

You can find courses, you can find a little bit more information about me and also information about working with me one-on-one and you can also find information about upcoming events, whether they’d be digital or in person. 

Drew Appelbaum: Well, Natasha, I just want to say that even though we just touched on the surface of the book here, writing this book to help people who are hurt and educating people on how not to get hurt again is no small feat. So congratulations on having your book published. 

Natasha Adamo: Thank you so much. I could not have done it without Scribe and the incredible people there. They are doing really God’s work there, allowing writers to own their own material, which is unbelievable and I did not use even 50% of all the incredible services they offer. They just merely published me and distributed me and they’re overseeing some of the marketing but they offer many services to authors and I can’t say enough about them. 

They are the kindest, most agenda-less people who are really on your side and they advocate for the author, which I couldn’t say personally with my experience in traditional publishing but again, I don’t ever want to dog on anyone’s decisions. I think it’s an incredible decision for many, many people. I was very inspired by David Goggins. We actually had the same literary agent and that’s how I found Scribe.

Drew Appelbaum: Oh yeah. 

Natasha Adamo: It’s been really great to see what he’s accomplished just by giving what he wished he had, you know? It’s an interesting thing about David. I don’t wake up in the morning thinking, “I need to read a David Goggins’ memoir,” but I do wake up in the morning and think, “Okay, I got to win my breakup.” However great or not great my book does, a lot of it is driven by this need that I see every day that people have but what he has accomplished is pretty unbelievable for a memoir.

He said many times, he couldn’t have done it without Scribe and the freedom they allotted him. So I’m very lucky to have come upon Scribe. 

Drew Appelbaum: Yeah, absolutely. Goggins’ three-year anniversary since he published his book. It’s great if you haven’t read it, Can’t Hurt Me, but let’s talk about your book. Natasha, it has been a pleasure and I’m excited for people to check out the book and everyone, again the book is called, Win Your Breakup, and you can find it on Amazon. Natasha, besides checking out the book, besides your website, is there anywhere else where people can connect with you? 

Natasha Adamo: Yeah, they can connect with me on Instagram. I’m just @natashaadamo. Twitter, I’m not as active but I am on there with the same exact handle and I do have a business Facebook. I don’t have any kind of personal Facebook or anything like that but that’s where people can connect with me. Instagram [is where] I’m definitely the most active.

Drew Appelbaum: Great. Well, Natasha, thank you so much for giving us some of your time today. Best of luck with your new book. 

Natasha Adamo: The pleasure is all mine. Thank you for having me on.