How Dorie Clark Went from Heartbreak to Writing a Bestseller

Dory, how are you today?

Hey, Terry Rice. I am good. It's so nice to be with you.

It is so great chatting with you. You are a mentor. You are a friend. If I look over my shoulder here, there are at least two of your books that you've written. I see the Long Game over here. As well as entrepreneurial. You so obviously a big fan of yours. And every time I get to chat with you, I still, like. I don't. I have, like, this fanboy moment, and it's hard to suppress. I remember the first time I met you in person. It was at a party at your friend's apartment, and I was just so, like, starstruck by you. I was, like, holding, like, two bags full of wine, and I'm just staring at you, and you're like, is that something you would like to put down? I was like, holy shit. You talked to me, like. So I'm trying to suppress my enthusiasm right now, but it's always great chatting with you.

Well, thank you, my man. And of course, I'm a fan. Right back. You were so kind to be the emcee for one of my book launch events. During the straitened circumstances that were pandemic book launches, I had, like, one thing that we were able to cobble together in New York, and it was this book talk at Saksworks, and you were so kind to run this show there for us, so I. So I really appreciated that. And, of course, you were one of the featured characters in the Long Game, so it's fun to have the chance to talk with you.

Yeah. And I was honored to speak with you there, too, and my wife let me go. Only because it was you, because it was still, like, kind of pandemicy.

It was kind of pandemic. Y. Y.

There's a slight chance I might die, but it's Dory, so she's like, okay, you can go. So, yeah. So. So thank you for that honor, but I have not even introduced who you are. Do you want to. Do you want to go ahead and do that yourself?

I. I write. I write books. The Long Game was the most recent one, and I do a little bit of business school teaching at. Formerly at Duke, now Columbia. And, yeah, I give talks. I do. I do online courses like you do, etc.

You're very humble as well, so I'm going to add that to the list. But. But, Dory, like, what's going on these days? I know you moved out of New York. You're down in Miami, but just how are things Going in general for you these days?

Things are pretty good. These days. I, I am enjoying life in the sun for sure. And I'm working assiduously to continue systematizing my business. You know, it's always, always the goal. Right. But how can you be thoughtful about building evergreen options and passive income streams? That was sort of the premise of one of my earlier books, entrepreneurial you that you referenced. And so I've been, you know, know, really working assiduously on, on all of those things. And personally, life is good. I get to spend time with my mom, who, who comes down sometimes because she loves Miami and I have a beautiful fiance, so. And, and, and two lovely cats.

Awesome. If anyone hears me say assiduously, it's because I learned that word on this podcast, so no idea how to actually use it, but. But yeah, I always learned something from you, so I appreciate it. And, you know, as you know, we're having a good time chatting right now. As you know, the premise of this show is for high performers like you to talk about a very challenging time in their personal or professional life. So I am going to open the door for you to do that now. And I'm thanking you in advance for your openness and your, Your willingness to share.

Yeah. Thank you, Terry. Should I, Should I just like monologue?

You should just monologue. I. I still have not come up with a good way to, like, transition into that. So right now we're just going to.

Jump into it and now we open the vein. Amazing. Yeah. So actually this is a good, this is a good bookend, and I like it already because it does have a little bit of a happy ending since I recently got engaged. But one of, I would say the really hardest times in my, both personal and professional Life came in 2013. There were some real highlights with that. That was the year that my first book, reinventing you, came out. So that was really exciting. And it opened up a lot more opportunities, especially around speaking or travel, international travel. So that was great. But I was coming out of a two and a half year relationship that ended literally on January 1, 2013. That is when we broke up. And it was. It was a very, very challenging time. We had just moved to New York together. We had decided to do that, rented a place, and then within like a week, we broke up. And it turned very, very kind of nasty. And I tried to be as magnanimous as I could, and I said, all right, you know, you pick. If you want to keep the apartment, I will move out, or I can keep the apartment and you can move out, like, you tell me what you want to do. And she decided that a really good way to get revenge on me was. Was not to make a decision. And so for two months, even though we were broken up and things were very contentious, we were still living together. And it was a time that I really should have been preparing for my book launch. I mean, you know how these things go. In the period before a launch, you need to be preparing things and getting your marketing ready and getting out there. And I really didn't and couldn't because I was so consumed with this extremely acrimonious turn in a relationship that I really, you know, at a certain point, that's. It's, you know, the only other one that I had had that I actually thought was going to be one that led to marriage. And so having that end was. Was really upsetting. Ultimately, I ended up moving back to Boston, which is where I had been living, and having to adjust to that. And it felt really kind of lame to have moved to New York and then have to, like, you know, be like, oh, hi, I'm back again.

And so everyone from Boston who just tuned out, hopefully you'll catch the next episode.

It was not. It was not Boston per se, to be fair, but. But, you know, to. To have made a sort of life plan and life change and then have to be like, you know, and like, you rewind and you're like, oh, actually, no, I'm not doing that at all. Felt I was. I was embarrassed and I was really, really upset at the. At the loss of the relationship and the fact that, you know, somebody that I had sort of relied on as, you know, your sort of primary emotional rock for the period of time that you were together, which had been several years, was suddenly gone. So I felt very lonely and, you know, upset about all of that in the midst of trying to, like, you know, sort of in this zombie like, fashion get through the. Get through the book launch. And then things honestly just became harder because later that year, my cat, who I was super close to, I had had him for. For 16 years. He was really my best friend. Ended up getting cancer and very quickly dying that fall. And so to go from having, you know, this. This relationship that I. That I thought was going to lead to marriage and, you know, your emotional support of this pet to not having any of that, it just felt so lonely. I was really depressed about that. And honestly, the one, two punch was. Was not fun. Probably the worst part was, was losing my pet because he was. He was just so amazing. He was such a great guy. But I'm even, you know, getting a little teary thinking about it. I mean, I went through a period, probably for about six months, where I was crying multiple times a day, just. Just really without warning, anytime I'd think about him. And so actually, that's why I decided ultimately to move back. Back to New York again, you know, sort of have a redo. Partly it was because, as I said, I felt a little embarrassed having, like, pseudo moved to New York and then having to, like, move back. But also, once Gideon, my cat, died, I. I just did not want to be in my house anymore. Like, I didn't. You know, I probably. It probably would have been a very good financial decision for me to have kept my apartment in Boston, which now is worth a lot more money. But I wanted to. I just wanted to get that shit gone. I wanted to rid of it, because I did not want one more reminder. I did not want to be in a place that I used to be with him, that he was not anymore. So I decided. I was visiting my mom over Christmas, and I. I thought about it, and I just literally decided in an instant. I'm like, I can sell it. I can get out of there. And so that's. That's what I decided to do. Fortunately, it was a, you know, reasonably hot market, and so the house sold in a. In a weekend, and it turned around pretty fast, and I ended up going back to New York. But, yeah, it was. It was a really. It was a really dark time because I felt. I felt really quite alone.

Yeah, I want to give you a break, and I just want to share some of my experiences. So first of all, thanks for sharing that. I know it's. It's. It's tough. I've lost a pet as well, and. And people don't get it until you. Until you're in it. You know what I mean? So I understand what you're saying. And what I was also thinking about as you're telling the story is, gosh, you must have been so proud to have your first book published. And it should be this amazing moment in your life, and everyone's congratulating you, and you just have this, you know, this emptiness inside, but you still have to be in front of people. And that, for me, that feels like the toughest part, because when I lost my son, T.J. i was still teaching. I was still teaching in person. This is back in the days when you taught in person. Right. So I remember one time I was in class Talking about my daughter, my oldest daughter, saying something, oh, she's running around doing xyz and someone's like, oh, I have a two year old and a newborn. Imagine if you had that problem. And I'm like, that's the problem I wish I had. That's the problem I wish I had. But like you, I had to keep on talking, I had to keep on teaching and pretending like nothing was wrong. But it was like a dagger that was just like unintentionally, you know, put in my heart. And there was a challenge because I had to become, I had to be functional. And as a result of that, I had to suppress some of the emotions. And I think that's the hardest part. Sometimes when you're supposed to be this engaging presenter who's like, you know, whatever. And you're like, I'm frickin dying inside right now. So when you were talking about still having to promote your book, book, I can imagine just like your publisher and your publicist, and everyone's like, hey, we got you booked on this show. And you're like, geez, man, I don't even want to get a bed right now. So I mean, how did you navigate that part where you're like, I don't want to get out of bed right now? Like, what was, what was that like?

Yeah, I mean, I think that a lot of it was just compartmentalization. And I think like a lot of things in life, a little bit is good and too much is very bad. I think compartmentalization is actually a very healthy skill that has gotten a bad rap in recent years. Yeah, I mean, the last few years has been the like, let it all hang out kind of thing, which I appreciate people talking about things and, you know, whatever. But it's also true that sometimes you just do have to do it. Like you, you gotta muscle through, and when you have responsibilities, you have to somehow make yourself do them. And to me, that's kind of the definition of, you know, really being an adult is like, all right, you have a thing, you're gonna do that thing. And I aspired to do that because for me, even though I was hurting a lot, I wanted to keep my commitments. I wanted to do right by myself in terms of promoting the book. Do right by the ideas in the book, do right by the publishers or by the, you know, the podcast host or the journalists or whoever that were interviewing me. And so I wanted to show them the respect of showing up and doing the work. And also, it's true that, you know, if all you do is sort of suppress things or repress things for a long time. That can become a pretty unhealthy way of life. And so you've got to find a way to let it out over time and. And find appropriate places to be able to kind of funnel it. I mean, in a really literal sense. I ran away. You know, I ran. Didn't want to be in my house anymore, so I sold it. I moved. And I don't actually think that was. That was bad. I think it was probably what I needed at the time. I mean, the metaphor that I always think about is how when somebody has really gotten, like, badly mangled in an accident or something, they put them into a forced coma because it's like, you know what? You can't deal with this right now. Like, we're going to put you to sleep for a while until your body can heal and get a little bit better, and then, like, you know, come back in a few weeks, come back in a month, and. And then we'll talk. Right. And. And I think it was. It was kind of like that, emotionally, like, you know, I did have to kind of just clamp down and focus. And then, you know, it's in the interstitial moments, of course, where it's like, you know, you're like, okay, on, on, on, on, on. And then you're. And then you're, like, in the shower and bawling, or you're in the car and you're bawling. But, yeah, it's. It. It took. It took about six months for me to stop being, I would say, extremely messed up, and about a year to really sort of genuinely not be messed up.

Yeah. When did your next book come out? Because that would have been entrepreneurial you, I believe. When did that come out? So were you writing it when you came out of the messed up phase or what?

The second book, actually, after Reinventing you was called Standout. And my. My.

Interesting for a person who does not want to stand out at the moment to write a book called Stand Out.

Yeah, yeah, it was. It was my. My somewhat underappreciated book that I still. I still love. It did not. Well, thank you. It never sold as well as its friends, but. But I think it was a very good book. Yeah, I mean, I was writing it during that time. It came out in 2015, which means it takes usually about two years for a book to come out. So Reinventing you was released in April of 2013. Standout came out almost exactly two years after that. And so pretty Much. As soon as the first book came out, I was out there with a proposal for the second one, trying to gin that up. So, you know, it was good. It gave me something to, to work on, to focus on. I think a project can help sometimes. I mean, I know, you know, in your great video that you did with ConvertKit, you talked a lot about how the gym became your project. So I think, you know, we need something, right? And, you know, the bad version of something is like, you know, drinking or whatever. And so we have to kind of pick our own good, good version of something to immerse ourselves in.

Yeah, I tried the drinking thing. That went on for like 10 years. Not a good idea. So less good direction. Yeah, yeah, yeah. Not recommended. But back to your point about compartmentalizing. And you're right, it gets a bad rap, right? But I think in doses it makes sense because on my end, like when I was dealing with the loss of my son, I was still doing keynote speeches, right? And I would say to myself, like, I know you're hurting right now. You got to be perfect for the next hour. That's it. You have to be perfect for the next hour. There's no options or else you can't support your family. That's how it goes. And I think that resilience, that stoicism, that this commitment to the task that you talked about is almost lost these days to an extent. And I don't want to say, like in today's society, because whenever you say that, it's like this sweeping statement, but it's like, yes, you shouldn't ignore it entirely, but if you have to get on stage, if you have another book deal, you got to push through that shit for a bit. And that's, that's it. I'm not trying to be insensitive, but the only way is through. And then take a break afterwards. Like, that's, that's, that's really it. So you said it more eloquently than I did, but I'm glad you brought it up because this is, this is what people need to hear more of. Like, again, you see Dory, she's amazing. Like, you know, she's also a stand up comedian, by the way, which you didn't mention. And you also produced a Broadway play, but she had to push through some shit to be the person that she is. And if you gave up back then, we wouldn't be talking right now. I never would have read your book, which is actually how I launched my business. So I do want to say thank you for that, for being able to push through and just highlighting how everyone else could do the same. But I also want to do this. I want to share an example of how your resilience helped you build your career. There's two stories that you tell that I love repeating. The one is about your mom and your brace. Her braces, we'll pause on that one. But the story of how you got a job writing for HBR by selling your bike, do you mind retelling that one? Because I just love that story for everyone's like, how do I do this? How do I do that? I'm like, I don't know, freaking try hard. And you're a really good example of what comes from that. So do you mind telling that story before I butcher it?

Yeah, of course. And, and I mean this, this is one of the stories that depending on the moral you want to extract from it, you, you could, you could take it in lots of directions. One, one way to take it is like, oh, you know, just, it's luck. Some people get lucky and it is that. But I, I also, I mean, perhaps self servingly in this instance, but I also happen to believe it's true. I also think that it, that it is an example of genuine luck meeting the preparation that's required for it. So the, the backstory was that I, I had started my business in 2006 and I was continuing to look for ways to raise my profile. And you know, one of the aspirations that I had, well, the big aspiration really was to write books. And so in 2009, I tried really hard to get a book deal. And everywhere I turned I kept hearing like, nope, nope, nope, you're not famous enough. And so largely the advice centered on creating, grow your platform. And you know, there's a lot of ways you can do it. But I centered on writing and figured, okay, if I start writing for high profile publications, that is a thing that I can do that can build my brand awareness and hopefully get a publisher interested. So that was really the goal. So I was trying everything. I was reaching out to different places and looking for opportunities. And I had been a professional journalist. I had spent a year, you know, writing full time for a, covering politics in Boston for an alternative newsweekly. So I literally used to get paid for writing. And so it was very humiliating. I was raising my hand. I'm like, hi, I would like to write for you for free. And everybody's like, f you, like, who are you? Like, go away. I'm like, really? Come on. But, but you know, that's, that's the reality. When nobody's heard of you, they really don't care. Like, it is just too much intellectual labor for them to even like, Google you. They're just like, no, go away. And so I think that, that sometimes.

People, for everyone listening, there is a happy ending to the story just to.

That's right. That's right, kids. Yes. I mean, I think that, you know, a lot of people understandably don't want to subject themselves to that because it does feel kind of terrible. So you just have to keep putting yourself out there. And so I was writing to Fast Company, to Inc. To all of these places and saying, hey, please, please, please. And occasionally I would get an editor who would bite in some way and be like, well, that's interesting. Send me some ideas. And then I'd send them some ideas and then I'd follow up 100 times. I'd never hear from them. They'd ghost me. So it was very dispiriting. So, but, you know, the plus side was that I had a list of a million ideas because I had written all of these things that nobody ever did anything with or nobody ever wanted to look at. So anyway, I was on Craigslist and I decided that I was going to sell my bike. I had previously run a bicycle advocacy organization and I had this actually really nice bike that I eventually decided was too nice. And I kept being scared people would steal it. So I'm like, I've got to get rid of this. I can't have a bike this nice. So I ended up selling it to a woman who, as it turned out, worked at the Harvard Business Review as like a copy editor. I didn't know she worked at the Harvard Business Review. She told me that because she had looked me up to make sure I was legitimate. And she's like, oh, I see you do business consulting. I work at the Harvard Business Review. And so at least at that point I had enough self possession to say, oh, how do you get started writing for you? And she was not the person, but she was willing. And of course I had to follow up a number of times, but she was willing to introduce me to the person. And eventually I got my first story in and I now have been writing for them for 14 years.

Wow. Love it. I love the serendipity. But again, like, luck is when opportunity and preparation are met with action. And you took that action. So I just appreciate you sharing that story because I tell it like it's my own sometimes because it's like there are no hacks. I mean, the hack is hard work. The hack is consistency. The HAP is preparation. And if you allow serendipity to occur by putting yourself in those situations, maybe you're selling your bike or whatever it is, then you can take advantage of it. But you can also.

That's like, that's like you. Right? You know, like, like shanghaiing Jason at the daycare to break into Entrepreneur. It's very similar.

Yeah. So if you want to become a writer for a well known magazine, either sell your bike or take your kids to daycare. And there you go. That's it.

Yeah, that's, that's the moral right there.

But Dory, you actually have courses and content on how people can write for high profile magazines, how they can build their brand online as well. So let's transition to that part where you plug stuff because I think a lot of our listeners are going to want to learn more from you.

Yeah, I absolutely. Thank you, Terry. I have several courses that are focused on this. And tune into the show notes folks, because Terry has an affiliate link and he will put it in the show notes so we can make sure you get the proper credit. But yes, I have a course called Writing for High Profile Publications that actually breaks down what I have Learned in the 14 years of meticulously crafting articles. I have now done more than 200 articles for Harvard Business Review. I spent a frenzied three year period writing more than 250 articles for Forbes. I've, you know, like Terry, I've written for Entrepreneur, I write for Fast Company, I've sort of done the circuit and I've taught a lot of people how to do it. In my recognized expert course in community that I run, we now are up to 62 people who have gotten published in Harvard Business Review. So we have systematized the process of writing for high profile publications so that people can really understand how to crack the code, how to hone your ideas and really do it as effectively and thoughtfully as possible. So check the show notes for Terry's link. And the other program that I run is called Recognized Expert, which is sort of broader focus. It's really a course about platform building and it's a long term community that people join. There's a course component, but really I like to think of it as a community because people buy it once they get lifetime membership. And it's actually really amazing, the friendship, the connections that people have built. But the goal is, is to help people on the journey and it is a bit of a long term journey to becoming a recognized expert inside your company or inside your field.

Dori, thank you for this. Thank you for everything you've done for me and by extension, my family and our audience listening right now. So I appreciate you and just thanks. I don't. I don't know what else to say, but thank you.

Well, thank you, Terry. You are such a bright light, and I always appreciate spending time with you. So this is really wonderful.

Awesome. You want to do it again tomorrow?

Absolutely. I'm in, man.

All right. Thanks, Dory.

Thanks.