Jackie Pilossoph – Creating Divorced Girl Smiling

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Episode Description

When journalist Jackie Pilossoph went through her divorce, the resources available to help people navigate divorce were practically non-existent. That prompted Jackie to start Divorced Girl Smiling, a blog that offers support, information and resources to women facing and dealing with divorce.

Today, Divorced Girl Smiling has grown from a personal blog into a media company. In this episode Jackie dives deeply into the decisions she made that led her to go from journalist to medial mogul.

Show Notes

Jackie Pilossoph is the creator and Editor-in-chief of Divorced Girl Smiling, a media company comprised of a website, podcast, mobile app and professional resources. Jackie holds a Masters degree in Broadcast Journalism and is a former television news reporter and features reporter and writer for the Chicago Tribune.

Where to Connect with Jackie
You can connect with Jackie on Facebook at Divorced Girl Smiling or in her Facebook Group, The DIvorced Girl Smiling Group. She is on LinkedIn as Divorced Girl Smiling. You can also find her on her website  at DivorcedGirlSmiling.com.

Special Offer:

The DGS Club offers support groups for women facing divorce and recovering from divorce. The Club runs in 4 week sessions. To find out more information and see when the next session begins go to Divorced Girl Smiling.com and click the tab "DGS Club".

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Creating Divorced Girl Smiling and Turning Your Pain Into Passion


divorce, people, karen, decisions, dating, writing, smiling, jackie, kids, job, bad, support, girl, books, feel, marriage, life, pioneer press, find, shameless plug


Karen Covy

Karen Covy  00:03

Hello everyone and welcome to off the fence, a podcast where we deconstruct difficult decisions so that we can discover what keeps us stuck and more importantly, how we can get unstuck. I'm your host Karen Covy, divorce and decision coach as well as recovering lawyer mediator, arbitrator and collaborative divorce professional. And on today's episode we have Jackie Pilossoph. Jackie is the creator and editor in chief of divorce girl smiling, a media company comprised of a website, podcast, mobile app and professional resources. Jackie holds a master's degree in broadcast journalism and is a former television news reporter and features reporter and writer for the Chicago Tribune. Her syndicated weekly column love essentially was published in the Pioneer Press, the Chicago Tribune, and all Tribune Publishing editions for six and a half years. Jackie was also a Huffington Post divorce blogger for five years. Jackie, oh, my gosh, welcome to the show.


Thanks for having me, Karen.

Karen Covy  01:04

I've been wanting to get you on this is from the minute I decided to do this. I was like, I have to have Jackie, because you are absolutely amazing. I told people a little teeny bit about you. But why don't you tell us more? And tell us about the media company that you run called divorced girl smiling. What is that? What does it do? What do you do? What's your mission?


Well, thank you. I don't think that you told a little bit about me, you really told a lot. And I appreciate all of the compliments. I decided to start divorce girl smiling a few years after my divorce when blogging got kind of big. So that was really the start of it. And the the reason behind divorce girl smiling was that when I was going through my divorce at 41, with two young kids, I felt like I was on an island. And back in 2008, there really wasn't anything, there were a few blogs. But I felt really alone and I didn't feel connected. And there wasn't a divorce community like there is now there was no such thing as a divorce coach, even that didn't even exist back then. And so I would have liked to have had the connections and the support and the professional resources. And I think I would have had such a better experience and a better outcome even and maybe for my kids too. And so that was the motivation behind divorce girl smiling. But when it really got to be a media company was a few years ago, when I started a podcast and videos and a mobile app and started partnering with all of these wonderful professionals so that I could help them get business but even more importantly, help my community of divorce men and women find good people to work with. So that's that's really what it is.

Karen Covy  02:59

Oh my there is so much in there. I can't wait to pick it apart. But I can so first of all I can so feel your your pain because I remember it was 2008 When my the first edition of my book when happily ever after ends was published. And there was a lot of nothing out there back then. I mean, it was there was just, you know, if you went to the bookstore, even just the bookstore, you would find books on like, you know how the shark tactics of how to take your spouse to the cleaners, or you could find like a memoir, and that was about it. I think the the only book on the market divorced book that wasn't worth anything at all at the time was divorced for dummies. So that kind of tells you something right? But and I know you know, aside from all the divorce girl smiling some of you have also written books to tell me about that. How did you decide to do that?


So I think he told the listeners before that I'm a former broadcast journalist and writer for the Tribune. And so obviously, I enjoy writing and I love writing. And so when I got divorced even before I got divorced, when I was unhappy in my marriage, writing became my outlet. It was like a water faucet of me expressing all these feelings on paper, which by the way, is why I suggest to so many people to journal journal your pain because it feels so good to get it out. And it's such a wonderful, healthy way to cope with your pain during and then after divorce. And so I started writing these novels, and all the characters were fake, but they were based on my story and stories of people around me and then I I've always been kind of like a humorous person. I kind of think I'm funny. I had like a really bad funny family and humor is such a great way to deal with pain also, I think and so I decided to make my books romantic and funny and sweet and inspiration. at all. And so I wrote, I ended up writing four novels really five, because one's in a drawer. And I just felt like I was helping people. It was like, my novels are like self help books in a novel. Exactly. That's,

Karen Covy  05:18

that's beautiful. And just, you know, to give, give a little shameless plug, where can people find these novels if they'd like yourself help.


Thank you. So if you go to divorced girl smiling, and you go to the tab that says books, it'll take you to Amazon. And then it will also take you to a page where you can get free ebooks that I wrote, and ebooks that you can pay for also.

Karen Covy  05:42

That's awesome. So how did you? How did you know you weren't always this media company mogul? Right? How did you make that switch? How did you specifically how did you decide because one of the things that I'm interested in here on this podcast and this video blog, whatever you want to call this is how people make decisions. And that's a big one. So how did you decide to go from a day job to a media company?


Good question. And you're so right. When people are going through a divorce, or they're just newly divorced, they don't really know what they're supposed to do in life, like, you know, let's say they haven't worked in a while or now that they're getting divorced, they have to change jobs because they have to make more money, or they want to go get another job and make less money so they can spend more time with their kids. So it's hard to figure out what you want to do. And that's kind of what happened to me. And so I had these backgrounds in sales, which I'm using now, broadcasting, which I'm using, right in which I'm using, and I feel like one thing kind of led to another, and Karen, I swear I'm using every skill I've ever learned in life. In this media company, I could never have done it if I wasn't in broadcasting or writing or sales, or marketing and all the things I've done in my life. I'm have kind of cult cultivated, I guess is the word into this one big passion project, which is divorce girl smiling.

Karen Covy  07:19

That's amazing. But you know, that's such, it's such a big leap to take right and especially, I'm sure that a lot of our listeners are in a similar position to where you were at one point where their marriage is ending. They're not sure about their career, can that support them? Do they need more? Should they start their own side business? What What would you say to somebody? How do you make those decisions? Well, it's


such an interesting question, because also, you're right, when people are unhappy in their marriage, or they're going through a divorce, they also have really little self confidence and self esteem. And so you're not your normal self. And you have all these other insecurities. And plus, if you were in a bad marriage, your husband or wife isn't really hasn't been saying the nicest things to you. So you don't feel good about yourself, and you don't believe in yourself. But what I would tell people is do what I did. Follow your passion, follow what you love to do. What were you good at that you don't do anymore? What do you enjoy doing? What do you think you could get a job as an I'll tell you this. It's not like I woke up one day and said, Oh, I'm going to start a media company. I started at the Chicago Tribune in the Pioneer Press, making $50 a week. And my job was to write down and submit like five things to do in Glenview this week. That was my first job after my divorce. And then it turned into the I was like the man on the street reporter and now I got to go to six towns and interview people and ask them what book they're reading or ask them like a question of the week. So I was doing a job that like a college intern would do. And I was like, 42 years old, and I wasn't happy about it. But I was like, this is fun. So what well, now I'm making 300 a week. So it all built up and it was little steps. And then they liked me enough and said, Hey, have you ever written feature stories are guys on vacation? Do you want to write a couple this week? I said, Sure. They said, you also have to take pictures. Can you take pictures? I said, Oh yeah, I'm great at that. Okay, do you know how to hold the camera, of course you can take pictures. So it just all happened organically. So what I would tell people is follow your passion and one thing you love if you work hard, it will turn into more and more and more.

Karen Covy  09:45

That is so important because, you know life is a journey and divorce is a journey and what you're saying is so important for people to hear that you know you don't start out at the top of the heap, right? You've worked your way in Do this and over time, one thing has led to another for you and then another and another, to the point where you're now you're realizing your dream, you can see it in front of you. And that's beautiful.


Absolutely. And you know, Karen, I was thinking when you were saying that, when you go through a divorce, you really have to be humble in many ways. And one of those ways is professionally. So what if you're older and you're doing this intern job? Look what it got me where it got me, I'm not saying you should do a job where you're gonna go to work every day and feel miserable. But it doesn't have to be this perfect ultimate job. As long as you know, you have a goal and you're going somewhere with it. Just stop it out for a while. And I remember once a long time ago, one of my still very best friends, I got this job in telephone sales. And I was like, Well, I really wanted to be in sales. I don't want to be in telephone sales. And she goes, Well, how long do you have to do it? And I said, well, they said you if you do it for a year, you can be promoted. And she goes, Do you know how long how quickly a year goes by just try it. And if you don't like it after six months quit. And sure enough, I did it. And I was promoted after a year and it all worked out.

Karen Covy  11:15

Oh my gosh, I never knew that you were a telephone salesperson. In my 20s. I have to tell you, I just going back quick story. I got a job as a telephone sales person. When I was 16 years old, it was selling tickets to the policeman's grand old Opry, I don't know who went to this thing. Nobody wanted the tickets, we would call off of like we had a phone list, you just keep calling the number number after I was so bad at it. I have never hated anything so much in my life. And there was a boy at the time who sat next to me. And he liked me. And he didn't. And there was a guy who was maybe a year older than the rest of us. And he was the boss and he would walk up and down the tables and say, Okay, anyone who hasn't sold one ticket in the next hour, you're fired, right? And I was like, Oh, thank you, God, I have a way out, right? And this kid would sell to when he gives me one. And so I wouldn't get fired. And I was like, no, please no, don't do. It sounds like such a nice kid. I'm sure he was. But that was so not the job for me. So I have tremendous respect for you. And anyone else that can do that. If that's just, that's amazing. Okay, so let's switch gears a little bit. And tell me about what decisions that you know what decisions you think divorcing people face, like their biggest challenges as they go through the process. Things that they might not realize in the moment are super important, but that you with all your experience now can look back and go oh, yeah, that's important.


All right. What did you ask me what choices people make? And then what?

Karen Covy  13:01

Yeah, what decisions they might have to make during the course of their divorce that are really important. And maybe they don't realize how important they are in the moment. I mean, big ones, of course, you know, it's important what schedule you see your children on, like, everybody gets that, but are some other decisions that people make that they might not think are so important, but the you know, really are?


Okay, your divorce lawyer is such a bigger decision than you think. If you don't feel right about it, you need to talk to Karen. And so, I mean, really, and also a divorce coach is vital. And by the way, I'm not just saying this, because I'm on your show, Karen, but they recommend you to anyone, I think you're a wonderful person, and you bring so much experience, like you were a divorce lawyer, you were a mediator, so you really do get it. So if you're not sure about your divorce lawyer, maybe interview a couple other attorneys and don't be afraid to change and also, having a divorce coach is a must. That's the first thing. Let's see other decisions that are important are who you date. So you you know, I wrote a blog post once on, are you getting divorced, don't do anything stupid. And I can say that because I did lots of stupid things when I was going through a divorce and one of the stupid things was I dated like all the wrong people. And so I think it's okay to date the wrong people just don't get into long term relationships with people who you know in your gut is not right, because then you're wasting all this time. And you're also like not living your best quality of life. So don't settle. You deserve to have it be really perfect this time around. Yeah, I love it, too. Right off the bat.

Karen Covy  14:55

I love that that you're you're so right. I mean you Your divorce lawyer is super, super important. And I hear from so many of my clients that they're concerned that they chose the wrong person. Right. And sometimes that's true. And sometimes it's not. And the challenge is knowing when it's true. And when it's not like is it just that your lawyer is busy? And there's nothing going on in your case right now? And that's why you're not hearing from him or her? Or is it because they're doing a bad job, and they're not paying attention to you like it? And so there are ways that you can kind of suss that out. But that's those are the kinds of things I mean, people don't realize the impact that the lawyer has, on how their divorce goes. And as far as dating, I love that advice, too. Right? It's about you know, making sure you don't, you don't have to only date Mr. or Miss right all the time. Like, that's impossible. But don't get involved in a long term relationship, for sure. Now, I'm gonna ask, I'm gonna put you on the spot and ask you a tough question. What do you think about dating during a divorce? Oh,


okay. So Karen, you wrote an article for divorce girl smiling about this? And I remember at the time, I was like, I don't know if I agree with this. I think it depends on the situation. So dating during divorce, you're talking about if you're not officially divorced, correct? Well, I just have heard of a recent person who is going through a divorce. And he put his profile on Bumble. And it completely made his divorce so much worse. Because the soon to be x saw him on Bumble. So that's something you really have to be aware. So if you're going to date during divorce, be really subtle about it, do not go on dating apps during divorce. I don't care even what your ex is doing. I just think it's so much better to wait until the divorce is final. Now, a lot of people are listening and saying, Well, I've already been going through a divorce for a year and a half. And I'm not How long am I expected to wait? So I guess my question is, Karen, what do you think about if people talk, if they're gonna date, talk to your ex spouse, if you can, and say, Are we going to agree that we're going to date and we're going to be okay with it, because our divorce is taking three years, you know, we have to know if we're going to be okay with it. Like, I just feel like the older I get, I get more and more upfront, put it out there, don't try to do something behind their back. Because they're going to find out from someone in your community, someone's going to see them at the bar on a day, or they're going to see your they're going to see you on these dating apps. So you got to really be upfront about it. And, you know, truthfully, when you're going through a divorce, you've probably been unhappy and felt alone for a couple years already. So maybe you are ready to date. So nobody should judge somebody for dating during a divorce. But I can see where your article would say that Be careful. Definitely.

Karen Covy  18:05

Yeah, I mean, I am with you 100%. I mean, nobody. I if I've learned one thing from my years on this planet, and the business that businesses that I've been in, it's that you can't judge anyone else, because you don't know what's going on in their life, you don't know what's going on in their heart or in their head, you haven't walked in their shoes, you just it's dangerous to judge other people. But that having been said, for the very reason that you pointed out dating during a divorce can come back and bite you, if your spouse doesn't know about it, or if you don't do it properly. But the other thing, the other sort of Robin there, too, is not only making sure that your spouse is on board, but that you know what you're going to say to your kids, too, right? Because if your kids are old enough to be aware of the fact that you're still married, and marriage means you're with just one person and now you're dating or like somebody else. How does that sit with your kids? And you know, especially when your kids are like teenagers, they get it and teenagers can be very judgy. Right? And you want to make sure you don't harm that relationship to


you know, I've never really thought about that. But I will say just having gone through a divorce with kids. The minute you tell your kids, you're getting divorced, and even more so the minute your spouse moves out, or you move out and you're living separate lives to the kids. That means you're already divorced. So a lot of times kids don't really know even if it's final yet. They really don't they think you're already divorced. That's it. But I will say if you start dating somebody, they're going to realize there's no chance mom and dad are getting back together and that can be devastating to kids. So think about that, too.

Karen Covy  19:56

Yeah, that's that's really, really good advice. For anybody, so, okay, switching gears a little bit, I'd like to just ask a couple questions just for fun. Okay, what is the best decision you've ever made in your life? Oh,


there's so many good ones. I've made many, many more bad ones. But the best decision I think I ever made was to have kids. I mean, how can I say anything but that that's literally the best decision. And I guess the way this is going to help people listening is that if you're getting divorced, and you're thinking, Oh, I made the hugest mistake by marrying this asshole, you know, you have kids, maybe with him or her. And I wouldn't change that for the world. So that's, that's one really good decision. And another decision, I would have to say, would be starting divorce girl smiling, because I feel like I'm on a mission to help other people. And it like really makes me feel like my life has meaning. You know, other than being an author, I would say it makes me I mean, you probably feel this way. Karen, what you do like really gives your life meaning. You are helping women, both of us, women and men who are in a horrible position. And if I can help somebody get through their divorce easier, that makes me feel really good about being on this planet. Yeah,

Karen Covy  21:40

yeah, that's, that's beautiful. But I did want to follow up on one of the things that you just said, it's like women and men, and the title of the site is divorce girl smiling, do you help guys too.


So I want everybody to know, if you're a guy listening, that divorce girl smiling, the stats show that 30% of my audience is men. So I really, really have a passion to help anyone getting divorced. And I mean men or women, transgender, any race religion, I am a very big proponent of helping people. Anybody who needs help, I am here for you.

Karen Covy  22:21

That that's awesome. And I know I'm the same way. It's like a the statistics show that there's a significant percentage, I think my breakout is 6040 women to man who go to the website, watch the videos on YouTube, do the whatever, all the things, right? Because men need help as much as women as much as transgender as much as like, everybody. Like if you're going through this major life event. You need help. Yeah, I don't know how you feel. But I'm a firm believer believer that nobody should go through a divorce alone.


I swear, and I did. I feel like I did. And it wasn't good. You know, it was probably one of the hardest times in my life. Yeah.

Karen Covy  23:05

So what decisions or recommend, let's put it this way instead of decisions, talk about recommendations that you hear other divorcing people tell each other because you you get a lot of comments on your blog and your Facebook group and people are talking all the time. And what are the the bad recommendations that you see people make to other people that you wish you could just go? No, don't do that?


Well, okay, on the divorce girl smiling facebook group page. So I have a group page and there's like, 3200 people on it, and they're talking to each other and somebody will post something, you know, my ex did this to me, and I'm so upset. I was crying all night. And then 15 People comment like, oh, that happened to me. And here's what I did. And honestly, Karen, I don't think people give bad suggestions. Like I can tell you what people do that is bad. But the people that I see making suggestions are they give really good advice, which really gives me hope. But I would say bad suggestions are like drinking like, oh, go have a couple drinks. Or oh, just the best way to get over someone is to get under someone else. I hate that saying. Yeah. You know, and so, you know, there's addictions drug addiction, sex addiction, drinking alcohol. There's no trying to get through something without getting support and help like you're just going to do your job and let time go by and get divorced. No, you need help. You need a divorce coach therapy support groups. I mean, I have a divorce girl smiling group where we meet and I only allow eight or less people in the group. We meet for four weeks on Zoom once a week. And it's just, I don't sit there and give advice. I don't really talk much. And all these women are supporting other women. So that was a shameless plug for the divorce girls. Find on divorce girl smiling in the DGS club tab. Okay. Anyway, my point is, is that you need support. If you're getting divorced, you need professional support, support from your peers. And you need to find healthy ways to cope with the anxiety and the pain, not drinking, getting into another relationship. Oh, getting remarried. Karen, when I got divorced, I was like, I'm gonna get remarried, I was on a mission. I was going to find husband number two, immediately. And all that did was make everything worse, put pressure on me and make me put up with very bad behavior from

Karen Covy  25:52

men. Who Yeah, that that is definitely a bad one. But I can't say no. I mean, you are welcome to make your shameless plug here. Because I have been, you know, I've dropped into your divorce girl smiling club. And it's amazing. I mean, just the feeling that you're not alone. Like, I think when when people go through a divorce, they feel like they're from another planet, right? And it's hard to talk to married friends, because they don't get it. They're still married. And you know, some of your friends kind of unfriend you. It's like, you've got the plague. Right. And so it's hard to get through that. And feel like you're not the only one on the planet that's faced these problems, right. So that I think support and support groups. So so very important.


Absolutely. And it's not expensive, either. Yeah, no, it's a really inexpensive way to get groups, not therapy. It doesn't replace therapy, but it makes you feel connected. And like you said, Karen, a lot of these people, you know, our best girlfriends, like, I know, my group, they're all married, you know. And so when I was going through a divorce, none of them really could relate. They love me, and they supported me, but it was in a very different way than if I would have had a divorce

Karen Covy  27:12

support group 100% 100%. Well, Jackie, this has been absolutely wonderful talking to you, you and I could probably talk for hours. I'm not sure who would want to listen to all of that. So I'm gonna bring it to an end and say, Thank you so much for being here. Where can people find you? What's the best place for people to reach you?


Well, first of all, Karen, thank you so much for having me. It's such an honor to be a part of anything you're doing. And I appreciate it. If people want to find me, you can go to divorced girl smiling.com. Really simple. It'll take you to the podcast, mobile app, sign up for the DGS club videos and a list of trusted professionals for any kind of thing that you need.

Karen Covy  28:01

That is awesome. And Jackie, thank you because you really, I think you really stepped into the gap. You have a beautiful mission and you're supporting so many people all over the world. So thank you, thank you. Thank you for being here. And for everyone listening go to divorced girl smiling.com You can find Jackie you can find your books and our work and our club and her all things divorce girl smiling. So thank you so much. And if you liked this video, like subscribe, come back and listen to the next episode. Bye for now.

Head shot of Karen Covy in an Orange jacket smiling at the camera with her hand on her chin.

Karen Covy is a Divorce Coach, Lawyer, Mediator, Author, and Speaker. She coaches high net worth professionals and successful business owners to make hard decisions about their marriage with confidence, and to navigate divorce with dignity.  She speaks and writes about decision-making, divorce, and living life on your terms. To connect with Karen and discover how she can help you, CLICK HERE.


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