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Published on:

11th Jul 2023

Heartbroken and Divorced? Let's Start Healing with the Divorced Girl Smiling

On today’s episode, I have the joy of speaking with Divorced Girl Smiling, Jackie Pilossoph. Jackie is such a light in this world, and a leader in helping connect those going through a divorce with the best resources out there. We talk about what it feels like to end any type of relationship, whether it be a friendship or a romantic partnership, the pain is similar and can turn your world upside down. Jackie talks about leaning in to your feelings and emotions in order to come out on the other side stronger. Tune in to hear the positivity that Jackie radiates and how to understand why the heartbreak hurts so much in the first place.


In this episode:

[2:10] Jackie shares what led her down the path to be the Divorced Girl Smiling. [5:10] What made Jackie write her article about heartbreak? [6:47] Understanding the why around heartbreak is the first step to working through it. [11:28] When to let go of the hope that things will change. [14:16] What does Jackie mean when she says she is tired of being hurt? [16:35] Breaking up with a friend vs. a lover - they are one in the same. [17:34] Jackie talks about how she was forcing things to be right even though they weren’t right for her. [19:25] What happens when you really love someone, but there is just no way to fix the relationship? [22:25] Understanding anxiety and how to manage it. 


Key Takeaways: 

The best thing you can do is to take care of yourself. You can only control yourself, you can make all the changes you want in yourself, but you can’t make your spouse change. Acknowledging all of your feelings and emotions are the healthiest way to get through the pain. People who don’t acknowledge all the feelings, they get angry and bitter. If you have the vulnerability and the guts to say what you are actually experiencing then it will help you in healing quicker. If you make little changes, one a week, and focus on that one change for the full week. If you have little changes, you’ll stick to them and then you can build on that new habit. 


Quotes: 

“Next time you feel that way, you should say to yourself, Don’t I deserve better? Do I really deserve to be treated this way?” - Jackie Pilossoph

“You finally come to this point where you realize that if it's not right it's just never gonna work no matter how hard you try. And the other thing I tell people is that both people have to really want it to work. And if they don't, you don't have any chance. If one wants it to work that's not enough. Commitment is the biggest force in keeping couples together. I believe that love is a choice.” - Jackie Pilossoph

“We fall in love and we ignore the bad behavior and the red flags because we, we don't wanna see that it's too painful. We're not ready to break up. We're still in love with a lot of other aspects of the person, so nobody's all good or all bad. And so we don't wanna see those signs.” - Jackie Pilossoph


Guest Bio: 

Jackie Pilossoph is the creator and Editor-in-chief of DIVORCED GIRL SMILING, a media company comprised of a website, podcast, mobile app and vetted, trusted professional resources.  DGS has a mission to empower, connect and inspire men and women before, during and after divorce. Pilossoph, who holds a Masters degree in Broadcast Journalism, 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 6 1/2 years. Pilossoph was also a Huffington Post divorce blogger for five years.


Resources: 

Divorce Girl Smiling 

Lesa Koski Website

Lesa’s Online Courses

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Mentioned in this episode:

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About the Podcast

Doing Divorce Different A Podcast Guide to Doing Divorce Differently
Divorce, co-parenting, menopause, marriage, and starting over after 40—Doing Divorce Different is your guide to a healthy, faith filled life transition.

Hosted by Family Law Attorney and Mediator Lesa Koski, Doing Divorce Different is a candid, empowering podcast designed to take the fear out of divorce and guide you toward peace—whether you’re navigating a split, working to stay married, or rebuilding a better life after a major transition. Each week, Lesa brings heart-centered legal insight, emotional support, and holistic wisdom to help you heal, grow, and thrive.

We cover everything from amicable divorce and co-parenting strategies to parenting plans that actually work and support kids in thriving through change. You’ll learn how to prepare for marriage with prenups, revisit your relationship with post-nuptial agreements, and understand what it really takes to stay married or rekindle love after a rough season. If you're in the midst of a grey divorce, wondering how to not get divorced, or questioning whether love can be found again, this show is for you.

Lesa also explores the emotional and physical changes that often accompany midlife and major life shifts. From navigating the impact of menopause on your health, marriage, and mood, to dealing with the loneliness that can come after divorce or empty nesting, you’ll find honest conversations that don’t shy away from real-life challenges. And for those of you in your 40s, 50s, or beyond, you’ll discover what it means to truly build a better life after 40.

Health and wellness are deeply integrated into this journey. Lesa shares insights on the benefits of rest, joy, nutrition, fasting, protein, and bone health, along with the power of movement, community, and exercise to support mental clarity and physical strength. You’ll learn how to take care of yourself with intention—because healing isn’t just emotional, it’s also biological.

Mindset work and self-coaching are recurring tools offered in episodes to help you reframe your story and shift from fear to freedom. And through it all, the show honors the role of faith, spiritual surrender, and letting God lead you through every season. Whether you're leaning into your relationship with God for the first time or deepening a lifelong practice, you’ll hear how surrender can bring peace even in the hardest moments.

You’ll hear real stories from people who have done divorce differently, saved their marriages, or found new love and purpose on the other side. Lesa also brings in conversations about marriages that have stood the test of time, co-parenting through complex seasons, and the realities of parenting after separation while maintaining stability for your kids.

This is not just a podcast about divorce. Doing Divorce Different is about taking back your life, rewriting your future, and trusting that you’re not starting over, you’re starting better. If you’re craving practical advice, soul-level encouragement, and real conversations about creating a healthy, joyful, purpose-driven life, you’ve found your community.

Subscribe now and join Lesa Koski for weekly episodes that will help you grow stronger in your relationships, your health, and your faith, no matter where you’re starting from.

About the Host:
I’ve spent over 25 years helping families navigate amicable divorce as a lawyer and mediator, always focused on protecting what matters most—your kids and your peace of mind. But my mission has expanded. Today, I support women over 40 not just through endings, but in building stronger relationships—and sometimes even saving their marriages. I’m a breast cancer survivor, a cowgirl at heart, a wellness advocate, and a follower of Jesus. My life and faith fuel my passion for helping women thrive.

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Lesa Koski