Sophie Elgort is a photographer, director, and award-winning television host. For nearly two decades, Sophie has photographed some of the world's most recognizable artists, actors, musicians, designers, and leaders. As the creator and host of Portrait Mode with Sophie Elgort, she's built a career around capturing not just how people look, but who they are.

In our conversation, we explore what it was like growing up in one of New York City's most creative families, how rejection became an unexpected teacher, and why the most successful careers are often built through curiosity, resilience, and a willingness to keep creating long before anyone is watching.

We also discuss the intersection of art and entrepreneurship, the lessons motherhood has taught her about intention and time, and why understanding people is at the heart of every great portrait.

Whether you're a creative, entrepreneur, or simply someone trying to build a life that's authentic to you, this conversation is a reminder that success rarely follows a straight line.

Watch Portrait Mode here

Sophie Elgort's Website

Follow Sophie on Instagram

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Mike Orscheln has spent more than four decades leading billion-dollar businesses, navigating corporate turnarounds, private equity transitions, and helping companies grow from good to extraordinary. Mike has served as CEO, president, and executive coach, building a career around one simple belief: people and purpose always come before profit.

But this conversation isn't really about business.

It's about what happens when you lose your mother at just three years old, spend decades never speaking about that loss, and then discover that grief has been quietly shaping every decision you've ever made. Mike shares the deeply personal journey behind his philosophy, "Be Aware 61," the synchronicities that changed his life, and how becoming emotionally conscious transformed not only the husband, father, and friend he became, but also the leader.

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

For the 100th episode of For Your Listening Pleasure, fashion stylist and founder of The Clothing Therapist, Dana Asher Levine, shares her remarkable journey of resilience, reinvention, and finding purpose through life's biggest challenges.

Known for styling some of Hollywood's most influential women, including a decades-long professional relationship with television powerhouse Shonda Rhimes, Dana has built a career helping women feel confident, authentic, and empowered through personal style. But behind her success is a story of profound loss, perseverance, and rebuilding. After losing both of her parents at a young age and later navigating divorce while raising three children, Dana found herself starting over at 40 and creating a business that would ultimately transform the lives of countless women.

In this heartfelt conversation, Dana opens up about grief, motherhood, entrepreneurship, finding love again, and the lessons she's learned from helping women show up as their best selves. She also shares behind-the-scenes stories from Hollywood, her approach to personal style, and why confidence has always been more important than following trends.

Episode Resources:

Follow Dana on Instagram

The Clothing Therapist Website

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

Marissa Isang is an Emmy-nominated storyteller whose career has taken her from Chicago newsrooms to the forefront of AI and tech communication.

Born and raised in Chicago, Marissa reflects on how the city shaped her understanding of family, resilience, and curiosity. We talk about the feeling of Chicago, navigating life between Bronzeville, the suburbs, and Rockford, and why the city never really leaves you.

We also dive into her journey through television news, producing live broadcasts, covering iconic Chicago moments like the Cubs' World Series run, and earning Emmy nominations for her storytelling. Then we explore her transition into the tech world, where she now helps make AI understandable, accessible, and human.

This conversation is about evolution, curiosity, storytelling, and learning how to navigate a rapidly changing world without losing sight of who you are.

Episode Highlights:

• Why “Chicago is a feeling.”

• Breaking into television news and sports broadcasting

• Covering Chance the Rapper and the Cubs World Series

• Transitioning from journalism into tech and AI

• Making artificial intelligence understandable for everyone

• Ethical AI and why representation matters

• The power of curiosity in storytelling

Episode Resources:

Marissa's LinkedIn

Marissa's Instagram Account

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

Jacynth Bassett is redefining what it means to age and challenging a system that profits from our fear of it. As the founder of Ageism Is Never in Style, she’s built a global movement dedicated to dismantling age bias and reshaping how we think about identity, beauty, and worth at every stage of life. What started as a deeply personal observation, watching her mother become increasingly invisible in spaces like fashion, has evolved into a powerful platform spanning community, consulting, and cultural change.

In this conversation, we unpack how ageism shows up everywhere, from the workplace to healthcare to the way we see ourselves in the mirror, and why women, in particular, are never considered the “right” age. We get into the concept of age confidence, the impact of social media and the anti-aging industry, and how internalized bias shapes our decisions more than we realize. Jacynth also breaks down why generational division is often manufactured, how these narratives are reinforced from childhood, and what it actually takes to unlearn them. This episode is about identity, power, and perception, but more than anything, it’s about reclaiming the right to exist fully, confidently, and unapologetically at every age.

Jacynth Bassett

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Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

Luke Corbett grew up in St. Louis in a conservative, values-driven household, eventually finding his way to Washington, D.C., where he worked on Capitol Hill at the center of American politics.

But what makes Luke’s story so compelling isn’t just where he started; it’s how his perspective evolved. From working inside the system to questioning it, from navigating his identity as a gay man within conservative spaces to witnessing pivotal moments in recent history firsthand, Luke’s journey is one of reckoning, growth, and ultimately, choosing to think independently.

In this conversation, we talk about what it’s really like behind the scenes on Capitol Hill, the tension between personal values and political environments, and the moments that force you to reevaluate everything you thought you knew. We also get into where the country is today, why so many people feel disconnected from politics, and what it means to step away and rebuild a life rooted in purpose, stability, and truth.

This is a conversation about identity, courage, and what happens when you decide to see things for yourself.

Connect with Luke on Instagram

Link to purchase:

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

Melissa Forman is a Chicago radio icon, television personality, and the kind of storyteller who has spent decades keeping an entire city company on its drive to work. Because Melissa’s career isn’t just about radio. It’s about what it takes to build a lane in a male-dominated industry, to go from being expected to be the “sidekick” to becoming the one driving the show, and to do it with warmth, humor, and that rare ability to make listeners feel like they’re talking to a friend.

We’re getting into her early days growing up, finding her voice, and the moment she heard a woman on morning radio and thought, that’s it… that’s what I’m meant to do. We talk about the behind-the-scenes grind people don’t see, the power of learning every button and every board so no one can ever tell you you don’t belong in the main seat, and what it’s like to hold space for a city when listeners call in with their funniest stories… and their heaviest ones.

Link to purchase:

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.

September is Suicide Awareness Month, and today I am honored to welcome Melani and Lenny Lighter to the podcast. In February 2023, their family was forever changed when their beloved daughter and sister, Lauren, died by suicide. In her memory, and in honor of the millions of lives lost each year, they created LIGHTER, a nonprofit dedicated to raising awareness and providing support for mental health.

Currently, they are leading the "Light in the Dark" fundraiser, with 100% of the proceeds going to the Lauren Lighter Fund. This fund directly supports NAMI Chicago, a local mental health organization, as well as the Douglas Mobile Outreach Program, expanding access to resources and care.

At its heart, LIGHTER is a candle project designed to bring light and comfort into people’s homes while honoring those who have struggled in darkness. Since its launch in August 2023, LIGHTER has raised over $1 million for mental health foundations in both Montreal and Chicago, offering communities not only resources but also awareness, compassion, and hope.

This episode serves as a reminder that we are all fighting battles that are unseen. I hope you find strength in Melani and Lenny’s story, and if you’re able, please consider supporting the Light in the Dark fundraiser with a donation.

Episode Resources:

Lighter Candles

Light in the Dark Fundraiser

Link to purchase:

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Download this episode of For Your Listening Pleasure wherever you get your podcasts! Make sure you follow us on Instagram @foryourlisteningpleasure

Click here to listen to the For Your Listening Pleasure Theme Song Playlist on Spotify.

To continue the conversation, feel free to DM me at https://www.instagram.com/foryourlisteningpleasure/ or email me at foryourlisteningpleasure@gmail.com.