Bound & Determined℠ with Meg McKeen

What happens when you gather a DJ, an insurance agent, and a sobriety and breathwork coach in a 50s-themed cooking school in Chicago and ask them about going against the grain? This. In this live recording from the Bound & Determined℠ Midwest Live tour, Meg is joined by Mary Nisi, Rosanne Boik, and Katie Tomaszewski for a conversation about how it feels to make choices for yourself that others wouldn’t make for you, how our definition of success changes as we do, and the importance of trusting our own knowing. Settle in for this one. It’s a masterclass in self-advocacy. And love. 

Mary Nisi founded Toast & Jam in Chicago, IL, in 2005, based on the idea that her clients and guests should be entertained, not overshadowed. Music-obsessed since childhood, Mary got her start in community radio and began DJing events when a listener called the request line and asked if she would DJ their wedding. Over the last 20+years, Toast & Jam has provided the soundtrack to thousands of weddings and events in Chicago and beyond. She is a founding member of the Chicago Independent Radio Project

(CHIRP) and currently hosts “The Noonday Underground” on Mondays from noon to 3pm on CHIRPradio.org. Mary is also the creator of the Toast & Jam Lab, an online course to help Mobile DJs grow and scale their businesses and is the host of the podcast, All Up in My Lady Business, Ever the innovator, Mary is the founder and sole DJ of Hot Flash Dance, a punctual party for rowdy women. In what spare time she does have she spends with her friends and family keeping bees, crafting and watching Jeopardy.

Rosanne Boik has been a commercial insurance broker for over 25 years, with her primary focus in the hospitality industry.  Her expertise has allowed her to maintain relationships with many of the most recognizable restaurant brands in Chicago, including Frontera Grill & Tortazo, SMG Restaurant Group (S.K.Y., Apolonia, Valhalla), Elske & Creepies, Cruz Blanca/Lena Brava, Bang Bang Pie, Pretty Cool Ice Cream, Tzuco & Ummo, m.f.k, Pangea Restaurant Group and across the nation - she’s currently working with a Michelin-starred taqueria in New York City. Rosanne is a long-term resident of the West Loop neighborhood of Chicago and she’s an avid traveler, loves hiking and cycling and hustles on the side, sitting for small dogs. Her current obsessions include works by both Gustav Klimt and Dale Chihuly.  

Katie Tomaszewski is a multi-passionate health and wellness educator dedicated to helping others feel and live better. With a degree in Health Sciences and extensive certifications as a breathwork educator and Pilates-based movement specialist, she brings a wealth of expertise to her work as the founder and lead coach of Deep Line Holistic Custom Fitness, the founder and lead coach of DryNamics - which is pioneering body-centered sobriety, and as a faculty member, The Language of Breath Breathworker School. With a deep understanding of the interplay between the nervous system, overall health, and quality of life, Katie provides the guidance and transformative strategies you need to start changing the way you *feel* the world around you. Through a holistic approach that integrates science, breathwork, meditation and small lifestyle adjustments, you can change the way you’re living, start feeling better and achieve lasting wellness.

Westfield is a property and casualty insurance company with more than 175 years of helping people protect what matters most - and a long tradition of creating spaces for women to connect and build community. Westfield believes that when women share their experiences and champion one another, they can inspire lasting change across the insurance industry. Learn more about Westfield.

• Join Postmarked: Bound & Determined℠ - and receive an every-other-month envelope of joy delivered to your mailbox
• Join Meg for an upcoming gathering:
  • Bound & Determined℠ Restorative Retreat, coming up in Michigan in November 2026
  • Join the waitlist for the next Bound & Determined℠ Founders' Retreat
• Have a question for Meg? You can send that to her here.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Jessica Hendricks has spent more than 18 years in property and casualty insurance, and now she is head of agency relations for Standard Lines at Westfield. In this live discussion, she reflects on challenging moments, such as when she dropped out of law school and, as a lifelong type-A planner, needed to figure out her life without a plan. Learning to trust her gut, Jess began getting comfortable with saying no and allowing herself to be ‘selfish’ within her career and personal life. We will also hear how Jess leads as her whole self, being comfortable not having all the answers, and finding her footing in the ‘messy middle’, from the boardroom to the ball field. If you are sitting at a crossroads, this discussion is for you.  

Jessica Hendricks is Head of Agency Relations for Standard Lines at Westfield, where she leads the Distribution Management team focused on strengthening agency relationships and creating a more connected, consistent experience for agency partners. Her team supports agencies throughout the entire lifecycle, from prospecting and onboarding to compensation, engagement, and strategic partnerships.

Jess brings more than 18 years of experience in property and casualty insurance, with deep expertise in agency distribution, sales strategy, and operational leadership. Before joining Westfield, she served as Vice President of Sales and Distribution Management at EMC Insurance Companies, leading enterprise-wide initiatives in agency compensation, contracts, national partnerships, and sales enablement. Based in Des Moines, outside of work, you'll most often find her cheering from the sidelines at her kids' sporting events and activities.

Westfield is a property and casualty insurance company with more than 175 years of helping people protect what matters most - and a long tradition of creating spaces for women to connect and build community. Westfield believes that when women share their experiences and champion one another, they can inspire lasting change across the insurance industry. Learn more about Westfield.

• Connect with Jess on LinkedIn
• Join Postmarked: Bound & Determined℠ - and receive an every-other-month envelope of joy delivered to your mailbox
• Join Meg for an upcoming gathering:
  • Bound & Determined℠ Restorative Retreat, coming up in Michigan in November 2026
  • Join the waitlist for the next Bound & Determined℠ Founders' Retreat
• Have a question for Meg? You can send that to her here.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Molly Stewart started in insurance just four days after her 16th birthday, and 27 years later, she is the Director of Sales and Distribution at Highstreet Insurance Partners, and she continues to pass on the vital information she has learned along the way. Molly looks back at the mentor who took a chance on her, the district manager who told her at 21 she would never make it, and the dollar bill taped under her chair at her first sales training and discusses how the “prove them wrong” fuel worked for her. She also acknowledges that this advice does not work for everyone, and what it truly means to coach each person with a different strategy. Molly opens up about helping her daughter Avery publish books written about living with anxiety and explains how anxiety can show up in the most mysterious ways. Listen in to learn more about the next generation entering the industry, the mentorship that is needed, and why it is okay for your life to form outside of your career. 

Molly Stewart is a passionate sales leader known for motivating teams, navigating challenges, and building strong, growth-oriented cultures through a collaborative and people-first approach. As Director of Sales & Distribution with Highstreet Insurance Partners, she brings over two decades of hands-on industry experience. Her career has spanned agency ownership, sales leadership, training, and business development. Giving her a uniquely broad perspective on growth and organizational success. Outside of work, Molly is a proud mom to three busy kids - Avery (11), Tatum (9), and Easton (7) - and shares carpool duty with her husband of 12 years, Troy. Faith and family keep her grounded, and she's always working towards that perfect balance of being able to do it all.

Westfield is a property and casualty insurance company with more than 175 years of helping people protect what matters most - and a long tradition of creating spaces for women to connect and build community. Westfield believes that when women share their experiences and champion one another, they can inspire lasting change across the insurance industry. Learn more about Westfield.

• Connect with Molly on LinkedIn
• Join Postmarked: Bound & Determined℠ - and receive an every-other-month envelope of joy delivered to your mailbox
• Join Meg for an upcoming gathering:
  • Bound & Determined℠ Restorative Retreat, coming up in Michigan in November 2026
  • Join the waitlist for the next Bound & Determined℠ Founders' Retreat
• Have a question for Meg? You can send that to her here.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Amy Crandall for a conversation about her gray hair transition - and so much more. Amy shares about the moment she looked in the mirror and thought - who am I fooling? - and we talk about what we find underneath (it's more than hair) and the feeling of knowing that the time is now. Amy gives us the permission we may not realize we're waiting for to make a change - or not - simply because it's right for you. 

Amy Crandall has worked inside the insurance industry for more than 30 years with roles in a family-owned agency, large carrier and industry vendors. Her expertise lies in service - and when she's not supporting guiding her team, she's walking her rescue pup and enjoying the majesty of the Pacific Northwest.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Ellie Platt - an insurance agency founder, community builder, and woman who has spent 15 years betting on herself as she goes - for a conversation about what it feels like to outgrow the pot you're in. We talk about the leap of faith it took to leave a good job with a two-year-old at home - the importance of saying what you mean, always, and why sometimes the brave thing isn't leaving - it's staying. Ellie is warm and generous in the most approachable way - and leaves us with a fun reflection on life through her lens today.

Ellie Platt is the owner and president of Platt Insurance, an independent agency she built from the ground up in Youngstown, Ohio. Now celebrating 15 years in business, she takes pride in leading a team of 12 and helping them grow while building a strong presence in the insurance industry. Ellie is also deeply committed to her community, serving in multiple leadership roles while balancing life as a dedicated mom. 

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Ema Roloff for a conversation about the uncommon courage it takes to build something before you know how it's going to turn out. We talk about reimagining the ways we gather, the accessibility gap in many professional events these days, and how it feels to take the first step when the noise around you tells you to wait  - or skip it altogether.

Ema Roloff is the Co-Founder of Roloff Consulting, where she helps business leaders navigate digital change with clarity, confidence, and a people-first approach. With more than a decade of experience in B2B enterprise software and complex enterprise sales, she translates topics like AI, digital transformation, and leadership into practical strategies that organizations can immediately apply. Through keynotes, workshops, research, and content Ema equips leaders to communicate change, build trust, and thrive in a digital-first world.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Melissa Barr, the founder of Sisu Insurance Services, for an honest, grounded conversation about the moment Melissa decided she was tired of her day running her. We talk about the non-linear, make-it-up-as-you-go reality of early entrepreneurship, the busy badge of honor so many of us have worn for decades without question, and what it looks like to finally - purposefully - start to uncrowd your life. 

Melissa Barr spent the last 24 years within the independent insurance agency operations space. Two years ago, she started her own company, Sisu Insurance Services, to help other independent agents and agencies build their businesses through enhancing workflows, building policies and procedures, employee and VA training and agency management system optimization. Fun facts about Melissa? She's a licensed massage therapist and has run the Detroit marathon; she also enjoys biking, hiking, running, yoga, barre and pairing great wine with great food! 

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here. Not following Meg on Instagram? You can find her here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Emily Merola, founder of the Blazer Society and leadership coach - for a conversation about what happens when we stop drifting and instead move with purpose. We talk about what happens when a woman finally gets clear on what she uniquely bring to the world, the courage it takes to bet on yourself after a lifetime of betting on everyone else, and why the women who need this support the most are often the ones who believe they deserve it the least. Emily is electric and so generous - this conversation will surely spark something in you, too.

Emily Merola is a former insurance industry executive – and today helps women leaders find the confidence to own the room and grow in their careers and lives. As a speaker and executive coach, she equips high-achieving women to move from overlooked to unmistakable through the power of presence. 

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Listen in as host Meg McKeen welcomes Julie Tomlinson for a conversation about the professional sabbatical that came when the job, the title, even the industry stopped fitting. We talk about psychological safety (it’s not a soft skill), what it means to mother a daughter as they both learn to take up space, and how confidence isn't a feeling - it's data, collected one attempt at a time. Julie is candid and wise, and reminds us that knowing who you are is a skill that will always be in demand.

Julie Tomlinson is a purpose‑driven insurance leader whose mission is to inspire advocacy and grace while empowering others with passion and respect. She serves on the Executive Board of the Girls Southeast Cincinnati Soccer Association, a nonprofit providing affordable recreational soccer to more than 1,000 girls across Greater Cincinnati. Before she joins Palomar Insurance in late July, Julie is currently enjoying a professional sabbatical, giving her the rare gift of time to fully soak in life with her wonderful family — Ryan (fellow insurance nerd and husband), Ellie (15), and Wesley (12).

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Join host Meg McKeen for a crossover podcast experience, featuring Kristin Heideman, the host of the Outspoken & Overbooked podcast. Recorded in front of a live, virtual audience, together we chat through our insurance career origin stories - and answer listener questions about moving from one role in the industry to another, and how to prep for the C-Suite, if that's what you decide is right for you. We already know it's who you know - but isn't it also how well you know yourself? 

With over a decade of hands-on experience in the insurance industry, Kristin knows what it takes to succeed in this space - because she's been there. After years as an Account Manager, she transitioned into recruiting to help others find the right fit and help firms build stronger teams.

Now, as the WBE-certified owner of The Brinkman Group, Kristin specializes in placing top talent across commercial lines, employee benefits, and wholesale brokerage. She works closely with hiring managers and candidates to make meaningful, strategic matches - not just quick placements.

Whether you're hiring, exploring new opportunities, or just want to stay informed about the market - Kristin is a resource you can trust.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!