Margo is joined by Anna Holzman, a therapist-turned-coach who helps sensitive creatives and entrepreneurs move through the fear of visibility and launch the work that feels most true to them. After 15 years in TV and publishing—and many false starts on her own creative dreams—burnout and chronic pain led Anna to discover nervous system tools that helped her unblock her voice and show up for the work she loves. Now she helps others melt through imposter syndrome, bring their creative visions to life, and share them boldly. She also hosts the podcast How to Trust Yourself.

Margo and Anna discuss:

• What’s happening in your nervous system when you want to launch something but feel stuck

• How to dialogue with fear instead of fighting it

• Why squashing fear often backfires

• The importance of social support and safety when showing up visibly

• Why sensitive voices are needed in today’s noisy world

• The perniciousness of comparison among creatives

• Graded exposure therapy

• Imposter syndrome, perfectionism, and creative blocks

• Understanding customer's perspectives
  
  

Connect with Anna:
www.annaholtzman.com
https://www.instagram.com/anna_holtzman/
How to Trust Yourself podcast: https://pod.link/1679033028

Connect with Margo:
www.windowsillchats.com
www.instagram.com/windowsillchats
www.patreon.com/inthewindowsill
https://www.yourtantaustudio.com/thefoundry

Margo is joined by artist and founder behind Beenanza Design, Bethany Andrews Nichols. A returning friend of the show, Bethany shares how her creative practice has evolved over the past few years—expanding her Burlington, Vermont studio into a hub for block printing workshops and collaborations with brands like King Arthur Flour and Cabot Cheese, developing her new DIY printing kit Coverall, and launching a block-printed fabric line with Stash Fabrics. Along the way, she opens up about navigating feedback, balancing motherhood and entrepreneurship, and the persistence it takes to keep moving forward.

Margo and Bethany discuss:

• How Bethany’s studio has evolved into a creative hub for workshops and collaborations

• Developing a DIY block printing kit

• Using feedback (even tough feedback) to refine ideas and keep creativity alive

• Building accountability and creative connections that move projects forward

• Balancing motherhood, entrepreneurship, and creative exploration

• Why starting before you’re “ready” is often the best way forward
  
  

Connect with Bethany:

https://www.beenanzadesign.com/partnerships
https://www.instagram.com/beenanza.design/
https://www.beenanzadesign.com/monthly-calendar/sept-25

Connect with Margo:
www.windowsillchats.com
www.instagram.com/windowsillchats
www.patreon.com/inthewindowsill
https://www.yourtantaustudio.com/thefoundry

Margo is joined by Cassie McDaniel, Head of Design at Medium, where she leads product design, brand, and research. Cassie has also brought her design expertise to companies like Lattice, Webflow, Glitch, and Mozilla Foundation, and she’s passionate about simplifying complex workflows while creating space for more meaningful design. Beyond her professional roles, Cassie is a painter, writer, DIY renovator, and environmental conservation group member—someone who embodies the importance of building a life rich with creativity both in and outside of work.

In this conversation, Cassie and Margo explore what it means to be a well-rounded creative leader, how personal passions fuel professional innovation, and why design belongs at the leadership table. Cassie also gives us a peek behind the curtain at Medium’s evolving design approach, including how her team thinks about content consumption, new UX navigation, and experiments with AI.

Margo and Cassie discuss:

• The case for doing things outside your job and how hobbies unlock new creative potential

• How writing serves as “exercise for the brain” and a counterbalance to a busy design career

• Cassie’s approach to mentorship, including hiring, coaching, and guiding designers at all levels

• A behind-the-scenes look at design at Medium, from flat minimalism to layered storytelling

• How a family legacy of persistence, from chicken farming to dentistry, shaped Cassie’s approach to creativity and leadership

• Lessons from Cassie’s career across Webflow, Glitch, Mozilla, and Medium, and why foundational creative skills translate to digital spaces

• What makes Medium unique as a platform for authentic stories, connection, and community

• The value of saying yes to new opportunities, co-designing with communities, and learning from every experience

• Balancing leadership, writing, and motherhood while still making time for passion projects at home
  
  

Learn more about Cassie here:

• Website: cassiemcdaniel.com

• Medium: cassiebegins.medium.com

• LinkedIn: linkedin.com/in/cassiemc

• Instagram: @cassiebegins
  
  

Connect with Margo:

www.windowsillchats.com

www.instagram.com/windowsillchats

www.patreon.com/inthewindowsill

https://www.yourtantaustudio.com/thefoundry

Save the date for Medium Day 2025: https://medium.com/blog/save-the-date-for-medium-day-2025-50b1f15de07d