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

In episode two of this two-part series, Margo continues her conversation with watercolor artist, creative mentor, and founder of Blue Pine Arts, Trupti Karjinni. In part one, Trupti shared her journey from building a thriving art supply and teaching business to experiencing burnout and rebuilding a more aligned, sustainable creative life. Here, the conversation shifts into the how: the mindset, methods, and strategies behind building a soulful teaching business that truly supports artists both creatively and financially.

Margo and Trupti discuss:

• Why “Big Box Mentor” launch advice often fails creative, heart-centered artists.

• Trupti’s Artist’s Launch Blueprint for burnout-free, spacious course launches.

• Building community and creative sovereignty through teaching.

• Navigating the emotions of entrepreneurship as a neurodivergent, heart-led artist.

• How teaching can be the most liberating and profitable step for artists.

• Encouragement for the artist who secretly dreams of teaching but feels overwhelmed.

Connect with Trupti:

Download Trupti’s free ebook Creative Teaching Stories
Blue Pine Arts
Follow Trupti on Instagram
Follow Blue Pine Arts on Instagram
Watch Trupti on YouTube

Connect with Margo:

www.windowsillchats.com

www.instagram.com/windowsillchats

www.patreon.com/inthewindowsill

https://www.yourtantaustudio.com/thefoundry

Margo is joined by watercolor artist, creative mentor, and founder of Blue Pine Arts, Trupti Karjinni. Since 2017, Trupti has taught over 45,000 students worldwide, guiding them to fall in love with watercolor while building confidence and creative joy. Today, she paints serene landscapes from the Canadian Rockies, creates handcrafted art supplies, and mentors artists who dream of teaching their art through courses, memberships, and retreats.

Together, they unpack Trupti’s journey from burnout to building a soul-aligned creative business that supports both artistic expression and financial freedom.

Margo and Trupti discuss:

• The path from making paints by hand to building Blue Pine Arts.

• Trupti’s transition from teaching on platforms like Skillshare to creating her own courses.

• What caused her creative burnout and how she rebuilt on her own terms.

• Why artists get stuck in hustle-mode (and how to break free).

• The importance of aligning your teaching business with your creative energy.

• How artists can honor both their creativity and financial goals.

Connect with Trupti:

Download Trupti’s free ebook Creative Teaching Stories
Blue Pine Arts
Follow Trupti on Instagram
Follow Blue Pine Arts on Instagram
Watch Trupti on YouTube

Connect with Margo:

www.windowsillchats.com

www.instagram.com/windowsillchats

www.patreon.com/inthewindowsill

https://www.yourtantaustudio.com/thefoundry