Sometimes the fastest way to clarity is to start drawing.

In this episode of How We Future, Lisa Kay Solomon sits down with visual thinking pioneer Dan Roam to explore how simple sketches can bring clarity to complexity. Dan, author of The Back of the Napkin and five other bestselling books, shares how visual thinking strengthens problem-solving, communication, and our sense of agency in an uncertain world.

In this conversation, you’ll learn:

• Why drawing helps us slow down and make sense of complex problems
• How Dan’s “six by six” framework supports clearer thinking and communication
• What visual thinking has to do with personal agency and influence
• Dan's philosophy on AI and its impact on storytellers

Lisa and Dan trace the roots of visual thinking back to how our brains naturally process the world, then bring those ideas into real life. The conversation also looks ahead as they reflect on what visual thinking means in an era of generative AI, and why human judgment, ethics, and curiosity still matter deeply.

Links from the show

• The Back of the Napkin: Solving Problems and Selling Ideas by Dan Roam
• Blah, Blah, Blah: What to Do When Words Don't Work by Dan Roam
• Show and Tell: How Everybody Can Make Extraordinary Presentations by Dan Roam
• Napkin Academy

In serious times, play can be one of our most powerful tools.

In this episode of How We Future, Lisa talks with Jill Vialet, social entrepreneur, author of Why Play Works, and founder of Playworks, about why play belongs at the center of how we lead, learn, and navigate complexity. Jill covers her journey to building an organization that transformed recess into a source of connection, trust, and resilience for millions of kids.

Their conversation explores how play helps people regulate their nervous systems, build relationships across differences, and see new possibilities when problems feel stuck. Jill shares lessons from Playworks, why trust is a prerequisite for learning, how unstructured play supports emotional growth, and what leaders can borrow from playgrounds.

You’ll hear about:

• How play helps us navigate chaos and uncertainty
• The connection between play, trust, and feeling safe
• How small, unexpected tweaks can unlock entirely new futures

This episode proves that creativity, empathy, and experimentation often emerge when people feel safe enough to engage. If you are leading through uncertainty or looking for new ways to bring people together, Jill offers practical insight and hopeful perspectives on how play can help us move forward.

Links from the episode:

Jill Vialet personal site

Jill’s Substack, “Workswell”

Jill’s Tee’s Shop

Why Play Works by Jill Vialet

Play: How it Shapes the Brain, Opens the Imagination, and Invigorates the Soul by Stuart Brown

Can changing your mindset increase your lifespan?

To kick off season two of How We Future, Lisa sits down with Chip Conley, entrepreneur, bestselling author, and founder of Modern Elder Academy. Chip has spent decades helping people rethink aging, midlife, and what it really means to live life to the fullest.

In their conversation, Chip and Lisa explore the idea of the “midlife chrysalis” and why the years around 45 to 55 can be a powerful period of transformation rather than decline. Drawing from his own near-death experience, his work in hospitality, and his time at Airbnb, Chip offers a hopeful and grounded reframing of aging.

You’ll hear about:

• How wisdom is distilled from experience and why it matters now more than ever
• How curiosity and energy can counter ageism at work
• What hospitality, community, and belonging have to teach us about the future

From emotional equations to regenerative communities, this episode is a reflection on learning, leadership, and designing a life with intention. If you are navigating change or wondering how to grow older with more joy and agency, Chip offers language, frameworks, and perspective to help you maximize your life.

Links from the episode:

• Modern Elder Academy
• Chip’s podcast, The Midlife Chrysalis
• Learning to Love Midlife: 12 Reasons why Life gets better with Age by Chip Conley
• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life by Chip Conley
• Chip Conley on Lenny Rashinsky’s podcast
• Chip’s post on LinkedIn celebrating his 65th birthday!
• 10 Commandments or Commitments, by Chip Conley