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

You can’t be a leader unless you’re a continuous learner.

In this special Season 1 closer, Lisa is joined by her mom, Dr. Bonnie Kay! Bonnie is many things: consultant, psychologist, continuous learner, competitive golfer, and lifelong inventor of her own path. Together, they revisit the choices, relationships, and philosophies that shaped Bonnie’s unconventional career and deeply influenced Lisa’s own work in futures thinking and design.

During the conversation, Bonnie shares stories from her early days as an English teacher, her leap into psychology during a major turning point for women, the “shortest dissertation ever” on gender roles and marital satisfaction, and her later career helping leaders grow through quality management and emotional intelligence.

You’ll hear:

• How “continuous learning” became her north star
• Why the circle of influence still matters in chaotic times
• The power of great conversations
• Her signature philosophies like “take the best and leave the rest”

It’s a warm, funny conversation about ambition, family, reinvention, and the lifelong practice of creating a meaningful life on your own terms. A perfect end to Season 1.

Some of Bonnie’s Favorite books and resources:

7 Habits of Highly Effective People Stephen Covey

Fierce Conversations by Susan Scott

Women Who Run with Wolves, by Clarissa Pinkola Estés

Think Again by Adam Grant (my mom literally gives everyone in her life Adam Grant’s calendar)

9 lifetime Hole in Ones, Impressive! An informal account of golf highlights by Bonnie Kay

The Rise of the full Stack Learning Organization, Lisa Kay Solomon