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

The future is being built in the spaces most of us never learned to see.

In this episode, Lisa talks with journalist and entrepreneur Jennifer Brandel. Jennifer is the co-founder of Zebras Unite, and creator of the Interstitium, a theory of the hidden connective work that keeps communities, movements, and systems alive. Jenn has spent her career naming the “in-between” roles that make change possible and giving shape to the people who do them.

They explore:

• The Interstitium Jenn's new framework for the unseen connective tissue of society
• Hexagon people those who bridge local life and global ideas
• Sacred hospitality how to create spaces where real transformation can happen
• Why connection is the real antidote to loneliness, polarization, and overwhelm
• Zebras Unite a model for building companies that are profitable and regenerative

Jenn shares stories from journalism, civic innovation, and community building, showing how naming and noticing these patterns helps people feel less alone.

This conversation is an invitation to reconnect with each other, design healthier ways of working together, and imagine futures built on reciprocity, meaning, and resilience.

Links from the show:

• Jennifer’s website
• The Intersitium
• Hexagon People
• Zebras Unite
• Zebras Fix what Unicorns Break