Chris Guillebeau, bestselling author and creator of The Art of Nonconformity, joins Lisa to explore what it really takes to build a self-directed life. He shares his unconventional path from high school dropout and aid worker in West Africa to global traveler, author of nine books, and entrepreneur. Chris unpacks the philosophy behind his work—why you don’t have to live your life the way others expect—and introduces the concept of time anxiety, the tension between the fear of running out of time and the paralysis of endless choices.

The conversation covers everything from the psychology of “enough” and how mortality awareness can sharpen your priorities, to practical strategies for leaving things undone, creating accountability structures, and decluttering your calendar. Chris also opens up about ADHD, therapy, and why you should ask yourself at the end of the day, “Did today matter?”

Behind his brilliance: Refusing to accept “no” and always looking for another way.

TOPICS COVERED

· The difference between traditional anxiety and time anxiety

· Why having more choices creates its own form of paralysis

· The two types of time anxiety: existential panic and decision overwhelm

· How ADHD diagnosis changed his relationship with productivity

· Why working for yourself is actually the conservative choice

· The myth that independent work is inherently risky

· Moving from "you can be anything" liberation to burden

· Why curiosity without follow-through is just floating ideas

· The seasonality of creative work and energy cycles

· How to measure success by what you control vs external outcomes

· The power of asking "Did today matter?" over productivity metrics

· Why leaving things undone is a radical act in completion culture

· The difference between hard work and passionate engagement

· How to use death as a clarity tool rather than anxiety trigger

· Platform agnosticism and the creator economy evolution

· The accountability structures that support independent creators

· Why caring about your work trumps optimization systems

· Moving from rules-based to values-based decision making

· The future self trap and why motivation doesn't transfer

· How to create enough-ness in a never-enough culture

THE SHOW
In this episode of Behind the Brilliance, entrepreneur and investor Sieva Kozinsky joins the show to share his journey from first-generation immigrant beginnings to co-founding Enduring Ventures, a holding company that acquires and grows businesses for the long game. Sieva opens up about the fear that fueled his early ventures, the lessons learned from failed startups and pivots, and why fundraising can sometimes blind founders to what really matters.

We dive deep into the psychology of selling a company, the art of negotiation with founders, and how legacy is built (or destroyed) in the years after an exit. Sieva also reflects on emotional discipline, meditation, and why surrounding yourself with the right five people may be the single most important factor in your growth. This conversation extends beyond building businesses to explore a useful philosophy for building a life you’ll still be proud of twenty years from now.

Behind his Brilliance: His mother and grandmother

TOPICS COVERED

• How Sieva’s immigrant upbringing shaped his resilience
• Pivoting from pre-med to entrepreneurship
• The pivotal college class that changed everything
• Why early failures were his best education
• Lessons from building and pivoting StudySoup
• Bootstrapping vs. raising venture capital (and why he regrets fundraising early)
• The psychology of fear as a driver in entrepreneurship
• Emotional discipline: responding instead of reacting
• The role of meditation in business and life
• The dangers of selling to universities (and what that taught him)
• Negotiating with founders who are selling their life’s work
• Why most entrepreneurs misunderstand exits and valuations
• The holding company model and why it’s different from private equity
• How to minimize regret when selling a business
• Finding the right cofounder and what to look for beyond skills
• The importance of discomfort in building a meaningful life
• Why you become the average of the five people closest to you
• Seeking serendipity and building networks through curiosity

THE SHOW

What happens when you build the company of your dreams, only to realize the dream came with tradeoffs you didn’t see coming? In this candid conversation, Rand Fishkin — cofounder of Moz and SparkToro — shares the pivotal moments that shaped his career: turning a $39 side experiment into a multimillion-dollar SaaS, raising venture capital for the wrong reasons, walking away from a $40M acquisition offer, and rebuilding his identity after leaving the company he founded.

Along the way, Rand unpacks the philosophy he lives by now: designing work around the life you want, not the other way around. You’ll learn why audience-first growth changes everything, how “dark social” can reshape your marketing strategy, and why the best companies aren’t built on hustle, but on thoughtful design.

If you’ve ever wrestled with status anxiety, questioned the pace you’re working at, or wondered what it would look like to run a business without burning yourself out, this episode will give you fresh perspectives and actionable ideas for building something that lasts — without losing yourself in the process.

BEHIND HIS BRILLIANCE: Empathy

TOPICS COVERED

· Status is a poor reason to raise capital – chasing external validation through VC can distort decision-making and undermine founder well-being.

· Audience-first beats product-first – building trust and reach before launching a product creates built-in marketing and faster adoption.

· Design trumps grind – thoughtful business and life design leads to better decisions, fewer hours, and more sustainable success than relentless hustle.

· Identity can’t be tied to one venture – detaching self-worth from your company enables resilience when endings or pivots come.

· Opportunity cost is real – turning down an offer (even for the “right” reasons at the time) can shape the trajectory of both the business and your personal life.

· Measure what matters, not what’s easy – “dark social” means a lot of word-of-mouth and share-driven traffic won’t show up in analytics the way you expect.

· Life design is part of business design – integrating personal goals, health, and relationships into work choices leads to richer, more fulfilling outcomes.

And much more!

Get the Show Notes here.

Dr. Rae Wynn-Grant is a wildlife ecologist, storyteller, and nature show host whose path to success defies every traditional metric of merit. In this candid conversation, Rae shares how she went from struggling in math and science classes to earning a PhD and becoming a leading voice in wildlife conservation.

We explore the pivotal role that belief, representation, and access played in shaping her journey from her first exposure to nature through television, to a transformative study abroad trip to Kenya, to an unexpected pivot from lions to black bears. Rae also opens up about hitting emotional rock bottom in her 30s, the identity crisis that followed, and how she rebuilt her life with honesty, humility, and hope.

This episode is a testament to what’s possible when we follow our passion, even when our performance or our path doesn’t fit the mold.

Behind her brilliance: Taking a non-traditional approach

TOPICS COVERED:

Why passion trumps performance - How to pursue your calling even when traditional metrics suggest you're "not qualified"

The representation breakthrough - Why seeing yourself reflected in expertise positions transforms what feels possible

Navigating productive discomfort - How to embrace stretching experiences that feel uncomfortable but lead to growth

Identity crisis as catalyst - Using rock bottom moments as launching pads for authentic reinvention

The marriage blueprint trap - Why relationships fail when one person brings a pre-drawn life plan instead of co-creating

Accountability without excuses - The liberation that comes from owning your choices and their consequences

Nontraditional paths to traditional success - How to thrive by refusing to fit conventional molds while still achieving recognized accomplishments

Environmental justice reframed - Why urban communities often care more about environmental issues than rural ones (despite stereotypes)

The privilege of starting over - Understanding what safety nets make radical life changes possible

Choosing authenticity over expectations - The courage required to disappoint others in service of being true to yourself

THE SHOW

Most of us are running on autopilot, checking boxes, chasing goals, and pushing toward some imagined finish line without stopping to ask if this is how we really want to spend our lives.

In this conversation, Jodi Wellman, author of You Only Die Once and founder of the 4,000 Mondays framework, makes the case for using mortality as a tool, not a threat. She shares why contemplating the end of life can snap us out of numb routines and guide us toward choices that create more vitality, meaning, and joy right now.

We talk about why achievement can feel hollow, how to spot the “dead zones” in your life, and the surprising power of small changes to make life feel bigger. Whether you have been wondering if there is more to life than your to do list or you just want to feel more alive in your everyday routines, this conversation is a reminder that your Mondays are numbered so make them count.

Behind her brilliance: Love and the Grim Reaper

TOPICS COVERED

· Mortality as Motivation: Facing the reality of death as a way to live more fully, not morbidly.

· 4,000 Mondays Concept: Using your finite number of Mondays as a framing device to clarify what matters.

· Vitality + Meaning = Fulfillment: Living wider (fun, novelty, aliveness) and deeper (purpose, connection).

· The Hedonic Treadmill: The idea that high achievers constantly move the goalpost and lose perspective on satisfaction.

· Experimentation as a Way of Life: “You don’t have to detonate, you can dabble.”

· Regret Minimization Framework: Inspired by Jeff Bezos and reframed here as: “What would you regret not doing?”

· Role of Rituals and Values: Structuring life around recurring rituals and clearly defined personal values.

· Self-Compassion and Inner Talk: The importance of being kind to yourself in the pursuit of growth.

· Redefining Success and Retirement: Moving from performance-based identities to interest-based living.

· Comparison and Individual Journeys: Why your life design has to be uniquely yours, and how social media distorts that.

Elaine Pofeldt, former Fortune Small Business editor, uncovered a hidden economy of one-person businesses quietly earning 7 figures and spent years interviewing the entrepreneurs behind them. In this conversation, she reveals the surprising industries dominating this space, why professional services often outperform tech, and the frameworks that actually work for building sustainable solo wealth.

From starting smart while keeping your day job to using AI as your secret weapon, Elaine breaks down the real strategies behind million-dollar one-person businesses. No hype, no hustle culture required. Plus: why health and boundaries aren’t “extras” but essential business infrastructure, and how to design a career that serves your life instead of consuming it.

Essential listening for anyone who wants financial freedom without chasing passive income or playing the venture capital game.

Behind Her Brilliance: Family

TOPICS COVERED

Elaine’s journey from fiction writing to journalism

The evolution of business journalism and rise of entrepreneurship in the public imagination

How AI and automation empower solo business owners

The origin story of The Million Dollar, One Person Business

Why peer learning and relatable case studies matter

Common traits among successful solo entrepreneurs

The emotional and mental stamina required to succeed independently

The role of physical health, boundaries, and self-awareness in entrepreneurial success

How older professionals and people with disabilities are reshaping the business landscape

Flexible business models that support life design

Building walk-away money and choosing clients wisely

The underestimated power of tools like planners, automation apps, and AI assistants

Lifestyle design, digital nomadism, and work-from-anywhere strategies

THE SHOW

Dr. Tal Ben-Shahar, Harvard-trained psychologist and author of multiple bestsellers including Happier, joins Lisa to explore the psychology and habits that lead to happiness in modern times. He uncovers the myths that keep successful people miserable and why our pursuit of the next achievement isn’t the answer. He shares his personal journey from academic achievement to profound unhappiness, breaks down the difference between experiencing emotions and being consumed by them, and offers a counterintuitive approach to emotional health through passive observation. The conversation covers everything from the achievement trap and social media's impact on happiness to practical parenting strategies and the future of leadership in a post-pandemic world.

Behind his brilliance: Curiosity and passionate effort

Visit BehindtheBrilliance.com for the show notes

TOPICS COVERED

Why successful people often feel secretly empty

The myth of constant happiness and toxic positivity culture

Passive observation: witnessing emotions without being consumed by them

The psychology of "enough" and escaping achievement addiction

Why fighting your feelings makes them persist

The role of curiosity in emotional wellbeing and personal growth

Social media's impact on perfectionism and life satisfaction

How to create space between stimulus and response during overwhelming moments

The difference between hard work and effort in personal development

Turning emotional dissatisfaction into positive life changes

Modern loneliness epidemic and the paradox of digital connection

Building authentic relationships based on values rather than demographics

The symbiotic relationship between leadership and management

Why power and control are ineffective leadership tools

Parenting strategies for raising emotionally intelligent children

The importance of modeling emotional regulation for kids

How to develop discipline without relying on motivation or willpower

Why retirement isn't the answer to work dissatisfaction

The value of experimentation and changing periods to question marks in life

SUMMARY

Anne-Laure Le Cunff, founder of Ness Labs and author of Tiny Experiments: How to Live Freely in a Goal-Obsessed World, joins Lisa to reveal her unconventional career journey from Google engineer to startup founder to neuroscience student to successful entrepreneur with Ness Labs. Growing up outside Paris with parents who prioritized financial security, she landed a dream job at Google with the status and paycheck that signaled success. But she soon realized that the ladder she was climbing was leaning against the wrong wall.

This conversation explores cognitive scripts that keep us stuck, the importance of experimentation over rigid goal-setting, navigating uncertainty, and designing a life aligned with internal rather than just external metrics of success. Anne-Laure shares insights on managing different types of burnout, the psychology of major transitions, and how she uses tools like journaling and AI to support her work and decision-making.

Behind her brilliance: Curiosity

Say hi to Anne-Laure on X/Twitter: @neuranne

TOPICS COVERED
Breaking free from cognitive scripts
The problem with traditional goal-setting
Building an experimental mindset
Why “feeling lost” is the price we pay for having freedom
Career transitions and identity beyond job titles
Navigating impostor syndrome
Burnout (including when you love your work!)
Redefining success using internal vs. external criteria
Managing time and energy without a corporate structure
Redefining the relationship between time, money, and personal values
Building a business organically and leveraging momentum
Using AI as a creative thinking partner
Growing up with multicultural influences
Examining default coping mechanisms like alcohol (and Anne-Laure’s journey to sobriety)
Letting curiosity lead personal and professional decisions
And much more!