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.