How to Not Know with Simone Stolzoff

Welcome back to Snafu w/ Robin Zander. 

In this episode, I’m joined by Simone Stolzoff – author of The Good Enough Job and the upcoming How to Not Know – and our opening keynote speaker at Responsive Conference 2025.

We explore what it means to have an identity beyond your job title, why rest is essential for high performance, and how ritual and community offer grounding in an age of uncertainty. Simone shares how Judaism and Shabbat have shaped his views on balance, the role of “guardrails” over boundaries, and how we can build more durable lives – personally and professionally. We talk about the future of religion, the risks and opportunities of AI, and why books still matter even in a tech-saturated world. Simone also offers practical writing advice, previews his next book, and explains why embracing uncertainty may be the most valuable skill of all.

Simone will be speaking live at Responsive Conference 2025, September 17–18, and I can’t wait for you to hear more.

If you haven’t gotten your tickets yet, get them here.

 

Start (00:00) Identity Beyond Titles (01:07.414)

• What identities do you hold that aren't listed on your LinkedIn?

• Simone’s Answer:

• Ultimate frisbee player – “the entirety of my adult life”

• Aspiring salsa dancer – taking intro classes with his wife

• Former spoken word poet – “It was the most important thing to me when I was 19 years old.”

• New father – navigating life with a five-month-old

• "I encourage people to ask: what do you like to do, as opposed to what do you do?"

Shabbat as a Sanctuary in Time (01:58.831)

• Robin references Simone's TED Talk, focusing on Shabbat as a metaphor for boundary-setting and presence.

• Simone expands:

• Shabbat offers a weekly rhythm to separate work from rest.

• Emphasizes the idea of "sacred time" and intentional disconnection from screens.

• Shabbat is a “sanctuary in time,” paralleling physical sanctuaries like churches or synagogues.

• Relates this to work-life balance, noting that intentions alone aren't enough – infrastructure is needed.

• "We have intentions… but what actually leads to balance is structural barriers."

Boundaries vs. Guardrails (04:44.32)

• Cites Anne Helen Petersen’s metaphor:

• Boundaries = painted lane lines

• Guardrails = physical barriers that actually keep you on the road

• There are calls for more guardrails (structural protections) in modern life.

• Examples:

• Airplane mode during playtime with his kid

• Attending yoga or activities where work can’t creep in

• "Individually imposed boundaries often break down when the pressures of capitalism creep in."

Religion, Ritual & Community (06:48.57)

• Robin asks how Judaism has shaped Simone’s thinking around work and life.

• Simone reflects:

• Religion offers a “container” with a different value system than capitalism.

• As organized religion declined, people turned to work for identity, meaning, and community.

• Religion can offer rituals to process uncertainty — e.g., mourning rituals like sitting shiva.

• Religious or community spaces offer contrast: they don’t care about your career success.

• "Religion is sort of like a container… with a value system that isn't just about growth charts."

• "It can be refreshing to say: Day 1, do this. Day 7, go for a walk."

• Personal journey:

• Simone reconnected with Judaism in his 30s as he built his own family.

• Once, went out of obligation, then rejected it, and now see beauty in ritual and intergenerational wisdom.

The Future of Religion & Community (09:12.454)

• Robin theorizes a future rise in spiritual and communal gatherings:

• Predicts new spiritual movements or evolutions of old ones

• Notes a hunger for meaningful in-person connection, especially post-AI and amid tech saturation

• "There's a hunger... as AI and screens define how we relate, people want to gather in person."

• "I don’t tend to make predictions, but I think this one’s inevitable."

• Simone agrees... but offers data as contrast:

• Cites the decline in religious affiliation in the U.S.

• 1950s: 3–4% unaffiliated

• Today: Nearly 1 in 3 identify as “Nones” (no religion)

• Notes reasons:

• Rising wealth tends to increase secularism

• The internet creates alternate identity spaces

• "I do believe there is inevitability in the growth [of spirituality]... But the data points the opposite way."

• Simone reflects on the factors behind declining religious affiliation:

• Doubt now builds community – the internet has enabled people to connect around leaving religion as much as practicing it.

• Political entanglement – many young Americans, especially, are alienated by the perceived overlap between right-wing politics and Christianity.

• Yet despite this secular trend, the need for meaning, ritual, and purpose remains universal.

• “There still is this fundamental need to find meaning, to find purpose, to find ritual… even if it’s not in the forms we’re used to.”

A Church in the Mission (13:07.182)

• Robin shares a formative experience from 2016:

• That year, he launched both Robin’s Café and the first Responsive Conference.

• When he walked into the theater space that would become his café, he encountered a young, diverse Christian revival group – live music, dancing, and energetic worship happening in a Mission District theater.

• This juxtaposition – a traditional spiritual gathering inside a modern, “hip” venue – left a lasting impression.

• “It felt like a revival meeting in the South… except it was full of people my age and younger, partying on a Saturday morning – and it just happened to be church.”

You Are More Than Your Work (14:51.182)

• Robin segues into the idea of multiple identities:

• He recalls how reading The 4-Hour Work Week helped him embrace not defining himself solely by his entrepreneurial work.

• Even on tough days running a business, movement and fitness have been a grounding force – something he does daily, independent of career performance.

• Quotes from Simone’s TED Talk:

• “Some people do what they love for work; others work so they can do what they love. Neither is more noble.”

• Robin asks Simone to share the origin of this line and how it connects to the poet Anis Mojgani.

• Simone recounts a pivotal conversation during college:

• As a poetry and economics double major, he was wrestling with career path anxiety.

• He interviewed his favorite poet, Anis Mojgani, asking: “Do you believe in the idea, ‘Do what you love and never work a day in your life’?”

• Mojgani’s response:

• “Some people do what they love for work. Others do what they have to so they can do what they love when they’re not working. Neither is more noble.”

• This countered Simone’s expectations and left a deep impression. He highlights two cases for cultivating a broader identity beyond work:

• Business Case:

• High performance requires rest.

• People with “greater self-complexity” — more identities outside of work — are more creative, more resilient, and more emotionally stable.

• Moral Case:

• Investing in other parts of ourselves makes us better citizens, community members, and humans.

• Singular identity (especially career-based) is fragile and susceptible to collapse — e.g., pandemic layoffs.

• Solely work-based identity also sets unrealistically high expectations that can lead to disappointment.

• “You’re balancing on a very narrow platform… You’re susceptible to a large gust of wind.”

• Robin reflects on how the Responsive Manifesto intentionally avoids prescribing one path:

• It's not anti-work or anti-grind.

• Recognizes that sometimes hard work is necessary, especially in entrepreneurship.

• Shares how his friend’s newsletter, Just Go Grind, embraces the idea that seasons of hustle are sometimes required.

• “Everyone figuring out their own boundaries is actually the goal.”

Work Isn't Good or Bad – It's Complex (18:34.436)

• Simone adds that society tends to polarize the narrative around work:

• Some say “burn it all down”, that work is evil.

• Others say, “Do what you love, or it’s not worth doing.”

• His book The Good Enough Job argues for a middle way:

• It’s not hustle propaganda.

• It’s not a slacker's manifesto.

• It’s about recognizing that we spend a huge portion of our lives working, so it matters how we approach it, but also recognizing we’re more than just our jobs.

• He introduces the concept of temporal balance:

• “There’s a natural seasonality to work.”

• Sometimes, long hours are necessary (e.g., startup mode, sales targets).

• But it should be a season, not a permanent lifestyle.

What’s the Role of Books in the Age of AI? (22:41.507)

• Robin poses a forward-looking question:

• In an age when AI can summarize, synthesize, and generate information rapidly, what’s the role of books?

• Especially nonfiction, where facts are easier to reproduce.

• Simone responds with both uncertainty and hope:

• Human storytelling as a moat:

• His work relies on reporting, profiling, and character studies — something LLMs can’t yet replicate with nuance.

• He doesn’t know how long this will remain defensible, but will continue to lean into it.

• Books are more than information:

• Books have utility beyond facts: they are entertainment, physical objects, and cultural symbols.

• Quotes the vibe of being surrounded by books: there's even an untranslatable word (possibly German or Japanese) about the comfort of unread books.

• A vinyl-record future:

• Books may become more niche, collectible, or artisanal, similar to vinyl.

• But they still hold society’s most well-formed, deeply considered ideas.

• The human touch still matters:

• A typed note that looks handwritten isn’t the same as a note that is handwritten.

• People will crave authenticity and human creation, especially in a tech-saturated world.

• “You can appreciate when something has a level of human touch, especially in an increasingly tech-powered world.”

• He closes with a self-aware reflection:

• “I don’t claim to know whether my career will still exist in five years… which is why I picked this topic for my second book.”

“Created by Humans” (25:49.549)

• Robin references a conversation with Bree Groff, who imagined a world where creative work carries a “Created by Human” tag, like organic food labeling.

• “I think we’ll see that [kind of labeling] in the next few decades – maybe even in the next few years.”

• As AI-generated content floods the market, human-made work may soon carry new cultural cachet.

• Simone shares a turning point: after submitting an op-ed to The New York Times, his editor flagged a bad metaphor. En route to a bachelor party, he opened ChatGPT, asked for new metaphors, chose one, and it made the print edition the next day.

• “Maybe I’ve broken some law about journalism ethics... but that was the moment where I was like: whoa. This sh*t is crazy.”

The Home-Buying Crash Course Powered by AI (27:57)

• Robin’s breakthrough came while navigating the chaos of buying a house. He used ChatGPT to upskill rapidly:

• Structural questions (e.g., redwood roots and foundation risk)

• Zoning and legal research

• Negotiation tactics

• “The rate of learning I was able to create because of these tools was 10 to 100 times faster than what I could’ve done previously.”

How to Live Without Knowing (29:41.498)

• Simone previews his next book, How to Not Know, a field guide for navigating uncertainty. In an age of instant answers, our tolerance for the unknown is shrinking, while uncertainty itself is growing.

• “We’re trying to find clarity where there is none. My hope is that the book offers tools to live in that space.”

• The “Three Horsemen of Delusion”:

• Comfort – we crave the ease of certainty.

• Hubris – we assume we know more than we do.

• Control – we believe certainty gives us power over the future.

• Robin asks how Simone finds his stories. His answer: chase change. Whether internal (doubt, transformation) or external (leaving a cult, facing rising seas), he seeks tension and evolution.

• Examples:

• A couple questioning their marriage

• An employee leading dissent at work

• A man leaving his religious identity behind

• A nation (Tuvalu) confronting its own disappearance

• “The story you find is always better than the one you seek.”

Want to Be a Writer? Start Writing. (36:50.554)

• Robin asks for writing advice. Simone offers two pillars:

• Ask These Four Questions:

• What’s the story?

• Why should people care?

• Why now?

• Why you?

• “Only you can tell the story of buying a café and selling it on Craigslist.”

• Build the Practice:

• Writing is not just inspiration—it’s routine.

• Schedule it. Join a group. Set deadlines.

• “Writing is the act of putting your ass in the chair.”

• Robin applauds Simone’s book title, How to Not Know, for its playfulness and relevance. He asks how Simone’s own relationship with uncertainty has evolved through his research.

• Simone reflects on how writing his first book, The Good Enough Job, softened his stance, from a hot take to a more nuanced view of work’s role in life. Similarly, with his new book, his thinking on uncertainty has shifted.

• “Uncertainty is uncomfortable by design. That discomfort is what makes us pay attention.”

• Simone once championed uncertainty for its spontaneity and freedom. But now, he sees a more complex dance between certainty and uncertainty.

• “Certainty begets the ability to become more comfortable with uncertainty.”

• He gives the example of a younger self traveling with no plan, and the maturity of seeing how some people use uncertainty to avoid depth and commitment.

Durable Skills for an Unstable Future (43:57.613)

• Robin shifts to the practical: In a world where stability is fading, what should we teach future generations?

• Simone shares three core “durable skills”:

• Learn how to learn – Adaptability beats certainty.

• Tell compelling stories – Human connection never goes out of style.

• Discern control from chaos – Use a mental decision tree:

• What can I control?

• If I can’t control it, can I prepare?

• If I can’t prepare, can I accept?

• “Often we’re more uncomfortable with uncertainty than with a certain bad outcome.”

• He cites research showing people are stressed more by maybe getting shocked than actually getting shocked.

AI as Editor, Not Author (47:23.765)

• Robin circles back to AI. Simone explains how his relationship with it has evolved:

• He never uses it for first drafts or ideation.

• Instead, AI serves as a “sparring partner” in editing – great at spotting drag, less useful at solving it.

• “People are often right about something being wrong, but not about the solution. I treat AI the same way.”

• Simone defends creative friction as essential to craft: rewriting, deleting, struggling – that’s the work.

The Chinese Farmer & the Fallacy of Forecasts (50:27.215)

• Robin expresses cautious optimism – but also fears AI will widen inequality and erode entry-level jobs. He asks what gives Simone hope.

• Simone counters with the “Parable of the Chinese Farmer,” where events can’t be judged good or bad in real time. His conclusion: we don’t know enough to be either pessimistic or optimistic.

• “Maybe AI ushers in civil unrest. Maybe a golden age. Maybe yes, maybe no.”

• He’s most hopeful about the growing value of human touch – gifts of time, love, and effort in an increasingly automated world.

Where to Find Simone (53:44.845)

• Website: thegoodenoughjob.com

• Newsletter: The Article Book Club (monthly articles not written by him, thousands of subscribers)

• Robin reminds listeners that Simone will be the opening speaker at Responsive Conference 2025, September 17–18.

 

People Mentioned:

• M'Gilvry Allen

• Anne Helen Petersen

• Anis Mojgani 

• Bree Groff 

• Tim Ferriss

• Steven Pressfield

• Ernest Hemingway

• Justin Gordon

 

Organizations Mentioned:

 

• Responsive Conference

• Zander Media

• Asana, Inc

• X, The Moonshot Factory (formerly Google X) 

• Waymo, 

• Jewish Community Centers (Boulder & Denver) 

• Robin’s Cafe

• Amazon

• Google / Alphabet 

 

Books & Newsletters

• The Good Enough Job 

• How to Not Know (upcoming book)

• The 4‑Hour Workweek

• Just Go Grind 

• Article Book Club