Doomer Optimism

One area where this podcast has turned its attention lately is the question of children, especially questions of schooling and parenting in The Age of the Machine. What follows is a conversation about free range parenting, and the importance of giving kids the freedom, outside the machine, to learn, grow and make mistakes.

I was lucky enough to have crossed paths with Lenore on Twitter The Everything App when she came across my viral post about my middle daughter’s “biker gang”:

I think my middle daughter is having the best summer of her childhood
She has this group of friends, they're all incoming 5th graders, and their moms and I have a big group chat going where a kid will ask their mom to say "anyone want to ride bikes" and then they start a little band of kids going house to house inviting others to play. Then they head to parks, to coffee shops, jump on the trampoline in their friends' yards.
One good thing though is that the moms are all in touch so even if the kids don't have phones or watches to communicate, we communicate with each other where they are/where they're headed.
They call it their biker gang.
My daughter has told me it is her favorite thing in the whole world, riding bikes with her friends. She says I'd rather do it than go to Disneyworld!
I asked her why and she said it's the freedom.
There is a certain age, I'd say something like grades 3 to 7, where it is essential kids get some independence. I think back to the times in my childhood where I was given some freedom to wander in those ages, and those are some of the best memories of my life.
It's so important we don't rob our kids of this. Make it happen by any means possible.

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Lenore is famous for letting her then 9 year old ride the subway in New York City alone. After teaching him how, she brought him to a designated spot and allowed him to find his way home. She was swiftly branded The Worst Mom in America.

Well, let all the Worst Moms unite!

In this episode we talk about the biker gang and her work in free range parenting which has now transformed into the Let Grow project which has all sorts of free materials for parents and teachers on building up confidence and responsibility in our kids.

Enjoy this episode, one of my favorites ever!

An old friend to the show, once maybe a foe for a while, back into friendly territory: Michael Thomas the Director of The Catholic Land Movement. I (Ashley) met Mike a almost half a decade ago, very early in my twitter days. It’s been a joy to see his vocation develop through the years and I am very glad Jason invited him back on the show.

In this episode, Mike and Jason discuss the development of the movement, Catholic Social Teaching, distributism, dignified work and practical action, the importance of in person connection, vocation, family, and love!

Enjoy!

I met Dwayne at a chance encounter at the Aspen Ideas festival in Chicago which my new buddy Samuel Kimbriel invited me to attend. I was feeling a little lonely and alienated there, lots of technocrats, and up to me walks Dwayne who saw my tag said optimism and he said “I am just about the most optimistic guy you’ll meet!”

I saw his tag from the Southeastern Grasslands Institute and I instantly knew this was someone I’d need to have on the pod. Unsurprisingly I tapped Peter Allen to co-host with me and these two were fast friends! Oak savannah ecosystem nerds unite!

Enjoy this episode!

If you want to support Dwayne’s work, consider attending the Eastern Native Grasslands Symposium conference: https://www.engsymposium.org/home or finding their work here: https://www.segrasslands.org/

I met Stephen this summer at the Woodcrest Bruderhof + DO + Savage Collective event in NY. Alan from Plough suggested Stephen for a panel and he instantly agreed! He gave a fantastic talk about the wonderful characters in his neighborhood, and the very real sense of place that happens when you invite the colorful characters into your life.

He had to run off to a family event after but he and I instantly hit it off and are slowly but surely planning a DO + Cracks in Pomo event in Manhattan, once we find the right format and speakers. In this episode we cover:

Stephen’s background

Postmodernism and the return of religion

Suburban disenchantment

Living tradition vs. traditionalism

Civic life over culture war

The Staten Island saint feast and MAGA

Roots, immigration, and integration

Humor, friction, and HR culture

Subsidiarity and overcentralization

The Catholic Worker and in-person events

Follow Stephen's work at: https://cracksinpomo.substack.com/

Jason initiated this get together of some of the original DO crew to discuss the life, work and legacy of Wendell Berry. It is no secret that Berry’s work has been an animating force for nearly everyone orbiting DO, especially those of us interested in food and ag systems. We discuss not only the legacy of Berry’s nonfiction work — how he suggested the agricultural system would collapse and so far it largely hasn’t, but also his fiction and poetry which actually has a great contribution on love, companionship, and romance.

Every once in a while someone comes into the DO world and it is so clear how well they fit in it’s amazing you hadn’t found them yet! This is true of Mike, Chicagoan, Northsider (boo!), who has a vision for how to make good things in the world and is working to do so.

Right now that looks like a manufacturing business he started, but Mike talks through his whole trajectory from fancy universities, working in politics, Chicago river ship boat captain, to trying to revitalize middle side American cities (with the help of Nick Offerman).

You can support Mike’s work here: www.wilmot-productions.com

This episode explores how Josh and Hannah Centers built Chapter House, a publishing project designed to restore beautiful, culturally literate children’s books to homeschool families. From Homer and Shakespeare to Beowulf, Greek myth, and Our Island Story, they explain why classic literature still matters for forming attention, imagination, and virtue in a distracted age.

They also share the homeschooling experiences that shaped their philosophy, including Hannah’s background as a public school teacher, their journey with a dyslexic child, and why Charlotte Mason’s ideas about habit training and whole-person education continue to guide their work. Josh makes the case that the liberal arts are even more important in the age of AI, while Hannah describes how the right book can open a reluctant reader’s world.

If you care about education, great books, or raising kids with depth and resilience, this conversation offers a thoughtful and hopeful vision for what learning can be.

"But at Least They're Human: Face-to-Face Living -- With Joy and Without Illusions"From the conference: Another Life is Possible co-organized by the Woodcrest Bruderhof community, Doomer Optimism and Savage Collective, July 2026https://doomeroptimism.substack.com/p/do-308-bill-kauffman

Tom and Jason talk to Lenny Wells - pecan farmer and extension agent - about growing pecans in Georgia, the cultural and ecological factors.

Along the way we also discuss:

-how he got into pecans

-his book on pecans

-consulting with a pecan farmer in Spain

-his love for Wendell Berry, and

-fly-fishing in Montana

Enjoy!

In this episode Ashley and Jacob discuss the concept of microcolleges, and examples of alternative educational models writ large.

Timestamps:

00:00 - Intro: Exploring education, community, and sustainability

02:27 - How a class on sustainable development shifted a life trajectory

04:02 - Higher education as transformative yet bureaucratic: a nuanced view

06:20 - The role of micro-colleges as laboratories for alternative education models

08:20 - Microcollege principles: human scale, place-based focus, holistic curriculum

10:12 - Experiential learning in agriculture and sustainability in Uruguay

13:19 - Moving to Uruguay: motivation, land, community, and self-sufficiency

16:26 - The influence of environmental sociology and fieldwork on education

18:13 - Rizoma and regenerative agriculture: connecting resources across bioregions

23:21 - Adapting the Uruguay model to local high schools and legislative advocacy

26:13 - The challenges of bureaucratic hurdles in US-based experiential programs

27:27 - The origins and evolution of Thoreau College in Wisconsin

28:05 - Deep roots in the Driftless region, organic farming, and educational experimentation

29:04 - Waldorf pedagogy, family-centered schooling, and youth leadership

31:51 - Deep Springs College: history, pillars, and self-governance

34:40 - The influence of Nicola Tesla and pioneering education in remote settings

36:27 - The unique, small scale, and community-centered design of Deep Springs and inspired schools

40:34 - Gender, environment, and community: reflections on co-ed versus single-sex models

41:26 - The importance of family and nurturing environments in education communities

43:11 - The role of place-based knowledge and historical understanding in cultivating belonging

45:27 - The holistic curriculum: arts, nature, and expedition-based experiential learning

48:45 - The ethics and profundity of slaughtering animals as a ritual of reverence

50:05 - Broadening perspectives: practical engagement over superficial debates

54:35 - The significance of embodied work, such as farming and outdoor survival skills

55:55 - Building agency through collective effort and sharing tangible skills

62:45 - The impact of experiential and community-based learning on resilience

65:05 - Ideals of subsidiarity and bioregional identity as anchors for local culture

66:39 - The cultural and environmental richness of bioregions like the Driftless

70:47 - The importance of place-based storytelling, native histories, and ecological literacy

75:34 - The power of local, tangible practices versus abstract ideologies

77:26 - The role of shared projects in dissolving superficial divisions

85:12 - Cultivating inner resilience and emotional strength through holistic education

87:11 - Moving from global scale despair to local scale action and empowerment

89:04 - The importance of facing difficulties together and growing through challenge

90:46 - The value of community hubs and bioregional identity in creating hope and agency