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BreadcrumbHome/Chicago/Higher Grounds Andersonville: Deeper Conversations
Higher Grounds Andersonville: Deeper Conversations
Sun 13 Sept, 10:00
Sun 13 Sept10:00Workshops

Higher Grounds Andersonville: Deeper Conversations

Sunday, September 13, 2026 · 10:00 – 11:30
Collectivo Andersonville
www.meetup.com/higher-grounds-chicago/events/315685121/
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About the event

Join us in Andersonville for conversations that go beyond small talk. **Higher Grounds – Andersonville** is a new satellite chapter of the group that started in DC a few years ago and has grown to nearly 600 people there. Whether we're exploring technology and AI, life transitions, spirituality, culture, relationships, or the search for meaning, every conversation is shaped by the people in the room. There's no set leader or rigid agenda, just a shared commitment to listen as much as we speak. * We start with brief introductions: everyone answers what makes you you (not your LinkedIn bio). * Job titles come later, if at all. * From there it's conversational jazz. No script, just people listening and following wherever the room takes it. But we tend to go deep. * The direction of each meetup emerges organically, so every event is unique. **MANDATORY: PLEASE REVIEW OUR COMMUNITY GUIDELINES IN THE GROUP DESCRIPTION.** Everyone is expected to engage in respectful conversations and listen deeply as well as share. We have a zero tolerance policy of sexual harassment and hate speech. Come ready to share, reflect, and connect with others in Andersonville who are also seeking deeper conversations. Most tables never need a prompt, the conversation just flows, but if one does, feel free to pull from the questions below. **Suggested Questions: Life Stages & Transitions** 1. What did you think you'd have figured out by now that you're still completely winging? 2. When did you realize your parents' advice was for a world that no longer exists? 3. What are you finally old enough to stop pretending to care about? Suggested Questions: Identity After the Roles 1. Who are you when nobody needs anything from you? 2. What dream keeps resurfacing even though the "practical" time has passed? 3. How do you handle having the freedom you always said you wanted? Suggested Questions: AI & Being Human 1. What human experiences will AI never truly understand? 2. If machines handled all your have-to's, what would you actually do? 3. What becomes more precious as everything becomes automated? Suggested Questions: Belief & Meaning 1. What certainties have you given up, and what rushed in to fill that space? 2. How has knowing someone who died changed how you live? 3. What do you believe now that would shock your younger self? Suggested Questions: The Modern Psyche 1. What anxiety do you carry that previous generations didn't have? 2. Which of your survival strategies are you ready to retire? 3. What uncomfortable truth about happiness did it take you years to accept? Suggested Questions: Work & Purpose 1. When did you stop believing that your job would complete you? 2. What would you do for work if money and status weren't factors? 3. How has your definition of "making it" changed over the years? Suggested Questions: Relationships & Connection 1. What relationship dynamic do you keep recreating, and why? 2. When did you realize your parents were just people trying their best? 3. What kind of loneliness doesn't go away even when you're with others? Suggested Questions: Time & Mortality 1. What are you running out of time to say or do? 2. How differently do you spend your time knowing it's finite? 3. What will you regret not trying, even if you fail? Suggested Questions: Society & Culture 1. What social convention do you follow even though it makes no sense? 2. Which generation do you understand least, and what might you be missing? 3. What aspect of how we live now will seem insane in 20 years? Suggested Questions: Personal Philosophy 1. What rule for life did you create after learning something the hard way? 2. When did you stop believing that everyone else had it figured out 3. What paradox about life have you learned to live with?

Found by Moments · Higher Grounds Chicago: Coffee & Deeper Conversations

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Location

Collectivo Andersonville

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SEPT13
Sunday, 13 September 2026

10:00 – 11:30

Location

Collectivo Andersonville

Link

www.meetup.com/higher-grounds-chicago/events/315685121/

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