September 2025
THEME: "Firsts"
Exploring the memorable “first times” that shaped who we are — from the lighthearted to the life-changing.
Hotseat Questions
Pick a question from the list below to ask the member next to you, then pass it along.
- What’s the first risk you took that made your heart race?
- Who was your first mentor or person who really believed in you?
- What’s the first time you surprised yourself with how strong you were?
- When was the first time you felt truly on your own?
- What was the first win that made you think, “I can actually do this”?
- What was the first time you really failed — and what did you learn?
- What’s a “first” you’re still chasing?
- What’s the first time you let go of something (or someone) you thought you couldn’t live without?
- Who was the first person you ever hired or convinced to join you?
- What’s the first city you felt at home in? Why?
- What’s the first book that rearranged your brain?
- What was your first big purchase with your own money?
- When was the first time you felt underestimated?
- What’s the first time you trusted your gut and it paid off?
- What’s the first time you ignored your gut and regretted it?
- Who was your first real friend — and what made that friendship stick?
- What’s the first time you surprised yourself?
- What was your first heartbreak or major disappointment?
- What’s the first time someone broke your heart?
- When was the first time you realized you were different from your peers?
- When was the first time you got in real trouble?
- What’s the first time a friend showed up for you when you really needed it?
- What’s the first time you realized your parents (or someone you looked up to) weren’t perfect?
- What’s the first time you hurt someone — and what did you learn from it?
- What’s the first time you felt proud of yourself?
- What’s the first major risk that didn’t work out?
- Who gave you your first real chance?
- What’s the first compliment you remember that meant something to you?
- Who was your first customer? Your first investor? Tell the story.
- What’s the first time you realized money doesn’t matter?
- What was your first big break in life or career?
- What’s the first time you stood up for yourself?
- What’s the first friendship that fundamentally changed who you are?
- When was the first time you felt like a leader?
- What’s the first time you felt like a fraud in your own life?
- What’s the first time you thought about quitting?
- What’s the first time you felt completely free?
- What’s the first time you put everything on the line — not knowing if it would work out?
- What’s the first time you met someone who completely inspired you?
- What was your first major conflict — and how did you handle it?
- What’s the first thing you ever lost that really mattered to you?
- What’s the first tough decision you had to make on your own?
- When was the first time you fell in love — and how did it change you?
- What’s the first time you felt unstoppable?
- What was the first moment you felt like an adult?
- What’s the first big mistake you made with money?
- What’s the first thing you’d do differently if you could go back?
- What’s the first time you made a bold ask — and got a yes?
- What’s the first adventure or trip that changed your perspective?
- When was the first time you felt completely unprepared, but somehow pulled it off?
