Week 11: The Conversation
Phase 3: Movement
George's Story
The conversation that changed everything for me was 15 minutes.
It was with a guy named Daniel — a founder who had exited his company 3 years earlier and was now doing high-end consulting. I'd known him vaguely through the Toronto startup scene.
I reached out with a simple message: "I'm navigating a career transition. You've been through something similar. Could I ask you a few questions?"
He said yes.
We got coffee. I asked him three things:
- "When you transitioned out of your company, what did you wish you'd known?"
- "How did you figure out what to do next?"
- "What mistakes did you make that I should avoid?"
His answers weren't revolutionary. But one thing stuck:
"The thing no one tells you is that the first thing you try probably won't work. The second thing might not either. But by the third thing, you'll know enough to get it right. Most people quit after the first failure because they expect to nail it immediately."
That was exactly what I needed to hear at exactly the right time.
Why Conversations Beat Content
I've read hundreds of articles about career transitions. Watched dozens of videos. Consumed endless content.
None of it was as useful as that 15-minute conversation.
Here's why: the best information isn't on the internet. It's in people's heads. And they'll share it with you — if you ask.
The people who are 2-3 years ahead of you know things that aren't written down anywhere. The real obstacles. The real opportunities. The shortcuts that actually work. The mistakes that look smart but aren't.
One conversation is worth 100 articles.
This Week's Tasks
Day 71 — The List (10 min)
List 3-5 people who are somewhere you might want to be. Or who've navigated something similar.
Day 72 — The Message (15 min)
Draft a short message to ONE of them asking for 15 minutes.
Be specific: "I'm navigating [situation]. You've [done X]. Could I ask you 2-3 questions?"
Reflect: "Drafting my message to ______"
Day 73 — Send It
Hit send.
Reflect: "Sent. 😬"
Day 74 — Community (5 min)
Review your conversation notes or prepare one follow-up question. If the other person has not replied, that is not a failed exercise; choose whether to follow up.
Day 75 — Prep (10 min)
Prepare 3 questions you actually want answers to.
Day 76 — Rest
Catch up or breathe.
Day 77 — The Conversation
Have it (or schedule it).
Reflect: What you learned. What surprised you.
Week 11 Complete
Next: Week 12 — The Commitment