Week 6: The Untethering
Phase 2: Identity
"Who are you when the job goes away?"
George's Story
A few weeks after I decided to shut down SimpleDirect, I was at a networking event in Toronto. Standard founder stuff — 50 people, bad wine, lots of "what do you do?"
Someone asked me. And for the first time in 4 years, I didn't say "I run SimpleDirect" or "I build fintech for home improvement."
I said: "I'm figuring that out right now."
The silence was awkward. They clearly didn't know how to respond. I didn't either, honestly.
But something interesting happened after: I felt lighter.
For years, my identity had been attached to SimpleDirect. "I'm George, I build fintech for home improvement companies." It was a clean story. Easy to tell. But it was also a cage.
Without that label, I had to figure out who I actually was.
The Exercise That Changed Things
Here's what I did: I tried to write my bio without mentioning my company, my title, or my industry.
First attempt: "George is a... uh... person who... likes business?"
Terrible. I literally didn't know what to say.
Second attempt: "George is someone who helps people see their situation clearly and make hard decisions."
Better. But still felt generic.
Third attempt: "George asks uncomfortable questions and doesn't let you hide from the answers."
That felt true.
It had nothing to do with fintech. Nothing to do with SimpleDirect. It was something that would still be true if I never worked another day in my life.
The Questions That Matter
This week, I want you to answer two questions:
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What were you good at before this career? As a kid, in school, in your early jobs. What did people notice about you?
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What do people ask you for help with outside of work? Not your colleagues — your friends, your family. What do they come to you for?
The answers usually reveal something real.
For me: I was always the kid who asked "but why?" I was the friend people called when they had a hard decision and needed someone to cut through the noise.
That's who I was before SimpleDirect. That's who I'll be after.
What I Want You to Feel
By the end of this week, I want you to have a sense — even a vague one — of who you are without the job title.
It might feel uncomfortable. "I'm a PM at Google" is a much cleaner identity than "I'm someone who figures things out."
But the clean identity is borrowed. The messy one is yours.
And when the borrowed identity gets taken away — which it might — you need something real to stand on.
Let's find it.
This Week's Tasks
Day 36 — The Bio (15 min)
Write your bio WITHOUT mentioning your company, title, or industry.
Who are you?
Reflect: Share it.
Day 37 — Community (5 min)
Review your Day 36 bio and name one concrete example behind it. Feedback from someone who knows you is optional; the archive has no shared bio feed.
Day 38 — Before the Career (15 min)
Two questions:
- What were you good at BEFORE this career? As a kid? In school?
- What do people ask you for help with OUTSIDE of work?
Reflect: 2-3 things from each.
Day 39 — Reflection (5 min)
Reflect:
"If I got laid off tomorrow, what would still be true about me:"
- A) I'm someone people trust
- B) I figure things out
- C) I build things
- D) I help people see clearly
- E) I don't know yet (valid answer)
- F) Something else: ______
Day 40 — Community (5 min)
Review your bio and Day 39 answer. Ask someone you trust for feedback if you want an outside perspective; posting is optional and no shared feed is provided.
Day 41 — Rest
Catch up or breathe.
Day 42 — The Experiment (10 min)
Next time you meet someone new, introduce yourself without mentioning work.
Reflect: "I tried it. It felt ______" or "What I'd say instead: ______"
Week 6 Complete
Next: Week 7 — The Inventory