The Grief

Week 2: The Grief

George's Story

After I decided to kill SimpleDirect, I didn't tell anyone for two weeks.

Not my team. Not my friends. Not my family.

I just... sat with it.

Here's what I realized: I wasn't just losing a business. I was losing an identity.

For 4 years, I was "the SimpleDirect guy." When people asked what I did at parties, I had an answer. When home improvement companies needed financing solutions, they came to me. I had a thing.

Without SimpleDirect, who was I?

27 years old. In Toronto. With savings in the bank but no clear direction.

I remember one night — maybe 10 days after I'd made the decision internally — I was at a dinner with some founder friends. Someone asked: "So what's new with SimpleDirect?"

I said: "It's going well."

Complete lie. But I couldn't say the truth yet. Because saying "I'm shutting it down" felt like saying "I failed."

The Part No One Talks About

Work is identity in the West.

"What do you do?" is the first question we ask strangers. Not "who are you?" or "what do you care about?" — "what do you do?"

Your job isn't just how you make money. It's how you make sense of yourself. It's your answer to the question of who you are.

So when your job is threatened — really threatened — it's not just your income at risk. It's your sense of self.

That's grief. Real grief. And it deserves to be named.

What I Want You to Feel

This week might feel heavy. That's okay.

If you are experiencing an actual loss or change, you can name it. If your work has not changed, treat the prompts as hypothetical or skip them; this chapter does not establish that your career is going away.

Don't fix it yet. Just notice it.

The people who skip this step — who jump straight to "what's my new business idea?" — usually end up right back where they started. Because they never processed what they were leaving behind.

Take the week. Feel what you feel. We'll start moving soon.

This Week's Tasks

Day 8 — Beyond the Paycheck (15 min)

Beyond money, what does your job give you?

Status (people respect the title)
Identity ("I'm a PM at Google")
Structure (reason to wake up, rhythm)
Community (colleagues, belonging)
Purpose (feeling useful)
Conversation fodder (something to talk about at parties)
Other: ______

Rank them. Which would hurt most to lose?

Day 9 — Reflection (5 min)

Reflect:

"If I couldn't tell anyone my job title for a year, the hardest part would be:"

A) Not knowing how to introduce myself

B) Feeling like I've lost status

C) Not having clear purpose

D) Losing my professional community

E) Something else: ______

Day 10 — The Human Story (20 min)

Research: What happened to people in disrupted industries?

Google "journalist layoffs personal story" or "manufacturing job loss experience" or similar.

Find ONE human story. Not statistics — a person.

Reflect: Link + one sentence about what resonated.

Day 11 — The Eulogy (15 min)

Write a short "eulogy" for the career path you thought you'd have.

3-5 sentences. This sounds dramatic. Do it anyway.

You don't have to post it. But you can.

Grief is appropriate. You're losing something real. The career path you imagined, the certainty you expected, the identity you built. Some of it is going away.

Don't fix it yet. Just notice.

Reflect: "This week I realized ______"

Week 2 Complete

Next: Week 3 — The Resistance