Week 4: The Money Question
Phase 1: Awareness
George's Story
When I was deciding whether to kill SimpleDirect, the biggest thing holding me back wasn't the identity stuff. It was money.
"Can I afford to walk away from this revenue?" "What if nothing else works?" "How long can I actually survive?"
Here's the thing: I had never actually done the math. I had a vague sense of "I'm fine" mixed with an underlying anxiety of "but what if I'm not?"
So one Sunday morning, I sat down and did the real calculation.
Liquid savings: about $1M (not bragging — I'd been grinding for 4 years and living cheap) Monthly burn: about $10K (Toronto isn't cheap, but I wasn't flashy) Runway: 100 months. Over 8 years.
I stared at that number for a long time.
Eight years.
I had been making decisions based on fear — "I can't afford the risk" — when the actual math said I had nearly a decade of runway.
Now, look: your numbers might be very different. You might have 3 months of runway. You might have 24. The point isn't the specific number. The point is that knowing the number changes everything.
In my case, after reviewing my finances, part of the hesitation was about identity. That does not establish the cause of anyone else’s financial fear.
The Real Fear
After I did the math, I had to ask myself: if money wasn't the issue, what was I actually afraid of?
And the honest answer was: looking like a failure.
I was afraid of telling people I killed my business. I was afraid of losing status. I was afraid of being "the guy who couldn't make it work."
That's not a money problem. That's an ego problem.
And once I named it, it lost most of its power.
What I Want You to Know
This week, you're going to do your own math. Not to freak yourself out. To see clearly.
Some of you will discover you have more runway than you thought. That's freeing.
Some of you will discover you have less. That's useful — because now you can plan.
Either way, you'll replace the vague dread with actual information. And information is something you can work with.
The question I want you to sit with:
"If I had enough money, what would I do? And is money actually the thing stopping me?"
For some people, money is the binding constraint. Debt, dependents, healthcare costs, housing and other obligations can make a transition unaffordable. A reflection exercise cannot remove them.
Let's find out what.
This Week's Tasks
Day 22 — What You Have (20 min)
Get honest about your financial picture:
- Liquid savings: Cash, easily accessible investments
- Monthly expenses: Real number, not the ideal
- Months of runway: Available savings ÷ expected monthly net cash outflows. For a no-income scenario, use expenses as the denominator. Exclude money committed to taxes, debt or other obligations; record uncertainty in asset values and costs.
Just calculate it. No judgment.
Reflect: "My runway in months: ______" (you can be vague: "3-6" or "12+")
Day 23 — Community (5 min)
Check the inputs to your Day 22 runway estimate for committed funds or missing expenses. Keep financial details private unless you choose to discuss them with someone you trust.
Day 24 — What You Need (15 min)
Two questions:
- What does your current lifestyle actually cost per month?
- What's the minimum you could live on if you had to? (Not forever — just for a transition period)
The gap between these two numbers is your flexibility.
Day 25 — The Real Fear (15 min)
Separate an affordable-loss calculation from how you feel about a change. Both can matter, and a genuine financial limit should be respected.
Journal (private): Which concerns are concrete obligations, which are uncertain costs, and which relate to identity or status? What would need to change before a risk became affordable?
Day 26 — Reflection (5 min)
Reflect:
"When I think about financial risk, my real fear is:"
- A) Not being able to provide for family
- B) Looking like a failure
- C) Losing lifestyle/status
- D) Having no safety net
- E) Not knowing how to make money differently
- F) Something else: ______
Day 27 — Rest
Catch up or breathe.
Day 28 — Reflection (10 min)
"How much is enough? Not to be rich — to feel safe enough to take a calculated risk. What's that number for you?"
Write it down. You might be closer than you think.
Reflect (optional): Share your thinking.
Week 4 Complete
Next: Week 5 — The Acceptance