I have a friend who makes $500K at Google. He's worked there 15 years, made Managing Director, and he told me: "I've basically given up and I'm just collecting my paycheck." This is what happens when you trade freedom for money.
The pattern I keep seeing across industries and countries:
- Waterloo classmate at Microsoft making $250K base - quit because he felt unmotivated
- Friend at Google for 15 years making $500K+ - gave up on career, just collecting paycheck due to office politics
- Investment banking friend making $400K after taxes - can't quit, can't move, can't take real vacation
- Works 80-100 hour weeks, checks emails at 11 PM and 3 AM, terrified of layoffs
- Both said the same thing: "I should have done a startup 10 years ago, but I thought I needed money first"
My own freedom mistake (even as an entrepreneur):
- Partnership with major US bank potentially worth $300K/year for early-stage company
- Came with strings: weekly mandatory calls, they approve our product roadmap, exclusivity clauses, response time SLAs
- Realized I was trading freedom for predictable money - buying myself a high-paying job with fancy title
- Walked away because if I wanted someone else controlling my time, I'd just work at Google for more money
The trap most people fall into:
- Think: "Trade freedom for money first, then use money to buy freedom later"
- Problem: By the time you have money, you've built a lifestyle that requires keeping the job
- $800K salary funds $600K lifestyle and traps you forever
- Add mortgages, car payments, private school, HOA fees - golden handcuffs get tighter every year
- Time is irreplaceable, money is replaceable - can't buy back decades spent asking permission
Wrong question vs right question:
- WRONG: "How much money is enough?" (No answer satisfies - $1M→$2M→$10M, target keeps moving)
- RIGHT: "How much freedom is enough?" (Start with 10%, 20%, 50% - even with full-time job)
- I turn down clients regularly - make more time by avoiding problematic people/companies, creates more value long-term
The three types of work relationships:
- Employee: Ask permission, trade time for money on someone else's terms, income stops when you stop
- Freelancer: More autonomy but still trading hours for dollars, fundamentally same problem
- Entrepreneur: Own the outcome, build assets that compound, can own something that works when you don't
The four freedom questions (rate yourself 0-4):
- Can you quit your job tomorrow? (6-12 months runway saved, skills to generate income quickly)
- Can you move anywhere next month? (Not tied down by lease, mortgages, office requirements)
- Can you say no without financial stress? (Turn down bad opportunities, walk away from toxic situations, have "F you money")
- Can you choose your own daily schedule? (Control calendar, work when most productive, take Wednesdays off without permission)
The reality check:
- Most people check zero boxes, some check one, very few check all four
- We've all optimized for income, not independence
- Society values net worth, job titles, salary, house, car
- But real questions are: Do I control my time? Can I say no? Am I building something that compounds? Do I own assets, not just income?
The middle ground nobody talks about:
- Not binary - don't have to choose between full-time employee or all-in entrepreneur
- Start consulting while working full-time, build to $10K/month in contract revenue
- Free ebook coming soon at founderreality.com on this approach
- There's always a middle path, always a way to start building freedom
Bottom line: I know people with $5M net worth who feel trapped. I know people with $100K who feel free. The difference isn't the money - it's their relationship with money and freedom. If you don't know what you want, more money won't solve that. You'll just build a more expensive prison.
New episodes Monday/Wednesday/Friday at 9am EST. Real founder lessons about building wealth and freedom without permission.
Daily thoughts: @TheGeorgePu on Twitter/X
Full episodes: founderreality.com
Email: george@founderreality.com
