E4: Work Shouldn't Feel Like Work (And Why I Just Said No to $5 Million)
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I just said no to $3-5 million.
Partnership came in last week. Two years of work for life-changing money. My spreadsheet said yes. My gut said absolutely not.
For the first time ever, I listened to my gut.
Here's the thing everyone gets wrong: If it consistently feels like work, you're probably doing it wrong.
Y Combinator says "do things that don't scale." VCs push "growth at all costs." LinkedIn is full of hustle culture bullshit.
But I've been building since 2019, and every time I followed "smart business advice" that felt wrong in my gut, it ended badly. Every time I trusted my instincts over my business plan, it worked out.
Real examples from this episode:
- The $15K Google Ads spend I refused to make (lost our major partnership, best decision ever)
- Why I've never spent money on ads in 6 years of building companies
- The payday loan company offering 30% commissions (immediate "absolutely not")
- Staying in Toronto instead of moving to Silicon Valley (felt like playing someone else's game)
The Sunday Night Test: How do you feel Sunday night? If you're dreading Monday morning, your spreadsheet might look good but your business is broken. Energy levels don't lie.
I can build AI tools for 12 hours straight and feel energized. Put me in a partnership call for 2 hours and I'm drained. That's not laziness. That's data.
Why this matters more than ever: AI is eliminating every excuse for doing work that drains you. Soon the only work left will require human creativity and passion. If you're not naturally drawn to what you're building, you're screwed.
Everyone can use the same AI tools now. The only differentiation left is you - your authentic perspective and natural strengths.
The framework: Four questions I ask myself: Does this energize or drain me? Am I delaying this decision because I don't want to face it? How do I feel about Monday morning? Is this who I actually am, or who I think I should be?
Bottom line: Work shouldn't feel like work. If it does, you're either doing the wrong work, or doing the right work wrong. Your gut reaction to opportunities tells you everything about alignment.
Think I'm crazy for walking away from millions? Email [email protected] - I'll read your take in the weekend bonus show.
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