Project yourself to age 80. "Will I regret trying this and failing?" -> Probably not. "Will I regret never trying?" -> Absolutely. This clarifies "safe" vs "risky". Staying in a boring job is actually the risky path (risk of regret).

Instead of asking "How do I make this company succeed?", ask "How do I kill this company?"

• Run out of cash.
• Fight with co-founder.
• Build something nobody wants. Now, avoid those 3 things. Solving problems backwards is often easier.

First Order: "I'm hungry, I'll eat a donut." Second Order: "If I eat a donut, I'll crash in 1 hour." First Order: "I'll ship this feature to close the deal." Second Order: "If I ship this custom feature, I'm now a consulting shop, not a product company." Always ask: "And then what?"