Strategy Should Hurt

This quote captures a fundamental truth about effective prioritization that many leaders struggle to embrace.

Core Meaning

• Prioritization requires sacrifice: True strategy isn't just listing everything you want to do—it's making difficult choices about what you won't do
• Pain signals effectiveness: If your strategic decisions don't feel uncomfortable or difficult, you're likely not making real trade-offs
• Discomfort is necessary: The emotional resistance you feel when cutting potentially valuable initiatives is a sign you're making meaningful choices

Why This Matters In Product

• Focus creates impact: Resources spread across too many initiatives dilute effectiveness and slow progress on everything
• Default is dilution: Without painful choices, teams naturally drift toward trying to do everything, resulting in mediocrity across the board
• Clarity emerges from constraints: When you explicitly decide what not to pursue, the path forward becomes clearer for everyone

How To Apply

For leaders:

• If your roadmap feels comfortable and includes everything stakeholders want, you haven't made strategic choices
• Force yourself to identify what you'll explicitly not do, even when those things seem valuable
• Communicate both your priorities and your deliberate non-priorities with equal clarity

For ICs:

• Recognize that the discomfort of saying "no" to good ideas is part of good product work
• Use the "pain test" to evaluate your own priorities—if dropping something doesn't hurt at all, it probably wasn't strategic
• Advocate for focus even when it means letting go of projects you personally value

The quote reminds us that strategy isn't a wish list—it's a series of difficult choices that create focus. The emotional discomfort of these choices isn't a bug; it's a feature that signals you're doing the hard work of prioritization.