The Destination Dilemma

How to make decisions and build a fulfilling life when you don't know what you want.

How can you plan for what you haven't experienced? Most people lock into goals—career paths, relationships, lifestyles—without testing whether those goals will actually bring fulfillment. They achieve success but wonder why it feels hollow.

The Destination Dilemma is the gap between achievement and satisfaction. You can't know what you truly want until you've lived it, yet you're expected to commit to major life decisions based on imagination alone. The solution isn't more planning—it's iteration. Test your assumptions, gather real data about what brings you satisfaction, and adjust your direction based on experience rather than guesswork.

These articles explore how to navigate uncertainty, align your life with your values, and build fulfillment through experimentation. Whether you're unsure what career fits you, unsatisfied despite achieving your goals, or overly certain about plans you haven't tested, you'll find frameworks for making better decisions when the destination isn't clear.

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Articles

Monk Week: Harnessing Solitude for Intentional Living

Discover how "Monk Weeks"—a purposeful period of solitude for deep reflection and life calibration—can help you live your life more intentionally. Learn science-backed benefits of intentional solitude and practical steps to improve clarity, creativity, and well-being.

An Equation for a Successful Blog (And Life)

Successful people are often successful in spite of the things they do. What are you trying to accomplish? What variables matter most in the equation for your success? Are there things that others say are essential that might not even be necessary?