Iteration Over Planning

Test your way to clarity through small experiments and continuous adjustment.

You can't know what you truly want until you've experienced it. Rather than locking into rigid plans based on untested assumptions, iteration lets you discover what works through action and feedback.

Small experiments compound into clarity. Test an idea for a week. Gather data about what actually brings satisfaction. Adjust your approach based on what you learn. This cycle of experimentation turns uncertainty into insight and helps you build a life aligned with what you discover matters most.

Whether you're exploring career options, testing relationship dynamics, or figuring out how to spend your time, these articles show you how to move forward without needing all the answers first. Start small, learn fast, and iterate your way toward a more fulfilling life.


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Articles

How to Improve Anything: Building a World-Class Feedback Loop

By building your own feedback loop, you can accelerate growth in any area of life. Find reliable, honest sources of feedback and getting as close to them as possible. Capture feedback quickly and intentionally, focusing only on what directly informs your improvement. Analyze the data to uncover patterns, root causes, and actionable steps.

Starting Successful Creative Projects

"If there is any magic in creative expression, it's how small, even silly ideas can become big, important, aw-inspiring works if a person invests enough time in them." - Ryan Holiday

One Email, One Idea, Every Week

Learn Agile Personal Development—the iterative approach to building a life you actually want.