Seeing the System
Why the books aren't working, and what might
Why I’m writing this
I spent eleven years at ThredUp, eventually running a $280 million P&L and helping lead the company from significant losses to profitability. Along the way, I did what a lot of ambitious operators do: I read the books.
Good to Great. The Lean Startup. Thinking, Fast and Slow. I could quote them chapter and verse. So could plenty of the leaders I worked with. And yet, the same strategic missteps kept happening.
Not because people were careless or unintelligent. And not because we hadn’t found the “right” framework yet. We had frameworks coming out of our ears. The issue was something more subtle and, once you see it, hard to unsee.
Over time, I started noticing a pattern. Smart people would reach for solutions before they could articulate what problem they were solving. One part of the business would “fix” something and another part would absorb the fallout. The organization would thrash: progress in one corner, regress in another. Everyone felt it, but it remained oddly difficult to name what was going on.
What I eventually came to believe is this: we are largely products of the systems we inhabit.
Systems shape what gets rewarded and what gets punished. They shape what information travels and what gets buried. They shape who feels safe telling the truth, and who learns to stay quiet. Most importantly, they shape the types of problems we can even see, let alone solve.
This is the persistent gap between theory and practice I’ve seen in every organization I’ve worked in or advised. Leaders read books about what successful companies do, but those books rarely examine the underlying structures that make certain actions possible in some contexts and impossible in others. They tell you what to do without helping you understand why you can’t do it.
Seeing the System is my attempt to close that gap.
This is the home for my long-form essays on how systems shape outcomes, and how leaders can act on those systems to create better results for their businesses, their employees, and themselves.
I draw on epistemology, sociology, and philosophy because those fields have spent centuries developing tools for exactly this: understanding the forces that shape human behavior while remaining largely invisible to the people inside them. Business writing has mostly ignored that tradition. I think that’s a mistake.
What to expect
I’ll publish long-form essays twice a month—the kind of pieces that take time to develop and reward careful reading. In between, I’ll share shorter observations roughly once a week as they occur to me: patterns I’m seeing in my consulting work, ideas I’m wrestling with, questions I don’t have answers to yet.
I’m launching with both free and paid tiers. For now, free subscribers will get access to everything. As the community grows, I’ll think more carefully about what lives where, but my bias is toward accessibility.
Who this is for
This is for people who want to go beyond frameworks to level up how they think and exercise judgment.
How we perceive what’s happening. How we reason under uncertainty. How organizations adapt, update, and refine their worldview. How incentives, status, and institutional physics shape decisions, even when everyone involved is trying to do the right thing.
I’m not here to tell you what successful companies do. I’m here to help you see what’s actually happening in yours.
Welcome to Seeing the System.
