Tuesday Email: Retrospects

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

Last week, a friend launched his consulting practice, and watching his excitement reminded me of every initiative I've ever started. The energy, the optimism, the meticulous planning—it's intoxicating. We pour ourselves into beginnings, analyzing every angle before we act. But there's a phase we consistently neglect, and it's the one that matters most: understanding what actually happened after we launched.

We've mastered the art of beginnings. We analyze, strategize, and optimize our way into action. We build spreadsheets predicting success and have endless conversations about potential outcomes. But when those outcomes arrive—whether triumphant or devastating—we do something peculiar: we shrug, label it "success" or "failure," and move on.

This isn't just inefficient. It's tragic.

The richest data about what works and what doesn't comes not from our initial planning but from the messy reality of execution. Yet we spend 90% of our time on the front end and virtually none mining the gold at the back end.

I learned this lesson the expensive way. Seven years into building a tech company, we were moving fast—too fast to stop and ask why things were working or not working. My instinct was always to provide answers, never to pause for questions. "We don't have time for project plans," I'd say. "We need results."

So we ran. And running felt like progress until it became chaos. People were building frantically, but nobody could clearly define "done." When someone thought they'd finished, there was always more to do. We never stopped to analyze why "done" worked sometimes and not others.

One week after we shut down—after the bank account hit zero and the doors closed—I drove to a lake for what I thought would be a weekend of sitting and thinking. Instead, I spent 48 hours typing. By the end, I had 70 single-spaced pages of insights about what had gone wrong and why. Those 48 hours of reflection on seven years of work taught me more about building businesses than the entire seven years had. The clarity was staggering. Every pattern, every recurring problem, and every missed opportunity became obvious in hindsight.

That's when it hit me: if I had spent just two hours each month doing this kind of analysis while we were building, I probably wouldn't have been spending that weekend writing the company's obituary.

Cognitive psychologist Amos Tversky captured this perfectly: "You waste years by not being able to waste hours." The ability to slow down allows us to speed up later. A race car driver who skips pit stops to save time will inevitably lose when their engine fails, while those who pause for maintenance zoom past them.

The U.S. Army figured this out in the 1970s with something called after-action reviews. After every mission—successful or failed—they'd gather to ask: What was supposed to happen? What actually happened? Why were there differences? The goal wasn't to assign blame but to institutionalize rapid learning.

Here's what I wish I'd known: retrospectives aren't about dwelling on the past. They're about extracting wisdom from experience before that wisdom fades. Without proper storage, old photos lose their color and detail over time. Our memories work in a similar way, simplifying complex experiences into basic success or failure narratives.

The deeper you probe, the more value you extract. The best retrospectives use the STAR framework: Situation, Task, Action, and Result. What was the context? What were we trying to accomplish? What did we actually do? What happened as a result? This systematic approach prevents crucial insights from getting lost in speculation.

Most of us do unconscious retrospectives all the time—we think about what went well or poorly for a few minutes, touch the high points, and call it good. However, without a process, consistency, and a framework to incorporate lessons into future actions, that time is wasted.

Think about your last major initiative. When did you last spend dedicated time—more than a few minutes—really diving into why it produced the outcome it did? Not just what happened, but why it happened the way it did? Whether you're building technology or building financial futures for families, nothing is perfect. There's always something to learn, always a way to improve the experience you deliver.

The most innovative companies have learned this: completion isn't the end of an initiative. It's the beginning of the real work—the work of understanding why things worked, so you can make them work better next time.

The question isn't whether you can afford to spend time on retrospectives; the question is whether you can afford not to. It's whether you can afford not to.

The best is ahead!

-Matt