Tuesday Email: Take imperfect action

Happy Tuesday!

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

I was standing in my kitchen, watching my six-year-old refuse to put on his shoes for the fourth time that morning.

My jaw was clenched. My hands were fists.

I knew exactly what I should do.

My wife had sent me many articles and podcasts over the past few months.

I could recite the principles: natural consequences, emotional regulation, and connection before correction. Perfect knowledge, zero application.

Then I yelled anyway.

That's when I realized I'd been asking the wrong question.

Most of us treat learning like preparation. We believe that if we research enough, study enough, absorb enough information, we'll be ready to act.

We're waiting for perfect knowledge before we take imperfect action.

But that's backwards.

The knowledge didn't stop me from yelling at my kid. The mountains' worth of wisdom evaporated the moment frustration hit.

Because learning doesn't happen when you read something, it happens when you try something and discover what you didn't know you didn't know.

Think about how you actually learned your job. Not from the training manual. Not from the orientation. You learned by doing.

By doing something badly, adjusting, doing it again slightly less badly, and iterating until it becomes second nature. Your mistakes were the curriculum.

Yet when it comes to matters that truly matter, such as parenting, business strategy, or innovation, we revert to a comfortable pattern: research, plan, perfect, then act.

Except by the time we feel ready, the moment has usually passed. The damage has been done.

Here's what changed for me.

After that kitchen meltdown, I decided to stop trying to think my way into being a better parent.

Instead, I picked one small tactic from a book I recently read — literally one thing — and tried it the next time my kids pushed their boundaries.

It felt awkward. I stumbled through it. My four-year-old looked at me like I'd started speaking Portuguese.

But something shifted.

Not in that moment, I'm not selling you a miracle here, but over the next week, as I continued to try that one small thing, learning from what worked and what didn't, adjusting as I went.

I wasn't becoming the perfect parent. I was becoming a parent who could learn in real-time instead of waiting for certainty that would never come.

That's when it clicked: Imperfect action creates insights that perfect knowledge can't.

You don't learn your way into better actions.

You act your way into a better understanding.

This isn't just true for parenting. It's true that innovation often dies in every industry where trust is fragile.

In wealth management, we've convinced ourselves that one wrong move could shatter decades of trust. We're not entirely wrong, trust does work like a coral reef, built slowly over years, vulnerable to sudden destruction.

But that fear has created a trap.

We won't act until we're certain, and certainty doesn't exist in an uncertain industry. We plan three-year strategies in an industry where no one can predict what the next three months will bring.

Ask any advisor what the industry will look like in three years. They'll say, "I don't know."

Now ask them their three-year goals.

See the problem?

Aviation and medicine face the same zero tolerance for mistakes, but they've solved for learning differently. They don't just analyze failures; they study near-misses, close calls, and moments when disaster almost happened but didn't. Every near-miss becomes a lesson that drives innovation.

What if we did the same? What if we looked at every hesitation, every moment we almost tried something new but didn't, and asked: what prevented us from learning there?

The shift requires rethinking three fundamental assumptions:

First: Stop calculating potential upside. Determine acceptable downside.

Most decisions get stuck in analysis paralysis because we're trying to predict the ROI of action. But in uncertain environments, upside is unpredictable. Downside is negotiable.

A surfer doesn't wait until they can predict the perfect wave. They ask: "What's the worst wipeout I can handle?" Then they paddle out.

What's the worst that could happen if you try that process change? If you can afford that downside and it moves you toward who you want to become, why are you still researching?

Second: Judge the process, not the outcome.

Outcomes contain luck. If you make ten decisions with sound reasoning and nine work out, you don't have a 90% success rate—you have a good process. If only three work out, you might still have a good process that got unlucky.

This matters because if you judge people on outcomes rather than process quality, you'll fire your best decision-makers during periods of variance and retain your lucky ones. Focus on the inputs: Was the information good? Was the reasoning sound? Were alternatives considered?

The basketball coach who fires players for missed shots while ignoring shot selection doesn't build a championship team. Neither does the leader who punishes good decisions that got unlucky breaks.

Third: When someone struggles, examine the system before you examine the person.

When one team member can't execute a process that "everyone else manages," the easy answer is that person needs more training.

The valuable answer might be that that person just revealed a broken system that everyone else was tolerating.

They're not the weak link. They're the canary in the coal mine, showing you which processes need fixing before they hurt everyone.

I still don't have parenting figured out.

Last Tuesday, I lost my patience, but I managed to hold back from yelling.

I now have something more valuable than a playbook: I have a way to learn. When I mess up, I don't just feel guilty and promise to do better next time. I ask: what did I try? What happened? What could I adjust?

The same is true professionally. We can't avoid uncertainty. We can't eliminate risk. We can't predict our way to safety.

But we can build a practice of acting small, learning fast, and adjusting often.

We can create systems that learn from near-misses rather than just punishing failures. We can replace the question "What's the ROI?" with "What are we willing to lose to find out?"

The alternative of waiting for perfect knowledge before taking imperfect action isn't safety. It's just a slower way to become obsolete.

The question isn't whether you're ready to act. It's whether you're ready to learn because learning doesn't happen in the research phase.

It happens in the kitchen, with the shoes, the fourth time that morning, when you try something different and discover what you couldn't have known any other way.

The best is ahead!

-Matt