Failing Forward: Mistakes I Made and What They Taught Me

Introduction

People love to talk about wins. Launches, promotions, revenue milestones. But the truth is, most of what I’ve learned in my career didn’t come from the victories—it came from the moments where I missed the mark, misunderstood the brief, or simply messed up.

Failure has been a consistent teacher in my journey, and the lessons I’ve gained have shaped how I lead, how I build, and how I bounce back.

Here are a few of the mistakes I’ve made, and what they taught me.

1. Mistake: Saying Yes to Everything

Earlier in my product career, I thought saying yes was a sign of being collaborative. Stakeholders wanted something? Yes. Engineering needed clarity? Yes. Leadership wanted a new report? Sure, yes.

What I didn’t realize was that every “yes” was a hidden “no” to something else. My backlog bloated. My focus scattered. My team lost sight of what actually mattered.

Lesson: Prioritization isn’t just a product skill—it’s a leadership responsibility. Saying no is an act of clarity.

2. Mistake: Falling in Love with the Solution

At one point, I became obsessed with a feature idea. I thought it would change everything. We spent weeks building it, polishing every detail.

When it launched? Crickets.

We hadn’t validated the problem well enough. The need wasn’t real. My bias had blinded the process.

Lesson: Fall in love with the problem, not the solution. Always.

3. Mistake: Avoiding Difficult Conversations

I once had a team member who was clearly struggling. Deadlines were slipping, communication was unclear, but I avoided addressing it directly. I was trying to be “nice.”

That delay hurt the team’s momentum and made the eventual conversation even harder.

Lesson: Clarity is kindness. Don’t wait to give honest feedback—it builds trust when delivered with empathy.

4. Mistake: Ignoring My Gut

There was a time when I felt something was off about a roadmap direction, but I let the majority vote win. I ignored my instincts, thinking I was being a good team player.

Turns out, my intuition was right. The initiative failed, and we ended up backtracking months later.

Lesson: Data matters, but so does your product sense. If something feels wrong, dig deeper.

Closing Thought

Failure is inevitable. But what you do with it—that’s what defines your growth.

The moments I’m most proud of aren’t when things went perfectly. It’s when I took ownership, learned quickly, and came back stronger.

If you're in the middle of a tough sprint, a missed goal, or a career setback—take a breath. There’s probably a lesson in there that your future self will thank you for.