Obstacles? Good. Now What?

This week marks 1 year since I took on a role that changed everything. While flipping through old files, I found notes from that exact week:

• “Key deal fell through.
• Partner backed out.
• Product dumped post-MVP — again.”

I remember that sinking feeling.
Frustrating? Absolutely.
Unexpected? Not really.

But that week, it didn’t end me.
It began me – a better version.

After two decades in product and ops, one truth stands out:
The obstacle is never the end. It’s the real beginning.

Back then, I used to panic when things collapsed.
But that moment taught me to ask a better question:

What is this trying to teach or unlock?

• Team messed up? → Great. Now, we build accountability.
• Tech failed? → Perfect. Time to fix what was fragile.
• Tough call? → Good. Let’s raise the bar on clarity.

Modern work is chaos. It always will be.
Most people expect smooth roads. They won’t come.

Resilient operators don’t avoid chaos. They convert it.

What separates them isn’t intelligence. It’s how quickly they flip friction into fuel.

So here’s what I’d say to the version of me from years ago
…and to anyone staring at a breakdown right now:

Next time something breaks, pause.
Don’t say, “Why me?”
Say, “Good. Now what?”

That’s not Stoicism.
That’s survival.
And with time, it becomes leadership.

Ever had a turning point disguised as a breakdown?