Design Playground: Musing 15: Some lessons you can only learn the hard way
A musing about the advice you can’t seem to follow — and how, no matter how hard you try, sometimes the only way to learn is through failure.
The advice you can’t seem to follow
Sometimes no amount of advice—no matter how wise or well-intentioned—can replace the sting of lived experience. Sometimes, you have to touch the fire yourself to truly understand it's hot.
That’s the bittersweet thing about good advice: you often know it’s right, but you’re not ready for it. So you kick the can down the road, telling yourself you’ll deal with it later.
And then one day, it hits you like a brick wall. That thing someone told you? They were right. You knew they were right. But you had to learn it on your own terms. And while part of you wonders why you didn’t listen sooner, another part feels deep gratitude—for the lesson you finally earned.
Why good advice isn’t always enough
There’s a difference between understanding something in your head and knowing it in your bones. Lived experience cuts deeper. It lingers, long after the moment has passed.
We all chase wisdom—but here’s the irony: you can’t shortcut your way to it. You might think you’ve figured it out, but life has a way of calling your bluff.
There’s a gap between knowing and really knowing. And that gap? That’s where the learning lives. It takes cycles. Reps. Humbling moments. The lesson almost never lands on the first try.
This isn’t failure. It’s the process. And don’t let anyone convince you otherwise.
Failure, reframed
Failure isn’t a detour. It’s the path.It turns theory into memory—into something real. It etches the lesson in a place we won’t forget.
Through failure, we don’t just learn. We understand. It becomes part of us. This is how wisdom is forged.
Reflection is what makes us stronger. What did I learn? What would I do differently?
Growth doesn’t come from avoiding failure. It comes from meeting it with curiosity. From staying in the game long enough to learn what can’t be taught.
The tender truth about resistance
We resist because of ego. Because of pride, hope, fear. All very human reasons. We tell ourselves it’ll be different. That we’ll find a way around the hard part. But instead of scolding ourselves for learning the hard way, we can offer grace. That version of us didn’t know better. Now we do.
Honoring the process
There’s a concept called Wintering—the idea that nothing in nature stays in bloom forever. Everything needs time to go quiet. To be still. To gather strength underground.
Wisdom isn’t about avoiding pain—it’s about learning through it. So one day, we can offer our hard-earned words to someone else. Knowing they, too, will learn in their own time.
The process isn’t a setback. It is the way.