The surprising joy hidden inside impossible problems

Have you ever felt stuck between two things that both have to be true? You know—the kind of tension that feels unsolvable because if you satisfy one side, you disappoint the other.

When Jeromy Wilson and I were building Niche Academy, we lived in that tension. We wanted to be a scalable SaaS company—build once, use many times. But our customers needed something different: personalized training content we didn’t have the capacity to produce. It felt like we had to choose.

Turns out, the solution was waiting in the paradox itself. The tension between product and service wasn’t a trap—it was a map. Once we stopped thinking either/or and started thinking both/and, everything changed. We discovered we could build reusable training content—custom enough to serve libraries, scalable enough to sustain the business.

That experience taught me something I’ll never forget: the feeling of stuckness is often a signal that something new wants to be discovered.

In my latest post, The Hidden Joy of Impossible Problems, I share how paradox-aware leaders can use Small, Affordable, Fast Experiments (SAFEs) to explore that space between opposites—and how Steve Jobs did the same when balancing design purity with engineering realism at Apple.

If you’re wrestling with a hard leadership paradox, this one might just help you find the treasure hidden inside it.

Read The Hidden Joy of Impossible Problems

Here’s to the quiet joy of discovery—
Jared