There’s a certain kind of joy that comes when you realize there is no problem you can’t find a solution to. It doesn’t come from easy wins or obvious answers. It comes from the surprising compatibility of things that you wouldn’t expect to work together. This post is about finding those hidden treasures.

Two weeks ago, I wrote about finding your highest-value goal and the crux barrier standing in its way. Last week, I showed how paradox—the pull of opposing necessities—creates the narrow, magical space where breakthrough solutions hide.

Today, I'm exploring the experiments where you actually discover your golden reward. I'll start with a personal experience.

The Gold Is Hiding in the Paradox

When Jeromy Wilson and I were building Niche Academy, we thought we knew exactly what kind of business we wanted to be—a SaaS company. The dream was clean and elegant: build a single platform once, and every library in the world could use it to train their patrons and staff.

But as we met with libraries, we discovered that very few had the time, expertise, or resources to create their own training content. If our platform was going to solve real problems, we’d have to build the training for them.

We felt stuck. To be sustainable and scalable, we needed a simple product model. To meet our customers’ needs, we needed a consulting service model. We had two necessary things pulling us in opposite directions. We were facing a paradox.

It took a while to see it, but our solution was hiding in the paradox itself. The tension between “build once” and “custom build” wasn’t a trap—it was a treasure map. 

As we looked for a way to meet both needs, we realized we could create a set of highly reusable training modules—content that served many libraries at once. When we packaged that content with our platform, everything clicked. We finally had a solution that addressed both necessary things and our sales took off. We couldn’t see it until we stopped thinking Either/Or and started thinking Both/And.

Paradox-aware leaders know that lasting solutions are always going to be waiting in the tension between opposing needs. Those solutions are never obvious, but we choose to look for them because we choose to believe they are there. Paradox-awareness shows us where to dig for the treasure.

Finding Gold With Experiments

Once we knew where to dig, we still had to figure out which tutorials to build and what they should look like. We found the gold with Small, Affordable, Fast Experiments—SAFEs. We tried different approaches in a way that kept costs low and learning high.

One experiment was a simple survey asking libraries which tutorials would be most useful. Another was asking a prospect to sign a contract that was contingent on delivering a defined set of tutorials. You only know people value something when they actually pay for it. To keep costs low and learning high, Jeromy and I created the first tutorials ourselves—no studio, no professional crew, just a microphone, a quiet room, and a learning curve with the video editing tools. That’s how we discovered what to build. That’s how we built a successful business.

Each experiment was a step of faith: small, cheap, fast, and designed to learn. Bit by bit, they led us toward a model that honored both sides of our paradox. Paradox-aware solutions require learning and discovery. Each SAFE is like tapping along the cave wall, looking for the hidden door.

You start with two questions:

1. What’s one small step that might move me toward my goal while honoring my opposing need?
   
2. How can I design this step so that even if it fails, the cost is low and the learning is high?
   

Paradox-aware experimentation isn’t reckless; it’s disciplined curiosity. It’s faith with a feedback loop.

Steve Jobs: A Both/And Visionary

Apple became a global icon through the productive tension between design purity and engineering realism. Most Apple competitors practiced tradeoffs and tended to favor engineering realism in their products. Steve Jobs differentiated Apple by insisting that both were necessary. And his success came from running deliberate experiments to find solutions that honored both.

Jobs insisted that Apple products embody clean, elegant design. He believed that beauty and intuitive simplicity were not bonuses but core to what a product should be. But real engineering constraints push back: circuits need structure, components need housing, signal paths need copper, antennas demand layouts, thermals need vents, screws provide rigidity. The engineers say “focus on function,” “pragmatism,” and “safety first.” The designers say, “strip everything to its essence,” “aestheticism,” and “beauty first.”

Jobs lived that paradox. He knew that leaning too far into design leads to products that fail practically. Leaning too far into engineering leads to ugliness, clutter, and blandness. All of Apple’s breakthrough products came from not choosing one side, but from methodically exploring how the two could support each other—through experiments.

Experiments at Apple

Below are a few concrete experiments (or iterative tests) that illustrate Jobs’s approach:

1. Iterative prototypes and foam models of the Mac enclosure
• Jobs would demand successive foam mock-ups from the industrial design team. Each iteration would be compared side-by-side with prior ones, and he would pick and critique fine details—radius of chamfers, curvature of faces, bevels, the feel of corners.
• Through these iterations, the design team would push for clean, friendly forms, while engineers would push for internal feasibility. The negotiation of what mass of electronics could fit inside those forms taught them the limits and possibilities.
2. Concurrent engineering / “deep collaboration” instead of serial handoffs
• Instead of handing the design to engineers only after the design was “done,” Jobs arranged a workflow where design, hardware, software, and manufacturing all worked in parallel—constantly feeding back to each other.
• In practice, that meant engineers would push back with feasibility constraints, designers would push back with form ideas, and they would iterate together, keeping the tension alive, not deferring one side or the other.
3. Dropping hundreds of hard drives to test the iPod’s durability
• As the team built early iPods, they didn’t just trust specs—they ran real-world destructive tests: drop tests of the drive inside the enclosure, stress tests, vibration tests.
• The aim was to let the demands of durability (an engineering constraint) push the design to adapt—not to compromise design, but to push design to absorb the constraint elegantly.
4. Killing the iPod-plus-phone (P1) experiment, then pivoting to full touchscreen
• One early path was to combine the iPod’s hardware with a dial-pad phone — a conservative incremental step. But Jobs and the team treated it as a working experiment. After months of prototyping, constraints emerged—it was awkward, limited, and forced too many compromises. So Jobs said, “Let’s kill this. We can do better.”
• That clearance allowed them to pivot into a more ambitious direction: full multi-touch, no physical keyboard, and rethinking the design/engineering trade space completely.
5. Antenna / signal design experiments (iPhone 4 “antennagate”)
• When Apple released the iPhone 4, they integrated the antenna around the stainless steel band of the phone—a bold move in design. Engineers warned of signal attenuation issues. Jobs and the design team nevertheless pushed forward, believing the integration was essential to the aesthetic and form.
• After early scores of reception complaints, Apple invited stakeholders to tour their radio-frequency lab and publicized that they had been performing extensive tests
• The resolution was not to abandon the integrated antenna design altogether, but rather to refine and tune it, improve shielding, offer free bumper cases (as a partial mitigation), and move forward with design fixes in subsequent models.

Through those experiments, Jobs and his teams absorbed engineering constraints without conceding design. They allowed tensions to live, not crush one side.

The Joy of Discovery

Every leader faces moments that feel impossible. But paradox-aware leaders learn to see those moments differently. They know that the tension between opposing necessities isn’t a dead end—it’s a compass pointing to innovation.

And when you choose to believe that a solution exists, when you design experiments to search for it, the feeling of stuckness turns into something almost holy: the joy of discovery.

Here’s my challenge to you. If you know your top priority goal and the crux barrier you need to overcome, if you’ve done the work to name the necessary opposites in play for you, then this week, design one SAFE.

Keep it small, affordable, and fast. Run it. Measure it. Learn from it. 

Because that’s where the breakthroughs live—between opposites, in the quiet hum of curiosity, faith, and motion.

Coming Nov 18!

The official release of my new book Tension—Mastering the Superpower of Paradox Aware Leadership