Day 45: The Constant Wrestle — Learning to Sit with Paradox

Day 45 of zero to one million, and something keeps bubbling to the surface as I work through these client projects: paradox.

I can't attribute the quote properly, but there's a definition of intelligence that's stuck with me — the ability to hold two opposing ideas in your head at the same time. That's become my working definition of paradox, and honestly, it's one of my favourite lenses for thinking about business challenges.

Right now, I'm wrestling with a classic one: attention to detail matters deeply, but you've also got to move quickly, ship things, and embrace failing forward.

Those two forces are constantly pulling against each other. You notice the details, the things that aren't quite right, but then you've got to counter that with just getting stuff out there and collecting real user feedback. It's a proper wrestle.

This tension shows up everywhere in business. Which got me thinking about other paradoxes I've encountered.

The Tough Love Paradox

Tough love came to mind immediately.

Here's the thing about tough love — it gets abused. Those narcissists we've all come across will frame meanness as tough love, but that's not it at all. Framing something as tough love doesn't give you permission to be an arsehole.

Real tough love, the way I'd define it, is balancing empathy with candour. Easily said, hard to do.

People want to be told straight. They want to hear exactly what's wrong and how they can improve. But that doesn't mean it can't be done with care and empathy. The paradox is telling someone straight whilst doing it with genuine care.

Confident Yet Humble

Another favourite: being confident yet humble.

Confident enough to know that when you're in the arena, you can execute. But humble enough to take feedback, look for your blind spots, and always improve.

I've heard this manifested literally as personas within athletes — one for training, another for competition. Kobe Bryant's "Mamba Mentality" is probably the most famous example.

Off the court: obsessive about training, convinced he wasn't good enough yet. This was the work in the dark persona.

On the court: fearless, supremely confident, wanted the ball, wanted to take the shot.

He literally coined these personas to handle the paradox between relentless self-improvement and absolute confidence in execution.

The Deliberate Approach

This is something I personally haven't done deliberately — creating conscious personas to handle contradictions. But I can see how useful this tool could be.

As a business owner wrestling with these constant tensions, maybe the answer isn't choosing one side or finding perfect balance. Maybe it's about getting comfortable with the wrestle itself.

Learning to sit comfortably with paradoxes feels like a skill that can be developed and should be developed. Not because it makes business easier, but because the tension between opposing forces seems to be where the real work happens.

The question isn't how to resolve these paradoxes. It's how to handle them deliberately, like Kobe did — with clear intention rather than constant internal conflict.

Starting Small

For me, I'm going to try naming the paradox when I notice it. Just calling it out: "Right, this is the detail versus speed tension again."

Then asking: what does this situation actually need right now? Am I in a "ship it and learn" moment, or do I need to slow down and get the details right?

It's not about solving the paradox. It's about choosing consciously which side to lean into for this specific moment, rather than getting stuck in the middle wrestling with both.

Small step, but it feels like a starting point for handling these tensions more deliberately.