No pain really is no gain.

And why even self-inflicted pain might be necessary for business survival.

When I started Pip Decks four years ago, it was a simple idea: a deck of cards to help folks run better workshops. No grand vision, no master plan. Just curiosity and a fair bit of naivety. And that naivety was a kind of superpower. It let me dive in headfirst without overthinking every risk.

Things took off faster than expected. I teamed up with a friend for illustrations, poured effort into making the content accessible, and before I knew it, people were buying the decks.

Along the way, I made some mistakes. I hired people too quickly, without proper vetting. I brought on someone because he had a flashy title and seemed like a good fit. Four weeks in, I had to let him go. Not fun. But it taught me to be thorough, to take my time with big decisions.

We also went through four accountants in as many years. Each time, we thought we'd found the right fit, only to realise they didn't get our business model or couldn't keep up with our needs. Frustrating, yes, but each misstep pushed us to find better solutions.

But the biggest mistake of all: i discovered Facebook ads. For every pound we put in, ten came back. It felt like magic. So we scaled up. Fast. We sold thousands of decks in no time. But that's when the wheels started to wobble—we ran out of stock. Not wanting to lose momentum, we kept taking orders, promising we'd fulfill them soon. Then COVID hit. Our stock was delayed, customers grew impatient, and PayPal froze our funds because we weren't shipping orders on time.

And now, four years later we have become too reliant on Facebook ads—a single point of failure. Nassim Nicholas Taleb, author of Antifragile (amongst many others in his “Incerto”) warns about over-optimising systems. When you fine-tune something too much, it becomes brittle. It works great for a specific set of conditions, until it doesn't. We'd optimised for sunny days, not storms. And this over-optimisation also reduced the optionality of our brand. Because our funnel, offer, price is optimised for a Facebook / Instagram ad conversion, we have locked ourselves out of wholesale or reaching “light” buyers.

Now, we're at a crossroads. We've decided to significantly reduce our Facebook ads. It feels risky, maybe even reckless. It’s like turning off the tap. But it's a self-inflicted pain—a way to become antifragile. Instead of waiting for the next crisis to blindside us (even something as innocuous as your ad account getting banned for an incorrect policy violation… it happens), we're choosing to challenge ourselves now. To find new ways to reach people, to diversify, to build resilience. To build play long-term games rather than short-term ones. The ultimate marshmallow test.

This concept can be neatly summed up like this: it’s the difference between being crushed by a one-ton boulder or getting hit by a thousand kilos of pebbles. The boulder flattens you instantly. The pebbles hurt, but they build callouses. They make you tougher. Those little shocks are what make you stronger. The same thing as tearing muscle fibres from weight lifting, and your body responding by making them stronger so it can better handle that weight again.

Ultimately, over these four years - I’ve learned that it's risky to play it safe all the time. Avoiding risk entirely leaves you unprepared for when the big shocks come. Mistakes and stress aren't just unavoidable—they're necessary. They push you to confront weaknesses, to learn, to grow.

So, dear reader (sorry it’s been a while huh!) take a look at your own projects. Where are you fragile? Where are you over-optimised? Maybe it's time to let the pebbles hit you. It might hurt, but the growth is worth it.

Maybe that was useful, maybe not. Let me know.

—Charles