The Contrarian Art of Planning for Bad Luck

The world loves a good success story. We're sold on the idea of the lucky break, the perfect timing, the stars aligning. But what about when the opposite happens? What about when luck works against you?

We plan for success. It's natural. It's optimistic. But it's also, in many ways, naive. We assume the best, neglecting the fact that life - and business - is anything but predictable.

"Luck is what happens when preparation meets opportunity," Seneca, the Stoic philosopher, once said. But let's flip that on its head. Let's prepare for when luck meets adversity. After all, adversity is merely opportunity dressed in work clothes.

Imagine a boat. Your business is the boat, and your plan is the route. The sea, unpredictable and fickle, is luck. You can't control the sea, just as you can't control luck. But you can control your boat. You can control your plan.

You set sail. The sea is calm. But then, out of nowhere, a storm hits. The sea is rough. It's working against you. Do you abandon your route? No. You adjust your sails. You ride out the storm. Because your plan was never dependent on the sea being calm. Your plan was dependent on your ability to navigate, no matter the weather.

That's the thing about planning. It's not about predicting the future. It's about being prepared to adapt, to pivot, to weather the storm when it comes. It's about building resilience into your strategy.

In the face of bad luck, resilience is your best friend.

So, how do you plan for bad luck? You start by acknowledging its existence. Don't dismiss it as a negative mindset. See it for what it is - a reality of life and business.

Next, you anticipate. You ask the tough questions. What if our biggest client pulls out? What if the market crashes? What if the product fails?

Then, you strategize. You identify your vulnerabilities. You create contingency plans. You build buffers. You diversify.

Finally, you remain flexible. You don't cling to your plan. You allow it to evolve. Because a plan that can't adapt is a plan that won't survive.

Planning for bad luck isn't pessimistic. It's pragmatic. It's strategic. It's the difference between being at the mercy of luck and being able to harness it, good or bad.

So, next time you plan, don't just plan for the best. Plan for the worst. Plan for the unpredictable. Plan for the sea, in all its fickleness. Because a boat that can weather the storm is a boat that can reach any destination, no matter the luck.