Why you should love to learn chaos

It’s where you win: Lessons from this year’s Round Ireland yacht race

Hi, Markham here. Thanks for reading Oscillations - a newsletter that looks for lessons in growth from all areas of work & life. Why ‘oscillations’? I explain it here. 

Let’s talk about why you need to lean into chaos.

⛵️ The Round Ireland Yacht Race took place week. It’s an ocean racing classic - 705 unpredictable offshore miles. You keep Ireland and all its islands to your right-hand-side (to starboard) as you lap Ireland, starting and finishing in Wicklow.

💨 There is always a sprinkling of chaos in this race, but the ideal situation for the Round Ireland is a classic west coast sleigh-ride, where the prevailing wind, blowing out of the south-west, scoots the fleet northwards from the bottom-left corner of the island near the iconic Fastnet Rock in a straight-line drag race round the top of Ireland. As the fleet nears the narrows between Northern Ireland and Scotland, tidal dynamics kick in and the race often goes into a different strategic phase. But until then, the fleet often surfs along the spectacular west coast, riding Atlantic swells with the wind at their backs.

NOT THIS YEAR.

🌊 As the fleet turned the corner at the bottom left, they split apart and pounded upwind, with lumpy Atlantic seas hitting them right in the face. That kind of sailing is called ‘beating’ for a reason - you take one as you fight to maintain momentum against both wind and waves, which want to push you backwards. It is a percussive, attritional, unpleasant way to sail, and the scattering of the fleet that comes with it is a kind of chaos that demands change, which creates opportunity. The race goes from a straight-line test of speed to a chaotic mess as boats’ paths scatter into disorganized upwind zig-zags. But that’s GOOD. That’s what we WANT. This is our time to shine.

In sailing, as in life, you rarely make gains while lining up with a bunch of other people in orderly fashion. The more chaotic portions of a race that disperse the competition are most often where the gains and losses play out, where the top and bottom tier are sorted from one another. It’s where you win.

☝️ This is how the tracks looked on the map. The fleet spread way out. All along the south coast they largely followed the same line, where they were competing on a single point of differentiation - speed. All of a sudden, everything blows up and the fleet is scattered. Before long, there’s an 80-mile east-to-west separation, representing the diversity of decision-making at play as crews decided on how best to navigate the turbulence. Speed is no longer the only factor. Multiple variables come into play.

🔀 During such chaos it’s often hard to tell who’s winning or losing in real time until things restabilize and everyone’s moving in the same direction again, or converging at a corner. You most likely can’t afford to look away from what you’re doing to benchmark against others. You have to spin all the plates, monitor for risks, live in the moment, keep moving forward. You have to do it solo. But so does everyone else. The people who can maintain momentum in choppy waters – a real-life metaphor that has become pretty common – and still have capacity to think, can expect to come out the other side of the chaos way ahead of the competition.

Sure enough, as the race started to revert to a straight-line drag race again off the coast of Galway, three boats emerged at the front of the pack. They would all end the race in the top four at the finish.

🧐 What separates the best from the rest? Mostly mindset. It’s how deeply you prepare ahead of time, and how you train yourself to react in the moment. The best will have prepared their team for myriad situations so that there’s a clear framework for action in almost any eventuality. They will have their maneuvers down, so that in the moment, the skipper can lead decisively, making calls on a few key pieces of clear, information before deciding on what tactics to deploy - even if people have barely slept. The best manage risk effectively and keep the bigger picture in focus. On the water, that means knowing the limits of your boat, reducing sail area early if dark clouds appear on the horizon to a level that’s safe for the boat and manageable by the crew, while still allowing you move forward. The best do all this by rote, enabling them to remain clear-minded about where the gains are likely to be made based on the weather forecast, tides, etc. They can then sail safely and smartly so their boat and team make gains while others fall apart. They get through the trickier conditions without breakages, in a good enough mental and physical condition to keep competing hard as things calm. The old axiom is that to finish first, first you have to finish.

All this assumes that you have built a team who thrive under pressure, keep cool heads and trust each other when they most need to. You need to collectively be in the frame of mind to calmly assess what’s coming your way, acknowledge what it will require in terms of change, then adjust early, without giving in to fear or lamentation: just change gears with purpose and drive on. If all that’s in place, when the dark clouds appear ahead, and you see the chaos coming, you know gains are likely coming your way. You love to see the darkness.

👔 How that translates to business is, I think, pretty clear, and plenty of people are thinking along these lines in the current downturn. Reducing sail as the storm clouds gather corresponds to reducing burn rate as credit tightens - bring it down to a level that allows you maintain momentum without burning out your remaining team. In sailing, you ideally switch from larger sails to smaller more manageable ones before the wind builds to a level where either the boat gets out of control or your sails shred. In business, if you’re running on investment money and aren’t at profitability, you risk running out of money if you don’t adjust costs early enough, and hit what Sequoia calls the ‘death spiral’. Managing for the forecast is the same whether it’s weather or macroeconomics. Be sure you’re preparing for what’s coming - don’t continue to adjust for the conditions you wish you had, adjust for the ones you can see approaching. Be clear to your team about why you’re making the choices you’re making so they’re aligned.

In the darkest moments, often the opportunity lies in simply out-surviving the others. As cheap money dries up and recession looms, you’re hearing VCs tell their start-up portfolio companies to do what they have to in order stay alive in the coming storm, which means cutting costs, focusing on revenue over all else, which has resulted in many, many startups shedding staff - the most recent being this email platform, Substack. From Y Combinator:

Remember that many of your competitors will not plan well, maintain high burn, and only figure out they are screwed when they try to raise their next round.  You can often pick up significant market share in an economic downturn by just staying alive.

😑 Chaos is hugely unsettling. Times of chaos can often make it hard to identify opportunity. Be calm. Keep your eyes out of the boat. Make your decisions rationally or not at all. The calmest heads will see and move to capitalize on opportunity first. The most experienced cool heads will revel in how hard it is for others to see it. As legendary Formula One driver Ayrton Senna said:

“You cannot overtake 15 cars in sunny weather…. but you can when it's raining.”

👹 Last word goes to the master of resilience, Homer Simpson, beautifully misquoting a mistranslation from JFK: