The Complexity Paradox

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Bob had heard it countless times before: "We're mostly on the same page. I think this should be pretty straightforward." Each time those words left someone's lips, he couldn't help but wince slightly. Years of experience had taught him something most people seemed reluctant to accept.

He'd noticed an inverse relationship that showed up everywhere in his life: the more straightforward someone insisted something would be, the more complex it invariably became.

He wasn't only talking about his own divorce, though that had certainly been a masterclass in misplaced optimism. He was talking about everything. His business ventures, family disputes, career transitions, even seemingly simple home renovation projects. He'd watched himself and others fall into the same trap repeatedly: wanting difficult things to be simple, wanting messy situations to have clean solutions, wanting good intentions and positive attitudes to somehow reduce the inherent complexity of whatever they were facing.

But he'd learned that optimism doesn't change the math.

When he and his ex-wife were getting along during their separation, he'd initially thought it would eliminate the need to untangle twenty years of shared financial decisions. It didn't.

When his business partner had approached him about dissolving their company on friendly terms, he'd assumed it would be straightforward. It wasn't, they still had to deal with contracts, assets, and future obligations.

Even when his father's estate seemed "simple" because the family got along, it still had tax implications, beneficiary considerations, and legal requirements that took months to navigate.

He'd come to understand that the absence of conflict doesn't create the absence of complexity. It just changes the nature of the challenge from adversarial to administrative, which, while certainly preferable, is still complex.

Looking back on his experiences, he realised that the people who had fared best in complex situations weren't the most optimistic ones. They were the ones who acknowledged the complexity upfront and built realistic timelines around it. They hoped for the best while planning for the actual scope of what they were facing.

He'd learned to value optimism for getting through difficulty, but he'd also learned it was terrible for estimating it. These days, when someone tells him something should be "pretty straightforward," he just nods and quietly starts planning for the complexity he knows is coming.