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Surviving Ambiguity

May 14, 2026 by Jennifer Cubino

While I have been fortunate to work across the areas of innovation for the bulk of my career, I would be lying if I didn’t acknowledge the anxiety created by ambiguity. Many moons ago, I was given the challenge of envisioning clinical operations changes needed for genomic in/ex criteria for precision medicine therapeutics. This started my middle of the night sketching on strategy; its where I bolt awake, somewhere between 2-4 AM, burning hot, with my mind whirring on connections, risk mitigations, actions, design and change. I used to try and not write my thinking down, but that failed rapidly as my brain would keep going until it was convinced I GOT THE MIDNIGHT MESSAGE. After all these years, I give in quickly now – sketching notes on any available paper, drawings with lines and arrows and swim lanes, risk tables and a giant list of questions / assumptions. I am a mix of absent-minded professor and crazed detective in these moments.

The most frequent reason for my crazed insomnia – ambiguity. From a systems view, whenever a new innovation is introduced (drug or tech or data), the whole operating model is at risk to hiccup and stop from the disruption. The ambiguity created by an innovation grinds operations to a halt. And without being too operationally nerdy, operations halting is bad. Hence why when I’m working on innovations, my brain’s safety valve triggers, waking me up to define all the places of ambiguity before the chance of hiccup. It’s really midnight risk management and operating model design. And for whatever reason, my brain won’t do this work in front of a laptop. Its either during sleep or on the trail. That’s it.

If I consider my ambiguity tolerance, I like to imagine this as a strength. Sometimes it actually is. Sometimes its torture. When other colleagues are happy to remain in the unknown ether, I am arduously working through design, options, risk, messaging, all while I should be sleeping. Is this really ambiguity tolerance? Or am I instead ambiguity intolerant and that is the source for my insomnia? Take a deal negotiation, for example: what are all the reasons the deal can fail to deliver value? The mitigations turn into contractual clauses and partnership structure. Or take a new digital endpoint: what are all the reasons pharma or a regulatory body would refuse? The mitigations turn into a go-to-market strategy, thought leadership and business model.

This past weekend, I found myself on the trail under highly ambiguous circumstances. There was a large patch of snow over a steep incline whose base was unstable scree. We needed to traverse without triggering an avalanche on the melting snow. My risk mitigation brain assessed slope angle, snow melt, past tracks and time to traverse. It was risk mitigation at its finest, with the reward of a rare view of a herd of mountain goats. Without fail, there is always an inspiring reward to surviving ambiguity.

jennifer.cubino [at ] littlecube.ch

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