Holding contradictions

I read Enuma Okora's column in the FT this week (behind the FT Paywall). One paragraph stopped me:

"I have a friend who, whenever I ask how he's doing, takes a moment before answering. Often he'll then express two seemingly conflicting feelings. 'A part of me is feeling grounded and engaged but another part of me is also feeling anxious because I'm concerned about [xyz].' I've grown to admire his willingness to sit with multiple realities, and even to begin practising it myself."

That willingness to hold contradictions, to say "both things are true" without rushing to resolve them, is rare. We aren’t always comfortable with it. We would much prefer coherence.

I wrote recently about the difference between clarity and certainty. That you can know where you're heading without being certain of outcomes. This is related but different. It's not just about accepting uncertainty but about holding multiple, sometimes opposing, truths at the same time, without needing to resolve them into a single story.

"How are you?" expects a single answer. "Fine." "Busy." "Good, thanks." Not "I'm both energised by the work and exhausted by it." Not "Part of me knows this was the right decision and part of me is still uncertain."

As I know only too well, the professional world particularly dislikes contradiction. We're expected to have a position, to sound confident, to present a clean narrative. It’s very rare for leaders publicly to hold doubt alongside conviction; consultants don't say "I'm not entirely sure”; and lawyers (and I spent 36 years as one) especially don't admit uncertainty.

But reality is messier than that.

In our work at Milestones, clients come wanting clarity. And clarity - knowing what you value, what you're looking for, what you're moving towards- helps. But insisting on a single, coherent story can actually obscure what's true.

Someone considering a career change might genuinely hold: "This opportunity excites me" AND "I'm anxious about leaving security." Both are real. Pretending one doesn't exist (usually the anxiety, because we're supposed to sound confident) doesn't make it go away. It just makes the conversation less honest.

It’s the same in my governance work. You can hold "this process is working well" alongside "there are risks here we need to monitor." You can think "this decision is right" and also "I have concerns about timing." These aren't contradictions that need resolving. They're simply multiple realities that need acknowledging.

When we insist on false coherence we risk losing nuance, honesty, and often judgment itself. Because good judgment rarely comes from certainty. It comes from weighing competing considerations and holding multiple possibilities. And then making the decision despite - not in the absence of - doubt.

Okora writes: "We are rarely just one thing at a time. None of us is just a husband or partner or just the strong one or just the sick one."

I feel that the same applies professionally. We are rarely just confident, just certain, just one thing. And to pretend otherwise, to smooth out the contradictions for the sake of a cleaner story, doesn't make us more credible. It just makes us less honest.