The decision you fear most in 2026

Author

John Drysdale
January 07, 2026 • Estimated Reading Time: 3 minutes

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What are you most afraid of deciding?

This is the question faced by Nora Seed , central character in the novel The Midnight Library, that I read over the holidays.

Nora finds herself in a mystical library where she explores books representing alternate lives she could have lived if she had made different choices.

Looking back, Nora sees a series of paths she once stood on the edge of: Olympic Swimmer, Rock Star, Glaciologist.

Each represents a version of herself that might have been more successful, more complete, more fulfilled.

She is then confronted by her own “Book of Regrets” in which she judges herself harshly for making the “wrong” choices.

She discovers that many of her perceived failures were based on misconceptions

Published by Penguin Random House

Looking back with regret and asking “ If Only’ Nora realises that she has overestimated the upside of unchosen paths and underestimated their costs. At the same time, she has undervalued how her actual lived experience has resourced her.

From “ If Only” to “ What If”

Nora was assessing the impact of her life choices but her learnings are also applicable to the types of challenges facing business leaders in 2026.

So here’s something you may find helpful when making tough decisions in the year ahead:

Resist the temptation to revisit past decisions through the “ If only” lens, e.g if only …. we had moved sooner, had chosen differently, had acted quicker, or pushed harder.

Over time, this habit quietly shapes behaviour: hesitation replaces conviction and decisiveness gives way to caution.

The shift that matters here is not about you finding better answers, but about changing how you relate to uncertainty.

“If only” is retrospective. It narrows attention, hardens judgement and quietly trains leaders to optimise for safety.

“What if” by contrast is about looking forward, getting curious. It accepts that decisions are made without full information and treats uncertainty as a condition of leadership rather than a flaw. It opens space for movement, learning, and deliberate choice.

What if you were able to frame the decisions that you regretted as sources of learning rather than failures of judgement ?

What if uncertainty is not something to eliminate, but something to lead through?

What if the year ahead is less about avoiding regret — and more about choosing clearly, even when outcomes can’t be guaranteed?

As leaders, we don’t get to choose perfect conditions. We get to choose our stance in the face of ambiguity. And often, the most important decision is simply the willingness to decide.

I hope you found this edition of my newsletter useful. If you have colleagues or associates who you think would also find it useful, please forward it to them.Or share on your own social media channels using the links at the top.

‘Til next time.

John