Is certainty the enemy of imagination?

It’s been over a year now since Ksenia and I published our first Doubt Club study. It’s been a year of change and growth for both of us – professionally and personally – and in and amongst it all, we’ve been continuing to noodle on the power of doubt in organisations and to have fantastic conversations with non-profit leaders and their teams about the tyranny of certainty.

And, oh my goodness, is certainty blowing up in our faces…?! At this point, March 2025, I think we can pretty much agree that the world order as we knew it, at least in Europe, has imploded. Mental models that we carried, that shaped our assumptions, are being challenged on a daily basis. And whilst all of this is distressing to the n’th degree, and causing direct harm to countless people, it has got me thinking about just what it takes for us to realise the mass assumptions we’re making – and how those assumptions limit our power to doubt collectively, and thus, and this is the leap I’m making in this blog, to imagine together different futures.

Here’s a story that will be familiar to many of you with elderly parents, relatives or friends. I was with my mum and dad recently. They’re in their 80s and their calendar is filled with various clinical appointments. In a typical week, it’s a couple of routine tests, a specialist surgeon or physician, and a little bit of light chemo thrown in for good measure. To make all this happen, my parents have to engage with tech. They’re told to scan a QR code to register for blood tests, to reply via an app to appointment invitations, to google their treatment pathways, and to arrange their hospital visits via Uber.

With all of this, last weekend, they’d pretty much reached boiling point. Two-factor authentication, plus phones running on old operating systems (and possibly that have run out of storage), meant that nothing was working. I was summoned, and after spending about an hour trying to calm them down, their tech was thrust into my hands. ‘Make it work,’ ‘we’re completely dependent on it and it’s not working…’.

This last comment from my mum ran through me almost like a knife. ‘We’re completely dependent on it…’ What? My family is super lucky (at least that’s my take on it most of the time) in that we all live – parents and 4 siblings – within a 10 mile radius of each other. My parents live in a block of flats with amazingly friendly and helpful neighbours and their community is strong. And yet, there’s my mum, a tough old bird, who’s lived through a lot, thrusting a lump of glass, metal and precious minerals at me and saying ‘we’re completely dependent on this.’

In that moment I had a dream – one of those moments when your imagination leaps 20 steps forwards in the blink of an eye. It went something like this:

  1. Mum, you are not dependent on this phone.

  2. The people who made this phone are dependent on you thinking you are dependent on this phone. A different thing entirely.

  3. You are dependent on your family, your friends and your community. Your phone is just a means of accessing them, which is technology you have had available to you since you were a small girl in Australia in the 1940s.

  4. So then, what other assumptions or mental models are the Big Tech oligarchs dependent on our holding, being certain of, to continue to tyrannise us?

  5. What would it look like for us to surface those assumptions or certainties in community? In our organisations, our families, our friendship groups? And in challenging those, and reducing our belief in our own dependence, what energies might be released, or what pathways might open up, for different ways of being, or of spending our precious time on this earth?

  6. Thus, the revolution began (and was complete, and a better world emerged, all in the blink of an eye).

So that was my flight of fancy… At the same time, there are some things I feel I have to believe, the certainties I am determined to cling to for now.

I believe that in governments, international organisations, think tanks and so on, there have been people for some time asking, whispering to themselves and perhaps their closest pals at the water cooler, ‘what if we’ve moved past the post-WW2 compacts? what if the death of living memories of WW2 means a precipitous fall away from commitments to the world order built in the 1950s?’

I believe that if the white noise of certainty (complacency?), the necessity of playing by the rules, and the inherent laziness of so many leaders (‘I’ve done my strategy, it’s on my powerpoints and on the website, so pipedown pipsqueak!’) had been forced aside, even for a short time, there would have been space to ask these questions and – critically – to start to imagine different futures.

I believe that in corporates and non-profits all over the world, there will have been people thinking to themselves, and again, chatting with their pals, along the lines of ‘well gee, these polls are pretty much 50:50, what we gonna do?’ (But I have little faith that time or space was created to imagine: ‘so what now?’)

I believe that every time an organisation undertakes a project or programme of work predicated off something that’s been sold as a ‘technological advancement,’ there have been people worrying away that this project might be based on an advancement in what technology can do – but that that is not the same as an advancement in justice or fairness in society, underpinned by technology. My mother-in-law and I recently sat with an official responsible for sorting out her ‘care’ following a hospital stay. He tap-tapped on his laptop, mumbled questions, didn’t look up once other than to reassure her that every visit from a ‘carer’ would be ‘logged on the system.’ Perhaps that essential ‘logging on the system’ is a result of technological advancement, but cannot possibly be considered an advancement in care (it’s a word with a meaning, and that meaning is not government agency risk management) for my elderly and infirm mother-in-law.

So, all to say, a year on and I am starting to think about doubt slightly differently. Where Ksenia and I started was reflecting on doubt’s role in key organisation systems and processes – how could the social process of doubt be surfaced and captured to serve as valuable critique of – and contributor to – say, strategy or planning. Where I’m at now is the prospect of it serving a deeper purpose – a surfacing of doubts not within the frame of the organisation’s current way of thinking – but within the frame of just how disastrous the next quarter of the 21st century is looking – particularly for minoritized and marginalized people everywhere. I’m interested in how the social process of doubt can be put to work not to refine the unworkable mess that got us here, but to imagine different constructs, of organisations, of partnerships, of ecosystems, of careers and so on and on…

So, what are the typical thoughts that hold us back from working the collective doubts out of the shadows and into the foreground?

  • “They won’t listen” (yes but have you worked your doubts in community, have you created space together for imagination, are you giving yourself space, with others, to create the possibilities of different?)

  • “We’ve always done it this way” (yes, but look where we are…)

  • “This is the norm in our sector” (see above..!)

  • “I don’t have time” (this is the hardest one, perhaps ask yourself [as I have been asking myself], how much time am I giving a day to the oligarchs? Inviting them in, to depress me, make me feel inadequate or envious or anxious, to outrage me or flatter me?)

  • “It feels weird… it’s not something I’d do…” (precisely! And that’s what tyranny relies on…and I believe – see above – that there are a lot of people around you feeling like you)

This is a feminist issue – I spend time every day with amazing women who in different ways are feeling both stunned and silenced. They are attending to the resilience of their families and communities – supporting mental health crises in the young, tech crises in the elderly, fragmenting communities and absences of hope and joy. It seems as though with a flick of a chainsaw, the last 50 years didn’t happen. That tiny erosion of patriarchal power since the 1970s seems to have been a chimera, it’s slipped through our fingers faster than I could ever have imagined. I don’t believe we can continue to try to improve what’s broken. We need to grasp our doubts, work with them together, and imagine the new. How otherwise to move from here?

PS The Imagination Deletion Machine ChatGPT was not involved in the creation of this blog – perhaps it would read better if it was but I don’t care!

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The paradox of leaders’ relationship with doubt