Wicked Money Questions

Wicked Money Questions: Holding the contradictions of being human in relationship with money

Isn't it interesting that we can hold two contradictory things about money at the same time?‍

For example, how is it that:

- You can both think about money constantly and feel embarrassed talking about it?

- You can both want financial security and feel safer not looking at your numbers?

- You can both pour everything into your work and feel awkward about what it costs?

- You can both want financial ease and feel nervous when things are calm?

- You can both believe in abundance and live inside a system built on scarcity?

Wicked Questions

I recently discovered that these paradoxical things formed as a question become 'Wicked Questions' - and they're rather intriguing.

In organisational and systems change work, they're used to surface the tensions that groups are stuck inside — where two opposite things are both true, and pretending otherwise just makes things worse.

A shout out to Ray Cooper's Holding Space series — a facilitation learning programme exploring different tools and practices for working with groups — as this was a practice we explored this week. Wicked Questions come from Liberating Structures, a framework developed by Henri Lipmanowicz and Keith McCandless, inspired by academics Brenda Zimmerman and Scott Kelso.

The format is simple:

How is it that I can both [X] and [Y] simultaneously?

Both sides expressed as real, valid truths. Not one good intention and one frustrating habit. Not a problem to solve. Just two things that are genuinely, honestly present at the same time.

You'll notice what makes these different from a normal question. For example, a normal question might ask: why do I keep avoiding structure when I know I need it? — which already assumes avoidance is the problem, and one side of the experience is wrong.

A wicked question asks: how is it that I can both want stability and resist structure? — which holds both as real, valid, and worth understanding.

Here are some Wicked Questions I came up with in the context of facilitation:

- How is it that I can both challenge systems and still unconsciously recreate them?

- How is it that I can both create safety and invite discomfort?

- How is it that I can both trust the process and panic when there's silence?

- How is it that I can both hold neutrality and bring my own values into the room?

- How is it that I can both facilitate vulnerability and avoid oversharing?

I really enjoyed this exercise. I love ambiguous things. I love when we finally name something that's been sitting unsaid. I love questions that don't demand a neat answer. And the whole point — the thing that makes these different — is that you're not trying to fix the tension. You're noticing it's there. And then, naturally, you start to get curious about the why (and what next).

And with my money and finance hat on — I immediately saw how relevant this is. Because money stuff is absolutely full of feelings, tensions and complexities.

Why money is full of wicked tensions

The usual advice about money tends to be things like tracking your spending, raising your prices, saving more, planning ahead, being disciplined, exercising self control. As if it's all just rational, logical, linear stuff. It doesn't invite questions - it just tells you what you're doing... wrong, and what you should do instead!

And yet the lived experience of money — especially for mission-led founders, business owners and creatives, who are very often in close proximity to money whilst carrying a lot of mixed feelings about it — is anything but linear. (And isn't that a wicked question in itself?)

While so many conversations about money flatten people into simplistic categories: disciplined or disorganised, abundant or scarce, good with money or bad with money. But most of us are holding competing needs, values, fears and survival strategies all at once. And often, what looks irrational from the outside makes complete sense when you understand the tension underneath it.

If you've ever listened to an episode of my podcast, The Money Story Project, you'll be well acquainted with this idea already — that money is layered.

Money carries the weight and depth of our experiences, education, family history, identity, culture, survival, beliefs and more. Money is entangled with worth and visibility and belonging and fear and... a great many other things. The narratives we have heard and lived through around money and meaning.

And of course naming that despite our own values and ways of being... we are (mostly) also operating within patriarchal societies, under late stage capitalism and amidst rampant consumerism, and oppressive political regimes. Is it any wonder we have complicated feelings about money in this world?

This is where Wicked Questions become particularly helpful in this context with money. They don't magically fix those tension — but they allow us to approach things with more curiosity and space for nuance.

Instead of asking: what's wrong with me? or what am I even supposed to be doing?

We begin asking: what tension am I inside? What else exists here?

And they grant us some breathing space and room for creativity in how we approach what emerges from the questions.

Wicked questions in practice

Take this one: How is it that I can both want financial stability and resist structure?

At first glance it can sound like self-sabotage. Surely if someone wants financial stability they should naturally want routines, systems, budgets, planning?

But for many people, structure doesn't simply represent safety. It may also represent control, restriction, burnout, rigidity, surveillance, pressure, or the loss of autonomy — particularly for people who for example are neurodivergent, recovering from burnout, or who grew up in environments where instability was the norm.

Sometimes people don't resist stability itself. They resist the versions of stability that once required them to abandon themselves in order to achieve it.

That is a very different thing. And understanding that distinction changes what actually helps, what they wish to lean into what greater harmony or alignment with this might feel like. Maybe someone doesn't need more rigid structure. Maybe they need gentler systems, more autonomy, flexible routines, financial practices that support their nervous system rather than overwhelm it.

The insight could even change you whole strategy. But you can only get to the insight if you're willing to sit with the contradiction honestly — without immediately deciding which side of it is the problem.

In this way they also give us space for our rebelliousness. To say — 'actually, maybe my resistance makes complete sense'.

Exercise: your wicked money questions

This exercise works beautifully solo — as a journalling practice — in conversation with a trusted friend, coach, or peer, or as part of a group discussion. If something surfaces that feels significant or tender, you might want to bring it into a supported space rather than sit with it alone.

Step one: come up with your own wicked money questions.

Think about your own relationship with money: What tensions do you carry? What contradictions feel alive for you right now?

Framing the contadictions in this format: How is it that I can both [X] and [Y] simultaneously?

Have a go at writing your own wicked money question.

And remember a truly 'Wicked Question' only works if both sides are given equal weight and equal curiosity.

This isn't "I have a good intention and a bad habit." It's "I have two real, valid but contradictory responses." That's what makes the question 'wicked'.

Experiment with coming up with some wicked questions of your own, if your would like a few to get you started, here's some I came up with that you could experiment with. Does anything take your fancy?

- How is it that I can both want financial security and feel safer not looking at my numbers?

- How is it that I can both value my work deeply and feel uncomfortable charging for it?

- How is it that I can both want more money and feel unsettled when it arrives?

- How is it that I can both crave stability and feel most constrained when things are actually stable?

- How is it that I can both need rest and feel most myself when I'm being productive?

- How is it that I can both see through the logic of capitalism and still measure my worth by its metrics?

- How is it that I can both want financial freedom and keep recreating the conditions of overwork?

- How is it that I can both want support and find it hard to receive?

- How is it that I can both want ethical business practices and feel pressure to constantly grow?

Step two: sit with your wicked question

Explore your question. What does it bring up?

Some prompts if they're helpful:

- Where do you feel each contradiction in your body?

- Do they bring up any particular memories, thoughts or images?

- Which side feels more socially acceptable? Which side do you tend to hide?

- Whose voice do you hear in relation to each side?

- What systems, experiences or relationships might have shaped this tension?

Step three: see where it takes you.

Let it percolate. There's no pressure to resolve or fix this contradiction— but you might find yourself wanting to explore what a resolution could look like, or talk it through with someone who is also navigating this or simply sit with it and see where you go with it over the next few days or weeks.

We're often trained — especially in financial and business contexts — to identify a problem and move immediately toward a solution. The discomfort of not-knowing is something to get through quickly, on the way to an answer. How often does this really work out?

Inviting in more contradiction

So much financial advice rushes straight to fixing. Telling you to just: 'Change your habits'. 'Raise your prices'. 'Track your spending'. But if we're carrying something more complex underneath (which most of us are on account of the human experience!), then seeking to fix it without noticing what's really going on probably won't stick — or feel good.

Wicked money questions create space to honour what's actually there — the complexity, the contradiction, the feelings that don't have a clean answer. And in my experience, that's not the soft option!

Wicked Questions offer an invitation to understand yourself and others more fully, without the pressure to immediately change. Providing space to notice and name what's going on, get curious about it — that's usually more effective, more stimulating, interesting and long lasting than rushing to fix a 'problem' in a way that is never going to work or feel good for you.

I'd love to hear about your experience with wicked money questions and where they take you!

Acknowledgement:

I first encountered Wicked Questions through Ray Cooper's Holding Space series, a facilitation learning programme I'd warmly recommend. The original framework comes from Liberating Structures, developed by Henri Lipmanowicz and Keith McCandless.

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