Many years ago a large non-profit organisation that I worked at got a new chief exec from the USA. She shocked us all by telling us that she wanted to see us all fail at least once in the next year.
At first I thought she’d mistaken us for a Silicon Valley startup rather than a slightly under-caffeinated, over-stretched British charity where the wildest thing we’d done lately was switch to fair-trade teabags.
Fail?
On purpose?
Some of the team looked like she’d asked us to steal stationery and admit it.
But once the initial horror wore off, her point started to make sense. Painfully, annoyingly, frustratingly good sense.
Playing It Safe: Our National Sport
If there’s one thing we excel at in the UK, apart from queueing and apologising when someone steps on our foot, it’s avoiding failure.
Especially in community or non-profit work.
- We cling to “how it’s always been done” like it’s an heirloom.
- We run every new idea past a committee, then a subcommittee, then a “quick working group” which lasts nine months.
- And by the time the idea finally emerges, it’s been smoothed, softened, and sucked dry of anything remotely interesting.
So when she said failure was not only acceptable but encouraged, it was as if someone had opened a window in a room we didn’t realise had gone stale.
The Right Kind of Wrong
Now, she didn’t mean the sort of failure where you forget to book the venue or send the newsletter to the wrong mailing list (we’ve all done that, once).
She meant the good kind of failure.
- The “let’s try this and see what happens” kind.
- The “this might just work… but probably won’t” kind.
The kind of failure you only get when you’re actually pushing at the edges rather than marching in circles inside them.
Open source folks should recognise this immediately. Half of our progress comes from things that “shouldn’t have” worked but somehow did. The other half comes from things that didn’t work at all but taught us something useful, usually in public and usually with someone watching.
The Slow, Quiet Culture Shift
Something interesting happened after her declaration.
People loosened up.
- They stopped treating innovation like a suspicious foreign substance.
- Ideas started appearing that weren’t already pre-approved by the ghosts of projects past.
- Some ideas were brilliant.
- Some crashed so hard we’re still finding the debris.
- And one or two were so baffling that no one to this day is prepared to admit responsibility.
But the point is: people tried.
In community-driven environments — whether charities, open-source projects, or volunteer gatherings held in rooms where the heating hasn’t worked since 1998 — the act of trying is half the magic.
Imagine If More Communities Allowed This
If failure wasn’t taboo…
If experimentation wasn’t treated like rebellion…
If people felt genuinely safe to say, “So, I had an idea…”
- We’d see more creativity.
- More collaboration.
- More weird and wonderful attempts.
- And, crucially, more things that actually move the needle.
Communities don’t grow by staying comfortable. They grow when someone experiments and pushes the boundaries. Sometimes gently, curiously, and occasionally disastrously.
A Small Invitation
So try something this month that might not work.
- Host the quirky event.
- Test the oddball idea.
- Start the conversation no one’s dared to start.
If it succeeds, brilliant. Tell everyone it was your plan all along.
If it fails, equally brilliant. You’ve learned something that you can only learn by doing.
Because the truth is simple:
Failure isn’t the opposite of success.
It’s evidence that you’re actually alive, awake, and giving things a go.
And honestly… that’s far better than perfect.
Acknowledge Your Failures
But here’s the caveat: I’m all for failing, but don’t keep banging your head against the same wall. There’s a difference between experimenting and just fumbling along, hoping a disaster will magically turn into a triumph.
When something clearly isn’t working, stop. Learn from it, yes, but then try something else.
Failing is useful. Repeating the same failure over and over? That’s just exhausting.
