Why Every Fundraising Team Needs a Rule Breaker
and what I've learnt from mentoring one
I’m currently working closely with a major donor fundraiser who, on paper, breaks almost every rule.
They have no formal fundraising qualifications.
No textbook pathway into the profession.
No neat CV showing a steady climb through “appropriate” roles.
Their experience is entirely on the job — driven by a personal crisis that pushed them into fundraising not as a career move, but as an act of necessity.
And yet.
They are securing meetings others insist are impossible.
They’re getting through to people most teams wouldn’t even try to approach.
They’re being invited into rooms — and conversations — that usually take years to access.
At first, I’ll be honest, it made me nervous.
When Professionalism Becomes a Constraint
Like many of us who’ve spent years in this sector, I’ve internalised a certain idea of how things are done.
There are rules:
Who you approach
How you approach them
When you should (and definitely shouldn’t) reach out
What is “appropriate”
What is “too direct”
These rules are rarely written down. They live in organisational culture, in professional norms, in the stories we tell ourselves about access and hierarchy.
So when I watched this fundraiser:
pick up the phone when others said “you won’t get through”
reach out directly when advised to wait
ask questions that cut straight to the heart of things
…I worried the approach was too haphazard.
Then I worried it wasn’t polished enough.
Adding Structure Without Killing Momentum
So we did what professionals tend to do when something feels uncomfortable: we added structure.
We started putting systems around the activity:
clearer tracking
more intentional follow-up
shared learning about what was working and why
Then we added polish:
supporting the development of a strong case for support
sharpening the articulation of impact
grounding conversations in strategy, not just instinct
What I was quietly worried about — though I didn’t name it at the time — was that structure might slow them down.
It didn’t.
Instead, something far more interesting happened.
What Happens When Rule-Breaking Meets Rigour
With their entrepreneurial, “why not?” approach and some professional scaffolding in place, the results accelerated.
We’re now seeing:
meetings with international, global funders
invitations to present at global conferences
genuine buzz at leadership level
momentum that feels alive, not forced
And perhaps most importantly, confidence — not just in the fundraiser, but in the organisation’s story.
This wasn’t luck. And it wasn’t chaos.
It was energy, paired with intention.
What I’m Learning (While Mentoring)
Working alongside this fundraiser has reminded me of something easy to forget when you’ve been doing this work for a long time:
Many of the rules we follow are inherited, not tested.
They’re often based on:
past gatekeeping
outdated power dynamics
fear of embarrassment
or assumptions dressed up as strategy
Entrepreneurial minds — especially those who come into fundraising from lived experience rather than formal training — don’t carry that baggage.
They don’t yet know who they’re “not supposed” to speak to.
So they speak to them.
They don’t assume access is impossible.
So they try.
And sometimes, they succeed precisely because they haven’t learned to rule themselves out.
This Isn’t an Argument Against Professionalism
To be clear, this isn’t a call to abandon rigour, ethics or good governance.
Fundraising still needs:
strong cases for support
accountability
clarity of purpose
respect for relationships
But it also needs courage.
And sometimes, courage enters the system through people who haven’t yet been told all the reasons something “won’t work”.
What Can We Learn From the Rule Breakers?
A few reflections I’m sitting with as we head into a new year:
Directness isn’t unprofessional — avoidance is.
Access often opens to those willing to ask, not those waiting to be invited.
Energy is an asset. Systems should support it, not suppress it.
Mentoring isn’t one-way. Some of the best learning comes from those doing things differently.
Early in the year is exactly the right time to challenge stale assumptions.
A Final Thought
At the start of a new year, when strategies are being refreshed and targets reset, it’s tempting to double down on what feels safe and proven.
But sometimes what we need most is a rule breaker in the room.
Someone who asks:
Why not?
What happens if we try?
Who says we can’t?
Paired with structure, ethics and intent, that kind of energy doesn’t destabilise an organisation.
It moves it forward.
And right now, that feels like exactly what the sector needs.
Love this: "Access often opens to those willing to ask, not those waiting to be invited"