the leadership dilemma
wholehearted possibility beyond the status quo
Next cohort: February 2026
one: what’s at the core of me?
three: participating in the world whilst staying sane and healthy
two: paying the mortgage and having a good life
we’ve all done values exercises before.
but what’s our real, unshakable truth - the part of us we will not compromise?
where do we find the solid ground that roots us in the world?
who do we believe we are? who are we becoming? and why?
two: paying the mortgage and having a good life
three: participating in the world whilst staying sane and healthy
two: paying the mortgage and having a good life
few dilemmas shape our choices more than paying the mortgage.
it’s a reason to stay in roles longer than planned, tolerate misalignment, or convince ourselves there’s no alternative.
here we explore what happens when ‘not enough’ dominates our decision making and limits our freedom.
what if the mortgage myth isn’t the fixed reality we thin
few dilemmas shape our choices more than paying the mortgage.
it’s a reason to stay in roles longer than planned, tolerate misalignment, or convince ourselves there’s no alternative.
here we explore what happens when ‘not enough’ dominates our decision making and limits our freedom.
what if the mortgage myth isn’t the fixed reality we think it is, but something we have more power over than we realise?
three: participating in the world whilst staying sane and healthy
three: participating in the world whilst staying sane and healthy
three: participating in the world whilst staying sane and healthy
the world’s problems can feel overwhelming.
it’s natural to focus on ‘looking after our own’ first.
but what happens when we step back from the bigger picture - or opt out entirely?
where do healthy boundaries end and avoidance begin?
how do we stay engaged in shaping the world and stay fresh?
do we really know how and when to draw the line?
four: the courage of uncertainty
three: participating in the world whilst staying sane and healthy
three: participating in the world whilst staying sane and healthy
at some point, wise leaders must accept a simple truth: we never truly know what’s coming next.
we do not control the universe.
what does it take to let go and embrace uncertainty rather than resist it?
how might that shift unlock a whole new way of leading?
five: do more with less
seven: when bad behaviour keeps winning
five: do more with less
we sit in permission queues—waiting for more people, more money, more resources. we stall when the answer is no.
what if we could lead the race by taking the path less travelled?
this masterclass invites us to play with the idea of doing more with less.
finding joy in simplicity and seeing where we love to create complication out of nothing more than habit.
six: leave no mark
seven: when bad behaviour keeps winning
five: do more with less
what if the greatest legacy we could leave is no mark at all?
what if enormous innovation could be unlocked as a consequence of striving to leave no footprint.
this masterclass explores the shifting ground of moral responsibility and the idea that innovation thrives in real constraints.
will we go first and set new priorities?
could that change the game in more ways than we can even imagine?
seven: when bad behaviour keeps winning
seven: when bad behaviour keeps winning
seven: when bad behaviour keeps winning
why does the world keep rewarding terrible behaviour?
why do we see some things clearly while remaining blind to others?
do good leaders go to war against it?
what happens when we do?
what are we missing - the thing that could finally turn the tide?
eight: driving the train
seven: when bad behaviour keeps winning
seven: when bad behaviour keeps winning
at some point, almost every leader will face an impossible choice.
we become the mythical train driver forced to decide.
do we divert the train and sacrifice one, or stay the course and let three perish?
what will we do in that moment?
just as importantly - who will we become because of it?
nine: how do we speak up safely and powerfully?
twelve: how do we release infinite possibility?
nine: how do we speak up safely and powerfully?
when and why do I give my voice away?
what makes me insist on going it alone?
how do I use my voice to deny myself or ignore others - what happens when I do?
Is there a way to speak up powerfully that shifts the tides peacefully and creates real change?
ten: compassion, love and commerciality
twelve: how do we release infinite possibility?
nine: how do we speak up safely and powerfully?
what is our professional narrative around compassion and love?
what makes us afraid to bring love to the table?
why does love so often feel inappropriate or unprofessional?
can we create a more powerful, human-centred approach to leadership?
and if so… do we really want it?
finally, what are ‘results’, and how does being a loving leader a
what is our professional narrative around compassion and love?
what makes us afraid to bring love to the table?
why does love so often feel inappropriate or unprofessional?
can we create a more powerful, human-centred approach to leadership?
and if so… do we really want it?
finally, what are ‘results’, and how does being a loving leader affect my reputation - will it stop me from succeeding?
eleven: there’s no time for the long game
twelve: how do we release infinite possibility?
twelve: how do we release infinite possibility?
when short-term results call loudly, how do we keep our eye on the long game?
what does it take to pause and create space when everything urges us to move faster?
and when we do, how do we use that space wisely?
do I have the courage to slow down when the world demands I speed up?
twelve: how do we release infinite possibility?
twelve: how do we release infinite possibility?
twelve: how do we release infinite possibility?
in a world with more possibilities than a single brain can handle, how do we break free from our own limited narratives?
how do we gather wisdom from the past while daring to build something new?
what does it mean to be a wayfinder and a trailblazer?
are we ready to step into the unknown?
danielle macleod
I know what it’s like to lead inside the arena.
For years, I played at the highest levels - leading 10,000 people, chasing results, making the hard calls, all while trying to stay true to myself. We broke records. It was fun. But something deeper kept calling, and it wouldn’t go away.
What really kept me up at night weren’t the numbers, but the dilemmas no strategy deck could solve. For the last eight years, I’ve been exploring and teaching leadership in a different way. We’ve only just begun.
This programme isn’t about answers. It’s about creating space for the questions we rarely name so that we can see differently, think bigger, and lead in a way that feels true.
It’s about evolving our impact to match a world that’s shifting under our feet.
If you’ve ever felt caught between what’s expected and what feels right - between security and possibility, between action and uncertainty - then you’re in the right place.
Shall we begin?
THE LEADERSHIP DILEMMA
£500+VAT
starts February 2026
- 12 x 90 minute online masterclasses (GMT weekday lunchtimes with recording)
- a curated reading and inspiration list
- a community of like-minded wise rebels
- 12 x 60 minute optional contemplation sessions to help you strengthen your reflection capability