Unlocking the effortless leader

Sometimes life doesn’t go as planned.

The picture we have in our heads gets trampled underfoot by the universe having something else in store for us.

Whether it happens in life or business, the mismatch between our dreams and reality can trigger fear, desperation, and shame.

But sometimes, just sometimes, not getting what we wanted or expected means we get what we need instead.

As was the case with this interview with one of our heroes, coach and entrepreneur Jerry Colonna.

The author of Reboot: Leadership and the Art of Growing Up and REUNION: Leadership and the Longing to Belong, Jerry has worked with CEOs and changemakers from around the world.

His work is deeply rooted in the concepts of radical self-inquiry and the healing journey towards becoming more conscious, aware, and compassionate leaders.

This interview was delayed by tech issues - the last thing you need when you’re interviewing your hero against the clock with an audience waiting.

Rather than talking about his past or his books, Jerry echoed Tolstoy’s Three Questions by grounding the conversation in the present moment, making Carlos’s suffering about the delay his top priority, and attending to it.

It brought Jerry’s compassionate intention behind his work and books to life in a more powerful way than any regular interview might trigger.

This one’s for you if…

You beat yourself up when things go wrong
You have habitual ways of being that don’t make sense given your current circumstances
You find leadership a struggle due to your own need to belong
You need a reminder to pause, take a breath, and slow down

Watch the full video here

Here are nine takeaways from the conversation:

1. A deeply compassionate vow

While many of us want to do good in the world, Jerry's life and work are guided by a profound purpose: the Bodhisattva vow of working towards the liberation of all beings from suffering.

“I am organised around what I would call my Bodhisattva vow.

And for those who don't know, Bodhisattvas are folks who have achieved enlightenment but, regardless, have chosen to take rebirth. Until all beings are free of suffering.

And so when we take a Bodhisattva vow, which is a thing that one does, you work towards the liberation from suffering of everybody.”

This vow sets a powerful intention that can be felt in both his work and his presence.

2. Attend to what is happening in the moment

It’s so easy to get caught up in what should be happening. This can block us from seeing what’s actually needed.

Carlos shared that the technical difficulties he experienced in launching the interview meant he could feel his anxiety reach his throat.

Jerry’s response was to speak more slowly, to slow the energy down, and to encourage Carlos to take a breath. As he explained later,

“If the folks recall, at the very, very start, I slowed us down and stopped to acknowledge and give some relief to Carlos's anxiety.

Which not only made Carlos feel better but, I’ll warrant, made Laurence feel better. It certainly made me feel better and probably made some of the folks in the audience feel better.

Totally unexpected, but the right thing to do in that moment.”

3. Beyond the “second arrow”

How many times have you made a mistake or had a painful experience and then berated yourself for it?

The true source of suffering often lies not in the initial challenge but in the stories and self-talk we attach to it – the "second arrow."

As Jerry reminds us, "The real source of suffering, the real source of the challenge, is, to use a Buddhist notion, our attachment to the way things are supposed to be."

Loosening our grip on how things are ‘supposed’ to be allows us to be more present to what is - and the opportunities it presents.

4. Acknowledge what’s going on inside us

When we look around at others, it’s so easy to feel inadequate. Jerry hasn’t been immune from struggling with his inner critic.

“In writing ‘Reunion’, one of the things I took on was this larger-than-life task: “What can I do to help heal the world?”

No big task. Just try to heal the world and stop us from trying to kill each other. That's all. And it's my Bodhisattva vow.

I lay awake at night after a weekend of trying to write and not getting the words right.

And the story starts flowing, “Who are you? You're not a writer. You're never going to be an author.”

Our task is to balance all these forces, to every day, lift up and acknowledge what is going on.”

5. We all long to belong

What often drives our “second arrow”? A fear of rejection and loss.

Underneath our individual stories and what Jerry refers to as “subroutines” lies a universal human longing for connection and belonging. As Jerry quotes from Frederick Buechner’s The Longing for Home,

“There lies the longing to know and be known by another fully and humanly, and that beneath that there lies a longing, closer to the heart of the matter still, which is the longing to be at long last where you fully belong.”

Knowing that we all share a need to belong helps you to understand your motivations better - and of those around you.

6. Carrying what went before us

Our longing for belonging often stems from ancestral experiences of loss and hardship, which are the genesis of many of our subroutines.

Jerry skillfully unpacked Carlos' anxiety around productivity, linking it to his family's history of losing comfort and security.

“‘If I move fast and break things, things won't get broken.’ That is not the logic of a fully actualised adult.

That is the logic of a child carrying the burdens of parents and grandparents, and great-grandparents, and great-great-great-great-grandparents.

It makes perfect sense. Until you examine it.”

7. Unlocking our stories through radical self-inquiry

As other recent speakers have noted, identifying and understanding our deep-seated belief systems and subroutines is key to our personal growth.

Jerry beautifully coached Carlos into exploring the effects that his family history have on how he acts today, demonstrating the power of radical self-inquiry:

“I think that you realise that if you take on the burden of that belief system, what I refer to in Reboot as a subroutine .. if you take that on, you know where you fully belong. You'll belong to your family.”

By taking ownership of how our lineage shows up in us, we can then find our place in it.

8. Longing for connection can fuel creation

Being a leader or founder can feel challenging. But true leadership isn't about relentless hustle and effort; it's about embracing the art of creating and enjoying the process.

Jerry reminds us, “Imagine the subroutines that are driving you. Imagine those belief systems, and just reframing the relationship with the assignment - with your core longing to belong.

It’s motivated by that wish for connection. And so the craft and the beauty are trying to create something out of nothing, which is the art of start-ups.”

9. Stories humanise and connect us

Knowing more about what may be driving our own and each other’s subroutines invites greater compassion, insight, and connection.

Because truly knowing and understanding each other's stories has the power to heal and bridge any perceived division.

As Jerry insightfully notes, “Let's imagine a world where we endeavour to really know each other. And see our own stories and their stories.

Let's imagine the effects of that world. It's kind of hard to dehumanise, push to the margins, systemically press or systemically ‘other’, those whose stories we actually know.”

Whose stories could you open yourself up to?

They say, “Never meet your heroes.” But Jerry Colonna’s wise and compassionate presence was a masterclass in embodying your values and allowing them to guide your actions.

And, by doing so, offering a masterclass in true leadership.

Do you want to join other like-minded people who want to make a positive difference in the world? Join our community, dip your toes in with a Masterclass, or dive into transformation at one of our life-changing events.