Go to main content Skip and go to the footer

It Wasn’t the Weather That Needed to Change

Caspar Craven

Creator of the Big Bold Mindset® | 2x Round-the-World Sailor | Former CFO (Multiple Exits) | Inspiring Businesses to Achieve Big Bold Goals by Stretching What They Believe Is Possible

It was our first time sailing a boat as a husband and wife team. The end of a long day on the water and we’d arrived at a bustling port rammed with other boats.

There was just one berthing spot left. It would have to be in the most awkward place! Right at the far end of a narrow lane lined with boats! Standard approach is reverse down the lane, at the last moment, take a sharp turn and calmly bring the boat to a stop wedged in between two other boats. Sounds easy right?

What didn’t help was the assembled onlookers watching and the strong cross winds blowing us sideways. The pressure was on.

The approach started well. As we neared the point to turn a gust of wind caught the bow and I shouted at Nichola to move the fenders to stop us hitting the other boats.

Her response: “don’t speak to me like that!”

In that moment I started to grasp the size of the challenge we had taken on to sail the world as a family team - my non-sailing wife, and my three kids under the age of 10 as crew.

In my working life as CFO, CEO and advisor I’d worked on many transformation projects where the stakes were high, the pressure was immense and resources were stretched.

Nothing came close to the scale of the challenge I was now facing. I’d built teams to tackle new markets, new projects and to scale and exit businesses but this was something else.

In that moment, I realised that the problem sat with me.

It wasn’t Nichola, the wind or the boat.

It was me and my approach.

If I couldn’t get that right here, in a relatively low-stakes moment, what chance did we have when it really mattered?

Culture reveals itself under pressure.

In the tone of voice. In the reaction. In how we show up when it matters. And in that moment, ours wasn’t where it needed to be.

Many teams don’t see this until it’s too late.

Up until then, I’d framed the challenge around the practical obstacles we had to overcome, not how we would actually work together to achieve it.

Things like we didn’t have the money to do this. At that point in my life we’d invested every penny in our business and I’d have earnt more money stacking shelves at the local supermarket. Nichola had only been on a boat twice, she’d been seasick both times and on top of that we didn’t have a boat either.

All very valid reasons why we should have scaled back the size of our challenge and settled for a more sensible 2 week holiday sailing the Greek Islands.

I see the same pressures in every business transformation where there are huge targets, massive uncertainty and the need for agility and resilience is extraordinarily high.

The pressure to scale back the size of the challenge and to settle more incremental growth rather than transformational growth.

We had made the choice to take on two parallel transformations. Turning around my struggling data analytics business in a rapidly changing market. And taking my family around the world.

We gave ourselves 5 years to complete both transformations.

That journey forced me to completely rethink how teams perform under pressure.

I realised that no-one was coming to save us and it was on us to figure out the shifts we needed to make.

Working with my family tackling the worlds toughest oceans gave me insights no boardroom ever did.

When the pressure is on, there’s nowhere to hide.

How you communicate, how you make decisions and how you show up determines whether you succeed or not.

And that changed everything.

These experiences became the foundation of the work I do today through The Big Bold Mindset® - helping leaders and teams navigate uncertainty, align around what matters, and deliver when the pressure is on.

 

Key Takeaways

These are just some of the core ideas that sit at the heart of The Big Bold Mindset®:

  • Thinking bigger stretches what you believe is possible
    And it’s in that space that creativity comes through. This is essential because you can’t navigate a new world using an old set of charts.
  • Culture reveals itself under pressure
    Not when things are going well, but in how people behave when it really matters.
  • Leadership is a mindset, not a title
    The story you carry shapes how you lead, especially when uncertainty is high and resources are stretched.

Send a request for Caspar Craven

Booking and request

Send a booking request here for Caspar Craven

Did you find the blog post inspiring? You can book Caspar Craven for your event. Contact us today to learn more about the possibilities.

About the author

Creator of the Big Bold Mindset® | 2x Round-the-World Sailor | Former CFO (Multiple Exits) | Inspiring Businesses to Achieve Big Bold Goals by Stretching What They Believe Is Possible

Go to the speaker's profile