Leading Successfully In Difficult Times: Lessons from a Frontier Explorer Part II

In part I of Leading Successfully In Difficult times, I talked about some of the lessons that I had learned from my record breaking expeditions. You might recall that my best mate Justin Jones (Jonesy) and I were the first to kayak unsupported from Australia to New Zealand, and then completed the first unsupported walk to the South Pole and back.

Hi, my name is James Castrission (Cas), and after my first adventure crossing the Tasman, I spent a good deal of time thinking about what I had learned. To make the 2000km journey, we faced dwindling food supplies, a string of technical problems, 14 days trapped in a whirlpool and two terrifying close encounters with sharks. When we finally made it to New Zealand, our friendship was stronger than ever.

What was fascinating to me was how every lesson can be applied to any difficult situation and anybody who wants to achieve something out of the ordinary. And that includes leading people through difficult times.


In this week’s article, I would like to drill down into some of the insights that I gained through the experience of our Trans-Tasman adventure and share some of the deeper principles that can help you become a successful leader in any conditions.

as a leader, sometimes you have to make the hard decisions to keep your ship running at its optimal performance.

Lead With Passion

Jonesy and I had a team spanning 17 countries but almost nobody’s involvement in the project was commercial. What attracted them was our authentic passion and commitment to the project. Our excitement was infectious and helped us attract a crew of equally motivated team members.

When we finally made it to New Zealand, our friendship was stronger than ever. We were sunburnt, bearded, physically and mentally wasted … but understandably jubilant. Helicopters hovered overhead and there were so many cameras pointed at us as more than 30,000 people welcomed us to shore.

Leading Successfully in Difficult Times

Be Honest and Authentic

Two months before we were scheduled to depart, having raised $500k in sponsorship, we finally put our custom made kayak in the water. And it flopped on its side. The rebuild took a year. What got us through was the honest, open and strong relationships we had built with our sponsors and stakeholders.

Be Accountable

Accepting responsibility for the bad/ugly defined our roles as project leaders. When our kayak didn’t work on first launch, the boat builder, marine architect, electrical engineer and kayak mentor all blamed one another. As the leader, I needed to be accountable for the failure before we could move on.

Leading Successfully in Difficult Times

The 40% Rule

The 40% rule dictates that when you think you are ‘done’, you’re only 40% done. Crossing this barrier was when we truly started to grow. Those few extra steps when we didn’t think we could go on were massive gamechangers.


For two weeks of our journey Jonesy and I were held captive, stuck in a massive current whirlpool in the middle of the Tasman Sea. In order to overcome this challenge, we had to paddle 150km back toward Australia before choosing a different route. As leaders, it was critical to realise progress isn’t linear.

Don’t Underestimate the Power of 1%

The success of our expedition came down to thousands of small modifications which accumulated to make a big difference. From major sporting teams to tiny companies, the culmination of small iterations and changes is the key to knocking off BHAGs (big hairy audacious goals).

Remove the Barnacles

By day 46, barnacles were slowing our paddling speed by 50%. We tried to ignore them and assign blame to something else (wind current, body fatigue) before realising that these inefficiencies need to be removed. The lesson was that as a leader, sometimes you have to make the hard decisions to keep your ship running at its optimal performance.

Social Capital Counts

Social capital is about coming together with shared values and understandings. It is the fabric that holds every high performance team together. It trumps individual talent and should be at the epicenter of every leader’s focus. A key driver of our successful crossing was action-orientated guiding principles. These aligned our international team and laid the platform for each member to go above and beyond.

Look Outwards, Look Ahead

Our position on the Tasman was being monitored by our support team and the best weather forecaster/ meteorologist on the planet. Receiving real time satellite imagery of localised current patterns allowed us to stay ahead of conditions, rather than react to them. It was important for us to leverage this data to drive decision making in a hostile environment that was changing rapidly.


We realised that when leading a team through a complex project, it is critical to reward and celebrate milestones and not just focus on the realisation of the goal. This proved that the growth mindset theory is true and paid massive dividends for morale and resilience. 

In 2013, I founded MyAdventure Group to allow executives and corporate groups to step into the unknown for themselves, and to harness the uniquely powerful lessons that can only be accessed outside of the office. The programs we offer are designed to develop teams and give them competitive advantage in one of the most confronting environments anyone will find; the business world.

If you would like to take you and your team on an inspirational journey in the spectacular Blue Mountains, where we apply the principles that I have talked about today, or book me to speak at your next event, just click on the link below.