Discomfort, Learning and Failing Forward

2 min read

Discomfort, Learning and Failing Forward


I am just back from a month of racing sailing yachts in the Caribbean. While that might sound like a luxury vacation, the truth is that the sport of offshore racing is highly uncomfortable, physically and mentally challenging, often scary, and downright exhausting. Layer that up with two disappointing results, and you’ve got, well, reality.  

Perhaps this is a metaphor for any high-level accomplishment. 

To accomplish new things, we must learn new skills.

While reality TV has many people believing they can fake it and pretend, this just isn’t true in the real world. The people that make it to the top of anything have put much effort into learning, and learning is complex.  

In a Harvard Business review article, Erika Andersen writes about the complexity of learning. She and her colleagues at Proteus International have identified four attributes essential for high-level learning. They are aspiration, self-awareness, curiosity, and vulnerability. Learning new skills requires us to resist innate biases, see new growth opportunities, become a novice again and be willing to fail – all very uncomfortable stuff for most of us.

In business, this type of learning is essential. The world is changing very quickly. New models are emerging, new technologies are being developed, and consumer behaviours are evolving.

We all know that changes are coming to the business world, including real estate. What they look like is uncertain, but now is the time to learn to learn. Knowing what we don’t know is tricky because we don’t know what it is that we don’t know.    

To excel in the emerging environment, the high-level skills needed won’t be specific knowledge but our ability to shift perspectives, adapt our beliefs, and pivot in the moment.

As I am learning new technology – both online learning platforms and sailing navigational software- I need to allow my brain to be elastic enough to see and understand things in a new dimension. This requires aspiration (Suze’s recent blog on aspiration) ,self-awareness, curiosity, and vulnerability. I can’t tell you how often I’ve just wanted to quit and pick an easier path. I won’t and if that sounds like you, let’s build our successful futures together.  

In one of the yacht races, I was assigned as navigator on a Volvo 70. This was a new position for me and while I understand a lot about sailboat racing, navigating on this complex, fast, and high-tech yacht required many new skills. I was a beginner again, and it was very uncomfortable. While I didn’t run this mega yacht up on any rocks, I also didn’t have any brilliant moments that put us at the top of the fleet. I was mediocre, and I’m not used to that.   

The learning opportunities in this experience are massive, and I am excited to fail forward. 

I have just received an invitation to be navigator on a more familiar type of sailboat close to home for a long-distance race in April. I see this as a valuable opportunity to consolidate my learning from the Caribbean and build new skills quickly and effectively. Maybe one day I’ll be a brilliant navigator. How fun would that be?

Over the coming months, I will be going deeper into the importance of learning to excel in business.  

Learning to learn is shaping up to be the critical skill in the new economy.