Charles Starrett


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Culture consultant & social tech teacher/facilitator at SoulCo & Northeastern University. He/Him. Dad, Harvard and NEC alum, visual thinker, dabbler in ukulele, electronic music, 한국어, and TTRPGs.


Choosing to fail again

Most of us got to where we are by being good at what we do. And we’re better at what we do now than we used to be. There were times when we struggled, stumbled, and failed. But we learned, got better, and now we enjoy the fruits of our success.

But what do we do if our achievement grows stale, or we start to discover that what got us here can’t get us any further? Most likely we need to learn new skills, which means that first we have to get used to failing again.

Having achieved success and enjoying the feelings of excellence and mastery, it can be difficult to leave the comfort and security of where we are and venture out into the dark forest of the unknown.

Doubts creep in: How long will it take to gain mastery this time? Will I be successful? Can I even do this?

And if we manage to convince ourselves to leave the comfort of our castle, the initial excitement of new adventure quickly gives way to that awkward “learning how to walk” feeling which comes with learning new skills. We fail. Often. And failure rarely feels pleasant.

What makes it worse is that repeated failure can feel like a lack of progress. Each failure may reinforce the belief that we’re not getting better. We can feel like we’re just walking in circles.

This is when we need to remind ourselves of why we’re doing this. Why are we putting ourselves through the pain of being a beginner again? What matters to us so much that it’s worth dedicating our life to this path, no matter how difficult?

Remembering why we chose this path of learning, and that failure is part of learning, can strengthen our commitment to keep going through the unknown forest when what might sound better is to return to the comfort of our castle.

I invite you to pause for a moment of stillness and ask yourself what keeps you going on the path of learning, especially when you fail?

3 July 2022

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