CategoryYear of Failure

Want to watch me squirm?

W

I love breaking rules. I love taking risks. I love risking failure. As part of the “scary conversation” series of chats I had this week, I challenged Frolic 100 member Leslie to pitch me on her current program. I was proud of her for stepping into her courage and doing so. But then she unexpectedly turned the tables on me and asked me to pitch her on my October program, which at this time was...

Let’s try a remix of transformation

L

Something I’ve learned about myself, and continue to learn, is how attracted I am to new creation, and not re-creation. That is why I don’t do nostalgia, and I’ve never had an interest in revisiting the chapters of my life. At least, not in the exact same way. I’ve also painted myself into a corner, where in recent years I will take on a topic or challenge, and then not feel any energy to return...

Why I’m Terrified to Host This AI Zoom (And Why That’s Exactly Why I Have to Do It)

W

Just over a week ago I challenged myself to come up with a topic that could put me on any stage in the world as an AI Expert. Leaning hard into my strengths, story, and interests, I came up with this title: A Rave Legends Guide to How to Be More Human in an AI World The thing is, I felt very confident in summarizing a bunch of thoughts, philosophies, best practices I have and present on this...

The Freedom Trap Nobody Talks About

T

First, an admission of failure. “The Big Drive 2025” for me is a complete bust. Making money for the sake of making money simply isn’t motivating me. There was value for me in analyzing my past processes, and writing them up in a series of articles for others, but returning to that specific playbook is not working. Because I’m not the same person. There’s an old quote that I feel is relevant in...

Failing at Failure

F

If I’m truly honest and open, I have an admission to make: I’m sitting here at my desk, trying to write about failure, and realizing I’m failing at failing. Not the kind of failure I promised when I declared this my Year of Failure. More like the embarrassing kind where I’m staring at my screen thinking “what the hell am I doing?” Last night I couldn’t sleep...

The Failures Have Begun!

T

I decided to start with an easy failure. Almost two years ago I was talking with a colleague and she suggested I get onto a TEDx stage, and I immediately responded with “No, it has to be TED. THE TED.” That thought lit me up. That was more my style – jump straight to the end. The idea went away until recently when we spoke again, and I found myself feeling the same way. Once I declared that...

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