How to Succeed at Anything



This week’s post is inspired by Tracking Wonder Quest, question number three, offered by visionary Debbie Millman, founder and host of Design Matters. Her question:


How would you do business as unusual in 2016 if you knew – no matter what you chose – you would not fail?


Frankly, I don’t like the question. Frankly, a lot of the questions on the Quest don’t sit right with me. That’s not a bad thing. I love getting them because they spur me to ask questions that resonate with me and that I hope will serve all of you. My question this week:


What if I allowed myself to fail?


Or better yet:


What if I did away with the dualistic notion of success versus failure and simply showed up for my work without judgment?


I’ve had a long and contentious relationship with the idea of success. Most of my adult life I have gone after the shiny things that called to me, from good grades to getting the initials, Ph.D. behind my name, from grants and fellowships to museum positions and bylines. Whatever I pursued, I gave it everything I had and collected the prize. Until it came to writing a book, post-graduate school, and I got lost.


I began with what appeared as success or at least the road to success. With only a vague idea for a book about Hannah Wilke aimed at a broad audience, I attended the Agents and Editors conference in Austin. On the first night of the conference at the opening reception, I snagged the interest of the first agent I met. I was so excited! After that it was all downhill. After rejecting proposal after proposal after proposal, my agent finally accepted one and went to market with it. Even before she came back with the long list of rejections, I knew it would fail. It wasn’t the book that I wanted to write.


In order to write the book that I knew was only mine to write, I’d have to give up the idea of success.


I’d have to let go of the agent, for a while anyway, and listen to the project that was calling, the topic that obsessed me since I began working on my dissertation nearly twenty years ago: Wilke’s legal and artistic complaints about her former lover, the pop artist Claes Oldenburg.  I’m writing that book now and having fun with it. I’m not sure I would be able to continue if I hadn’t given myself permission to fail — at least according to my old way of thinking that required the bling of representation and promise of publication.


A few days ago, I was at Garcia Street Books in Santa Fe and noticed a small book by Pema Chodron at the check-out counter titled, Fail, Fail Again, Fail Better. The book is a transcript of Pema’s speech at her granddaughter’s graduation from Naropa. No one prepares us to fail, she writes, “how to get good at holding the rawness of vulnerability in your heart.” How to be comfortable with being uncomfortable, necessary for any artist in any media. She then quotes Joyce, who claimed in Ulysses that mistakes can be portals of discovery. She says,


It’s a little hard to tell what’s a failure and what’s just something that is shifting your life in a new direction.


For artists, that shift is key. To show up without expectation of success or failure, to arrive in an open state where the work can flow through you and surprise you. That is the fun, that is where wonder resides, in the surprises and discoveries.


If success is a mirage, then failure is also a myth. We all know by now there is no there there, only this moment, only this one step forward in the direction of a creative dream. We never know where we’re going to end up. If we’re doing our job, it will be somewhere we never imagined.


What about you? What is your relationship to success? What if you allowed yourself to fail in 2016? Could you give yourself permission to step into the wild unknown?

2 thoughts on “How to Succeed at Anything

  1. Pingback: Daydream Believer | Lauren McLean Iuppa Ayer

  2. Marisa

    I love that you’ve stood up to say the Quest questions haven’t been resonating. The rich uncle prompt knocked me off course and I haven’t recovered.

    After years of refusing to believe such advice applies to me, I’ve embraced my “I don’t know” and recognize how a fear of failure has straight jacketed me. It feels desperately important that I’ve decided to step into the stories I am truly called to tell.


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