Safe to Fail: A Journey in Reviving My Creativity

How I’m designing a series of public experiments to make it safe to fail and break out of my default patterns

Two weeks ago, I came out of a mastermind group with a powerful piece of feedback:

I needed to feel safe to fail.

To be honest, I’ve been feeling somewhat stuck creatively for a couple years now.

I’d experience sporadic creative spurts here and there — but nothing like the inspirational muse and sustained devotion to my life’s work I once felt in the years prior.

And that’s been hard.

Growing up, I got straight A’s in school from third grade onwards, even through MIT. The behaviors that led me to academic excellence gifted me with a really successful career and oriented me toward a high quality bar for anything I produced.

But they also had a cost — the bar for my own quality and performance deprived me of the safety to fail.

In particular, my over-attachment to spending my time and energy on doing the “right” soul-aligned projects made it difficult to work on anything when nothing felt quite “right.”

And that’s been the invisible thread underlying my creative struggles the past couple years.

Quantity Creates Quality

In their book Art & Fear, authors David Bayles and Ted Orland share an insightful story about this phenomenon.

A ceramics teacher divided his class into two groups.

One group would be graded on the quantity of ceramic pots they created over the semester — the more they created, the higher the grade.

The other group only needed to produce a single pot — and would be graded on its quality.

Come grading time, the highest quality pots actually came from the “quantity” group. The “quantity” group — in creating large amounts of work — had created opportunities to learn from mistakes and discover what worked. The “quality” group, in just theorizing about how to perfect clay, didn’t actually get as far.

Quantity breeds quality.

Clearly, to actually do the work I wanted to do in my life, I needed to create more and allow more room for failure.

I recently read Nicolas Cole’s The Art and Business of Online Writing. Cole’s the founder of Ship 30 for 30, a program dedicated to helping people create and publish 30 pieces of published writing in 30 days.

I’ve always felt some trepidation at the idea of committing to doing writing at such high frequency. Some of my most popular pieces of online writing, ones that generated 1M+ views, took me weeks to write.

If it felt challenging to even write a piece a week, how would I write a piece a day?

And yet, some part of me that I if I could accomplish that, it would break through several limiting patterns.

Inspired by that idea, the path forward became clear.

I needed to intentionally design a series of public experiments for myself to break my default patterning.

Experiments where I followed my impulse to create. Experiments where I allowed for expression without attachment to outcome. Perhaps even experiments where I explicitly disallowed myself to focus on the long-term impact of things.

The public piece was important because it would be the crossover point for breaking instilled patterns.

Those experiments would then become both a personal and spiritual practice in cultivating my creative expression.

My Ship 30 for 30 Journey

For my first experiment, I decided last Monday to embark on my own Ship 30 for 30 journey and committed publicly on Twitter to publish one short-form (250+ word) essay a day for 30 days.

I’m using Twitter as my publishing playground, experimenting with both Twitter threads and long-form tweets.

Eight days in, and I’m feeling surprisingly lighter.

I’ve been able to write for 30-45 minutes per day and then hit publish — without feeling attached to whether people would read it and without needing to edit each piece of writing into the perfect essay.

I’m starting to find my voice back again and letting more creativity flow without needing the output to necessarily be anything.

And I’m gradually discovering the unique perspective I want to bring. Right now, I’m resonating with my journey of understanding the different emotional and relational pieces of the human operating system and how to self-debug them and even rewrite the internal code for them.

If you’d like to follow along, you can follow me on Twitter:

Or check out the thread here:

Some ideas might stick and make it into longer-form pieces of writing — but I also don’t need them to do.

Expect more public experiments to follow.