Failure as a Tool – Life Lessons From Singer/Rapper Dessa

As a fan of every opportunity to better understand failure and the powerful role it can play in our lives a friend recently sent me the recording of Dessa Darling’s (a.k.a. Margret Wander) 2012 commencement address to the College of Liberal Arts at the University of Minnesota.  Dessa earned her degree in Philosophy from the school and is a member of the indie hip hop collective Doomtree, proving that you can actually make money with a Philosophy degree.  An interesting side note on Doomtree is that they truly a collective of seven members who come together to make both music and money with no contract.  If a member chooses to leave the band they are free to leave with no strings attached and they will be replaced with a new member.  Even before forming they seemed to understand that most bands don’t survive when one person leaves and contracts need to be unwound so they created a more fungible organization that will survive and potentially flourish with artists coming and going.  This is a great example of creating a structure or process that supports a more natural state of the world.

To be honest I hadn’t heard of Dessa or Doomtree (several of their videos are available on YouTube and the music is really good) prior to seeing her commencement address but I was pretty impressed with both her delivery and her content.  The speech was not quite as polished as the addresses from J.K. Rowling (Harvard 2008 address: The Fringe Benefits of Failure, and the Importance of Imagination) or Steve Jobs (Stanford 2005 address: You’ve Got to Find What You Love) but Dessa was amazingly authentic and wonderfully perceptive.  I have included three of the what I felt were her most notable insights: embrace failing as a tool, strategies that help support failing, and re-framing your life through a lens of “Charitable Interpretation.”

1) Failing is a tool so start now: In enduring failure you are able to tolerate the prospect of failure, you become bold enough to be appropriately ambitious when selecting your future objectives.  If you pursue only those goals which you know you are really likely to achieve, you live like an iceberg with the vast majority of yourself undiscovered and unknowable even to yourself… Failure is the tool that we use to demarcate the edges of our abilities.

2) Two small strategies to start failing: 1) keep your overhead low – the more money you spend the more time you have to spend earning the money to pay those bills, 2) life’s most precious commodity is time – you will find no one willing to share out his money but by how many does each of us divide up his life.  People are most wasteful of the one thing for which it is right to be stingy – time.

3) Embrace “Charitable Interpretation” as way to re-frame your thinking to move your life (and the world) forward: “I am not trying to get to right, I am not trying to win the life, but to make the argument better, to find the better idea, to have a better resolution, that to relinquish my desperation to be correct and instead to find a solution to the problem whether personal, academic, or vocational.”  Just think how this re-framing could improve our political dialog where today we seem to be locked in a zero-sum “game” where one party wins only by the other party loosing?  Instead could we begin our discussions by interpreting the other side’s arguments in a way that maximizes their truth or rationality to find common group rather than residing on the polar extremes?

The truth is that many of these lessons transcend both our personal lives and our work lives.  I would highly recommend that you take 22 minutes out of your day and enjoy the journey.

YouTube – Dessa 2012 Spring Commencement: Keynote Address


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