Commiting to a Year of Risk-Taking and Failure

Commiting to a Year of Risk-Taking and Failure

I am committed to changing my relationship with failure.  Failure was something I was deathly afraid of for most of my early life.  I think I was 30 years old before I took any serious risks at all and that included leaving a secure job at IBM, moving to Chicago, and getting divorced.  That year of risk-taking was one of the most important and formative years of my entire life.  But before we go further into failure and risk taking, I have a small confession.

I think that I love Seth Godin.  Yes it is true.  I don’t mean that I am in love with Seth Godin, just that I love what he writes and find myself inspired by it.  Every day I find myself excited to find something from his blog in my inbox.

Lately I’ve been struck how often Seth writes about failing.  Maybe I even love him more when he talks about failing.  It may be that I have been thinking about failure more or that my mentor Rich Blue has been talking more about failure, and all of a sudden I am  seeing it everywhere.  In any case, I noticed what seemed like a trend so I went back through Seth’s blog posts to see what he had actually written about failure.  Here is a somewhat random dozen of my favorites snippets from his blogs on failure:

1/17/2008: Is it worthy?
Our birthright is to fail and to fail often, but to fail in search of something bigger than we can imagine. To do anything else is to waste it all.

1/18/2010: Unrealized projects
[writing about director Tim Burton] One key element of a successful artist: ship. Get it out the door. Make things happen…The other: fail. Fail often. Dream big and don’t make it. Not every time, anyway.

2/27/2010: Genius is misunderstood as a bolt of lightning
Genius is actually the eventual public recognition of dozens (or hundreds) of failed attempts at solving a problem. Sometimes we fail in public, often we fail in private, but people who are doing creative work are constantly failing.

7/16/2010: A hierarchy of failure worth following
Not all failures are the same. Here are five kinds, from frequency = good all the way to please-don’t!

FAIL OFTEN: Ideas that challenge the status quo. Proposals. Brainstorms. Concepts that open doors.
FAIL FREQUENTLY: Prototypes. Spreadsheets. Sample ads and copy.
FAIL OCCASIONALLY: Working mockups. Playtesting sessions. Board meetings.
FAIL RARELY: Interactions with small groups of actual users and customers.
FAIL NEVER: Keeping promises to your constituents.

1/17/2011: Cashing the check
The opportunity to step up and to fail (and then to fail again, and to fail again) and to continue failing until we succeed is greater now than it has ever been.

4/14/2011: How to fail
All of us fail. Successful people fail often, and, worth noting, learn more from that failure than everyone else.

5/3/2011: Hard work vs. Long work
Hard work is frightening. We shy away from hard work because inherent in hard work is risk. Hard work is hard because you might fail. You can’t fail at long work, you merely show up. You fail at hard work when you don’t make an emotional connection, or when you don’t solve the problem or when you hesitate.

10/5/2011: Failures and the dip
In the Dip, I’m arguing that big successes happen when people with good taste see the failures, evolve and keep pushing anyway. The good taste comes when you know the difference between failures that are better off forgotten and failures that are merely successes that haven’t grow up yet.

12/18/2011: The difference between a failure and a mistake
A failure is a project that doesn’t work, an initiative that teaches you something at the same time the outcome doesn’t move you directly closer to your goal. A mistake is either a failure repeated, doing something for the second time when you should have known better, or a misguided attempt (because of carelessness, selfishness or hubris) that hindsight reminds you is worth avoiding. We need a lot more failures, I think. Failures that don’t kill us make us bolder, and teach us one more way that won’t work, while opening the door to things that might. School confuses us, so do bosses and families. Go ahead, fail. Try to avoid mistakes, though.

1/9/2012: Out on a limb
That’s where artists do their work. Not in the safe places, but out there, in a place where they might fail, where it might end badly, where connections might be lost, sensibilities might be offended, jokes might not be gotten.

1/29/2012: Prepared to fail
“We’re hoping to succeed; we’re okay with failure. We just don’t want to land in between.”
–David Chang
He’s serious. Lots of people say this, but few are willing to put themselves at risk, which destroys the likelihood of success and dramatically increases the chance of in between.

Which brings me back to my mentor Rich Blue and his recent failure kick.  He keeps encouraging me to live a big life by saying, “if you aren’t failing then you are not taking enough risks”.  (I would also mention that I love Rich Blue but I don’t want you to get the wrong idea about me!)  It was Rich that introduced me to the Mindset book by Carol Dweck.

In this book, Dr. Dweck thoroughly explores our beliefs about our abilities, our growth, and about learning new things.   These beliefs form the ‘mindset’ that we carry about ourselves and others.  There is a fixed mindset that says that people are born with certain traits and abilities and that defines the full extent of their capabilities.  Then there is a growth mindset which believes that people will continue to grow and develop through their own efforts.

Individuals with a fixed mindset tend to avoid failure at all costs.  To fail means to define yourself as a failure.  So as you can imagine, taking risks or trying something new isn’t practiced by those with a fixed mindset.  I think this pretty well describes the first 30 years of my life.

Individuals with a growth mindset tend to value taking risks and being willing to fail.  They see failure as an opportunity to learn about what is not working or to adjust their approach.

The concept of failure is also pretty big in agile development, an area that I have been exploring a lot lately.  In fact, a key saying from agile is “fail fast”.  This is often used to justify pulling the plug on risky projects sooner rather than before a major investment has been sunk.  (Note:  I think we have to be cautious about this application because it could also lead to pulling the plug too early, or not fully throwing yourself into a project or initiative, just because it is risky.)  I think the description from James Shore in the Art of Agile Development is the one that I like the best:

Failing fast applies to all aspects of your work, to examples as small as buying a bag of a new type of coffee bean rather than a crate. It frees you from worrying excessively about whether a decision is good or bad. If you’re not sure, structure your work so that you expose errors as soon as they occur. If it fails, let it fail quickly, rather than lingering in limbo. Either way, invest only as much time and as many resources as you need to be sure of your results.

With these principles guiding your decisions, you’ll fear failure less. If failure doesn’t hurt, then it’s OK to fail. You’ll be free to experiment and take risks. Capitalize on this freedom: if you have an idea, don’t speculate about whether it’s a good idea—try it! Create an experiment that will fail fast, and see what happens.

I just spent the previous 3.5 years doing so-so consulting work for a great client. Unfortunately, I became quite complacent during this time and I took very few risks. I wrote less than previously, spoke less, and read less. I CREATED LESS!  I was not challenging myself, I was not taking risks, and I was not failing fast. When a colleague mentioned to me last year that he was reading one business book a week, I was incredulous. “It can’t be done” I thought as I silently reflected on my own 1-book-every-2-months pace. (Since the beginning of this year, I have put myself to the task and found I could actually complete 2 or even 3 books in a week when I applied myself.)

I am committed to changing my relationship with failure.  2012 is going to be a year of ramping up the risks and the failure rate.  I am going to live like it is 1993 again (sans the painful divorce!).  I am going to fail fast.  I started last month with a new certification and partnering with two different consulting firms.  I am reading, and writing.  (If you are an agile enthusiast, please note that I have launched a new blog specifically about agile and program management at: It might fail, but I am going to learn a lot in the process.)

Stay tuned here for more.  And do please let me know what risks you are taking this year.  I hope they are big ones!


This Post Has 2 Comments

  1. I am inspired by your courage and faith to risk going all out and possibly failing–you are living by what Carol Dweck calls the growth mindset. I am throwing my hat in the ring with you for 2012.

  2. Thank YOU Rich for being such an inspiration to me and so many others. You have impacted a lot of lives!

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