I read Nick Milton’s Must you fail in order to learn? post on Friday with trepidation.  I have written of the importance of failure a few times (In praise of failureRyan’s rules for projects) and I talk about it all the time.  I often say my philosophy is ‘to fail quickly’ and after reading Milton’s post, I stand by that.

It’s not that I strongly disagree with anything he says, I don’t really.  He’s right about nearly everything. Personal failure is absolutely NOT necessary in order to learn, but he tacitly concedes that knowledge itself always comes from failure; either your’s or someone else’s.  

As Milton says:

Learn from the failures of others, not your own failures.

Now, I could be pedantic and argue that learning from the failure of others constitutes true opinion rather than knowledge. But that’s silly. There is a very good argument to be made that in everyday life, true opinion or belief is just as valuable as personal experiential knowledge.

Milton continues:

Learn, try, succeed (then learn again) is a far better approach than try, fail, learn (then try again).

Again, I generally agree, however this approach presupposes that others have failed before you in a similar task and have published or recorded their failure so that you may learn from it.  One should always begin a new task with research to determine if others have attempted what you are trying.  There is no sense reinventing the wheel if it’s already been done, and there is no sense in recreating other’s failures, unless you are looking to confirm their findings.

Milton closes:

Let’s sever this implied link between learning and failing. Let’s embrace “learning to avoid failure”. Let’s not punish failure if it is the result of informed risk taking, but lets not expect it either.

It’s the second sentence that bothers me most.  Embrace “learning to avoid failure”.  In my experience, most people already do this instinctively. They take the route they believe is least likely to fail and avoid the one with the highest potential reward. This is risk aversion causing sameness, stagnation, and a near total lack of innovation. Or, in other words, the legal industry for a long time now.  If you only build on the failure of others, then you will only go so far as they have already gone.  Worse yet, and more relevant to the legal industry, if you only attempt to replicate the success of others, you will undoubtedly fail. Situations are always unique and success is rarely replicable in different environments.

When I say my philosophy is ‘to fail quickly’ it doesn’t mean I am actively trying to fail so that I can learn something, it means I recognize that any project looking to do more than simply maintain the status quo, will have the odds stacked against it.  People will actively try to kill it, unknown unknowns will rear their ugly heads, and sometimes I’ll just screw it up. If that is going to happen, I would rather that happen as quickly as possible, so that I can learn from what went wrong, try to fix it, and go again. To that end, yes, I will try to stress my projects, push them harder than I should, break them if I can, because if I can’t break them, then the partner in the corner office won’t be able to either.

People who are concerned with avoiding failure, do not think this way.  They sweep inconsistencies under the proverbial rug.  They ignore new information that doesn’t fit their current hypothesis.  They rarely admit when they fail, let alone learn anything from it.

Let’s sever this implied link between failing and incompetence. Let’s embrace the ‘learning opportunities that failing can offer’.  Let’s not expect failure, but let’s not fear it either.

Let’s do our research, plan our path, and go confidently into the unknown to learn new things.


We can “embrace ‘learning to avoid failure'”.

Photo of Ryan McClead Ryan McClead

Ryan is Principal at Sente Advisors, a legal technology consultancy specializing in innovation strategy and cross-platform solutions and support.  He has been an evangelist, advocate, consultant, and creative thinker in Legal Technology for more than 15 years. In 2015, he was named a FastCase 50 recipient, and in 2018, he was elected a Fellow in the College of Law Practice Management. In past lives, he was an Innovation Architect, Knowledge Manager, a Systems Analyst, a Fashion Merchandiser, and Theater Composer, among other things.