Image Credit: StartupVitamins

Failing Fast, and the baggage therein.

james helms
6 min readFeb 15, 2019


I did not get up today to fail. I am not raising my son to fail. I do not want my marriage to fail. I would prefer my kidneys not to fail.

Failure is bad. Synonyms include: lack of success, nonsuccess, non-fulfillment, abortion, miscarriage, defeat, frustration, collapse, foundering, misfiring, coming to nothing, falling through. It is incredibly hard to find the silver lining in failure. It feels very final. It feels very desperate.

Failing was the worst thing you could do for 16 to 20 years of education. Failing was considered the opposite of learning in primary school. There is tremendous shame associated with failing, being wrong, acting wrecklessly or disappointing yourself and others with your inability to succeed. We all know this. We are all clear. So when we ask our teams to fail fast — we should understand perfectly the baggage they are associating with the term.

Not all failure is learning

A LOT of failure is simply that. With the wrong mindset — without the proper tools — failure is depressing, morale-dampening, momentum-killing and career-stifling.

Some people rise from the ashes, dust themselves off, note where they probably went wrong, chalk it up to experience and get back on the bike. Others collapse in a heap, drink themselves into a hole or lash out with blame and anger. Failure is emotional and unpredictable like that.

There are things like bias and attribution errors that can cloud the waters. Did I fail? Or did someone or something else? Am I victim of circumstance? Did events conspire against me?

It’s important, and difficult, to separate the failure of an experiment or project from the person. One who fails is not a failure. One who fails continuously, but learns and educates and adjusts and keeps going is not a failure. One who fails and fails to learn, and eventually just gives up… may become a failure. But the product and the person or team should be judged independently.

Most failure is an opportunity–if you believe in that kind of thing

Developing and maintaining belief is a critical component to transforming abject failure to a learning opportunity. Belief that you are inherently a good person, that your heart is in the right place, that you are intelligent enough to learn from your mistakes and have been put in this place and time to feel this moment because it will spur you on to do something with this new knowledge. Sometimes that realization takes a while. Sometimes it takes years to exit the ditch. Sometimes a few failures pile up at the same time and that belief is shaken. When it does, failure might turn one into a victim.

I don’t consider myself a risk-taker — I just like to try stuff

Some people might look at my behavior, as a designer and as a father and as an artist, and chalk what I do up to scientific method: Curiosity, hypothesis, experiment, analyze and reflect, Repeat. But I’ve only recently, in the last 5–10 years, started to connect the behaviors of “just trying stuff” with formal experimentation, risk-taking, and “failing fast.”

Boldly trying stuff has served me well since I graduated from college. In 1997, I talked my girlfriend into packing all of our stuff into a U-Haul and we drove from Philadelphia to Dallas without a job offer. Without even a lead. It was a risk — and that risk paid off (Thank You, God, Tom Hansen, Tim Murphy and Jim Wegerbauer). It could have gone horribly wrong in any number of ways. I didn’t think much about the danger of a cross-country drive or the fact that this girlfriend of mine might grow to hate Texas (or me) or that 4 years of advertising design classes might not have prepared me land, much less do the job I was hoping to get. I maintained a bias toward action: I made calls. I interviewed. I did research. I made more calls. A combination of persistence and luck (and perhaps a little pity) tipped in my favor and I got a job.

And I just kept doing all that stuff, every day: trying things, learning what worked, discarding what didn’t. I failed all the time, but it always felt like trying stuff. No one was going to die if my little experiments didn’t yield tremendous gains. I’d just try something else.

Gradually that behavior formalized as a learning mindset. An experimentation framework. It went from just being brave to being intentionally bold.

Coaching teams to fail is confusing

You don’t actually want teams to fail. You want them to learn as much as possible, as fast as possible. You want them to share “good enough” sooner instead of holding ideas back until they are perfect — and perfectly wrong. You want them to think boldly and dangerously but work fast and simple, down and dirty. You want them to go find out they are wrong, and learn what is right. You want them to make things continuously, understanding that some of those things will be bad but others will yield unexpected results. And celebrate the surprises and discoveries — not just validations.

You tend to learn less from successes

Validation is a tricky thing. We tend not to question our successes. “Of course it went well. I’m right.” I’m smart. I’m good. I’m worth my salary. I work hard. I am thoughtful. It’s too easy to connect the dots of qualified success. It’s much harder to pick apart the nuances of where things went right. In fact, you can end up creating big, elaborate systems to replicate being right, versus breaking a problem down into small chunks to inspect where it went wrong. Quite honestly, sometimes success is less interesting than failure. Failure draws our attention and curiosity. It makes for better stories. Great success stories tend to be defined by the failures that preceded them.

Failing fast may be necessary, but it never feels good

It’s very hard to convince a team that failing fast is a good thing.
“Of course it failed. We rushed into it. We shipped it before it was ready.” Rationalizing failure is a defense mechanism. Because I’m smart. I’m good. I’m worth my salary. I work hard. I am thoughtful.

Coach and encourage the quality of learning per second

Create space for teams to share what they are learning daily or weekly — not just during monthly check-ins. If your teams only get an audience with you once every two weeks or once a month, there’s weird pressure on them to have “succeeded” once versus “failing and learning” 20 times. Or 100.

Make to think, it makes failing feel less disappointing

There’s a lot of weight put on thinking things through. And reflection and consideration is a deep and important part of the creation process. But tangible, concrete ideas (things) tends to engage more regions of the brain then abstract ideas:

Relative to concrete words, abstract words activated left inferior frontal regions previously linked with phonological and verbal working memory processes. The results show overlapping but partly distinct neural systems for processing concrete and abstract concepts, with greater involvement of bilateral association areas during concrete word processing, and processing of abstract concepts almost exclusively by the left hemisphere. J Cogn Neurosci. 2005 Jun;17(6):905–17.

I’m not a neuroscientist, but “greater involvement of bilateral association areas” seems to mean “both the left and right hemispheres of your brain” — where the complex stuff happens. Like learning and understanding and building neuroplasticity by making new connections. Which make sense: tangible prototypes have more sensory “data” to consume to give an idea shape and intention.

Plus, prototypes feel “productive” — part of a learning process — which softens the blow of failure. “Yeah, but look at all the different things we MADE!” I coach teams to make their first things as quickly as possible. Drawings that provoke a discussion, and spur action.

So if you want teams to Fail Fast, might I suggest:

  1. Coach teams to use quick, simple prototypes to test their assumptions. The sooner the better. Being wrong fast is always better than being wrong slow.
  2. Separate the team from the outcomes. Good teams don’t fail. Good teams learn and keep moving.
  3. Be clear that learning is a key element of success, and a desirable business outcome in its own right. Energize teams with the prospect of experimentation, versus pressuring them to immediately deliver business value at scale.
  4. Be clear that “being right” doesn’t absolve you from deeply and cautiously understanding why
  5. Make space for teams to share how they feel about the work. Understand the psychic toll of being wrong (even if you’re learning) repeatedly. We weren’t wired for that, and it’s a magicians trick to find the silver lining in consecutive adverse outcomes.



james helms

Design Leader, Advisor, Speaker, Student, Advocate, Enabler.