The Value of Failure

tl;dr Celebrating success is always a welcome thing. But in a lot of ways, the people we should be celebrating are the ones who failed, and then learned from it. As a matter of fact, there’s a reasonable correlation to be drawn here—that those who are truly successful are the ones who failed first.

This is actually a post that I’ve been holding on to for a while now, having originally been inspired by a Harvard Business Review article that goes into this more deeply. In it, the author states:

One intriguing feature of these enormous success stories is that so many of them are little-known companies in ordinary, sometimes downright boring industries: railroads, health insurance, back-office automation. … But the more important part of the story… is that every one of these star performers faced at least one “near-death experience” during the course of its long-term success. I don’t mean a few quarters of sluggish growth or a one-time product flop, but a radical shift in its market, a major technology disruption, or a disastrous strategic bet that threatened the company’s very existence.

Many, many years ago, when I was contracting for this guy Mike Cohn, he mentioned to a good friend of mine (who was working there with me) that “Ted needs to fail. Twice.” Needless to say, Mike didn’t say it to my face. I wouldn’t have heard it for the advice that it was—I’d have seen it (as many people do, when I tell this story) as a desire to see me brought low or something. In truth, it was anything but that. Mike also was the guy who told me that, “You have so much book knowledge, people forget that you don’t have a lot of experience, and expect a lot more out of you than you’re capable of delivering. It’s like being 6-foot-4-inches at 13; you look like an adult, but you’re not one, yet.”

In other words, Mike was channeling the old adage: “Good decisions come from wisdom. And wisdom comes from bad decisions.”

(And, sure enough, once I had failed, twice, it was then that I started making real progress in my career as a programmer/consultant/architect. Mike had that one absolutely spot-on.)

The HBR author talks about how companies trying to avoid this near-death experience just somehow don’t seem to “get it”:

In an effort to understand the new logic of change and the emerging rules of success, we convened a conference around the theme “How Do You Overthrow a Successful Company?” …. It was a gathering of executives, strategists, and change agents from illustrious big companies who sensed that there were massive shifts on the horizon and who were determined to reckon with those shifts and embrace a new generation of business models, a new era of technology and communications, a new level of customer expectations and sophistication. … In other words, they were leaders who wanted their companies to win big in fast-moving times without a near-death experience. It was a great idea for a conference, yet it amounted to a hill of beans.

He goes on to point out that all of the named companies in attendance, and how they were struggling or had met with nothing but struggles and difficulties—clearly the conference didn’t really help them all that much.

So what is it about failure that is necessary for success?

Failure forces retrospection

First of all, far more than any success, failure forces players to examine what’s going on and why they’re not being successful. We see it all the time in sports: the first-round draft pick gets to the big leagues, and doesn’t really seem to take the whole thing seriously, and (not surprisingly) performs disastrously. They’re accustomed to success, so they don’t bother with the kind of internal reflection and retrospection that is necessary to get better.

This happens with companies, too. When a company is successful, the investigation as to the mechanics of that success are limited, or else captured as part of the company’s CEO tossing off some sound bites. “We are a company of passionate individuals who are committed to our firm’s success” seems to be the phrase du jour. Success has everything to do with the company’s effort, and nothing to do with any sort of external factors that might have affected the results.

When you fail, though, suddenly people want answers, and the usual raft of platitudes don’t hold up anymore.

Failure creates desperation

More importantly, though, when the company’s on the brink, there’s a sense of focus and desperation that says “Well, we’ve got nothing left to lose, so let’s go all-in on this and see what happens.” This isn’t a new idea; Cortez used it in his conquest of the Aztecs. By “burning the boats” (though history actually records that he scuttled the ships, rather than burned them), Cortez created a “We have no road back, we have to go forward, or die” mentality among his men. Their options were thus narrowed down to exactly two: conquest or death. Robert Greene, in his book “The 33 Strategies of War”, calls this “The Death-Ground Stragegy”.

Quite often we feel somewhat lost in our actions. We could do this or that–we have many options, but none of them seem quite necessary. Our freedom is a burden–what do we do today, where do we go? Our daily patterns and routines help us to avoid feeling directionless, but there is always the niggling thought that we could accomplish so much more. We waste so much time. … Over two thousand years ago, the Chinese strategist Sun-tzu came to believe that listening to speeches, no matter how rousing, was too passive an experience to have an enduring effect. Instead Sun-tzu talked of a “death ground”–a place where an army is backed up against some geographical feature like a mountain, a river, or a forest and has no escape route. Without a way to retreat, Sun-tzu argued, an army fights with double or triple the spirit it would have on open terrain, because death is viscerally present. Sun-tzu advocated deliberately stationing soldiers on death ground to give them the desperate edge that makes men fight like the devil. … The world is ruled by necessity: People change their behavior only if they have to. They will feel urgency only if their lives depend on it.

Obviously, we’d prefer not to hold death to peoples’ faces in order to get them to better react at work, but sometimes, when the chips are down, the best thing to do is to simply state, “This is the only path forward, we either march, or we die.”


… what’s the takeaway here?

Actually, it’s pretty simple: Do you really want to succeed? The Death-Ground Strategy says that you should basically put yourself into a position where you either succeed, or die. If you’re contemplating becoming a technical speaker, quit your job and throw “all-in” around speaking at technical conferences and what-not. Either you will speak at the user group, or you will starve.

Yeah, I’m not a huge fan of that. Try it if you like, but that seems like huge downside for very small upside. Maybe for an army trapped in a foreign land whose only hope for survival is to fight its way back home, it works, but for most of the rest of us, who are nowhere close to trapped behind enemy lines, much less staring death in the face…. yeah, not so much.

But there is value in failure, if only because it forces us to engage in that reflective and introspective process that helps us emerge stronger and better over time. Which then suggests to me that practically speaking, the takeaway here is to Put yourself into failure-potential situations. Take those risks. Put your career and credibility on the line. Engage in things that you aren’t sure you can do, and because nobody likes to fail (including you!), you’ll put forth much more effort into the exercise.

“33 Strategies” offers the following:

  • Stake everything on a single throw.
  • Act before you are ready.
  • Enter new waters.
  • Make it “you against the world.”
  • Keep yourself restless and unsatisfied.

So, for example, if you want to be a technical speaker, stand up and volunteer to give a talk at the local user group. Matter of fact, volunteer to do four talks over the span of the next year. (“Four talks?! Are you out of your mind?!? That’s like one every three months!“) Don’t do just the same talk four times—do four completely different, separate talks, which will then force you to figure out how to write good talks in a compressed period of time.

Or, if your desire is to get a startup off the ground, commit to having an MVP ready by the end of the calendar year 2016 without leaving your job yet. Because let’s face it, if you can’t get the MVP done in six months while holding down a regular full-time job, you won’t be able to handle working the 80 hours a week that a startup will demand of you during the early days. And you’ll need that MVP before you can get any kind of angel or seed funding anyway.

And when (not if!) you fall, figure out why, get back up, and keep going.