Why Try?

The ‘Pain’ of Failure

Keith York
4 min readApr 15, 2021

Several years ago, I was talking with a recent hire at the bloviated Fortune 50 company at which I was then working. The company was stalled amidst an endless barrage of changes, (changes that would result in the end of both of our jobs within weeks of this event) and she was very bright, and as a result I was having a hard time keeping her engaged. So, at one point, I suggested she download a bunch of data from one of our systems and begin to familiarize herself with it. Being the smart person she is, and having been there long enough to have heard complaints about that particular system, she asked “Is the data any good?” I answered without hesitation and, if I know me, a bit smugly, “No”, with an air that should have been followed with “what’s that got to do with anything?” but wasn’t. (Missed opportunity). She laughed and asked “What’s the point in looking at it then?”

At that moment I had an epiphany that I suspect is responsible for my new direction in life. (It was either the epiphany or ‘Fast and Furious, Tokyo Drift’). I turned to her and asked, “How will we know what ‘good data’ looks like if we don’t know what ‘bad data’ looks like? (I find it hard to believe that I was laid off shortly after that.) The more general form of that question is — How do we know what ‘right’ is if we don’t know what ‘not right’ is? Fast forward 5 years and I’m increasingly appreciative of how relevant that question is; Not just in business, but in life. And I’m increasingly aware of the role it has played in shaping my life, and those of many of the people I’ve met down here.

It’s a well-known joke among the sailors I’ve met in the last couple weeks that owning a boat is 20% boating and 80% fixing things. The above sentiment, then, usually comes in a form similar to “Well, if you hadn’t broken it then you wouldn’t know as much as you do now about how to fix it”. A similar comment is, “if you hadn’t made that HUGE and possibly disastrous mistake today, you wouldn’t know what you need to do differently next time. Now try again”. Nobody ever says “I can’t believe you did that” or “Damn, do you know how stupid you looked just now?” because they’ve all done something similar, or worse. In fact, every night at 5PMish people start gathering in the cockpits or salons of their neighbors’ boats and the conversation on every one is either what they broke, what they fixed, or how they survived a dicey situation. (Still eager to find an editor willing to correctly punctuate my sentences.)

What I realize is, at a much larger scale, every person I’ve met here has taken a chance and leapt into the unknown to learn if it’s right for them or not. Some are still in the orientation phase (like me) and others have been doing it for years. Of course, there are still others, who I won’t meet, who gave it a shot and didn’t stick with it. They’re the owners of the many boats we see at the Marina, and in dry dock, that are for sale or were simply abandoned. And, besides the fact that some let their boats just rot, nobody faults them. They tried, they learned, they moved on. It’s not a failure — but a lesson. Either way, each of them changed in the process and now knows what it’s like to take big risks. They won’t judge anyone who risks and fails because they, too, have made the effort.

We’ve heard it said in many different ways. “Fail Forward”. “What doesn’t kill you makes you stronger”. “If you fall off the horse, get back on”. The point is — if you don’t take risks, you’ll never know. If you do, and fail, don’t stop trying. Only the people who’ve never tried will judge you negatively.

So, yeah. We got laid off from that company 5 years ago. But that recent hire I mentioned earlier, and I, know what’s wrong with the data she looked at. I’m guessing that the people who are still at the bloviated company still haven’t figured it out because it’s a waste of time looking at data you know is wrong. Right?

Keith

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Keith York

If I’m honest with myself, I write about being human as a way to validate for myself that I meet the qualifications.