Successful Failure: Reflections from the Chessboard

I face crippling failure every day. And by that, I mean I lose at chess daily. But as I’ve been checkmated daily and gone through the grieving cycle of anger, disbelief (he cheated!), sadness, and resignation, I’ve wrestled with the question of what it means to fail well. And whether it’s chess, misunderstanding an assignment, letting a ground ball roll through your legs (which has happened way too many times to me on the baseball diamond), or screwing up at work, we all face failure daily. There’s no escaping it! The solution cannot be to simply try harder. That just invites more self-criticism. Rather, we must learn to fail successfully.

From my many, many failures at chess, I want to share three thoughts on how to fail successfully.

Failure and Expectations

Sometimes, I would look back on my chess games and wonder, “How in the world could I miss that move?” Or, “How could I possibly have thought that was a good idea.” As I dejectedly tried to learn from my mistakes, I realized that failing successfully requires you to take a closer look at your expectations.

I think it is helpful to make a distinction between objective and subjective failure. Objectively, failure is when you fail to meet an expectation. Subjectively, failure is when you fail to meet your expectations. And it turns out that our subjective standards are often silly and unrealistic. My standard of not missing any of the right moves in chess really is the unrealistic standard of playing like a chess grandmaster.

While having high expectations helps to drive you onward, too high of expectations can be unhelpful. It is in fact possible to set unreasonably high subjective standards that are far beyond objective standards. And, might I suggest that these unreasonably high subjective standards might not be motivated by desires for excellent service for the Lord (who gives us an easy burden and light yoke). Could they spring from the pride in thinking that “we can handle it,” the idolatrous desire of worship, or validation from others covered up with a thin veneer of “it’s for the Lord”? The other implication is that often what you perceive as failure is really not a failure at all. If you impose your subjective standards on reality, you might think you failed when you really succeeded. With this skewed view of reality, no wonder we can be so quickly discouraged. How do you think we could press on when we see success from the Lord as a miserable failure? And how can we keep moving forward when it seems that all we do is fail?

Failure and Sin

I never thought I was an angry person before chess. Fiercely competitive? Definitely. But most assuredly not angry. But after a couple of loud exclamations of “aarrrgghh!!!” after throwing the game away or some harsh self-talk of “I can’t believe you made that terrible move! How could you think that,” I realized how much anger was in my heart. Failing successfully means that you pay attention to the sinful tendencies that are revealed.

Failure often weighs down on us, cracking our shiny exteriors and exposing our ugly side. Failure helps to reveal what is in your heart and gives you the opportunity to grapple with your negative emotions. Successful failure, then, involves taking responsibility for your sin instead of blaming the circumstances or other people.

Failure hurts the most when it is accompanied by sin. The pride of high expectations and the idolatrous desire of worship from others (or “people pleasing” as we like to call it to soothe our consciences) makes failure ever so painful. Perhaps the pain of failure can help pinpoint where our idols in our lives are. For me, I’ve realized that I feel stupid when I lose at chess. A defeat at chess tells me my opponent thoroughly defeated me while I made mistake after mistake. The sting of intellectual failure helps to pinpoint where my idolatrous idols lie. And maybe you can resonate with something similar: the crushing pain of disappointing someone that you care about or the agony of embarrassing yourself in front of others.

Failure and Humility

There’s almost nothing more humbling than walking away from the chessboard after being intellectually dominated by your opponent. Losing again and again at chess almost made me step away from the game. Then I realized that successful failure requires that you be humbled by your failure.

Failure is an object lesson in humility. Failure forces you to come face to face with your own finitude. Failing well means reminding yourself you are just human. And, since our high expectations are often rooted in pridefully thinking “we can do it,” failure will force us to re-evaluate our sinfully high expectations.

Humility should actually have us expect and allow for failure. If failure is inevitable, then to not expect failure is to (quite literally) make a plan to fail both because your plan is so bloated with pride that it doesn’t allow room for failure. Humility means I should expect to lose at chess and not always make the best moves. Sometimes, you just get outsmarted and outplayed.

Of course, having this humility doesn’t always insulate from the sting of failure. And adjusting your expectations and growing spiritually from your failures don’t always take the edge off failure. At the end of the day, you must analyze your game even when it hurts to see your mistakes. You must go back and watch your sermon to see where you could have communicated better. You must retry tomorrow after today was a flop. But I think that thinking through these three things when you fail will you help grow in the grace and the knowledge of God. And as we grow and strive to live out our salvation, may we remember the grace Christ extends on the cross and eagerly await the day when he transforms our bodies in glory.

Photo by Louis Hansel on Unsplash