Finding the Courage to Fail

I am afraid of many things – tarantulas, large groups of extroverts, in-sink garbage disposals – but one of my very worst fears is regret.

As long as I can remember, I have taken cautionary tales seriously. Even as a child, whenever a pastor, friend, or relative began a statement with “I wish I had…” or “I wish I hadn’t…”, my ears perked up. I took every nugget of rueful wisdom and turned it into a new rule for myself. 

  • I wish I’d said ‘I love you’ more. Ok, fine, I’ll say I love you at the end of every visit or phone call. Check!

  • I wish I hadn’t worried so much during my 20s. Umm, ok, harder, but I guess I’ll practice gratitude, and do more deep breathing. Check!

  • I wish I’d taken better care of my neck skin. Get at me, moisturizer with SPF 15+. Check!

I thought that if I gathered enough information on other people’s regrets, I could avoid their mistakes and live the best possible life.

And there it is: that tiny, terrifying word. Best.

I didn’t aim for a good life. I aimed for the perfect life, the right life. The life that earned a “well-done-good-and-faithful-servant” post-funeral (the heavenly version of a gold star on a math quiz).

Evangelical Christianity taught me to be a perfectionist. So much of church teaching was concerned with the right and wrong way to do things – dress, speak, work, and relate to other people, for example. Good behavior didn’t come in degrees: it was either righteous or sinful (and, given humans’ purportedly wicked hearts, usually the latter).

To an evangelical, regret is usually a sign of sin – that is, failure to live that best life. Failure to live up to God’s standards. Sure, evangelicals might talk about grace, but what they mean by that is usually a nebulous concept that certainly doesn’t offer a pass on devastating divine “consequences” for our failures.

It’s no secret that the evangelical Church considers some sins as worse than others, and that sexual sin was the worst of them all. This meant that one of the things I was most afraid to fail at was romantic relationships.

A few months ago, I was puzzling over my passivity in dating relationships. Even though I identified as a feminist and had a strong sense of what I wanted, I was always the last person to make conversation, the slowest to flirt, the first to cede control and make myself small. I never took risks or initiative in dating, and even went several years turning down second dates, always wondering if a more ideal option were just around the corner.

Slowly, I began to wonder if my play-it-safe behavior had something to do with my fear of failure and regret.

Then a new question bubbled up: What does it even mean to fail at a relationship?

In the secular world, it’s common to label breakups and divorces as “failed relationships.” But Evangelical teaching expanded on that definition, making relationship failure both more likely and more of a disaster. According to the Church,

  1. If a relationship doesn’t end in marriage, it’s a failure.

  2. If a marriage doesn’t last till death, it’s a failure.

  3. If either #1 or #2 occur, those failures reflect poorly on your spiritual wellbeing, and may even be sin.

I’ve already written about how the church’s goal for dating was marriage, and how that pressure made romance impossible for many of us. The goal of marriage was even weightier: according to the Bible, marriage is meant to be a symbolic picture of Christ and the Church. You and your partner were supposed to grow into Christ-likeness and “do Kingdom work” together – preferably while having as many babies as possible. To fail at this high calling was to bring dishonor on not only yourself, but also Christ. (Plus, re-marriage was forbidden in some denominations, so if you screwed up your one shot, you were condemned to a sexless, lonely life ever after. Talk about high stakes.)

Faced with these prospects, I grew risk-averse. Like a track athlete about to run the 100-yard dash, a perfect start could be the difference between success and failure. For me, that knowledge meant simply never starting at all: always waiting, always wondering if a more perfect setup was just around the corner.

I began to come to grips with my fear of failure when I encountered the book Mindset by Dr. Carol Dweck. Dr. Dweck posits that there are two perspectives people can hold about skill and success.

The Fixed Mindset assumes that talents and abilities are inborn. Whether or not we are successful or unsuccessful at anything is for the most part a result of the propensities written into our DNA.

The Growth Mindset, by contrast, assumes that humans have incredible power to develop skill over time. Practice will make, if not perfect, at least good enough.

From the Fixed Mindset perspective, failure is terrifying because it is final: it indicates you are inherently “not good at” something. The End. The Fixed Mindset and evangelical Christianity draw the same conclusion in this case: If my relationship fails, that indicates something about my identity. Something is very, very wrong with me. I am broken, and may even be unfixable.

In the Growth Mindset, however, failure is understood as not only an inevitable part of life, but also an opportunity. Each failure offers valuable information about ourselves as well as information about the skill we are trying to cultivate.

Jalaja Bonheim takes this view in her book, The Hunger for Ecstasy.

The sooner we discard the oppressive assumption that an ended marriage is a failed marriage, the better. If we approach relationships as opportunities for growth, it would serve us better to view the end of a marriage not as a failure, but as a milestone signaling that two people have reached the limits of their ability to serve as teachers for each other. it is time for them to bless the path they have traveled together and enter the paths they will henceforth travel separately.

What if, Bonheim wonders, we shifted our perspective so we could view the end of a relationship as not a failure, but a completion? What if we realized that we come into each other’s lives to teach each other something, and a parting is only a sign that we have learned what we can and are ready to move on?

Vision shifts like these have revolutionized the way I date. I’ve realized that I have to give up trying to be good at love before I’ve been bad at it. I have to be willing to try and perhaps “fail.” The goal is no longer to force something to be perfect or to last longer than it should; the goal is simply to learn.

Most of the times I’ve actually tried in relationship, I have, by evangelical standards, failed. Every single one has ended in ghosting, cheating, lost interest, or mismatched expectations. In my experience, trying is strongly correlated with disappointment, hurt, and humiliation.

But as my therapist likes to say, we humans are big enough to hold more than one emotion. I can refuse to excuse shitty behavior – my own and others – and still be grateful for what I gained through difficult relationships. When I walked away from those experiences, I carried with me moments of joy that I get to keep now, knowledge about myself I wouldn’t otherwise have. I’m proud that I refused to settle for what couldn’t serve me anymore, but I’d fight anyone who tried to take these complex, multifaceted pieces of my past away.

Cheryl Strayed expresses what I mean beautifully in Wild, when she muses about her own mistakes:

What if I was sorry, but if I could go back in time I wouldn't do anything differently than I had done? … What if yes was the right answer instead of no? What if what made me do all those things everyone thought I shouldn't have done was what also had got me here? What if I was never redeemed? What if I already was?

When the goal is no longer perfection, but rather a step-by-step journey towards a larger, freer, more whole life, you come to see: you really can’t lose. And when you look back at the life you’ve lived, you might even see and accept it as it is. No regrets.