The Wisdom of Regret

Last week, our family was playing a game called “Couples Quiz,” which is supposed to be for two married couples to see how well they know each other, and how compatible they are. We play it with our daughters, and it’s hilarious because they answer questions about each other as if they were married, and they always beat us – showing that though you can’t always tell, they actually know and love each other, and are more alike than they are different.


One of the questions was, “What is your partner’s greatest regret,” which is not really a very light, party-game kind of question. Jeff and I didn’t guess right on each other’s answer, which is a subject for a whole other blog.


But I woke up at two a.m., which I do often, roiling around in my head over some times in my past that I regret. Author Kate Bowler once wrote on Instagram that after nine at night her mind turns into Nietzsche, so she goes to bed. Imagine how dark my thoughts are at two a.m. I began to think about myself in my twenties and early thirties, and felt not just regret, but humiliation! I thought of how insufferably certain I was of things when talking to my in-laws when my husband and I were first married. I thought about myself as a leader in my early thirties with other young moms – before I had been through Twelve Step Recovery from codependency. And, oh, I thought, how embarrassing it is that I was so out front with hundreds of women when I had so many issues that I wasn’t even aware of yet.


I ended up confessing all these past sins to God from my rumpled sheets around three, and finally fell back to sleep.


I was still feeling spiritually squirmy when I woke up in the morning, and I told Sophia, my seventeen-year-old, at breakfast what had happened in the night.


“Well,” she said, “if you look back and feel embarrassed about how you were acting ten years ago, that just means you’ve grown as a person.”


I didn’t name that girl “wisdom” for nothing.


How true that is! And conversely, if you don’t look back decades and squirm a bit over what you used to do, say, and feel, does it stand to reason that you have not grown as a person? I’m sorry to say that I do know a few people (just a few), who haven’t changed in 30 years and that is not exactly a compliment.


I asked a much older man once – who I admire – what he would have done differently as a parent. His answer was, “Absolutely nothing.” Now, I do admire this guy, but I know his kiddos well, and I think they would probably find it healing if he could tell them one or two things he wished had gone a different way in their household. Though it may not be productive to agonize over our past, there is some wisdom in regret. There is wisdom and spiritual maturity in grieving how our past actions hurt other people -- and maybe even ourselves.


As a Christian, I regularly want to look back and ask, “What could I have done differently?” Not as an exercise is self-flagellation, but for a few concrete reasons.


First, I want the freedom brought to me through confession to God and forgiveness for my sins and mis-steps. Psalm 103 says that God has compassion on those who fear him because he remembers that we are dust. God looks at my early-20s arrogance and says, not just “I forgive you,” but also, “Well, yes, I expected you to act that way. That’s what dusty 22-year-olds are like.” This exercise keeps me humble; I’m still getting lots of things wrong. I hope, in fact, to be in my sixties, look back on my forties, and say, “Well, I’ve come a long way since then.”


Secondly, I want the option to do better in the future, to be matured spiritually, to love more like Jesus loves. In my twenties, I ran with a rather legalistic circle of believers, and they talked a lot about becoming less like ourselves and more like Jesus. Since I was still trying to figure out who I was, I bristled at that! I see know that becoming more like Jesus doesn’t actually mean losing my own personality. As I mature, I become both more like myself and more like Jesus. But it’s the myself that Christ intended, my gifts, desires and perspectives being just a little bit more like the tiny sliver of the image of God that I bear.


And third, I ask myself “what could I have done differently?’ because I want to go back and

repair the damage I’ve done if I can -- by apologizing and making amends. I can live a spiritual life by ignoring how I hurt people.


I recently bought a new bicycle, and for the new bicycle, some artist-drawn stickers. My favorite one pictures a seam ripper that says “No regrets.” Do you see the irony in this? As a seamstress, do I have no regrets when I look at an imperfect project because at least I got something finished? Yes, sometimes. But more often, I have no regrets because I used the seam ripper to go back and fix my mistakes if I can.

In the Twelve Steps, everyone’s least favorite is Step Nine: Made direct amends to people wherever possible, except when to do so would injure them or others. It’s not super fun to go back through your life and admit where you were wrong – and sometimes even make restitution for your wrongs. But the Twelve Step program also lists promises: what you will experience when you “work the steps,” things like serenity, renewed relationships with equal partners, and an ability to know what to do “in situations that used to baffle us.” (from The Big Book of Alcoholics Anonymous) Most Twelve Steppers will tell you that you don’t really experience the promises until after you’ve done your Step Nine.


Step Nine is my seam ripper. And, also, actually, Step Ten: We continued to take personal inventory and when we were wrong, promptly admitted it. We call this keeping a short list. The hope is that by doing this, the two a.m. squirm in ten years will be a little less squirmy, and the damage I do to those I love will be minimized!



After my new sticker, my favorite ironic image with no regrets are those memes of the tattoos that say “no regerts.” I found this on a tattoo removal website. If it weren’t for the grace of Jesus, my past mistakes would be this permanent. I wouldn’t have the strength to look back. I wouldn’t have the strength to admit I was wrong. And I wouldn’t, frankly, have the strength to keep desiring growth. His grace keeps me from being crushed by my issues, my sins, my mistakes, my foolishness. At the start of Holy Week, as we move through the last week off Lent and toward the glory of Easter, may we reflect on the God who say us in all our dustiness, loved us, picked us up, and helped us more forward without regret.



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Above all else guard your heart, for everything you do flows from it. ~Proverbs 4:23