A conversation I had with a high school senior last school year is sticking with me, rattling around in my heart. Really it isn’t even the whole conversation itself. What lingers was really just a passing footnote to her larger point, but after it was said, it was all I could think about. She said in the midst of her thought:
…I know you’re not suppose to have any regrets in life…
I think this is popular culture worldview that sounds like it should be Biblical but isn’t necessarily so. Often times our “life without regrets” is rooted in “Hall of Fame” verses such as Romans 8:28 which says, “And we know that in all things God works for the good of those who love him, who have been called according to his purpose.” We read this and say, “Well, if I could do it all over again…I wouldn’t change anything because I can see now how God used it to make me the person I am today.”
To that person I would say this: I am thankful for the ways that God has used the good and the bad in my life to shape me into the person I am today…but there is plenty that I wouldn’t do again if I had the chance. I have plenty of regrets.
The way I treated my brother in middle school, the way I treated my parents in high school and the ways I viewed girls, sex, and dating in college. The friends I gave up on. The faith I lost hope in. The ambition I failed to cultivate. The people, politics, and issues I never cared for. The time I allowed to pass by. There are so many things that I look back on and regret either doing or not doing. And guess what, I feel these regrets are worth remembering and talking about.
I don’t believe that Jesus takes away my regrets. I don’t think Jesus wants us to forget the things that we’ve done or didn’t do that caused us to miss the fullness of life He intended for us. Here’s what I do believe Jesus does with and to my regrets. He removes the chains and crippling effects of shame, embarrassment, and worthlessness that come hand-in-hand with the brokenness of our past.
To say I have no regrets is basically the same as me bringing my own Get Out Of Jail Free card to authentic Christian community. It gives me a pass from being honest, vulnerable, and broken before you. The truth is, in my marriage, I still have to work and make sacrifices because of poor choices I made before I vowed my heart, life, and eyes to Christina. I wish I had more freedom from the detrimental relational habits and tendencies that I established before I met my wife. But because of the death and resurrected life I share with Jesus’ I am free from the shame of these habits. Together with my wife we can talk about the realties of my past brokenness in a way that pushes us toward Jesus as opposed to avoiding the topics for fear of shackling me to my past.
I have plenty of regrets in my life. What makes my regrets different is that in Jesus, they’ve become pillars of wisdom and discernment for my future, not chains of shame that keep me bound or ignorant of my past.
Uncomfortable Middle 
Well said. Thanks for sharing.
Thanks – It’s a topic that hits close to home…
”But I think if you ask anybody that’s honest about it, there has to be a number of choices they’ve made in their life that they wished they’d made the other choice. They wished they had bought the house or didn’t buy the house or didn’t marry the girl or did. So I have plenty of regrets. And I never trust people who say, ‘I have no regrets. If I lived my life again, I’d do it exactly the same way.’ I wouldn’t.”
http://www.miamiherald.com/2013/08/04/3539035/play-it-again-woody-blue-jasmine.html
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Five years after graduating college, for me, a big one right now is “career choice” / “college major”.
I wish that I would have had a specific understanding of what jobs were in demand, instead of the 20-year-old belief of “I’m smart, employers will want to hire me.” …… Career-wise, a lot of friends have had easier career journeys than me so far because they had the “certifiable skills” that are in high-demand, like a CPA (accounting certification) that is very helpful in getting established in the business world for the first few years.
Having said that, graduating during the worst recession in 70 years didn’t help the cause either.