Regret Expressed as Grief Versus Regret Expressed as Feeling Crushed

There is a difference between regret expressed as sadness/grief for what might have been and regret expressed as a crushing weight of hopelessness.
May 15, 2024

In a recent sermon by Pastor Travis, John 15:1-8 was the passage (see sermon and sermon notes here). This was part of the “I Am” series, highlighting a host of statements from the gospel of John in which Jesus compares himself to various metaphors, for the sake of revealing something important and precious about his character and his mission. In John 15:1-8, Jesus calls himself the “vine” (15:5) and he calls his followers the “branches” (15:5). A branch must be connected to the vine in order to survive and produce fruit. The main point of this agricultural metaphor is that connection to Jesus is the only way to live life in a way that ultimately is pleasing to God and in sync with how we’ve been made by him to flourish. 

However, for many who are on the “back nine” of their life span – especially if they have made foolish or unwise choices in the past – recognition of the time that was lost can be a source of bitter heartache. They are thankful to be currently and eternally connected to life and hope, but sadness is not totally displaced. What might have been! What could have been enjoyed (grieving the absence of joy in the past that was missed out on)! The pain that could have been avoided (grieving the presence of heartache that had enduring ripple effects)! These regrets are painful precisely because they are not limited to the past – individuals continue to live with the consequences of their decisions from years before in tangible ways.

A quick word about defining regret. I am defining regret as “wistfully wishing past events had turned out differently.” There’s not a single person who cannot relate to such a definition. Sometimes regret involves serious things like a relationship, financial choices, or an addiction. Other times it’s a bit less sobering, such as wishing in hindsight that a different destination had been chosen for the annual family vacation. On the more serious end of the spectrum (e.g., relationships, career aspirations, personal life-altering decisions), regret can easily turn from understandable sadness to a life-dominating and crippling depression.

Many times, the admonition for such individuals from well-meaning Christians sounds something like, “That’s your past. But now you can be thankful for the present and future. After all, Christ has saved your soul and given you hope going forward.” This is true and right, insofar as it goes. My concern, however, is that Christians often are uncomfortable with grief, and therefore fail to discern “good regret” from “harmful regret.”  It feels awkward. We don’t have a functional category for lament. We know Christians are supposed to be defined characteristically by joy. We remember the jubilant psalms (e.g., Psalms 34 and 100), but we forget the psalms characterized by hard emotions (e.g. Psalms 42, 43, 73, 88). For Easter, we spend a bit of time on Friday (Jesus’s death), focus a lot of attention on Sunday (Jesus’s resurrection), and typically give Saturday (a time of devastating grief for Jesus’s disciples in which their worlds were absolutely rocked) short shrift or no attention in our imaginations. We know Job’s three friends were not very helpful, but that doesn’t stop our impulse of discomfort at some of Job’s own words. 

There is a difference between regret expressed as sadness/grief for what might have been and regret expressed as a crushing weight of hopelessness. We must learn to be comfortable with the former, even as we very much want to resist the latter. We must be patient with regret expressed as grief. Part of living in a fallen world is that sin and its effects make life less than God originally intended it to be. We grieve this. To not grieve would be more strange than grieving. 

When speaking of one’s own past (and the pain associated with it), there does come a place for moving on, but not in a “suck it up and get over it” kind of way. Moving on from crushing regret is rooted in God’s forgiveness and acceptance. What does this mean? It means believing that God really has forgiven any past sinful actions on our part (1 John 1:9–2:1); we need not add anything to the work of Jesus. It also means believing that God has not only forgiven, but he has accepted and loved us. To borrow imagery from the story of the prodigal son (Luke 15:11-32), God has seen us, run towards us, hugged and kissed us, welcomed us with unforced glad-heartedness into his family, and given us all the rights and privileges of being one of his children. Out of these realities comes a trained thankfulness for the way God has made your life matter from this point forward. This is a discipline. 

For the person wrestling with regret that feels crushing:

  • Cling to the objective forgiveness and acceptance God has given you. 
  • Get busy serving other people. Don’t give Satan a foothold by isolating yourself. You will turn inward if you do this, and this kind of introspection will cripple you. 
  • Take your heartaches to Jesus. The pain is real. But Jesus promises to give you rest that goes deeper than the pain of regret (Matt 11:28-30).
  • If your regret fails to give grace and mercy the primary “seat at the table,” then this form of regret is not from God. God is never out to crush you.

For the person who is a friend to one experiencing crushing guilt:

  • First, be patient. Be comfortable being uncomfortable. Sometimes words absolutely need to be said, but your patient presence may be what is needed most. Don’t feel a need to respond to every little thing your friend says that is not “theologically appropriate.”
  • Discern whether this is regret expressed as grief or regret expressed as crushing hopelessness. A “red flag” should go up for the latter, but don’t be alarmed by “clean” grief.
  • Point them to Christ. He is who your friend needs the most. 
  • Try to get your friend outside themselves. In other words, encourage them to love God by serving others or enjoying life-giving activities. There are times for introspection or taking stock of the past, but that is a slippery slope right now for your friend. Introspection can be deadly.