Woulda, Coulda, Shoulda: A Thief Named “Regret”

A few weeks ago I started my day with a feeling of sadness.

It was an early exercise day so I put my bike in the van before sunrise and went to meet a friend.

I have been a little extra contemplative these days.  The main reason right now is we have, what is to us, a major transition coming up.  Our oldest daughter, Brianna, is about to move out of the house to start college and will be living on campus.  Granted, it is only a few miles down the road, but the fact is life will never be the same as it has been for the past 18 and a half years.

Transitions and change have a way of causing us to evaluate some things.  As I was riding, I was thinking about some things I wished I had done differently or better as a father.  I was beginning to feel like Eeyore on a bike and then my best Friend whispered to me, “Do something about it.”  It was like a light bulb turned on.

  “Do something about it.

It was so obvious, yet it completely took me by surprise.  It’s not too late.  I have today!  The possibilities for today are endless.  Anything I wish I did in the past I can still do today (except maybe play basketball really well).

There is a fine line between healthy evaluation and regret.  If we never take inventory of what needs improvement, we will always stay the same.  Regret and evaluation seem similar but are actually much different.  Regret has a paralyzing effect that immobilizes us in the here and now.  Regret never ends with hope and action.  It says, “it’s too late, you are a failure.”  The ironic thing about listening to the voice of regret is we wish we had done something to make yesterday better while stealing our ability to improve today!

Philippians 3:13 But one thing I do: Forgetting what is behind and straining toward what is ahead, 14 I press ontoward the goal to win the prize for which God has called me heavenward in Christ Jesus.

I love Philippians 3 when Paul is reflecting on his history.  There were some things in his past that were horrible and some things that his peers would have praised him for.  His conclusion on the matter was to press forward by the grace of God toward the prize.

Maybe you have been tempted to believe, like me, that it’s too late?

Don’t get stuck in regret.  There is hope for the future and you can do something about it right now.  Do something. Anything!  Send a text message, call that friend.  Apologize for something you needed to take responsibility for.  Set a goal and take one simple step today!  Even better?  Invite some friends to encourage and help you along the way.  Today is not over yet, hope and action are the anecdote for regret!  ** Discussion guide below ….

Next in series: Overcoming Regret pt.1: Good Grief

Related StuffGotta Let Go To Grow;    3 Things I Would Say To My Younger Self – by guest Christina Lewis;  Your Happy Brain, Connection and the Science Behind ItDaily Post

BREAK IT DOWN:   Process it some more with coffee or friends!

  1. Have you ever found yourself contemplative or dealing with regret in a season of change (a loss, a move, a change of job or relationships)?  What was happening in your life that caused you to reflect?
  2. What is one thing you wish you had done differently personally, professionally or relationally?
  3. Take a look at 1 Corinthians 4:Now it is required that those who have been given a trust must prove faithful. I care very little if I am judged by you or by any human court; indeed, I do not even judge myself. My conscience is clear, but that does not make me innocent. It is the Lord who judges me.Therefore judge nothing before the appointed time; wait until the Lord comes.
    • According to verse 2, is there a reason we need to evaluate what we have done or are doing?
    • How should we apply verse 3 in regards to regret and self-evaluation?
    • When is the appropriate time for judgement?
  4. Do you find regret to be a positive motivator or something that causes you to be stuck in negative thoughts and emotions?
  5. What is one simple thing you could do or step you could take to make progress instead of remaining immobilized?
  6. Pray, ask Father God for direction and strength to do something about it!



  1. There will be no regrets if we press on toward the goal for which God has called us heavenward in Christ Jesus! He is always working for our good!


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