It’s gotten under my skin, this quote. Yes, there are positive ways to mean/understand it, but I think it’s too easily skewed.

Never regret anything because at one point in your life it was exactly what you wanted.

(I don’t even know to whom to attribute the quote, so I extend my apologies for not noting it. Whomever you are, I wish I could hear the way you intended it because I think I beg to differ with you. Respectfully, of course.)

My deepest regrets in life are over the very times I did exactly what I wanted instead of what was wise. At the ripe age of 16 I can remember articulating this very notion. I sat on the floor of my family room and uttered the words to my mother. I cited it as an over-arching tenet by which to live my life: I wouldn’t regret anything I’d done in the name of ‘love’ or ‘youth’ or ‘adventure.’ It was my license to sin. And it stayed in my wallet for seven years, corners dog-eared, folds creased and print worn from my long succession of years pulling it out to trump better judgement.

• I wanted to be physically involved with that boy.
• I wanted to try those drugs.
• I wanted to stay out dancing instead of studying.
• I wanted to sleep in instead of attend class.
• I wanted to eat that bottomless basket of fries. By myself.
  (Please pass the Ranch dressing.)

When I have made decisions that were absent a moral component, then my ‘regret’ is simply a wistful reflection on what might have been. I certainly have my fair share of those. But I think this turn of phrase is too easily erected as a flippant barrier to God’s wisdom.

To look back without regret on choices made without regard for God’s instruction is essentially to stand willing repeat the experience simply because we ‘wanted’ it at that point in time. The Bible calls this foolishness.

Like a dog that returns to his vomit
is a fool who repeats his folly.
— Proverbs 26:11 ESV

We are to acknowledge that our desires are of a carnal nature, contrary to the Spirit (Galatians 5:16-24, Isaiah 55:8, Romans 8:1-8), and to be grieved because our actions grieved God. If we cannot, we’ve cheapened the sacrifice of Christ to be only for the sins we are willing to call sin.

I don’t believe we should be crippled or paralyzed by the sins of our past; they are covered by the blood of Christ and we are new creations (2 Corinthians 5:17). Our regrets must send us running unabashedly into the arms of our Heavenly Father. He will redeem them and use them for His glory, but we’ll never see it unless we repent of the sin. Without regret, there is no repentance.

So, I’m okay with regrets. They tell me my desires are no longer that of a fool and that my heart looks a little more like Christ’s than it once did.

Thanks be to God.

 Not that I have already obtained this or am already perfect, but I press on to make it my own, because Christ Jesus has made me his own.  Brothers, I do not consider that I have made it my own. But one thing I do: forgetting what lies behind and straining forward to what lies ahead,  I press on toward the goal forthe prize of the upward call of God in Christ Jesus. 
— Philippians 3:12-14 ESV