How to make choices you won't regret

I’ve often been asked about my years in Afghanistan and the fallout I’ve lived with since. “Knowing what you know now, would you do it again? Would you make the same choices?”
I’ve struggled to answer in a way that makes sense. On the one hand, I have no regrets. I’m glad I chose as I did then. On the other, I’ve grown, and I recognize that not all of the choices I made then fit well with what I’ve since learned of God and of myself.
It’s sometimes hard to hold these two pieces together, to believe that neither the way I chose then nor the way I’m choosing now are of less value than the other. And it’s not always easy to know, looking forward, how to make new choices that will leave me with no regrets regardless of the outcome.
I find help—both in living with past choices and in choosing well in the present—in a surprising spot. Paul has just spent eighteen hundred words arguing in the strongest terms that the Galatians must resist the demand to live under the details of the old law, marked by circumcision. But then he surprises me with this:

“For in Christ Jesus neither circumcision nor uncircumcision has any value. . .”

“Now wait a second, Paul,” I want to say. “You’ve just spent more than four chapters arguing the dangers of letting our lives be ruled by a list of shoulds. But now you’re saying that living free is no better?”
Neither fasting nor feasting has any value.
Neither keeping Sabbath nor not keeping it.
Neither doing the dishes right after dinner, nor choosing to rest and do them later.
Slowly I realize that Paul is removing yet another layer of distraction so he can lead us to the core of choosing well. Quiet, contemplative living is neither holier nor less holy than years of long nights trying to help half-dead patients in a mud hospital because, as we live our life in Christ,

“. . . the only thing that counts is faith expressing itself through love.” (Galatians 5:6)

Does my choice flow out of faith in Jesus? Does it help me trust him more?
And does it express that faith through love—for God, for others, and for myself in a healthy, respectful, stepping-into-God’s-love-for-me way?
Then it is a good choice.
In my twenties and early thirties, driven and anxious to make a difference in the world, and loving God as best I knew how in the midst of that, faith expressed itself in love to God and others by my commitment and determination to keep serving in the midst of craziness and huge cost in Afghanistan.
In these past seven years since God closed the door on that way of loving him, faith is expressing itself through love by learning to live within my limitations and offer back to God and others the gentle, grace-filled space God has been offering me. Now, drivenness and the previously unrecognized self-abuse of constantly ignoring my limitations would be neither faith (trusting God’s love for me) nor love (respecting God and His treasured possessions by caring gently for people who matter to him—myself as well as those around me).
So the question, “Would you do it again?” Not now, but I’m glad I did it then. Then it was the best way I knew to offer God my faith and love. Now He’s asking me to express my trust through love in different ways.
Choosing to live by "faith expressing itself through love" doesn't guarantee a smooth path or a comfortable outcome. It does mean that, whatever the outcome, I can trust that the God who has made me His has received my offering of faith and love with the delight of a mother receiving her toddler's first dandelion bouquet. And God's smile is what leaves me with no regrets.