On Living With Regret

Lent Day 13

Early on in my Professional Cancer Patient days—back when my life still felt like it was happening to someone else—I was forced to make a series of impossible medical decisions with very little information. These were not the kind of decisions people imagine when they talk about being proactive about your health, but the kind where every option comes with a long list of side effects, no guarantees, and almost no research on what the best course of treatment should be.

Choose this drug and risk one future. Choose that treatment and foreclose on another. But decide now, because waiting is also a decision. It felt like a terrible game of Life. Except that Life was mine.

At some point, someone wiser than me said something that I haven’t forgotten:

Today, you have to decide that you did the best you could with what you knew.

Those words felt like manna, sustenance enough to face the next day, and the next.

Because not only is regret debilitating, the fear of living in regret is too.

If only I had known.
If only I had waited.
If only I had acted sooner.
If only I had trusted my instincts.
If only I had ignored them.

Georges Seurat, A Man Leaning on a Parapet, 1881–82, oil on panel.

Regret tries to convince us that we could have known. In fact, we should have.

But here is what we don’t like to say out loud: every meaningful choice requires us to foreclose on other possible futures. No decision preserves all possible outcomes. Eventually, you must choose, and choosing will always come at a cost.

When I replay those early medical decisions now, what tempts me most is the fantasy that clarity was available and I simply missed it. That the data was there. That wisdom was just out of reach. Regret loves this story. It gives the illusion that the future was readable and I failed to interpret it correctly.

But regret is often a delusion of control.

What that sentence—I did the best I could with what I knew—gave me was permission to tell the truth about time. About information. About limits. It reminded me that hindsight is not a moral achievement. It is just… what comes later.

In the story of Lent, we will see Jesus move toward the cross with an enormous sense of foreboding. Our Jesus walks toward his own death, not with an eerie calm, but so much fear that he sweats blood. Some people try to prevent his suffering, while others will betray him. It’s a story steeped in almosts and should-haves and I-wish-it-wasn’t-so. But I find that, in particular, there is something especially fitting about allowing the darkness of this story to speak to us about our own limitations. We are imperfect and our knowledge is partial. Our bodies are fragile and our choices deeply limited. We were always and forever human, so omniscience is off the table. We must make do with lives that are scarred by regret.

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Not all regret is the same.

Now, that doesn’t mean all regret is a misunderstanding to be therapized away.

Some regret is real. And it needs attention.

An apology left unsaid.
A relationship quietly abandoned.
A boundary incorrectly set.
A truth delayed until damage settled in.

Christian theology has always known this difference, even when modern spirituality prefers not to. Thomas Aquinas argued that confession is not primarily about punishment, but about truth rightly ordered. To confess is to bring disordered love back into alignment—to name where we aimed ourselves poorly, even if our intentions were mixed.

Martin Luther went further. Confession, for him, was not a one-time clearing of the ledger but a daily practice of honesty. The Christian life, he said, is one of continual repentance—not because we are uniquely terrible, but because we are perpetually unfinished. (Because, you know: “If we claim to be without sin, we deceive ourselves and the truth is not in us.” 1 John 1:8–9.) Sigh.

And John Calvin—our favorite Terrifying Reformed Uncle of the Faith—believed confession was the doorway to freedom. Until we stop defending ourselves, he argued, grace remains theoretical. Confession is how we stop editing the story.

Which is to say: Christianity does not imagine wholeness without regret. It does not offer absolution as a shortcut around responsibility. It assumes that naming what we have done—clearly, without excuses—is part of how repair begins.

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Repair is still possible.

Last week, we talked about the things that were done to us.

The unfairness that was never acknowledged.
The harm that lingered without repair.
The moments that still ache because no one ever said, That shouldn’t have happened.

We talked about complaint as a form of faith—about telling the truth before we rush toward forgiveness, meaning, or spiritual improvement. We practiced naming what hurt without immediately managing it. We filed our grievances. Some of us added a few things to The List.

This week, Lent asks us to turn slightly—and carefully—and ask: is anyone rightfully filing paperwork to the Complaints Department about me?!

Because alongside the things that happened to us are the things we have lived with ever since: the choices we made under pressure, with partial information, imperfect motives, and very human limits. The words we didn’t say. The risks we took. The boundaries we failed to hold. The damage we wish we could undo.

If last week was about truth-telling without self-blame, this week is about blame without despair. The things we knew—and chose anyway.

The risks we understood and took.
The relationships we entered.
The boundaries we failed to set.
The truths we delayed telling.

These are not mistakes born of ignorance. They are decisions made under the pressure of love, fear, longing, or hope. Lent does not let us look away from these moments—but it also does not collapse us into them.

Because while we cannot return to the moment of decision and choose again, we can choose now.

Sometimes repair looks like a message sent without knowing how it will land.
A name spoken honestly in prayer.
A sentence that begins with: I was wrong.
Or: I’m sorry.
Or: I still care.
Or even: I forgive you.

And sometimes repair looks like letting ourselves off the hook for doing the best we could with what we knew then.

This is the strange mercy of Lent.

It does not ask us to live in permanent self-accusation.
Nor does it allow us to bypass responsibility.

Instead, it invites us to inhabit the present honestly—to tell the truth about what happened, what failed, what was lost, and what still aches. It asks us to act with the humility that comes from knowing we are finite, and the hope that comes from knowing we are not done yet. And God is not done with us.

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Let’s give each other some advice about how to say sorry. Regardless of how it turned out, what’s the best version you’ve gotten or given of being wrong?

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This week’s reflections:

For ease, refer back to this post for this week’s reflections. The links will go live each morning:

• Thursday, March 5 - Lent Day 14: The Grief Without a Ceremony

• Friday, March 6 - Lent Day 15 : The Futures That Never Arrived

• Saturday, March 7 - Lent Day 16: Let us repair.

• Sundays during Lent are mini-feast days. No Lent Reflection.

• Monday, March 9 - Lent Day 17: Both Things at Once

• Tuesday, March 10 - Lent Day 18: The Randomness We Don’t Like to Admit