Forgive Yourself For Not Knowing

We evaluate our past decisions under conditions that would be thrown out of any fair court.

The evidence: everything that happened after the decision. The hire didn’t work out. The strategy was wrong. The conversation you avoided festered. In retrospect, the warning signs were clear. The right move is obvious.

But the evidence was generated by the consequences of the decision itself—consequences that, by definition, your past self didn’t have access to when they acted. You hired the wrong person? You know that now because you saw what happened. The version of you that made the hire was working with incomplete information, which is what every hire actually is. You spent a year on the wrong strategy? You know it was wrong because you ran the experiment. The version of you that chose it didn’t have the data yet.

The defendant is your past self. The judge is your current self, armed with all the information the defendant never had. It’s a rigged trial, and we run it on ourselves constantly.

Drag, Not Wisdom

Most people carry a portfolio of these. Past decisions that look obvious in hindsight, generating a persistent guilt that masquerades as conscientiousness.

The problem is that this weight doesn’t function the way we think it does. We imagine it makes us wiser—more careful, more attuned, better at pattern recognition. Sometimes that’s true. But more often, what I observe is something that looks like learning but functions as drag.

Making a bad call on a hire makes you overly cautious in all hiring, not just analogous situations. Trusting the wrong person makes you slower to trust anyone. Making a bold move that didn’t work makes you allergic to boldness itself, even when boldness is exactly what’s called for.

The guilt doesn’t sharpen judgment. It blunts it. It introduces hesitation into decisions that don’t deserve it—not because the current situation warrants doubt, but because a past situation taught you that your own judgment can’t be fully trusted.

That’s not wisdom. That’s an old wound leaking into the present.

What Self-forgiveness Actually Is

Kristin Neff’s research on self-compassion reframes this usefully. Self-compassion isn’t self-indulgence. Neff defines it through three components: self-kindness rather than self-judgment, recognition of common humanity rather than isolation, and mindfulness rather than over-identification with painful thoughts.

The research is consistent and counterintuitive. People with higher self-compassion don’t have lower standards. They tend to have higher personal standards and greater motivation to improve. What they have less of is rumination. They spend less cognitive energy replaying their failures and more energy learning from them and moving forward.

This maps onto something I notice in practice. The people who’ve found a way to forgive their past decisions aren’t the ones with lower standards. They’re the ones with more available capacity. They’re not spending energy relitigating old calls, so they have more to invest in current ones.

Self-forgiveness isn’t softness. It’s the removal of a structural impediment.

Lessons vs. Weight

The practice is distinguishing between the two.

The lessons—what to watch for next time, what patterns to recognize earlier, what instincts to trust—those stay. Those are the return on the painful experience. They earned their place.

The weight—the guilt, the replaying, the “I should have known”—that’s what can be set down. Not because it doesn’t matter, but because it has stopped producing anything useful. It’s taking up space you need for the decisions in front of you.

Forgive yourself for not knowing what only time could teach you. Embedded in every regret is the belief that you should have known better. Sometimes that’s true—sometimes you ignored clear evidence, and honest accountability for those moments matters. But more often, the knowledge that would have changed the decision simply wasn’t available yet. You hadn’t lived through the experience that would generate it. You were an earlier version of yourself, operating with an earlier version of your understanding.

Expecting that person to have made a better call is expecting them to have been someone they weren’t yet.