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Retroactive Omniscience and Having Your Own Back

by Dr. Tonya Caylor
May 23, 2026

Over the past few weeks, we’ve been following “John,” a fictional physician trying to sort through the emotional aftermath of multiple job changes and the growing belief that maybe he was just bad at choosing jobs.

In the first edition, he recognized the story he was telling himself and how it was warping his emotions, behaviors, and decisions.

In the second edition, he stepped back as the compassionate, objective observer and looked for patterns, blind spots, and lessons with more self-awareness and less self-criticism.

This week, John is learning something different: Having his own back.

With a few moments of active reflection, John realized he had slowly started treating every difficult job discovery as evidence that he couldn’t trust himself.

The unexpected sense of chaos and overwhelm in an FQHC with complex patients without any resources, the lack of effective processes and policies in another setting, the patient volume expectations in yet another setting. Each new frustration became additional “proof” in the mental case he was building against himself.

Not: “This is new information.” But: “How did I miss this again?”

Those are two different perspectives that lead to different internal experiences, and influence choices differently.

One creates curiosity, adaptation, and discernment. The other creates shame, paralysis, and self-doubt.

While putting this together, I reflected on an early leadership experience of my own.

Years ago,when we started an indigent care clinic, I placed two people into leadership-type roles based on what I knew about them at the time. One had previous office manager experience before retirement, so that felt like the obvious fit. The other had strong community connections so she seemed to fit the role for our connector to local social services.

Both very reasonable decisions.

As time went on and I got to know both women more fully, it became increasingly clear they were not really a fit for the roles I had placed them in.

The woman in the office manager role was a social butterfly. Patients and staff felt instantly seen and cared for around her. But because she connected so deeply relationally, she sometimes struggled with the operational follow-through and hard conversations the role required.

The other woman was a worker bee. Organized and direct. Comfortable making hard decisions. But that same style didn’t always land as well when vulnerable patients were unloading complicated personal struggles and resource needs.

Over time, it became obvious that each woman naturally carried strengths the other role needed most.

Thankfully, both were open to the switch.

But I still remember the sinking feeling in my stomach: “Oh… I really messed this up.”

At the time, I didn’t yet have language for what I now think of as “retroactive omniscience” (once we know the outcome, we act as though we should have known it all along.)

I see it differently now.

I really had made the best decision I could with the information I had at the time - the work was new, the volunteers were new, and we were opening for service soon. Then I learned more information.

Sometimes physicians (and leaders in general) confuse hindsight with failure.

John started realizing that having his own back didn’t mean refusing to examine his decisions honestly. It didn’t mean pretending every choice had been perfect or every frustration was someone else’s fault.

It meant recognizing that he had, in fact, done meaningful due diligence each time. He had asked questions, reflected, sought advice, considered his family, thought about finances, schedule, mission, and long-term goals.

And then he made the best decision he could with the information he had at the time.

That didn’t mean circumstances couldn’t change or that hidden realities wouldn’t emerge. Or even that his own priorities and needs wouldn’t evolve.

It just meant those future discoveries didn’t have to become evidence that his ability to find a job was broken.

Now, he is building the pattern of remembering to approach it as new information. “Well… this is new. What do I want to do with this information now?”

His unnecessary suffering eased, even while the stress remained, and then he made the next best decision from a better place. Whether he stayed, or left, or made adjustments, doesn’t matter. What’s important to know is increasingly, his decisions came from clarity rather than self-condemnation.

We treat adaptation as proof the original decision was flawed, rather than evidence that we’re paying attention and willing to adjust. The goal was never omniscience. The goal was thoughtful decision-making and the willingness to adjust when needed.

Being able to put your head on the pillow knowing you made the best decision you could with the information you had on hand and that you’ll have your back should you find out new information tomorrow is very grounding.

Reflection:

What changes when you replace “How did I miss this?” with “What do I want to do with this information now?”

What would it look like to trust that your future self can handle new information when it comes?

Responses

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