Seeing Sideways - “I Knew It” – The Lie Your Brain Loves to Tell (The Hindsight Bias)

“Resilience isn’t built on perfect foresight. It’s built on honest hindsight.”

In this episode of Seeing Sideways, I explore the Hindsight Bias—how the brain tricks us into thinking we “knew it all along.” I share tools to help you separate real insight from illusion, so you can reflect more clearly, lead more fairly, and build true resilience.

Have you ever looked back at a decision and thought, “I should’ve seen it coming”—but did you really?

Key Takeaways and Tools

• What Hindsight Bias Is—and Why It Feels So Convincing
  After something happens—especially something negative—my brain tries to convince me that I saw it coming. But that’s not insight. It’s a trick of memory.
  [01:01]
• Why the Brain Does This
  From an evolutionary point of view, rewriting the past helped us feel more in control. But in modern life, it often keeps us stuck or overly critical.
  [02:52]
• Reconstruct the Moment, Not the Myth
  I’ve learned to challenge hindsight bias by revisiting notes, emails, or journals to remember what I actually knew at the time—not what I think I knew.
  [04:46]
• Separate Outcome from Judgment
  A good decision can still lead to a bad result. That doesn’t mean I made the wrong call. I focus on whether I was thoughtful with what I had, not whether I turned out “right.”
  [06:00]
• Catching the “I Knew It” Reflex
  That inner voice saying “I saw this coming”—I now pause and ask, “Did I really know this before, or am I rewriting the story now?”
  [06:55]

Resources & Practices I Shared:

• Revisit the Record: Go back to notes, messages, or conversations to remember what you actually knew at the time.
• Use Reflection Prompts: I asked, “What did I know? What was unclear? What did I do well, even if the result didn’t land?”
• Shift from Outcome to Process: Judging decisions by results alone distorts learning. I now reflect on my thinking, not just the ending.
• Normalize Uncertainty: I remind myself and my team that “not knowing” is part of the deal. Most meaningful choices live in the gray.
• Pause Before “I Knew It”: That little pause helps me stay honest—and grounded.

7. A Thought Exercise I Left You With:

Think of a moment that didn’t end well—where you’ve told yourself, “I should have seen it coming.”
Now ask:

• What did I truly know at the time?
• What was unclear or incomplete?
• What assumptions did I make?
• What did I actually do well, even if the outcome disappointed me?

Next week, I’ll explore how the brain’s love of pattern-seeking and apophenia can lead us to see meaning where none exists—when connecting the dots becomes creating illusions.

If this episode gave you something to reflect on, share it with someone who might need it. These biases aren’t flaws—they’re part of how we make sense of the world. But the more aware we are, the more clearly we can think, choose, and lead. Because after all, it’s all an inside job.

Chapters

• 0:10 Introduction to Cognitive Biases
• 1:01 Exploring Hindsight Bias
• 8:19 Reflecting on Lessons Learned

Transcript

0:07

Ever catch yourself focusing on what's wrong instead of what's possible? Or judging someone too quickly only to realize you were off? That's not a flaw. It's your brain doing what it was wired to do, taking shortcuts. In this special series, we're walking through my book, Seeing Sideways, One Chapter at a Time. Each episode explores a powerful cognitive bias that quietly shapes how we think, choose, and connect. These mental shortcuts helped our ancestors to survive. But today, they can cloud judgment, limit perspective, and chip away at well-being. So this isn't about fixing your brain. It's about understanding it so you can lead yourself with clarity, respond with intention, and build resilience from the inside out. Well, welcome back to Seeing Sideways, a short series on It's an Inside Job podcast. Now, last week we explored the negativity bias and how it affects perception. This week we're going to explore the hindsight bias, how we trick ourselves into thinking we knew it all along. The hindsight bias is the brain's habit of rewriting the past to make it feel more predictable. After something happens, especially something negative or surprising, we tend to believe we knew it all along. Our memory reshapes itself to match the outcome, giving us the illusion of foresight when what we actually had was hindsight. Now, it's comforting to feel like the signs were always there, But this illusion distorts our memory, our confidence, and our decision-making. Our judgments were sharper than they were, our predictions more accurate, and our awareness, well, more complete. It feels like clarity, but what it really is, it's a trick of reconstruction. You watch a project fail and say, I knew this would happen. Or a relationship ends and you retroactively identify all the red flags. After a market crash, it suddenly seemed obvious that the signs were there. But if you check your notes or your honest memory, you'll realize you didn't know. You had doubts maybe, but they didn't feel like certainty at the time. Hindsight bias makes us overconfident. It leads us to judge others harshly. They should have seen it coming, and ourselves unfairly. How did I not know? It erases ambiguity and complexity that were real at the moment and replaces them with neat, tidy narratives that often ignore how uncertain we actually felt. The Twist. From an evolutionary perspective, hindsight bias helps us learn from the past. If we could reconstruct events into cause and effect stories, well, we'd feel more in control and better prepared for the next time, telling ourselves, I knew it. Well, it helps us feel competent and safe in an unpredictable world. But today, this mental habit, this cognitive bias, well, it oversimplifies the truth. The world in actuality is messy. decisions are uncertain and we rarely have a complete real-time information. Hindsight bias hides the truth behind a curtain of false clarity, which can stop us from learning, empathizing, or improving. The cost. When you fall for hindsight bias, you distort your learning. You think you've made a bad call because you should have known better, even if the information wasn't available then. This can lead to rumination, regret, and self-doubt. It can also make you intolerant of uncertainty or overly critical of others' decisions. The hindsight bias can damage trust, either through leadership or through collaboration. They can make you dismiss team members' honest efforts or frame others' mistakes as incompetence instead of complexity. They create the illusion that success is linear and failure is obvious when in reality most meaningful choices live in the gray zone. The contrarian move. Hindsight bias isn't just a memory glitch. It's a confidence trap. It replaces the uncertain you once felt with the illusion that it was all clear from the start. That might feel comforting but it robs you of honest understanding of how decisions are actually made in real time. To build true insight, you need to separate what you knew from what you know now. And then you have to honor that difference. Reconstruct the moment, not the myth. When something goes wrong, your brain rushes to create a cause and effect story. But most decisions are made in a fog, that fog of uncertainty, not with floodlights. To challenge hindsight bias, take a moment to revisit what the situation looked like at the time. Pull up emails, journal entries, meeting notes, anything that helps you step back into the real context. Next, ask yourself, what were the facts available to me then? This process, well, it enables you to recover the uncertainty you forgot. It reminds you that you likely made the best call you could with the information you had. Decouple outcome from judgment. Hindsight bias often leads us to judge a decision by its results rather than its reasoning. But a good decision can have a bad outcome. And a bad decision, well, it can get lucky. Instead of asking, was I right? Instead, ask, was I thoughtful or did I weigh what I could? Let your standard for reflection be a process, not perfection. This is especially important in leadership where poor results don't always mean poor judgment. When you reflect this way, you don't just learn more. You lead more fairly and empathetically. Build tolerance for uncertainty. One of the costs of hindsight bias is that it makes you forget how complex most decisions are. It erases the ambiguity that was present and replaces it with artificial clarity. To resist that, well, start normalizing uncertainty. Remind yourself and your team that not knowing isn't a weakness. It's the default setting of reality. Most meaningful decisions live in the gray. Embracing that helps you move forward with humility and courage, not just hindsight-driven critique. Catch the I knew it reflex. That voice that says, I knew this would happen. Interrogate it. Ask yourself, did I say that at the time? Or am I saying it now that I know how things turned out? Often you'll find your memory has been quietly edited to fit the outcome. That doesn't make you a liar. It makes you bloody human. But calling it out keeps you honest. And honesty is what turns experience into actual growth. Clarity is resilience. Resilience isn't built on perfect foresight. It's built on honest hindsight. The strongest leaders and thinkers don't pretend they knew it all along. They own the fog of uncertainty that they walked through. They honor the process, not just the result. Doing that builds trust in your past, confidence in your present, and adaptability for whatever's next. So this week, I'd like to leave you with a little thought homework. I want you to think of a situation that ended badly, where one you've told yourself, I should have seen it coming. Now write it down. And ask yourself, what did I know at the time? What was unclear? What assumptions did I make? What did I do well, even if the result didn't land? Let that be your new story. Not cleaner, just more actual. And remember this, the next time you feel the urge to say, I knew it, pause. Ask yourself, or do I know it now? That pause is going to make you wiser over time. Next week, we're going to look at the twin cognitive biases of pattern-seeking and apophenia. Our brains love to find patterns in the chaos, in the uncertainty. But sometimes our brains connect the dots, but the dots lead to no picture. Thanks for listening to this episode of Seeing Sideways. These biases aren't flaws. They're part of how our brains make sense of a complex world. But with awareness, we can move from reaction to reflection, from assumption to intention. So if today's episode offered you a new perspective, please share with someone who might benefit. Because the real work of thinking clearly, choosing wisely, and leading with purpose, well, it's all an inside job. See you next time. Music.