Is It Time to Rethink That Decision? How Cognitive Bias Shapes the ADHD Entrepreneur’s Choices

How Our Mental Shortcuts Shape, Support, and Sometimes Sabotage Our Business Journey

For ADHD entrepreneurs, learning to recognize and recalibrate cognitive biases transforms mind traps and thought loops from hidden hazards into conscious, strategic tools.

If you've ever invested time or money into a "sure thing" that fizzled, or found yourself insisting, "this time I will stick to my schedule!" (despite reality), you're not alone. In her latest ADHD-ish episode, host Diann Wingert peeled back the layers on a topic that hits home for so many entrepreneurs with ADHD: cognitive biases—those sneaky mental shortcuts that shape our decisions, our stories, and, sometimes, our downfalls.

Armed with insights from Vicky Tan's book Ask This Book a Question, Diann explores exactly how these mind traps and thought loops impact the ADHD brain, and—importantly—how we can work with them instead of against them.

What Are Cognitive Biases? The Brain's "Helpful" Shortcuts

Cognitive biases aren't unique to ADHD brains; they're a universal human feature. The cognitive bias definition that resonates most with entrepreneurs? As Diann puts it, these are "mental shortcuts that our brain takes to process information quickly." In other words, they're the tools evolution handed us to avoid being overwhelmed by data, allowing for snap decisions. But for those of us with ADHD, these shortcuts don't always get us where we want to go. Sometimes, they spark innovation; other times, they lead us straight into frustration or failure.

Instead of seeing biases as flaws, Tan and Diann encourage us to view them as potential assets—quirky friends who are fun at parties, but whom we shouldn't always take too seriously.

ADHD and Optimism Bias: The Double-Edged Sword

Perhaps the most familiar cognitive bias for ADHD entrepreneurs is optimism bias: our tendency to overestimate positive outcomes and underestimate the risks or effort involved. It's the voice that promises, "This project will only take two days!"—when reality (and history) say otherwise.

Diann highlights how this optimism fuels necessary bravery, creativity, and risk-taking in business. But unchecked, it also leads to overcommitting, under-planning, and disappointing results. The solution isn't to squash your optimism; instead, it's about "calibrating" it. For Diann, this means relying on external accountability (like business besties who question her estimates), breaking projects into smaller parts, tracking her actual time, and leveraging tools like Goblin Tools and project management systems.

The Fundamental Attribution Error: Judging Others, Forgiving Ourselves

Another hidden snag is the fundamental attribution error: attributing other people's mistakes to their character, while excusing our own as situational flukes. Imagine labeling an employee as lazy for missing a deadline, but seeing your own missed deadline as the result of overwhelm.

Diann warns this cognitive bias is "relationship poison" for ADHD entrepreneurs, especially since we already struggle with consistency and time management ourselves. The antidote? Practice perspective-taking: ask yourself how you explain someone's actions, how you'd explain the same thing if you had done it, and what three other explanations are possible. This simple shift can save business relationships and foster more empathy all around.

The Sunk Cost Fallacy: Throwing Good Resources After Bad

ADHDers are especially prone to the sunk cost fallacy—the impulse to keep pouring time, money, or energy into something just because you've already invested so much. We cling to ideas or relationships that aren't working, often driven by our difficulty with transitions, emotional attachment, and the fogginess of working memory.

Diann offers the "fresh start decision framework": If you were starting today, with what you know now, would you still choose to pursue this thing? That clarity can break the spell of sunk costs and make pivoting possible when needed.

Putting It Together: Practical Steps for Self-Awareness

So, how do ADHD entrepreneurs create a decision making process that harnesses the power (not the pitfalls) of these mind traps? Diann recommends:

• Recognize the Story: Pause to ask what narrative you're telling yourself about a decision or situation.

• Spot the Bias: Name which cognitive bias might be at play—optimism, attribution error, sunk cost, or others.

• Reframe the Perspective: Use ADHD creativity to see the situation from multiple angles.

• Reevaluate the Decision: Make choices with fuller awareness, not just gut instinct.

Add in external accountability partners, decision journals to track outcomes, enforced "cooling off" periods before big choices, and visible reminders about optimism bias, and you're well on your way to a more intentional decision making process that actually works with your ADHD brain.

Conclusion: Embracing Your Quirky User Manual

Cognitive biases aren't character flaws. For ADHD entrepreneurs, learning to recognize and recalibrate them transforms mind traps and thought loops from hidden hazards into conscious, strategic tools. As Diann so wisely concludes: "The stories we tell ourselves shape our reality… With the right awareness, these patterns become your entrepreneurial advantage."

So, next time you feel yourself looping or leaping, remember: the ADHD brain is wired for both brilliance and blind spots. Your job is to read your own user manual—and keep rewriting it with every lesson you learn.

Want to get better at spotting your cognitive biases and make better decisions as a result? I created a free companion handout with the various patterns discussed in this episode, plus my four-step framework for rewiring your biases. Grab your copy right here.

Feel free to DM me on LinkedIn or send me an email at diann@diannwingertcoaching.com. I'd love to hear your thoughts! If you'd like to hear the full episode on the ADHD-ish Podcast, you can do that here.