More Than Imposter Syndrome: How Conditional Thinking Holds Us Back

More Than Imposter Syndrome: How Conditional Thinking Holds Us Back

More Than Imposter Syndrome: How Conditional Thinking Holds Us Back

Mental Health

Mental Health

/

Douglas Voon

Douglas Voon

/

22 May 2025

22 May 2025

/

Thoughtful professional man in office setting, representing imposter syndrome, leadership anxiety, and internalised self-doubt in the workplace.
Thoughtful professional man in office setting, representing imposter syndrome, leadership anxiety, and internalised self-doubt in the workplace.
Thoughtful professional man in office setting, representing imposter syndrome, leadership anxiety, and internalised self-doubt in the workplace.

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More Than Imposter Syndrome: The Hidden Rules That Quietly Shape How We Show Up


The Moment That Changed How I Worked


Years ago, after my first promotion to a managerial position, I was required to attend monthly meetings where other managers and I were expected to report on our team’s performance. I remember obsessing over plans, reports, and stats — trying to be ready for anything that might come my way. By the end of those two-hour meetings, no matter how well my team had performed, I’d walk out completely drained. Not just tired — mentally fried.


One day, having noticed this, a senior manager pulled me aside. She simply said: “You’re doing good work, but please don’t kill yourself over it. We don’t expect you to have all the answers on the spot — we just want to know you to know where to look if we ask.”


At the time, I think I nodded politely while silently calculating what else I should’ve prepared. But something about her tone stuck with me. That quiet moment marked the start of one of the most impactful mentor-mentee relationships of my career. And looking back, I realise how much her words have stayed with me since.


When Self-Doubt Becomes an Identity


I now see elements of what I’d later recognise as imposter syndrome — the belief that “I have to know everything to do my job well.” If I didn’t, I wasn’t just underprepared. I was letting people down. Maybe even proving the promotion had been a mistake.


In a post I wrote not long ago, I unpacked a pattern I see often in coaching: the hunt for a “regret-proof” decision. As if there’s some version of perfect thinking that shields us from doubt. That was me too. I wasn’t just afraid of getting it wrong — I was terrified someone might find out I didn’t belong.


People talk about imposter syndrome like it’s a skill issue. It’s not. It’s an identity issue. It tells you your value is conditional — only as secure as your last answer, your last win, your last moment of competence. It disguises itself as diligence, but underneath is a deeper fear: if I’m not perfect, I don’t belong. That’s what makes it so draining — you’re not just working hard; you’re working to prove you deserve to exist in the room.


The Trap of Biconditional Thinking


Maybe that’s why I used to find comfort in rules. I come from a tech background — logical if-this-then-that flows made sense. Predictable, clean and manageable. Life didn’t always follow that logic, but my mind clung to it. What I’ve just described isn’t conditional thinking. It’s something more rigid: biconditional thinking. In formal logic, biconditional means both sides must be true — “if and only if.” If X, then Y. But also: if Y, then X. It’s airtight.


In life, that thinking gets messy, take this for example: “If I hit my monthly target, I’ll order takeaway to celebrate.” Then later, you see me eating pizza at my desk. It’s easy to assume I've hit the target — as if pizza only follows success. But maybe I was just hungry. That’s the trap: we mistake one thing as evidence of another, when life has way more variables.


In psychology, it’s worse. We don’t just observe the rule — we internalise it. “If I’m confident, I belong here,” turns into, “If I don’t feel confident, I must not belong.” We stop testing the belief. We just live it.


How These Rules Shape Our Behaviour


These kinds of rules don’t just shape self-talk — they shape behaviour. I’ve seen senior leaders avoid asking for input because they believe needing help undermines authority. I’ve seen people hesitate to speak up in meetings, not because they lack insight, but because they’re afraid one awkward sentence might discredit their credibility.


That’s what biconditional thinking does. It keeps us in performance mode. Everything becomes a test, a signal, a risk. It tells us we have to earn our right to be here — again and again and again.


Funny enough, the best leaders I’ve worked with weren’t flawless, they were grounded. They didn’t panic when they didn’t know something, they just said, "Good question," and moved the conversation forward. They weren’t performing certainty — they were modelling steadiness.


Years ago, one such leader told me I didn’t need to have all the answers — just the ability to find them. At the time, I didn’t realise how liberating that was. But now? It’s a mindset I return to more than I’d like to admit.


Loosening the Grip of Invisible Rules


You don’t need to be someone’s boss or have a fancy title to change how you show up — for yourself or for others. One of the most powerful shifts is simply learning to notice when those old rules start speaking on your behalf.


Ask yourself: What are the quiet rules I live by? What do I believe I have to do, be, or prove in order to be enough?


These questions aren't abstract. They show up when you don’t speak up. When you hesitate to ask for help. When you win something and still wonder if you deserve it.


A Gentle Challenge


So here’s a small challenge:


Think of one rule that’s running the show. Maybe it’s: “If I’m not the smartest in the room, I don’t belong.” Or: “If I slow down, I’ll fall behind.”


Now gently test it. Where did it come from? Is it true? Has there ever been a time when you didn’t follow that rule — and things still worked out fine?


You don’t have to demolish it overnight. Just start by noticing it. Then question it. Tug at the edges. You might find the confidence you were chasing isn’t on the other side of getting it perfect — it’s in not needing to anymore.


If this sounds familiar — if you’ve found yourself caught in these patterns and you’re ready to make sense of them — I’d be glad to help you explore it further.


Curious to Explore Further?


If this article stirred something and you're the kind of person who likes to connect the dots, here are a few threads worth pulling:


  • The term imposter syndrome has been around since the late '70s — first noticed among high-achieving professionals who felt like frauds despite plenty of evidence to the contrary.

  • Some of these mental patterns overlap with what psychologists call cognitive distortions — things like "all-or-nothing" thinking or rigid inner rules that shape how we interpret success, failure, and everything in between.

  • And if you’ve ever wondered why some teams feel safe to admit mistakes and others don’t, there’s growing research around psychological safety and how leadership tone sets the stage.


You don’t need to dive into textbooks — but if you're interested in understanding how beliefs shape behaviour, these areas are full of insight. And if you're someone who prefers working through it in dialogue, that’s what coaching is for.


If you're curious about how this might apply to your own experience, get in touch to arrange a free discovery session. I'd be happy to explore it with you.

More Than Imposter Syndrome: The Hidden Rules That Quietly Shape How We Show Up


The Moment That Changed How I Worked


Years ago, after my first promotion to a managerial position, I was required to attend monthly meetings where other managers and I were expected to report on our team’s performance. I remember obsessing over plans, reports, and stats — trying to be ready for anything that might come my way. By the end of those two-hour meetings, no matter how well my team had performed, I’d walk out completely drained. Not just tired — mentally fried.


One day, having noticed this, a senior manager pulled me aside. She simply said: “You’re doing good work, but please don’t kill yourself over it. We don’t expect you to have all the answers on the spot — we just want to know you to know where to look if we ask.”


At the time, I think I nodded politely while silently calculating what else I should’ve prepared. But something about her tone stuck with me. That quiet moment marked the start of one of the most impactful mentor-mentee relationships of my career. And looking back, I realise how much her words have stayed with me since.


When Self-Doubt Becomes an Identity


I now see elements of what I’d later recognise as imposter syndrome — the belief that “I have to know everything to do my job well.” If I didn’t, I wasn’t just underprepared. I was letting people down. Maybe even proving the promotion had been a mistake.


In a post I wrote not long ago, I unpacked a pattern I see often in coaching: the hunt for a “regret-proof” decision. As if there’s some version of perfect thinking that shields us from doubt. That was me too. I wasn’t just afraid of getting it wrong — I was terrified someone might find out I didn’t belong.


People talk about imposter syndrome like it’s a skill issue. It’s not. It’s an identity issue. It tells you your value is conditional — only as secure as your last answer, your last win, your last moment of competence. It disguises itself as diligence, but underneath is a deeper fear: if I’m not perfect, I don’t belong. That’s what makes it so draining — you’re not just working hard; you’re working to prove you deserve to exist in the room.


The Trap of Biconditional Thinking


Maybe that’s why I used to find comfort in rules. I come from a tech background — logical if-this-then-that flows made sense. Predictable, clean and manageable. Life didn’t always follow that logic, but my mind clung to it. What I’ve just described isn’t conditional thinking. It’s something more rigid: biconditional thinking. In formal logic, biconditional means both sides must be true — “if and only if.” If X, then Y. But also: if Y, then X. It’s airtight.


In life, that thinking gets messy, take this for example: “If I hit my monthly target, I’ll order takeaway to celebrate.” Then later, you see me eating pizza at my desk. It’s easy to assume I've hit the target — as if pizza only follows success. But maybe I was just hungry. That’s the trap: we mistake one thing as evidence of another, when life has way more variables.


In psychology, it’s worse. We don’t just observe the rule — we internalise it. “If I’m confident, I belong here,” turns into, “If I don’t feel confident, I must not belong.” We stop testing the belief. We just live it.


How These Rules Shape Our Behaviour


These kinds of rules don’t just shape self-talk — they shape behaviour. I’ve seen senior leaders avoid asking for input because they believe needing help undermines authority. I’ve seen people hesitate to speak up in meetings, not because they lack insight, but because they’re afraid one awkward sentence might discredit their credibility.


That’s what biconditional thinking does. It keeps us in performance mode. Everything becomes a test, a signal, a risk. It tells us we have to earn our right to be here — again and again and again.


Funny enough, the best leaders I’ve worked with weren’t flawless, they were grounded. They didn’t panic when they didn’t know something, they just said, "Good question," and moved the conversation forward. They weren’t performing certainty — they were modelling steadiness.


Years ago, one such leader told me I didn’t need to have all the answers — just the ability to find them. At the time, I didn’t realise how liberating that was. But now? It’s a mindset I return to more than I’d like to admit.


Loosening the Grip of Invisible Rules


You don’t need to be someone’s boss or have a fancy title to change how you show up — for yourself or for others. One of the most powerful shifts is simply learning to notice when those old rules start speaking on your behalf.


Ask yourself: What are the quiet rules I live by? What do I believe I have to do, be, or prove in order to be enough?


These questions aren't abstract. They show up when you don’t speak up. When you hesitate to ask for help. When you win something and still wonder if you deserve it.


A Gentle Challenge


So here’s a small challenge:


Think of one rule that’s running the show. Maybe it’s: “If I’m not the smartest in the room, I don’t belong.” Or: “If I slow down, I’ll fall behind.”


Now gently test it. Where did it come from? Is it true? Has there ever been a time when you didn’t follow that rule — and things still worked out fine?


You don’t have to demolish it overnight. Just start by noticing it. Then question it. Tug at the edges. You might find the confidence you were chasing isn’t on the other side of getting it perfect — it’s in not needing to anymore.


If this sounds familiar — if you’ve found yourself caught in these patterns and you’re ready to make sense of them — I’d be glad to help you explore it further.


Curious to Explore Further?


If this article stirred something and you're the kind of person who likes to connect the dots, here are a few threads worth pulling:


  • The term imposter syndrome has been around since the late '70s — first noticed among high-achieving professionals who felt like frauds despite plenty of evidence to the contrary.

  • Some of these mental patterns overlap with what psychologists call cognitive distortions — things like "all-or-nothing" thinking or rigid inner rules that shape how we interpret success, failure, and everything in between.

  • And if you’ve ever wondered why some teams feel safe to admit mistakes and others don’t, there’s growing research around psychological safety and how leadership tone sets the stage.


You don’t need to dive into textbooks — but if you're interested in understanding how beliefs shape behaviour, these areas are full of insight. And if you're someone who prefers working through it in dialogue, that’s what coaching is for.


If you're curious about how this might apply to your own experience, get in touch to arrange a free discovery session. I'd be happy to explore it with you.

Let’s talk

Contact Cross Horizons today, and let's start the conversation about transforming your life.

info@crossinghorizons.com

(+61) 458 884 950

Contact

Site designed and built by shaunxwong

All rights reserved.

Let’s talk

Contact Cross Horizons today, and let's start the conversation about transforming your life.

info@crossinghorizons.com

(+61) 458 884 950

Contact

Site designed and built by shaunxwong

All rights reserved.

Let’s talk

Contact Cross Horizons today, and let's start the conversation about transforming your life.

info@crossinghorizons.com

(+61) 458 884 950

Contact

Site designed and built by shaunxwong

All rights reserved.