Maybe you’ve hit send and immediately wished you hadn’t? Fired off an email that missed the point but showed what you really felt (cringe), responded to a post without fully reading it, made a decision based on partial information we could have caught if we’d slowed down. We’ve all probably paid dearly.

These moments create regret, friction in relationships, at work, online. In aggregate, they undermine our collective capacity to communicate and cooperate at a time when we can least afford it. With AI amplifying both possibilities and risks, we need to up our cognitive game; we need to be smarter to work with smarter tools. We need to both speed up and slow down. Maybe we need to take a simpler approach to get it right. We catch a lot more detail, like watching the winning score or the crushing miss in slow motion in the post-game post mortem.

Being Securely Insecure?

What I call "secure expertise" isn’t just competence—it’s competence plus awareness of the limits of one’s knowledge, a kind of being secure about insecurity. It requires emotional stability: As James Carse might frame it in his work on finite and infinite games, finite players play to win the round; infinite players play to get to a better place over the long-haul.

Secure expertise also requires epistemological comfort with uncertainty—being clear about what we don’t know and using that ambiguity productively rather than defensively. When these capacities fail, we miss things. Here’s what might be going on under the hood.

**Executive function and inattention. **Sometimes the issue is straightforward: difficulty with baseline attentional control, time management bottlenecks, poor task planning, or simply not slowing down when the situation requires it. The brain’s executive attention networks help us inhibit hasty decisions and discriminate among competing stimuli, though it needs to be engaged with the right timing and switching to properly create the world we want to inhabit, rather than the one we find ourselves in.

What helps: Timers can pace us; built-in review steps before finalizing important communications catch errors before they escape. Mindfulness meditation, practiced over time, strengthens these networks—neurons that fire together wire together, as the Hebbian doctrine reminds us.

**Emotional interference. **There are more ways this happens that we can fully cover here. Psychodynamic conflict, anxiety, narcissistic vulnerabilities—these can hijack attention without our awareness. When ego is on the line, we’re more likely to react than respond, to defend rather than understand. The bluster that often accompanies insecurity serves some other agenda than the proposed one: face-saving, dominance, discharging anxiety, or shoring up a fragile sense of self.

What helps: Developing tolerance for self-conscious emotions like shame and embarrassment—rather than needing to feel right all the time—allows learning from mistakes. Healthy self-esteem regulation, built through experimenting with ourselves over time with a scientific attitude, is key.

**Habit. **We develop ways of operating with information that become automatic: scanning rather than reading, responding before processing, prioritizing speed over accuracy. These patterns may have been adaptive once, though they no longer serve us. Muscle memory makes us repeat the same context we needed at some earlier stage, a one-trick pony operating system which doesn’t work for different contexts.

What helps: Give yourself the gift of giftedness1. Deliberately practice new behaviors—including the mental habit of taking multiple perspectives—until they stick. Re‑read the post before you reply; make “slow down” the default, not the exception. Remember that context matters, and habits steal contextual awareness by swapping complexity for misleading simplicity. Weigh multiple contexts, while respecting that the old operating system still has its uses. Cultivate cognitive flexibility—openness to new experience—a trait strongly correlated with giftedness.

**Interpersonal Factors. **Communication distortions are common; we perceive others not as they are, rather through the lens of past relationships and expectations, applying familiar templates from prior experience to current interactions2. Not liking someone, social anxiety, being triggered by who they are—these all shape what we notice and miss. Our own insecure insecurities warp our filters and we "project" onto others, straw-man them, and then often attack or retreat. We are shadow-boxing.

What helps: Recognizing that our reaction may reveal more about our history than the moment creates room to reconsider. Before replying—especially in high‑stakes exchanges—get a second opinion for external calibration. Notice when the past is shaping your perception more than the present; over time, that reduces error and updates your educated guesswork with fuzzy, Bayesian logic. Even if you’re right about the other person, that very certainty can signal what’s keeping you stuck in an old pattern—especially when it comes with righteous indignation or a sense of victimhood.3

**Motivational interference. **Sometimes we harbor overlapping motives we haven’t recognized; inner conflict creates ambivalence that clouds judgment. Clashing thoughts and desires, clashing directives and goals, doubt about authenticity4,5, imposter syndrome, all spring from and foment cognitive dissonance. This dissonance is the signal to self-interrupt and consider alternatives, after restoring equanimity.

What helps: Noticing when we feel activated is itself a skill, taking distress and confusion as signal rather than noise, pleasure in curiosity rather than pain in disorientation. Treating dissonance as information rather than something to resolve quickly, and asking ourselves what we actually want to happen. The "self-compassion break"6 can do wonders: This is a moment of pain; I am suffering. All human beings suffer ("common humanity"). What do I really need right now?

**Impulsivity. **Anything that boosts impulsivity can worsen all of the above: ADHD, anxiety, intoxication, sleep deprivation—even excitement. Don’t confuse impulsivity with spontaneity or intuition; those are useful and different. Impulsivity is an accelerant, not a brake. Think the regrettable late‑night post, or the quick reply that chases a laugh to impress rather than the kind of humor that builds connection. It’s decisions made without enough context.

What helps: Knowing our vulnerabilities. Building in structural safeguards—waiting periods, review protocols—or simply asking: "Is this urgent, or does it just feel urgent?" Learning the crucial difference in how impulsivity feels in the moment, as contrasted with true spontaneity.

**Resource Depletion. **Even people with excellent attentional capacity can fail when running on empty. Fatigue, crisis mode, cognitive overload—these situational factors deplete the resources needed for careful processing.

What helps: Preemptive steps to keep the tank full. Protecting sleep. Recognizing when we’re depleted and deferring important communication and decisions whenever possible. Does it really need to go out now?

Embracing Complexity

These factors rarely operate in isolation; most behavioral failures in communication involve some combination—emotional reactivity amplified by fatigue, habitual patterns triggered by interpersonal dynamics, attentional lapses worsened by anxiety. Understanding our particular constellation is the beginning of change. What seems hopelessly complicated starts to make sense, over time. Learning effective self-governance7 is a key organizing schema, starting with assessing your own ego functioning8 to make effective choices in the "timeless present moment".

We learn what we can and can’t do by experimenting with ourselves over time, with a scientific attitude. That’s the work. If these patterns cause significant distress or dysfunction, consultation with a mental health professional can help identify what’s driving them and develop targeted strategies for change.