Awkwardness Is Usually Smaller Than Regret

People sometimes tell me that I seem to collect unusual stories.

I understand why.

I can tell several stories from the same month that sound as though they should have happened across several years. Unexpected conversations. Decisions made with little preparation. Encounters with people I did not know. Situations that became memorable partly because many people probably would not have entered them in the first place.

For a long time, I thought unusual things simply happened to me.

I do not think that anymore.

I think I have more of these experiences because I have developed a habit of walking towards some of the moments that make me uncomfortable.

Not recklessly. Not every time. I am still capable of hesitation, embarrassment and fear.

But when I notice that fear is becoming the main reason I am avoiding something, I become curious.

What would actually happen if I did it anyway?

I do not want fear making too many decisions for me

There is a difference between being afraid of something and having a good reason not to do it.

Some fear protects us. It tells us that another person is behaving unpredictably, that a situation is unsafe or that the consequences are greater than we are prepared to carry.

I have no interest in becoming fearless in that sense.

Courage without judgement easily becomes recklessness.

But much of what stops us in ordinary life is not danger.

It is awkwardness.

What if I say the wrong thing? What if somebody thinks I am strange? What if I admit what I actually think and they disagree? What if I ask and they say no?

What if I look foolish for thirty seconds?

Those possibilities can become surprisingly powerful when they remain untested. The imagined situation keeps growing because reality never gets the opportunity to correct it.

That is where this connects with Thoughtfulness Needs a Stopping Point. Thinking can prepare me for a situation. It can also make the situation larger while nothing outside my head has actually happened.

Sometimes the only way to discover the true size of an awkward moment is to enter it.

Usually, I have found, it is smaller than I imagined.

Sometimes I simply say what I notice

I might pass someone and think she looks beautiful.

If the moment feels appropriate, sometimes I say it.

You look beautiful.

That can be the entire interaction.

I do not say it because noticing someone gives me any claim on her attention. I am not expecting a telephone number, a conversation or anything in return.

Sometimes appreciation can simply remain appreciation after it has been spoken.

Naturally, the moment may become slightly awkward. She may look surprised. She may ignore me or simply continue walking.

If she keeps walking, I keep walking too.

That is part of the interaction.

But another possibility exists. She smiles, says thank you, and for a few seconds two strangers have a kind exchange before continuing in different directions.

What interests me is not really the compliment.

It is how much psychological weight we can give such a tiny social risk before anything has happened.

The imagined rejection can feel enormous.

The real rejection may simply be somebody continuing with her day.

Straightforwardness only works when the other person remains free

This distinction is important to me.

Being willing to express myself does not mean another person has to receive that expression in the way I hoped.

If I tell somebody how I feel, my honesty does not create an obligation for them to feel the same.

If I ask for an opportunity, somebody can refuse it.

If I start a conversation, the other person can decide not to continue it.

If I challenge an idea at work, I can be wrong.

Courage cannot mean being brave enough to ask but too fragile to accept the answer.

Otherwise straightforwardness becomes something else. It becomes an attempt to control another person’s response while presenting myself as courageous for speaking.

For me, the freedom comes from being able to say:

This is what I think.

This is what I feel.

This is what I would like.

and then allowing reality to answer.

That does not mean every answer is easy.

A no can disappoint me. Someone may misunderstand me. Another person may decide that what I want is not what they want.

But their answer does not have to become a judgment about everything I am.

That is part of the distinction I explore in When Other People’s Behaviour Becomes a Verdict on Us. Someone else’s reaction contains information. It does not automatically contain my value.

Embarrassment became cheaper when I stopped treating it like an emergency

I think many experiences never happen because we place an unusually high price on looking foolish.

We rehearse conversations instead of having them. We wait for perfect circumstances and try to know the outcome before deciding whether something deserves an attempt.

It is understandable.

Nobody particularly enjoys embarrassment.

But a life organised entirely around preventing uncomfortable moments can become very predictable. There may be fewer embarrassing stories.

There may also be fewer surprising ones.

Over time, I became more willing to pay the small price of occasionally looking strange, being misunderstood or discovering that an idea did not work.

What surprised me is how rarely the actual price matches the imagined one.

Most uncomfortable situations become ordinary once I am inside them.

An awkward conversation becomes a conversation.

A difficult question receives an answer.

Someone says yes.

Someone says no.

Someone laughs.

Someone looks confused.

And life continues.

This does not mean people are always kind or that every social risk is sensible. Context matters. I still need to notice when another person is uncomfortable and recognise when persistence would stop being courage and start becoming disrespect.

But embarrassment itself no longer feels like sufficient evidence that I should avoid something.

Courage includes the possibility that I am wrong

Most of these situations have produced good experiences for me.

But I do not think that can be the argument for entering them.

If courage were worthwhile only when it produced the outcome I wanted, it would not really be courage. It would be a successful prediction.

Sometimes I will misread a situation.

I will ask something I later realise was unnecessary. Someone will not appreciate what I say. An idea I defend will turn out to be weaker than I thought.

There will be moments when I walk away thinking:

I could have handled that better.

I have become more comfortable with that possibility because being wrong no longer needs to become a complete judgment about me.

A strange thirty seconds can remain thirty seconds.

A rejection can remain one person’s answer.

An unsuccessful attempt can become information.

A mistake can require an apology without becoming proof that I should stop taking risks altogether.

That distinction matters because otherwise courage becomes impossible.

I would have to know that I was right before taking the action that reveals whether I am right.

Silence should have to justify itself too

I recognise the same pattern when the uncomfortable action is not approaching somebody but saying something that matters.

There are situations where remaining quiet feels safer.

I may need to admit that I disagree. Tell somebody that something hurt me. Say that I want something, or that I no longer want something I previously accepted.

Silence can feel responsible because nothing visibly difficult happens while I remain quiet.

But silence has consequences too.

If I postpone a necessary conversation because I am waiting to feel completely comfortable, I may eventually start communicating through distance, hesitation or changed behaviour instead.

That is why Silence Can Become a Conversation of Its Own became an important distinction for me.

I do not believe everything needs to be said.

Sometimes silence is wise.

But I increasingly believe silence should have to justify itself in the same way speech does.

Why am I not saying this?

If the answer is consideration, timing, privacy or safety, waiting may be completely responsible.

If the main answer is:

Because this might feel awkward.

I want to examine it more carefully.

Fear alone is rarely enough.

The same thing happens in leadership

This part of me does not disappear when the situation becomes professional.

There are moments at work when the easiest option is to remain quiet.

A decision may not make sense. An idea everybody has accepted may deserve another question. Someone more senior may be confidently moving in a direction I think contains a problem.

Sometimes the uncomfortable thing is admitting that I do not know.

Sometimes it is saying:

I disagree.

Sometimes it is taking responsibility before I know whether the eventual result will make me look good.

The same choice appears in a different form.

Do I protect myself from discomfort, or do I enter the situation and find out what is actually there?

That does not mean saying everything that enters my mind. Straightforwardness without judgement becomes carelessness very quickly.

Timing matters. Evidence matters. Other people matter. Authority changes the weight of what we say.

That is one of the reasons Quiet Leadership Is Not the Absence of Authority matters to me. Leadership does not require speaking first or speaking most. But there are moments when restraint has done its work and the responsible thing is to become clear.

A leader who never risks an uncomfortable sentence may look calm while leaving everyone else to carry the uncertainty.

Courage at work is not volume.

Sometimes it is simply accepting the social cost of saying what the situation requires.

There are risks I should not romanticise

I do not want to turn discomfort into a rule that says:

If something scares you, do it.

That would be a poor rule.

Some hesitation contains important information.

There are situations where another person is clearly uncomfortable. Situations involving real physical, financial or professional risk. Moments where the possible consequences are much greater than embarrassment.

Sometimes the courageous decision is leaving.

Sometimes it is saying no.

Sometimes it is refusing the invitation to prove something.

The distinction I care about is whether I am responding to the actual consequence or to an imagined social humiliation that has grown far beyond it.

Before I act, I sometimes ask myself:

What am I actually risking?

If the answer is safety, somebody else’s dignity, a serious responsibility or something difficult to reverse, the fear deserves much more attention.

If the answer is:

I might feel awkward for a minute.

then fear does not automatically get the final vote.

Regret is not only about the things we did

We often think about regret as something created by action.

I should not have said that.

I should not have gone there.

I should not have taken that risk.

Those regrets exist.

But there is another kind.

I should have asked.

I should have said what I felt.

I should have tried.

I should have told that person what they meant to me while I still had the opportunity.

Those regrets are quieter because nothing dramatic happened.

Life simply moved on.

The conversation never existed.

The question never received an answer.

The possibility stayed a possibility until eventually there was no longer anything to decide.

That is the kind of regret I have become more aware of.

Not because every possibility deserves pursuit.

But because I do not want fear of a temporary feeling to repeatedly decide which parts of life I am allowed to discover.

I do not know whether tomorrow comes

This can sound dramatic, but I mean it quite literally.

None of us knows exactly how much time we have.

I do not use that thought to justify recklessness. If anything, it makes me more interested in distinguishing risks that matter from discomfort that merely feels important in the moment.

If there is something meaningful I want to say, why am I postponing it?

If I appreciate someone and the context allows me to say so respectfully, why must the appreciation always remain private?

If I want to try something and the main consequence of failure is embarrassment, what exactly am I protecting myself from?

There will always be another reason to wait.

Better timing.

More certainty.

More confidence.

A future version of ourselves who finally feels prepared.

But much of life seems to happen before that person arrives.

At some point, waiting for fear to disappear becomes another way of allowing fear to decide.

I still feel afraid

I do not think courage is the disappearance of fear.

Fear is often what makes courage visible.

There are still situations where I hesitate. Things I write and rewrite before sending. Conversations where I can feel myself searching for one more reason to postpone them.

I do not always choose action.

But each time I enter a situation I once imagined as enormous, fear receives a more accurate measurement.

Sometimes the situation really is difficult.

Sometimes I realise my instinct was protecting me from something important, and I listen.

But surprisingly often, the thing that looked enormous from a distance becomes very ordinary once I am standing inside it.

A conversation.

A question.

A compliment.

A refusal.

A disagreement.

A possibility I would never have discovered if certainty had been the price of entry.

Maybe that is why I have so many stories.

It is not because extraordinary things continually happen to me.

Sometimes I simply walk into the moments that fear would have preferred I passed by.

And more often than not, the awkwardness is smaller than the regret would have been.