The Paradox of Communication

The easiest thing to do. The hardest thing to do well.

We’re born knowing how to communicate.

There’s no instruction, no vocabulary, and no real understanding of language, but the message still gets across. A newborn cries, and the world responds. Before we ever speak a single word, we already know how to express need, discomfort, frustration, and fear. It’s instinctive. It’s natural. It just happens.

But as we grow, something shifts. We develop language. We gain the ability to reason, to persuade, to shape our thoughts with precision. In theory, we should be getting better. In reality, most of us get worse. We hesitate. We say too much or too little. We avoid hard truths or bury them under sarcasm, silence, or deflection. We misunderstand and get misunderstood. And the more we care about what we’re trying to say, the harder it seems to say it well.

That is the paradox.

Communication is the most natural skill we have, and yet it's one of the most difficult to do well. It's something I’ve been thinking about a lot lately, not because I’ve figured it out, but because I haven’t. There are moments when I say the wrong thing, or say nothing when I should have spoken, or realize too late that what I meant wasn’t what was heard. It’s frustrating. And it matters more than almost anything else. Every relationship, every opportunity, every conflict or resolution rests on this one ability.

I want to get better. That’s what sparked this. Not some abstract idea, but the realization that improving how I communicate might improve everything else. Every man, every woman, every parent, partner, and friend needs this. And the better we get at it, the more connected, clear, and grounded our lives become.

Looking for Answers

When I don’t understand something, I start researching. I read. I study. I look to the great thinkers of our time and the ones who came long before us. I try to find out what they saw that maybe I’m missing. That’s how I approach most problems in my life, and communication has been no different.

Naturally, I hoped there would be some guiding principle or forgotten wisdom I could put into practice. Maybe a single sentence that unlocks everything. Something elegant. Something clear. But that didn’t happen. What I found was a wide range of views, many of them conflicting. Some focused on structure. Some focused on tone. Some questioned whether true understanding between two people was even possible at all.

The more I read, the more it seemed like there wasn’t a solution. Not a fixed one. Not something you could simply learn and then master. There were tools, sure. There were insights. But there was no magic phrase, no absolute rule that worked for everyone, every time.

And maybe that’s the point.

Maybe communication isn’t meant to be a rigid structure, and maybe it’s not about finding one perfect style. We all have our own way of speaking, just as others have their own way of interpreting what we say. That gap between intent and perception is where so much of the difficulty lives. Maybe communication isn't about getting it right—it's about getting closer.

So instead of trying to build some perfect method, I started with a simpler question: why is something we’re born able to do so easy to lose? Why do most people get worse at it over time, not better? What happens along the way that makes us stop saying what we mean, or hearing what others are really trying to say?

That felt like the right place to begin. Not with a solution, but with the problem. Not with mastery, but with a willingness to ask why we drifted.

So I went looking there. Back into the writings of the people who spent their lives trying to understand human nature. The ones who thought deeply and wrote clearly. The ones who didn’t try to sell a solution, but instead tried to reveal something true.

What I wanted to know was simple: why do we get worse at this?

If we start out so good at it—pure, instinctive, unfiltered—why does growth so often bring confusion, distance, and miscommunication?

Turns out, a few of them asked similar questions.

Ludwig Wittgenstein, one of the most influential philosophers of the twentieth century, believed that language was a tool, not a perfect mirror of the world. He thought the issue wasn't that we couldn't speak clearly, but that we asked too much of language. Over time, we stop using words simply and begin trying to sound more refined, clever, or impressive. We build layers between what we mean and what we say. We assume people understand what we intended, even when we haven’t said it directly. In trying to sound precise or thoughtful, we often drift away from being clear or honest. The message gets lost in how carefully we’re trying to deliver it.

Søren Kierkegaard took a different angle. He believed that as we become more self-aware, we also become more fearful. Not necessarily afraid of others, but afraid of being fully seen. He called this the anxiety of selfhood. That fear makes us speak indirectly. Instead of saying what we really feel or think, we imply, we deflect, we joke. We start playing defense even in everyday conversation. It's not that we lose the ability to communicate. It's that we become afraid of what might happen if we do it too well, if we say the thing and can't take it back, or if it’s met with silence.

Martin Buber talked about presence. He believed communication suffers when we stop seeing each other as people and start treating each other as problems to solve or roles to manage. In his view, most of us shift from what he called real, relational communication to a more transactional one. We become strategic, measured, and controlled in our speech, and in doing so, we lose the connection. What begins as something natural slowly becomes a kind of performance. We worry about how we sound instead of what we’re really saying, and somewhere in that shift, authenticity gets lost.

None of them offered a perfect solution, but each pointed to the same root issue. We don’t get worse at communication because we stop trying. We get worse because we start carrying more. More ego. More fear. More pressure to get it just right. We learn to protect ourselves. We want to sound smart. We want to avoid pain. And in all of that effort to be careful, we stop being real.

That doesn’t fix the problem. But it gives me something solid to stand on. Because if that’s where it breaks down, maybe that’s also where it can be rebuilt.

So where do I land on all this?

Like most things, I don’t think the answer fits neatly into one box. I see truth in what they each said. I’ve felt it. The fear Kierkegaard described is real. There have been moments where I didn’t say something because I didn’t want to be exposed, even if that exposure would have brought clarity. I’ve tried too hard to sound right and ended up not saying what I meant at all, just like Wittgenstein warned. And I’ve absolutely caught myself performing instead of connecting, playing out conversations like a script instead of showing up fully present, which is exactly what Buber pointed out.

But I also think there’s something missing from their observations. Something less abstract and more grounded in everyday life.

I don’t think we get worse at communicating just because of fear or ego or philosophy. I think part of it is that we stop practicing. As kids, we’re constantly expressing ourselves. We say what we feel, when we feel it. We ask questions without shame. We speak up because we haven’t yet learned to shut down. Somewhere along the way, life starts rewarding restraint and punishing honesty. So we adapt. We pull back. And over time, we just get rusty.

Like anything else, communication is a skill. And like any skill, if you stop using it the right way, it decays. You get sloppy. You develop bad habits. You convince yourself that you're good at it because you talk all the time, but talking isn’t the same as communicating. If anything, the people who talk the most are sometimes the ones doing the least actual work when it comes to clarity, connection, or impact.

So yes, I agree with the philosophers in many ways. But I also think the breakdown is practical, not just existential. We don’t study how to communicate. We don’t reflect on how we come across. We rarely stop and ask, “Did what I say land the way I meant it?” Instead, we just keep moving, keep talking, and wonder why we feel distant from the people around us.

I’m not trying to become a master communicator. I’m just trying to get better. To be more aware. To tighten the gap between what I mean and what gets received. And to stop assuming that because I speak often, I’m saying something that actually matters.

Where it Shows Up

I started paying more attention to the people around me. The ways we all trip over communication without meaning to. Sometimes it’s obvious. Other times it’s quiet.

There’s someone I know who’s incredibly sharp. Witty, quick, always has something clever to say. But he can’t be serious. Anytime a conversation starts to drift toward something personal or real, he sidesteps it with humor. He’ll crack a joke, change the subject, make everyone laugh. And he’s good at it, which makes it harder to notice what’s really happening. But the deeper truth is that you can never get past a certain point with him. That discomfort blocks the connection. You can feel it. He isn’t doing it to avoid me, he’s doing it to protect himself. But it means there’s always distance that shouldn’t be there.

Then there’s someone else who struggles on the receiving end. She’s emotional, deeply sensitive, and always seems ready to defend herself, even when no one’s attacking. You can bring something up calmly, gently, with no edge at all, and she’ll brace for impact. Everything gets taken personally. Every word feels loaded. Conversations that should be simple turn into tense exchanges because no matter how you try to reach her, she hears judgment. And once that wall goes up, it’s almost impossible to get through. You’re not solving anything. You’re just trying to prove you’re not the enemy.

Neither of them are bad people. They’re both thoughtful, good-hearted, and want connection like anyone else. But somewhere along the way, how they learned to protect themselves ended up getting in the way of actually being understood.

And that made me turn the lens back on myself.

I’m not someone who holds back. If anything, I lean too far in the other direction. I’ve always been direct, often to a fault. I speak clearly, I get to the point, and I don’t waste time softening what I think. That works in some environments, but not all. There have been times where my words were sharp when they didn’t need to be, or landed harder than I intended. And I’ve learned that being right isn’t the same thing as being effective.

So I’m not trying to become more blunt. I’m trying to become more aware.

I want to get better at understanding how what I say is received. I want to stop assuming clarity is enough, and instead consider timing, tone, and how much weight the other person might already be carrying before I add anything more. I want to listen longer before I respond. I want to resist the urge to fix everything or frame everything with logic. Some things don’t need a solution. They just need space.

I don’t have a process. I just know that when communication improves, so does everything else. And if I want better relationships, better leadership, better outcomes, I can’t keep doing it the same way and expecting different results.

We’re all born knowing how to cry when we need something. Somewhere along the way, we forget how to say what matters without breaking the connection in the process. That’s what I’m trying to work on now. Not speaking louder. Just learning when to speak, how to speak, and when it’s better to simply be quiet and let someone else be heard.

Buried Beneath Experience

The more I think about it, the more I realize communication isn’t something you master. It’s something you carry. It’s there from the beginning, raw and instinctive, and then slowly, life starts getting in the way. The more you live, the more you experience, the more guarded you become. You get hurt, misunderstood, dismissed. And without even realizing it, you start to speak less freely. You shape your words to protect yourself, not to connect with someone else.

We’re all born knowing how to cry out when we need something. To ask. To express. To be heard. But over time, that clarity erodes. Not because we lose the ability, but because we build layers on top of it. Some of those layers help us survive. Others just make it harder to say what matters.

Getting better at communication isn't about learning something new. It's about remembering something old. Stripping it back down. Paying attention again. Choosing presence over performance. Connection over control.

For something we’re all born knowing how to do, it’s surprising how much work it takes to do it well again.

-Gino