“The most terrible poverty is loneliness and the feeling of being unloved.”

- Mother Teresa

I’ve dealt with loneliness my whole life.

In one way or another I’ve often felt like an outsider.

Too black for some spaces. Not black enough for others.

Too nerdy for some spaces. Not nerdy enough for others.

Too successful for some spaces. Not successful enough for others.

To be clear, I have some great friends that I’ve known for 10, 20, and even 30 years.

I’m absolutely grateful for them.

But as we get older it’s inevitable that life happens. Some people move away. Others get consumed by career obligations. Others have personal or family health challenges. And some, you realize you never had that much in common to begin with.

That’s life.

As I get older (and hopefully wiser), I become increasingly aware of what actually matters in life and try to be as intentional about “keeping the main thing, the main thing”. And relationships are absolutely something to prioritize.

And as a founder, I’m definitely aware that entrepreneurship can be incredibly lonely. I owe it to myself, and the company to be more thoughtful about creating community to increase my odds of success.

This is partly what led to me reading, Belong, a book from Radha Agrawal, about creating intentional community. It’s anchored in her own story of loneliness, building community and living an intentional life. She now runs a company called DayBreaker that puts on sober, morning dance parties, and is the founder of Belong Center; an organization focused on the loneliness epidemic. Her new book, How to Be A Friend, comes out in October.

The stats about loneliness and relationships are undeniable.

Harvard’s 85 year study proves that relationships are the #1 predictor of happiness.

In 2023, the U.S. Surgeon General, Dr. Vivek Murthy, declared loneliness a public health epidemic.

Not metaphorically. Literally.

It’s the same category as tobacco and obesity.

The numbers are staggering:

Read that again. Half the country. We're not talking about feeling a bit blue on a Sunday night. We're talking about a population-level health crisis that's quietly killing people, and almost nobody is treating it like one.

Take a minute to look at the chart below.

It shows how we spend our time as we get older.

There’s a reason why dating coach, Logan Ury’s book is called How To Not Die Alone.

I've spent more time than the average person sitting with this data, and I’m convinced I we're labeling this thing wrong.

Read the Surgeon General's own definition of loneliness carefully. It's not "being alone." It's:

The key word is meaningful.

Loneliness isn't a shortage of people. It's a shortage of people who you have meaningful connection with. You can be lonely in a crowded room, in a packed open office, in a 14-person family dinner, in a marriage.

The disease isn't a lack of bodies in your vicinity.

It's a lack of relationships with depth.

Which raises the obvious question: why are so many people short on depth? It's not for lack of opportunity. The average adult crosses paths with thousands of potential connections every year. Coworkers. Neighbors. School parents. People at the gym. The whole internet.

Depth doesn't fail to happen because we run out of candidates. Depth fails to happen at three specific moments. And every one of them is gated by something we don't talk about enough: Courage.

1. Starting is a courage problem.

Every meaningful relationship in your life began with someone — you or them — choosing to break the social ice. Saying hello. Asking the question. Reaching out after the meeting. Sending the "hey, want to grab coffee?" text.

When young men are

That move is small in execution and enormous in nervous system. Because to reach out is to risk rejection. To risk awkwardness. To risk being the person who cared more.

Most people, most of the time, don't make the move. Not because they're unfriendly. Because the cost of looking foolish feels higher than the cost of staying alone.

Multiply that by a population, and you get an epidemic.

2. Deepening is a courage problem.

Once a relationship exists, its depth is a function of one variable: how much truth gets shared.

If two people only talk about sports and the weather, they will know each other for thirty years and still be acquaintances. If they trade something real — a fear, a regret, a thing they've never said out loud — the relationship can move ten years deeper in a single conversation.

But going first requires courage. Vulnerability is the cost of admission to depth. And most adults, once they've collected a few wounds in life, decide quietly that the cost is too high. So they keep their guards up. They stay pleasant. They stay polished. They stay alone.

Brené Brown has spent twenty years saying basically one thing in different ways: vulnerability is what makes connection possible, and most of us are too afraid to do it. The data backs her up. So does my own life.

3. Maintaining is a courage problem.

Every real relationship eventually has friction. A misunderstanding. A hurt feeling. A drifting period. A moment when one person was wrong and the other knows it.

What happens next is what determines whether the relationship survives.

If you have the courage to say I was wrong, I'm sorry, can we talk — the relationship gets stronger. If you don't — if you let it sit, get awkward, become the thing we don't talk about — the relationship slowly suffocates.

Most relationships don't end in a fight. They end in silence. In a "we just drifted" that's actually "neither of us had the courage to address the thing."

Add up enough of those silent endings across a life, and your circle of meaningful relationships shrinks every year.

Put those three together — starting, deepening, maintaining — and we don't just have a loneliness epidemic. We have a courage crisis that's expressing itself in a variety of ways; which includes loneliness.

Half the country isn't lonely because there aren't enough people. They're lonely because the muscles required to connectwith the people who are already there have atrophied. We've outsourced courage to algorithms. We swipe instead of approach. We text instead of call. We ghost instead of close.

Each of those choices is, individually, a small protection from a small risk. Compounded across a culture, it's a society of people who feel surrounded but unknown.

This is why I’m so passionate about building DailyCourage. It’s not about helping people with the big heroic acts of courage, but about helping people develop the willingness to do the slightly hard thing instead of the slightly easier thing. To go first. To be honest. Every day.

Courage is a muscle and every day we have the opportunity to get stronger. If we don’t use it, we’ll lose it. Yes, there’s some discomfort required to grow muscle, but the reward is worth it, because as Anais Nin so eloquently put it:

“Life shrinks or expands in proportion to one’s courage.”

Here's your reflection for the week:

Pick ONE relationship that you’ve been resisting being vulnerable in. There’s something you haven’t shared but know you should. If you or they were to die next week, would you regret not having the conversation with them?

Here's your challenge for the week: Go First

In one conversation this week, share something you'd normally keep to yourself. Not a trauma dump; just a real thing. Something you're scared of, struggling with, or quietly proud of. Whoever goes first sets the depth of the conversation.

With courage,

Jonathan