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Living deliberately

When were you happiest?

It’s the kind of question that shows up late at night, often uninvited. Maybe after a long day, a tough week, or one of those slightly-too-honest catch-ups with an old friend. And the answers come in all shapes.

Some people default to the past. They’ll say: school, definitely. Or university. Those long, hot summers. The sense of possibility. A time when the biggest decision was whether to go out again or actually study. Life hadn’t started yet, and that somehow made it feel more full.

Others swear by the present. Right now, they'll say. Because everything they’ve done: the mess, the risks, the lessons. It's all led them here. And that has to count for something, right?

Both of these answers sound reasonable.

Both of them can feel true.

And both, if you look closely, are wrong.

The Illusion of a Peak

We tend to imagine happiness like a mountain. There’s a high point. Somewhere.

We either haven’t reached it yet, or we hit it years ago and didn’t realise until we were on the way back down.

This is a dangerous metaphor.

If you think your happiest moment is still ahead of you, you’re always chasing. Always thinking the real thing is just around the corner. One promotion away. The next relationship. The next job.

You end up living in the “almost.” The prelude. Happiness becomes a moving target. One that keeps shifting just as you get close.

But if you think your happiest moment is behind you, that’s no better.

Nostalgia starts to turn into grief. You stop seeing possibility in the present. You start treating your own life like a story that’s already been written. That’s even more dangerous.

So I think we need a different way to look at happiness.

The Myth of Constant Joy

Here’s the first truth I’ve had to learn (and relearn): happiness is not a permanent state.

It’s not something you achieve, and then live in, like a well-decorated house.

It’s fleeting. Intermittent. Often subtle. Sometimes loud. It doesn’t arrive with a bang.

Sometimes it doesn’t even feel like happiness at the time. It just feels like presence. Or peace. Or being so absorbed in something that you forget to check your phone, for a minute or two...

And those moments happen at every stage of life, not just in your highlight reel.

I’ve had deeply happy moments whilst sitting in traffic. While unloading the dishwasher. While walking back from the gym, tired but proud. They don’t look like much from the outside. But they’re real. And they count.

Which brings me to a second truth.

The Happiness of Becoming

There’s a very specific kind of happiness that doesn’t get talked about enough: the joy of not being there, but heading in the right direction.

That middle bit, the stretch between where you were and where you’re going, is full of tension. But it’s also full of energy and progress. It's full of tiny wins.

Think back to any time you felt like you were really growing. Learning something hard or building something new. Those times often felt stressful, even chaotic. But they were also intensely meaningful. And in hindsight? Pretty happy.

So maybe we need to stop equating happiness with comfort. Or with certainty. Sometimes, being in it is where the good stuff is.

Nostalgia Isn’t the Enemy

Now, let’s talk about nostalgia.

It gets a bad rap. We’re told to live in the present. To stop romanticising the past. And there’s truth to that. Living in the rear-view mirror can rob the present of colour.

But nostalgia isn’t foolish. It’s informative. It shows us what mattered. The times you look back on fondly? They leave clues. Maybe it wasn’t the setting, but the people. The energy. The sense of openness. The freedom to fail without consequence.

That doesn’t mean you should try to recreate those exact conditions. You’re not that person anymore, and the world’s not the same either. But you can take the essence of what made those years feel rich and inject it into your now.

Maybe that’s the real use of nostalgia. Don't idealise the past, but learn from it.

So, What Is Happiness?

After all this, I still don’t have a clean definition for you (sorry). But I’m less convinced that I need one.

What I’ve come to believe is this: happiness is not one thing. It’s a collection of moments. A rhythm. A feeling that you’re living in alignment, even if just briefly, with what matters to you.

Sometimes it’s loud and joyful. Sometimes it’s quiet and still. Sometimes it doesn’t look like happiness until much later.

And maybe most importantly, it changes. What made you happy at 20 might bore you at 35. What terrified you then might calm you now. That’s not a problem. That’s growth.

The Happiest Times Are Not Always Obvious

I think we underestimate how often we’re happy without noticing. We assume it should feel bigger. Brighter. More cinematic.

But most of the happiest people I know don’t walk around beaming all day. They just know how to notice the small stuff. The moments in between. They don’t wait for the perfect conditions. They build little rituals that make space for joy.

And they don’t treat happiness like a final destination. They treat it like a companion. One that comes and goes, but always leaves something behind.

What To Do With All This?!?

If you’re wondering whether your best days are behind you or still to come, here’s my take: that’s the wrong question.

The better one is: how do I create more conditions for happiness today?

Not big, sweeping changes. Just small shifts. Here’s where I’d start:

  • Notice patterns: Think of three moments this month when you felt happy (even briefly). What do they have in common? Time of day? People? Activities? Repeat them.
  • Rethink nostalgia: Choose a period you idealise. Write down what you loved about it and what you didn’t. Then look for ways to bring some of the good stuff back, without pretending life hasn’t changed.
  • Make space: Happiness needs room to show up. That might mean saying no more often. Or turning your phone off for an hour. Or making time for things that don’t have a productivity angle.
  • Redefine the question: Instead of asking “Am I happy?” try “When was the last time I felt happy?” or “What would make me feel more like that this week?”

Because happiness isn’t a point on a timeline. It’s not a prize for getting everything right. It’s a practice. It's the art of noticing. It's a choice, to be made over and over again.

And the good news? You can start today. Right now.

Until next time,

Jon "Clap along if you feel like happiness is the truth" Kaye

Finding meaning in Moments

P.S. Shared experiences can give you joy. Phone a friend. Meet up in real life. Make sure to notice someone. Anyone. Share the joy. Spread the love.

Original newsletter disclosures

DISCLAIMERS & DISCLOSURES This content is for education and entertainment purposes only. Jon does not provide tax or investment advice. The information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. Past performance is not indicative of future results. All investing involves risk, including the possible loss of principal.