I had one of those life conversations with a friend last week. “Do you know the story of the ant and the grasshopper?” he said. “You guys are the ants, and I’m the grasshopper.”

He meant it about money. My husband and I aren’t working for a pay cheque anymore — we’ve been travelling for months now, going wherever we like — and that ease is exactly what he doesn’t have yet. He was putting himself in the fable as the one left out in the cold.

Here’s who he actually is: talented, more than I could manage myself, honestly. He works long hours. He’s a genuinely good person, with real integrity, gentle and sensitive, creative and artistic, carrying a strong sense of responsibility toward his job, his friends, his family. None of that fits “grasshopper.”

Our freedom, and his lack of it, isn’t a story about one of us working harder and the other one lazing around.

I let him finish. Then I told him he had the wrong bug.

A quick refresher, since the Aesop may be rusty

You know the story. The ant spends the summer hauling food back to her nest, one grain at a time, while the grasshopper, carefree, dances around and plays the fiddle  in the shade and tells the ant to relaz. Well, winter comes. And the ant is warm and fed. The grasshopper is standing in the snow with an empty stomach and a fiddle nobody wants to hear anymore.

Not lazy. Undirected.

My friend wasn’t skipping the work. He never has. If I counted the hours strictly, I’d bet he’s put in more of them than I have. What separated us wasn’t luck, and it wasn’t really the money either, though that’s part of it. In my experience — coaching people, and just living life amongst each other — it’s rarely the amount someone earns that decides this. It’s the relationship we have with money in the first place.

I think of two people I know, doing the same job, one senior to the other in the same department. The senior one earns more. The junior one is the one who becomes financially free. That’s not the exception, in my experience — I could tell you a handful of stories that go the same way.

What my friend didn’t have was the winter he was working toward — a shape to all that effort, an answer to “storing up for what, exactly?”

That’s a different problem than the one the grasshopper/ant fable is telling. The ant isn’t virtuous because she’s busy. She’s envisioned her winter and built toward it. Take away the vision, and the ant is also just out in a field, working just as hard, with nothing waiting for her in November either.

What I told him, more or less

I told him to ask a different question. Not “am I working hard enough?” but “what am I working toward?” And underneath that, more quietly: what would this year, this month, this week look like, if that picture were actually the one I was building toward?

It’s a harder question to sit with. Lazy has a clean fix — you just try harder. It’s harder to admit you’ve been sprinting all along, just toward nothing in particular.

The beauty of a specific dream

My wish for him, and maybe for you too: if you haven’t already, let yourself dream up the picture. What are you actually looking forward to having, one day? For my friend, it’s not having to think about money at all, so he’s free to just make his art.

A wish on its own doesn’t do much, though. I’ve found it needs a year attached to it, or it stays a daydream. I know because that’s what I did — in my early thirties, I picked an age, somewhere around 45, and told myself that’s when I’d be financially free. I got there close enough to call it on schedule. A wish with a number attached becomes something you can actually walk toward, not just something you hope for.

Aesop’s story, I think, is telling us something in both directions: work hard, and work toward a picture. That’s how I read it, anyway.

I still think about him, my creative good friend, working toward a life where the only work left is the art. I wonder what yours looks like.