The Remarkable Fools Letter

The Remarkable Fools Letter

How I stopped worrying and learned to love the lotto

A fool’s guide to financial independence through unemployment

Jim Dalling's avatar
Jim Dalling
Jan 25, 2026
∙ Paid

Unemployment is a weird kind of freedom. It’s kinda like a snow day until you remember: oh shit, I still gotta shovel the driveway.

The relief of unemployment comes with the panic of will the next plan work out?

A guy can lose a lotta sleep worrying about his financial stability.

That’s why I decided to take action.

I went out on a walk to buy a lottery ticket.

Normally, I wouldn’t buy a lottery ticket, but for Christmas, Laura gave me a scratch and win ticket.

It was a $20 ticket, you know, the deluxe kind.

But from that $20 ticket, I won $50.

Well done eh?

A more responsible person might consider this win good enough. They would use this windfall to cover a bill. I used it to buy ten weeks of hope. Ten tickets for ten draws, ten weeks in a row.

In leaving a job though, I’m left dreaming:

What do I have?

What do I need?

What can I get?

What am I gonna do with this?

An outta work fool has neither money nor structure.

That’s a bit of a problem.

But right now, I’m enjoying a wealth of time - a wealth …

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