🎲 You can't win if you don't play

Welcome to the Freaking Nomads Newsletter, your weekly dose of stories, insights, tools, and opportunities for digital nomads and remote workers building a life without borders.

Hey Freaking Nomads,

A few months ago, while I was still in Oman, I saw an open call for a photography contest. The theme was life in the Middle East. Submit your best shots, a small prize, some exposure.

I had photos. Actual good ones, from markets, from the coast, from that strange golden light Oman does right before sunset.

My first thought wasn't yes. It was who am I to enter this.

I'm not a photographer. I take pictures on my old and half-broken phone. Real photographers submit to things like this.

So I sat on it for three days. Photos picked, never sent.

Then I thought about how many opportunities I've skipped exactly like this. Not because I got rejected. Because I never even tried.

I hit send at midnight, mostly to stop thinking about it.

I won.

I still can't fully explain how. But that's not really the point of this newsletter.

The point is: I almost didn't play.

And I think that's true for so much more than photography contests.

It's the sponsor you don't pitch because they'll probably say no anyway. The city you don't move to because what if you hate it. The person you don't message because it's been too long and it'll be weird now. The idea sitting in your notes app because it's easier to imagine it working than to test it.

Rejection has an ending. You know exactly where you stand. Not trying doesn't. That one just sits there. Forever unresolved. Forever maybe.

I used to think I was being careful. Now I think I was just protecting myself from a no I hadn't even earned yet.

Five years ago, I left a stable job in London with zero freelance experience and no plan beyond let's see. That decision terrifies me more in hindsight than it did in the moment, mostly because I know now how badly it could've gone.

But it didn't. And the only way I found that out was by playing.

So here's my actual question for you this week: what have you not applied for, pitched, messaged, or tried, purely because you assumed the answer was already no?

Hit reply. I want to know what you're sitting on.

Until next week,

Irene

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Who is hiring this week? Here are some top roles to check out:

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