Freelance freedom’s cute until…


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Hi Reader,

This past weekend was a long one here in Canada, and honestly? It was a great one.

I went to a friend’s wedding, deep-cleaned my apartment, and went on a few long, sunny walks with my fiancé.

But returning to work mode reminded me of how blurry time can feel when you’re self-employed.

Without a regular 9–5 rhythm, holidays, weekdays, and weekends start to blend together. And that made me think about how easy it is to confuse freedom with flow.

There’s an idea ingrained in freelance culture that freedom is the ultimate goal.

If you can work from anywhere and set your own hours, you’ve made it. Even if you’re highkey stressed and quietly spiralling.

But the truth is, freedom without structure turns into chaos real fast.

That hit me while reading the book 4,000 Weeks a few years ago.

The author, Oliver Burkeman, discusses how pursuing total time freedom can make you more anxious, rather than less.

Because yes, you can do whatever you want.

But what do you do first?

What do you do when you’re tired?

What do you do when nobody’s watching or expecting anything from you?

For me, the answer’s been simple (but not always easy): routines.

Not rigid ones. But soft structures that give my days a bit of shape.

Like front-loading my days and weeks with high-focus work. Hosting coworking focus sprints so I’m not relying on willpower alone. And most recently, creating monthly messaging themes to reduce the “what should I post today?” spiral.

If freedom is the dream, I’ve found that structure is the scaffolding that holds it up.

Of course, what works for me may not work for you.

But if you’re a creative with a flexible schedule, consider adding an ‘anchor’ to your week.

It could be soft time blocks. A daily walk. A “no meetings” morning.

Nothing fancy. Just something steady.

A little structure goes a long way.

‘Til next time!

Big (virtual) hugs,


✨ What’s happening inside The Reach

Our Unmute Yourself visibility challenge is still going strong. Last week was all about turning ideas into content, and members delivered! Two members revived their newsletters, and another scheduled three LinkedIn posts and kicked off a new content series. 👏🏾👏🏾👏🏾
This week's theme is "Set It and Forget It," and it's all about batching and scheduling.
P.S. Speaking of content creation, I’m looking for a visual content partner to help bring The Reach’s social channels to life. Apply here—the deadline is May 22.
P.P.S. Feeling the Unmute Yourself FOMO? Start your trial today and catch the last two weeks of the challenge.

💡What I'm loving right now

Contracts Market Spring Sale!* If “sort out my contracts” has been on your to-do list forever, now’s the time to cross it off. Now until May 20–27, you can save:

👉🏾 30% off all templates
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Fun fact: The founder, Jaime, is a past client turned good friend, and I’ve been a longtime fan and customer. I use their Client Services Agreement for every new consulting project, and it has saved me from SO many messy client situations.

👩🏾‍💻 Your website copy should work as hard as you do.

If it still sounds like version 1 of your biz, you’re probably overdue for a messaging refresh.
I’m booking spring/summer Content Strategy Intensives (for folks who want clarity and a plan) and full website copy projects (for when you’re ready to hand it off completely).
Book a call and let’s make sure your words match the work you’re doing now.

1719 Lawrence Ave E, Scarborough, ON M1R 2X7
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Jasmine Williams Media is a company that was founded and primarily operates within the ancestral, traditional and unceded territories of many nations, including the Mississaugas of the Credit, the Anishnabeg, the Chippewa, the Haudenosaunee and the Wendat peoples, also known as Toronto, Canada. This land is now home to many diverse First Nations, Inuit and Métis peoples.

Freelance Curious

Freelance freedom doesn’t have to mean chaos. Join 1,500+ creatives getting honest stories and strategies for building a more structured, sustainable business—that still feels like you—every Tuesday night.

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