- Writing newsletters, including her personal weekly that just hit its 5th year anniversary
- Advising and angel investing in developer and productivity-focused teams, namely Contenda, Centered, Netlify, and Polywork
- Producing content for developers across livestreams, podcasts, TikTok, and more
We sat down with Cassidy to dive into how she’s designed, scaled, and monetized her content engine throughout the years — as well the pressures and fulfillment that come with it.
What Are You Polyworking On?
The brief answer is: “Well, I make memes and code on occasion.”
If someone asks for more detail, I’ll say:
- I’m a software engineer. At my day job, I’m the Head of Developer Experience and Education at Remote.
- But I’m also a startup advisor and investor.
- I create content across platforms and mediums to help people learn to code.
Making jokes on the Internet is obviously not my main line of work, but it’s become almost equally important — it’s what people recognize me for.
On the other hand, I’ve been working with developers for years and years. I love doing it. So I pitch myself as a developer experience expert.
That combination of silly and serious is how most folks have come to know who I am.
When Do You Polywork?
My workflows have changed a ton throughout my career.
But I’ll say that I enjoy my current day job at Remote because we’re a pretty asynchronous company. That means very few meetings and much more space in my calendar for actually producing more work.
These days, the consistent parts of my schedule look like:
- Mondays – Dive into my to-do list, whether for Remote or other content creation, with a ton of flow time
- Tuesdays & Thursdays — Speak on the Stack Overflow podcast
- Wednesdays — Meet with my manager and write the Stack Overflow newsletter
- Thursdays — Livestream for about two hours
- Saturdays & Sundays — Write my weekly newsletter
I’ve also been able to work out certain systems, like for the Stack Overflow newsletter:
- I begin prepping to write on Monday, just by gathering links and notes.
- Once Wednesday comes, I can bang out the writing, ship it, and be done.
For my personal newsletter, it used to take me a solid eight hours to write it — but having preparative systems in place means I spend less than two hours writing each newsletter these days.
I’ve gotten far better at the time management element of polyworking.
And I’m way less stressed at the end of the day, which frees up time and mental energy for just having fun.
When Do You Step Back From Creating?
The tough thing about building up this consistency is usually something that sounds silly — like wanting to go on a vacation.
If you’re accountable to other people, whether that’s your readership or the company you create for, you never want to miss a beat or unplug.
- With my weekly newsletter, not only do folks look for it every week — they’ll also start sending messages if I upload it even three hours late.
- With my livestreams, I get messages saying, “It’s not a real Thursday if you’re not streaming. So will you be streaming today?” And if I won’t be, I have to make sure I announce why and explain myself.
I appreciate it, but it creates an element of pressure.
Of course, I could take more breaks. I also don’t mind, though, because I know it provides value to people.
From day one, the most important thing for me has been knowing that the content will probably be useful or instructive to at least one person.
So that’s one thing about content creation: I do it for fun and maybe an extra buck here and there, but I’m not truly reliant on it for income on purpose.
My situation is not like consultants and freelancers who have to go through calculating, like, “How do I book time off? Every week I take off is a week without income.”
Luckily, I don’t feel that deep reliance — but I do feel the pressure of folks relying on me.
So that’s probably the biggest question for me lately: If I took an entire month off someday, which I don’t see happening soon, would I just stop the whole content machine?
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