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Cassidy Williams: Learning to negotiate like a pro

Cassidy Williams: Learning to negotiate like a pro

Cassidy Williams is the Head of Developer Experience & Education at Remote, as well as a self-described meme-maker on the web.

In Part II of our deep dive with Cassidy, we unpack her top three learnings from polyworking: including valuing her work product, asking for help to negotiate, and staying curious along the way.

Let's get into it.

1) Never undervalue yourself

I didn’t realize I was undervaluing myself for a long time. I would say, “Whoa, I’m making $100 every month on this,” or, “Wow, they’re gonna pay me $50 to speak at this conference.”

Then I spoke to other people who also had newsletters and livestreams. I realized that, even though we produced about the same kind and quality of content, their checks had way more zeros on them than mine did.

Another time I told someone how much I charged for conference appearances, which didn’t include travel and lodging costs — and she essentially yelled at me over my Twitter DMs.

So I said, “Wow. I don’t know what I’m doing. I’ve just been working in my silo.” I didn’t know how much I could get paid for the longest time because I didn’t ask.

2) Ask for what you want

Eventually, I also realized you could get other folks who do understand your worth to negotiate on your behalf. It felt unbelievable when I first heard about it.

  • One of my friends had her partner negotiate her job offer on her behalf over email. She got paid about $70,000 more than she’d anticipated.
  • When a friend of mine negotiated on my behalf for a newsletter sponsorship, I received more money than I ever had for a newsletter before.

To this day, it can be so difficult to negotiate for myself. I thought about how it might be cool to have groups of people negotiate on each other’s behalf… then I realized I invented unions.

3) Always ask questions

Maybe the common thread is that I’d tell younger Cassidy to just ask for advice from so many more people. It does not require a full mentor-mentee relationship to ask a question. The worst they can do is say no, or ghost you.

But the best thing they can do is give life-changing advice within a few minutes of their time, or if you’re speaking to a company, they can supplement really helpful income. It’s obviously easier said than done.

But every time I’ve asked questions of anyone who’s further ahead in some aspect — maybe they’re more consistent or confident in their content, or they’ve made X amount of dollars from teaching, or they’ve written a book — I’ve been able to gain something.