What ChatGPT told me about my writing style

And what we can learn about brand voice.

Maybe you’ve heard about my newsletter, it’s been called “addicting,” “rave-worthy” and “one of the best newsletters out there,” and as of today, we’re only 30 weeks in.

My newsletter STILL boasts an average 70% open rate, week after week.

My subject lines sound something like this:

  • I’m Here So I Won’t Get Fined
  • “Do you think I need to get him to break up with me again?”
  • Soulmate Critera

It gets silly, personal, vulnerable, and if you’re not already 10,000% clear on this; it’s about connection rather than sales.

As I’ve started writing more and more copy for clients, and defining their brand voices, I went to the internet’s wizard (the modern “Ask Jeeves”) to analyze my writing style.

First, I opened up an email that I sent earlier in the day, and copied the “professional summary” section. The email was for a podcast pitch, and this is what I included.

Resume-adjacent things you *might* want to know:

1. My first internship: While studying abroad summer after my freshman year of college, I stole a pair of office keys, arrived first thing in the morning to make coffee in the office, and started calling myself an intern. The next summer I was offered said internship and I did make coffee + dozens of other things.

2. My first big-girl job: After interning with the company for 2 years, I moved to Costa Rica for the summer 48 hours after college graduation. I worked there for 4 years full time, beginning as “Assistant Program Manager” and ending at “Strategic Initiatives Assistant & Marketing Manager.” AKA brand manager for 3 brands, managing 2 websites, marketing materials, recruiting, hiring processes for a fellowship that I launched, and managing my own sales portfolio.

3. I wanted health insurance: After 4 amazing years (7 total), I needed a bit more regularity and structure (as well as to move back to Seattle) so I got a job as Executive Coordinator to the VP of University Advancement, at Seattle University. It was a culture shock. And, incredibly fun. I was called a tyrant on multiple occasions (which I am told is a good thing), managed a hiring process for the executive team, saw my first “org chart” and learned that I was the 3rd highest ranking EA on campus.Oh, and got health insurance.

4. Accidentally moved to Los Angeles: One of my best friends had a room open up in her beloved apartment, and when I came down to visit, I landed a job interview…and then the job. After working in hospitality and facilities management for 10 months, I can tell you, I am not built to be front-facing 40 hours per week. I moved a lot of furniture on the days that I was feeling introverted.

5. Ruby Works was born:

After doing a few websites on the side, or on “sick” days, I took this gig full time. It’s been a wonderful, scary, eye-opening time of personal development and growth. I’m really happy here, and it’s hard.

Then I asked ChatGPT the following prompt:
Please analyze the following writing sample and tell me about the author’s writing style.

Here is what little miss GPT had to say:

The author’s writing style is refreshingly candid and full of personal anecdotes. They communicate their professional journey in a casual, almost storytelling manner, which makes their experiences engaging to read. They transitioned from a self-proclaimed intern to diverse roles of increasing responsibility, displaying adaptability and resilience. Their move towards entrepreneurship with Ruby Works reflects an entrepreneurial spirit and a willingness to embrace challenges for personal growth. The narrative is marked by humor, self-reflection, and a non-linear career path.


I’ve done this before with my newsletters and gotten similar results. I will specifically take newsletters or Instagram captions that do really well (i.e. lots of engagement) and ask ChatGPT to concisely analyze the writing style, tone, and voice.

What we learn from doing this:

Because writing about yourself is nearly impossible, or at least hard to do without cringing; it’s incredibly helpful to have AI tell you about yourself. It allows you to see your writing from a different vantage point.

Then consider the following:

  • Is what ChatGPT is saying how I want to be perceived?
  • Is this style what resonates with my client base/audience?
  • Do I like the traits associated with this voice/tone?
  • Are there different emotions that I want to evoke?

How to Implement:
Take a moment (or use the audience development worksheet in my website copy template) and get clear on how your want your brand and business to be perceived. Then, take an existing writing sample (or 7, like I’ve done), and give ChatGPT a holler.

Then, please tell me what you come up with! Lessons, changes, and how spot on (or cringe) ChatGPT analyzed you.

If you want strategy or copy help, reach out! I offer 90 min strategy sessions where we can take a look at your branding, website or copywriting. Anything goes, but… not in a weird way.

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