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How Chrissy Hennessey Grew Her Substack To 2,000 Subscribers With A Full-Time Job


Chrissy Hennessey has a Master’s Degree in Creative Writing, and is the founder of the So Relatable newsletter on Substack that has close to 2,000 subscribers. She’s written three novels and a short story collection–all of which haven’t been published yet–and she works full time as a Manager of Writing and Content Strategy for a company called nCino, a fintech organization based in Wilmington, North Carolina. 

She started So Relatable in 2019 as a safe haven for creatives who want strategies to help them navigate the creative process. Tucked inside her posts, however, are always useful lessons you can take with you to live a healthier, more fulfilling life in general. And her writing is always so fun, funny, hopeful, and down to earth. I hope in this conversation, you'll begin to understand why her writing has captivated nearly 2,000 subscribers over the past five years.

Useful Timestamps

For your listening pleasure, I’ve “bolded” my favorite parts of our interview down below. I feel Chrissy and I really started getting on a roll around the 19 minute mark.

1:19 When Chrissy fell in love with writing
3:43 How Chrissy defeats the comparison game online
5:42 Focusing on your “true fans” helps, too
7:40 Write to your top fans instead of the masses
9:30 Why Chrissy started ‘So Relatable’
12:04 Does writing what you want lead to a bigger impact with audiences?
14:19 How does Chrissy deal with burnout?
16:50 Two hours of reading = One hour of writing
17:35 Write through the white space
18:53 Would Chrissy even want to be a full time Substacker?
25:15 How Chrissy survived “starting small” as a creator
26:52 How Chrissy found the “sweet spot” in her newsletter
29:45 How Chrissy’s book failure led to her best posts
30:48 How Chrissy got through book publishing failures
33:12 If Chrissy never got a book published, would alll this still be worth it for her?
34:41 2 secrets to growing a Substack newsletter
36:51 Two moments Chrissy had a big bump in subscriber growth
39:55 Why “word of mouth” is king on Substack
42:20 Does Substack have higher quality writing than Medium?
45:50 Finding something you love to write about will take you take you far


So Relatable (Chrissy’s newsletter)
Chrissy on Instagram

Here’s links to a few newsletters Chrissy mentioned during the interview:

Nisha’s Internet Tote Bag with

My Sweet Dumb Brain with

Mind Of A Writer
Mind Of A Writer Podcast
A podcast about writing and how to grow on Substack, featuring interviews with Subtack's most popular creators.