37: Jenny Blake's Non-Linear Writing Process: On Books, Blogs, & Substack
Explore Jenny Blake's journey as an author, speaker, and strategist, covering her writing process, books, and insights on navigating a creative career.
" I cannot imagine not writing another book because it is such a soul project and it is just one of the artifacts in the world that gives me life every day, physical books. And I want to contribute to that, no matter what the math says on paper." Jenny Blake
Some fun numbers for you on today's podcast guest:
27 nos and one yes, which is all Jenny needed to land a publishing deal.
200,000 words written on Substack in 2 years, showing an impressive commitment to her curiosity and craft.
15 minutes a day was all it took to build the momentum needed to write her first book.
You'll hear more numbers in today's episode. What these show me is someone who cares.
When a friend sent me a Voxer message one day, "You HAVE to follow Jenny Blake! I think you'll love her."
One long, deep, and winding rabbit hole later, I devoured her book, Free Time (her third), binged podcast episodes, and signed up for her newsletter. Just one newsletter in, and I felt such a connection with her that I asked to be on her Free Time podcast.
Perhaps a little forward (we just met!), but I knew she was a kindred spirit, and I wanted to be in the virtual room with her.
Spoiler, she said yes (find my interview with her below).
Some key takeaways from our coffee and salty almond butter-fueled chat:
Writing prompts on Jenny's old Apple computer as a kid sparked a deep love for following a story seed.
Post-It notes or Kanban boards in Notion support her non-linear, yet tactile writing process — and she took a different approach for each of her three books:
Life After College (first book): Started as a blog, written with short tips, quotes, and questions, like "Twitter meets What Color Is Your Parachute?".
Pivot: The Only Move That Matters Is Your Next One (second book): Developed while self-employed and short on money, requiring her to balance writing with running her business.
Free Time: Lose the Busywork (third book): Written during the pandemic, allowing for a dedicated five-month period of focused writing.
Daily writing habits — think just 15 minutes a day can give you huge progress with your writing projects
in the personal essay genre, you're not supposed to be an expert,
That challenging moment when finishing a book and shifting your focus to marketing
Insights into why Jenny runs a social media-free business
The evolution of her Substack publications, like "Rolling in Doh," focuses on personal essays and the "stickier sides of self-employment"
How writing from the "wound" rather than the scar can be a nurturing way to explore issues, challenges, and life experiences without needing to wrap up the lessons in a tidy little bow for readers.
If you've got a blog, memoir, or business book on your heart, enjoy this episode!
Timestamps:
00:00 Introduction to Guest: Jenny Blake
02:15 Early Writing Memories and Inspirations
04:23 The Role of Books and Memoir Writing
08:56 Navigating Personal Essays and Vulnerability
17:56 The Fascination with Elizabeth Gilbert's Memoir
22:10 Writing Process and Inspiration for each of Jenny’s Three Books
33:47 The Power of Small, Daily Writing Habits
36:01 The End of NaNoWriMo
39:08 Challenges in Book Writing
42:20 Social Media and Book Publishing
48:26 Substack and Subscription Fatigue
52:51 Exploring Personal Essays
54:00 Current Writing Projects
01:01:42 Writing Rituals and Final Thoughts
About Jenny Blake:
Jenny Blake runs a Delightfully Tiny media and IP licensing company. She loves helping people set their time free through smarter systems, and is the author of three award-winning books: Free Time: Lose the Busywork, Love Your Business for leaders and small business owners; Pivot: The Only Move That Matters Is Your Next One high net growth individuals navigating what’s next; and Life After College, a portable life coach for twenty-somethings. For nine years, she hosted two podcasts with over two million downloads combined. Jenny also publishes personal essays about the stickier sides of self-employment at Rolling in Doh, a 2024 featured Substack publication.
Connect with Jenny Blake:
Jenny’s website: https://jennyblake.nyc/
Jenny's Books:
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