Somehow, This Is Working
21 Questions with Jenny Lawson
How do you keep going when your brain won’t cooperate?
That’s the question Jenny Lawson has been answering for years, first on her blog, then in a series of books that combine humor, honesty, and hard-won survival strategies.
Known to many as “the Bloggess,” Lawson has built a devoted following by writing candidly about depression, anxiety, chronic pain, and the absurdity of everyday life. Her books—including Let’s Pretend This Never Happened, Furiously Happy, and Broken (in the best possible way)—have all been instant #1 New York Times bestsellers.
Her new book, How to Be Okay When Nothing Is Okay, gathers more than a hundred of the tools and tricks she relies on to get through hard days, keep creating, and find moments of joy, even when everything feels impossible.
In her Author Insider questionnaire, Jenny gets real about what the writing life actually looks like…
21 Questions with Jenny Lawson
1. I couldn’t have written my last book without…
A cat on my lap. And coconut rum.
2. What’s your most common form of procrastination?
Convincing myself that something else NEEDS to get done first before I can work. My house is never as clean as when I have a deadline.
3. Do you read your reviews?
Never read your own reviews. Have someone you love read them for you and show you the best ones. Have them also honestly but kindly share with you any criticisms that might be valid and fixable.
Bad reviews are inevitable. When I start to doubt that I do read the one-star reviews of my favorite books of all time and remember that you can’t be everything for everyone. I’m not for everyone and that’s how it should be.
4. What’s the first thing you do after you finish a draft?
I send it to my agent and then try to forget that I’ve sent it but inevitably panic and become convinced that she hates me now even though she’s been my agent forever. Then I remind myself that drafts are supposed to be messy and weird and that good editors and agents can see the gold inside all of the sludge.
5. Kiss, marry, kill: podcasts, newsletters, and speaking gigs.
They’re all hard and all fantastic so I would kiss them all and then slap them in the face. And then kiss them again.
6. What’s a writing habit you’re embarrassingly superstitious about?
I avoid anything with the unlucky number in it whenever I can. I’ll change deadlines if I can. It’s ridiculous.
7. What’s something you wish you’d started doing five years ago?
I can’t think of anything. Five-year-ago me was overwhelmed and I’m just proud of her for surviving. I don’t think we always give ourselves enough credit for what we’ve lived through.
8. Where do you find new ideas, and how do you keep track of them?
My brain is full of ridiculous nonsense, and I tend to write ideas down on my phone and then later think, “What the hell did this mean? Who wrote this??” It’s like a psychopath is leaving me notes and that psychopath is me.
9. What’s the best piece of professional advice you’ve ever received?
Whatever way works best for you is the best way. It’s okay to look weird.
10. And the worst?
“If you share these crazy thoughts in your head you’re going to scare people away.”
11. Whose career do you most admire and why?
Judy Blume is a real hero. Not only did I love her books growing up, she’s also a lover of books and of authors. She helped me in real life and she didn’t need to do that. I try to pass that on to others…helping as much as I can.
12. What’s on your nightstand right now?
A cat. And about a dozen books. And my night guard. The book I’m reading right now is The Curse of Hester Gardens. So good.
13. How did you find your agent?
I went to a writing conference about 15 years ago and embarrassed myself in front of a ballroom of people, and instead of seeing an awkward girl fucking things up, she saw an awkward writer fucking things up. Forever grateful she reached out to me. (Thanks, Neeti!)
14. What’s a writing rule you’ve happily broken?
All of them. I love to write run-on sentences or sentence fragments that work in my head (and hopefully readers’ minds) even though they would make my English teachers cringe. I make up words if I can’t find one that fits better. I have a Journalism degree, which was helpful because I was able to recognize all of the rules that I was breaking and sometimes that convinces the powers-that-be to let you do what you want. The rules are just suggestions.
15. What tech tools (AI included) do you actually use—and which ones do you actively ignore?
I am fanatically against AI for all creative endeavors. I’m a bit of a Luddite and easily intimidated by most tech, but there are a few tech tools that I lean on, including this one, which I cover in my upcoming book.
When I’m struggling to put something on an empty page, I’ll go for a long walk, pull up my notes app to transcribe what I’m saying, and then just pretend I’m talking to an imaginary friend and telling them everything I want to write about. I go through the details and go off on tangents, and when I get back to my desk, I have a document I can use to start the work. It’s really helpful.
16. What’s the best non-writing skill that’s helped your writing career?
Embracing whimsy and joy and silliness. I write about very dark things sometimes, but I am not afraid to be ridiculous and weird and unhinged because life is very short and joy is necessary. I think that shows up in my writing and invites others to be silly with me. It’s a gift I give myself.
17. Can you describe your ideal workday?
Ideally, I would wake up at 9 am, write for four hours, and love what I’ve written. Have a taco and pet a cat. Edit that writing. Finish the day pleased with myself and ready to do more tomorrow. Watch The Gilded Age while drawing on the couch with family. Be asleep at 10 pm. I have never experienced this sort of day even once in my life.
18. How does that compare to your actual workday?
A normal workday is more like…I wake up at 3 am. And 6 am. And 9 am. And get caught doomscrolling until 10:30 when I panic. I’m at my desk by 11 am and then convince myself I need lunch. Back at work at 12. Write for an hour. Delete everything. Write for another hour. Edit it. End up with two paragraphs I really like. Watch 90-Day-Fiance while playing a computer game because my cat is on my sketchbook, and I can’t possibly move him to draw. At 11 pm my cat moves and I start drawing and my husband says it’s time to go to bed but I don’t because I’m too into my drawing even though I need to be sleeping and then I have an idea on how to finish the next chapter and rush into my office before I can forget it and then it’s 3 am again.
19. If you could write one book in a totally different genre than you usually do, which would it be?
I LOVE horror. Like, so much that I run a horror book club called Nightmares from Nowhere. One day I’ll try it out myself.
20. What’s something about the writing life that still surprises you?
How it brings us together. How I can hear from people on the other side of the world who are touched by my writing. And how I can be changed by the writing of others. We’re all stories in a way.
21. What is your new book about?
It’s about all the tips and tricks I’ve collected to keep going both mentally and creatively. It’s basically my toolbox of how I’ve lived with depression, anxiety, ADHD, chronic pain, and the assorted bullshit of life and still managed to keep creating. It’s easy to read and ridiculous and weird as hell, but I’m really proud of it.
Bonus: Anything you’d like to ask or crowdsource from fellow authors in the Author Insider community?
One of the reasons this book exists is because I’m forever sharing my tips and tricks and asking other authors for theirs, so I am all ears for any tools that help in writing. Particularly regarding fighting procrastination. I’ve found that often the tip that works for a year or two can lose its oomph so refilling that toolbox is a forever-act of self-care.
Looking forward to your answers!
More from Author Insider
Author Insider is where writers get the real story of publishing—thoughtful conversations with bestselling authors and industry insiders, clear-eyed analysis of where the market is headed, and practical strategies for building a sustainable writing career. Whether you’re just starting out or several books in, the goal is the same: helping you make smarter decisions about your work.
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Until next time,
Panio Gianopoulos
Editorial Director, Author Insider & The Next Big Idea Club
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I love the combination of smart and funny Jenny brought to this and brings to her other writing. This line especially stood out to me (and is much easier said than done): "Five-year-ago me was overwhelmed and I’m just proud of her for surviving. I don’t think we always give ourselves enough credit for what we’ve lived through." And wow do I relate to this real workday schedule, which we don't hear enough about when most online advice is about how to optimize every second of the day.
This book told me about substack. I don't do social media so I didn't have a way to regularly see and hear from her. Her books have helped me. In many many many ways. So I'm so excited to be here and give her six bucks a month. 😁