Oh, Please!
Interview with Malaika Simmons | vol. 010
Welcome to Oh, Please!—where reformed (or at least reforming) people-pleasers spill the tea on learning to live their own lives without apologizing for breathing. Breaking the habit of putting everyone else first is no joke, and I’m eternally grateful to these brave souls for sharing their journey back to sanity right here at DPP. Trust me, you don’t want to miss this series—subscribe and cheer on these heroes as they finally learn to say “no” without a panic attack!
Learning to say “No” is the only way you can create the space to give your full energy and attention to the things that deserve your “Yes.”
-Malaika Simmons
Welcome back to our Author Interview series, Oh, Please!
I am so excited to introduce you to someone whose presence is equal parts grounding and electric — Malaika R. Simmons. She’s the founder of The Writer’s Block Party, and an expert at writing with clarity, confidence, and unapologetic joy.
In this conversation, we talk about the courage it takes to stop people-pleasing, the magic of intentional living, and what it really means to own your story.
Get ready for an honest, energizing, and heart-opening chat with a woman who embodies what it means to show up fully.
About Her:
Malaika Simmons is a former corporate attorney turned writer, committed to storytelling that asks critical questions, seeks truth, and inspires change. After leaving the corporate world to pursue writing, Malaika suffered a life-altering brain injury, which helped bring into focus the importance of prioritizing her passions. She writes women's fiction with an element of suspense, nonfiction essays, and short stories exploring resilience, identity, and personal evolution. Her Substack, The Writer's Block Party (linked below), is a community of critical thinkers, change agents, and truth-tellers who believe both life and literature are cause for celebration.
Welcome to DPP, Malaika! Can you please share when you realized your “yes reflex” was becoming a problem? Where were you, and what was the incident that made you think, “Wait…why am I baking 100 cupcakes for Karen’s third cousins cat’s birthday?”
For me, I don’t think it was one single moment, but rather the accumulation of several incremental steps in the wrong direction over the course of life, and specifically, my career as a corporate lawyer.
As a result, I slid so far out of alignment that I barely recognized myself, running from work to home frantically, unable to get back to baseline, perpetually some version of sick, and sitting trying to play with my kids only to notice, even when I was physically present, I was a million miles away.
Work was draining me, and I felt totally out of sync with my core values. Realizing I was past the point where small corrections could help, I made massive changes in my life, which I’m still in the process of seeing through. But I’m so thankful I made them.
Do you have any Mentors/Gurus/Greek Philosophers who have supported you on your journey? Tell us about them.
My list of mentors and supporters has been exceptionally long. And I’ve been pleasantly surprised to find that the more I step into my purpose, the more support floods me from a host of directions, which includes the insanely encouraging Substack community.
As far as personal values, my mom has always been a phenomenal mentor.
But quite candidly, she knows less about the path toward becoming a writer, so for those insights I’ve built an amazing writing community, which includes my agent, Taj McCoy, a writing mentor, Celestial, and a host of other supportive friends who I trust and rely on to help guide me.
And, of course, I’m always devouring the work of other amazing writers, philosophers, and creatives for inspiration.
How did it feel the first time you said ‘no’ and didn’t follow it up with an apology? Was it like discovering a superpower, or did it make you want to hide under a blanket?
I hated it!
And there were numerous instances where I fell into a bad habit of saying “no” and then walked it back to try to escape the discomfort of standing my ground. Now, it feels more like a superpower, but that “no” muscle was one I took a long time to build. And like any muscle, it shrinks if you don’t consistently use it.
When you feel yourself slipping back into people-pleasing tendencies, what do you do to reset, besides searching Zillow for the cheapest deserted island?
When I’m overwhelmed or sense myself sliding to a place I don’t like, I tend to withdraw at least initially. Pulling back allows me time to reflect, reset, and strategize in developing a path forward.
But I’ll be honest, if you checked my browser history, you’d almost certainly find searches for a faraway beach hut.
Since you stopped being an expert “yes-person,” what’s been your biggest self-care indulgence (and how much do you love it)?
Massages have always been the way to my heart. I love them and make a point of getting them pretty regularly.
The other thing I did for the first time recently, which was totally trippy, was floating in a sensory deprivation chamber. A couple of friends gave it to me as a gift, and I loved it. It’s certainly not for everyone, but if the idea intrigues you, try it. I’m told it’s a powerful tool, especially for writers and creative types.
If you could give one piece of advice to fellow recovering people pleasers, what would it be (besides faking bad cell reception)?
Learning to say “no” is the only way you can create the space to give your full energy and attention to the things that deserve your “yes.”
RAPID FIRE ROUND:
Kryptonite. What (or who) is yours when it comes to pleasing?
Opportunities with potential prestige attached get me every time. Think: corporate speaking engagements or conference presentations. Things like that pull me back toward my old life and always feel easier to justify than I want them to or then they should. I guess old habits die hard.
Do you have a favorite Book or TV Show/Film?
The Alchemist! (Note from Kaylen: I too, LOVE this book!!)
What is the best advice you have ever received?
“Leap, and the net will appear.”
It’s not advice per se, but the concept has always felt both powerful and empowering to me. It’s on us to take the first step. Then and only then will life, God, the universe, etc. open our circumstances in service of our dreams.
Where can we find you and your work from here?
I’m in love with Substack, so you can find me here at The Writer’s Block Party. I’m also on IG and Bluesky (both searchable as Malaika R. Simmons). I’m working to get my first novel published and am currently drafting my second, so stay tuned for details on those.
As much as I’m a passionate creative, I also pride myself on building community, so I also host several writing groups and events. Malaikarsimmons.com has all the details!
And I love an individual message, so please reach out! We’re all in this together.
Thank you for connecting with us here at DPP, Malaika! Excited for your novel to be published- keep us updated!
May we all start to say “No” to the small things, and lean into “Yes” for the big TRUE things,
K. Alexandra
🐣 P.S. RECOVERING PEOPLE-PLEASERS: If you have walked through fire and have tips to share with the rest of us, I would LOVE to interview you! Please submit your contact information (safely) here: Interview Me! 🐞
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In love with the work you’re doing, K. Alexandra. In a time when too many are sharing their highlight reels, you’re pushing people to dig deep and share struggles. And we’re all better for it.
It’s a pleasure to work with you. And it’s even better to know you and have you as a friend. Our community and my writer life is made better by people like you who thoughtfully and lovingly push us all to create something real. 🖤✨
"That 'no' muscle was one I took a long time to build. And like any muscle, it shrinks if you don’t consistently use it." SO GOOD