Writing Through Heartbreak, Finding Voice in Vulnerability

Want to grow your Substack community? Matt shares hard-earned wisdom from building a global readership, one honest sentence at a time.

Welcome. We’ve saved you a seat under the Palm Tree. This week I discuss writing, mindfulness, and the creative process with

Matt Lillywhite 🇬🇧

of Writing Wednesdays.

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Olu: Welcome Matt, to Writing Under the Palm Tree. I love how you keep it real about the process of writing. Your work is vulnerable while maintaining a sense of direction.

Revealing your writing voice

Olu: Your writing has a distinct feeling of propulsion that brings the reader along as you drive toward your point.

My first question is, how did you develop your voice? Is there a pivotal memory or set of pivotal memories that come to mind?

Matt: Thank you so much for having me, and I appreciate the kind words. I used to write short stories all the time, even if they were just scribbled-down daydreams in notebooks. I’d invent worlds, characters, and scenarios that were sometimes based on reality, but more often than not, they were just my way of processing my feelings. I think that’s where the beginnings of my voice came from. Writing to make sense of things that didn’t always make sense.

Olu: What brought you to Substack? Do you feel there is something unique about this space?

Matt: I’ve been a full-time writer on Medium for six years. Almost seven. Built a following of over 45,000 people, and I’ve been able to travel the world thanks to writing. But I joined Substack because I heard so many amazing things about the community and wanted to be a part of it.

Every day, I check my notifications and see long, thoughtful comments from people who said my work made them feel seen. If that’s not a reason to get up every day and write, I don’t know what is.

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From Invisible to Unshakable: How to Stop Feeling Like You Don’t Matter

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Writing through heartbreak

Olu: Have you experienced deep heartbreak when it comes to your writing? How did you process it? How did you grow from that experience?

Matt: My mom had cancer a few years ago. I remember coming home, holding her hand, and telling her everything was going to be okay. I didn’t know if it was true, of course. But I wanted to be strong. For both her and my family.

Writing was my way of processing everything. Of making sense of the world, so to speak. Each evening, when she was asleep, I’d write in my journal about everything that was on my mind. And even though I couldn’t say much of it out loud, I felt like I could confide in someone, even if it was actually a pen and paper.

Create shared value first; community will follow

Olu: You are creating a special space here on Substack. You’ve welcomed thousands of new Substackers into your community. As of this publication, you have close to 8k subscribers. Major congrats on that. What’s been your philosophy or mindset when promoting your writing and making meaningful connections here on Substack?

Matt: The biggest thing is always giving more value than I receive. For example, I want to make sure I go into every interaction with the mindset of helping someone as much as possible. Sometimes, it’s answering a philosophical question about finding their voice.

Other times, it’s something more practical, such as getting more engagement on Substack notes, or increasing the number of subscribers. Ultimately, I’ve noticed that when I provide value to the Substack community (without expectation), people often want to engage and read my content, as well.

Olu: What are the core things you try and do each week to build community here on Substack? How do you maintain a healthy proportion so you don’t burn out?

Matt: It really varies week to week. I try to be as active as I can in my private community for paid subscribers. That often involves answering questions, providing insights, etc.

I also write 10-15 notes per workday as a means of testing the waters. Basically, if I have an idea for a future newsletter, I’ll write down the central point in 5-6 lines and see the response.

If a note performs well, it goes in the pile of newsletters to write in the near future (as I just expand on the idea and make it a long-form article). If it doesn’t, I take it as a sign that a specific topic or perspective might not be as useful to my community as others.

Words to thrive by

Olu: Thank you for talking with me and sharing your experience and writing process with the Palm Tree community. I have to say, encouraging, collaborative voices like yours are part of what makes Substack unique and vital. It's tradition here to conclude with a quote or proverb that resonates with you. Is there one you’d like to share?

Matt: There’s a quote by Ryan Holiday which I live by. “Wherever we are, whatever we're doing, and wherever we are going, we owe it to ourselves, to our art, to the world to do it well."

That applies to everything in life, whether it’s writing, relationships, or even something as simple as treating servers with kindness in a restaurant. Wherever I am, I try to be a good person, and the rest falls into place.

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What is one thing you want to do to be more creatively daring?

Share your thoughts below. Your words may be what someone needs to hear to take that life-changing, routine-shifting, career-changing next step.

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When I hear that quote, this comes to mind. Whatever lights you up in the place where you are, pursue it bravely, pursue it with daring, pursue it like this is the only life, the only time, and the only space you have to do so. Take a risk, and leave no room for regret. Your art is worth it.

In solidarity,

Olu

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