This June marked eight years since I said “screw it” and jumped into self-employment.

Eight years ago, I ditched my cushy tech job. Dreams of starting my own thing were buzzing around—and, let’s be real, I was dragging a ton of emotional baggage with me. If you'd told me then where I'd end up now, I’d probably have laughed right in your face. Or cried. Probably both.

Before I quit, I’d spent eight years hustling up the ranks from software engineer to engineering manager to product manager. On paper, I was killing it. But in 2016, everything just fell apart.

Burnout knocked me flat. Like, “quit-my-job-with-no-backup-plan” kind of flat. I had enough savings to keep the lights on for a bit, but emotionally? I was a mess.

About a year after walking away, I wrote my first newsletter about making shit that matters (cut me some slack on the writing—it was rough). It was me trying to sort out the craziness—the highs, the lows, and those “what the hell am I doing?” moments you get when you flip your career upside down. People started noticing my writing, but honestly, I had no idea why I was writing or who was even reading it. I was just trying to find something that felt like… me. But man, it took way longer than I'd like to admit to figure that out.

Then I wrote about my burnout. I mostly wrote it for myself—a time capsule to remember where I’d been. But holy crap, did that piece strike a chord. It landed on a few tech news sites, and suddenly tens of thousands of people were reading my story. I was pumped and scared shitless all at once.

But it was the responses that really hit me. Hundreds of emails from folks—maybe even you—sharing their own stories of burnout, career shifts, and the endless struggle to make work, well, work. I read every single one, tried to reply, but it got overwhelming fast. On one hand, it showed me how powerful words can be in connecting people. On the other, it piled on the pressure to keep delivering insightful stuff.

Eventually, the initial buzz wore off, and I found myself stuck. Afraid I couldn’t live up to that one big hit, terrified I had nothing valuable left to say, convinced I was a fraud all along. So, I did what felt easiest: I stopped writing. For years, this newsletter just sat there, a nagging reminder of my fears and insecurities.

But I couldn't just stop working altogether—bills don't pay themselves. So I dove into client work, anything to stay busy and, you know, eat. Mostly odd jobs—a bit of editing here, a blog post there. Nothing too personal, nothing that felt risky. But as I helped more businesses find and tell their stories, something clicked: I was actually pretty good at this. More importantly, I was enjoying it.

Then I hit a turning point that really hammered home what I valued in my work. An agency I'd freelanced for in the past reached out with a massive offer—a six-figure editing deal, starting immediately. It was more money than I'd ever been offered.

But as I dug deeper, I started hearing unsettling things about how they were treating their team—layoffs, dubious practices, the works. My LinkedIn feed blew up with people affected by their shady moves—folks looking for work, reaching out. So there I was: Do I grab the money and ignore the warning signs, or do I do what’s right and walk away?

In the end, I said no. Wasn’t easy—who turns down that kind of cash? But I figured if I was gonna build something that lasts, it had to feel right. People before profits, you know?

Saying no really made me think about the kind of work I wanted to do and who I wanted to do it with. That's when I realised: I wanted to help the folks who actually give a damn—the businesses that care about their people and their customers.

Without really planning to, I started leaning into brand writing. And I know what you're thinking: "Brand what now?" Yeah, I had the same reaction. Basically, I help businesses talk about themselves without putting everyone to sleep.

Every business has a story, but let’s face it—most are terrible at telling it. That's where I step in. I help them figure out not just what to say, but how to say it so it sounds like them. No BS, no cookie-cutter crap. It's about uncovering the real story and telling it in a way people actually care about—not just spouting marketing buzzwords.

Maybe that means coming up with a cool name for a new product, shaping a brand’s "voice," or telling a founder's story so you can’t help but cheer for them. Sometimes it’s about explaining a complex tech product so simply your grandma would get it. But always, always, it's about being real and creating something that resonates with actual people.

The cool part is how it blends all these random skills I’ve accumulated almost by accident. I'm mixing my tech background with my love of writing and tossing in all those hard-earned lessons about what makes people and businesses tick. It's kinda like being a mix of psychologist, storyteller, and business nerd—all mashed together.

Right now, I've got a few things on the go in this space. First off, there's my work at Lede & Kicker. That's my brand writing studio where I help businesses find their authentic voice and craft stories that connect. It's not just about pretty words (though I do love that part)—it's about using those words to make people give a damn.

I'm also gearing up to launch another newsletter called Motormouth. It’s all about helping creatives and marketers be bolder with their words. I’m leaning into a no-nonsense, dry, and direct vibe for that one. Kind of like my own little playground for brand writing. I'm also hoping it’ll kick off chats about the stuff we don't talk about enough in the creative world—burnout, ethics, all that juicy stuff. If that’s your jam, come along for the ride.

Oh, and I'm moving away from the B2B-tech-writing grind to work with local Aussie spots in food, wine, travel—you know, the good stuff. Since moving to Australia for a slower pace of life with my family, this shift just feels... right. Working about 3-5 hours a day on client projects that align with my values has given me the flexibility to spend more time with loved ones and reignited my creativity. These industries have such rich stories to tell, and they actually touch people's everyday lives.

What I love most about brand writing is that it's never just surface-level. To do it well, you have to dig deep—into what makes a business unique, what their customers care about, and where those two things meet. It's about finding that sweet spot where a company's true identity clicks with what their audience is looking for.

This work isn't just about slapping together pretty words or clever slogans. It's about designing change. Helping brands ditch the boring, forgettable, eye-roll-worthy stuff and make something that actually clicks with people. ‘Cause really, that's what it’s all about—creating brands for real folks, not just chasing profits.

And yeah, I get the irony. Here I am, helping businesses find their voice when I spent years too chicken to use my own. But maybe that's why I get it. I know what it's like to feel silenced—by others, by life, by my own fears. I’ve been through it all. Now, it feels like I've finally figured out how to be the real, unfiltered me I always wanted to be, and how to help others do the same.

It’s wild to think eight years ago, I was a burnt-out engineer with no clue what was next. Now? I'm helping others tell their stories. Life's funny like that—the story you think you're writing turns out to be just the first draft of something way better.

Maybe that’s what these Dispatches are really about. I’m not claiming to have all the answers, but I’m up for asking the hard questions out loud. Your stories, your replies—they've shown me we're all in this together, stumbling through our messy, imperfect lives.

Because really, those are the stories that count.