I've been writing professionally for sixteen years (which qualifies me as an original gangster of self-publishing), operating nine pen names across fiction and nonfiction that generate consistent income. I specialize in image marketing under my own name, teaching people how to make their content, books, and marketingvisually compelling in a world drowning in poorly designed everything.

I love talking about email marketing, Pinterest, book covers and formatting, and storytelling—you could call them my passion topics. And once you get to know my background, you'll understand why I may have some solid opinions and takes on marketing in these areas for indie authors, because I've been at this game since before most people knew self-publishing was a viable option.

But this podcast isn't about me flexing my credentials. It's about calling out the fuckery in several creative spaces and what it is to live the life of a writer—the myths, the bad advice, the realities vs. fantasy, and the bullshit that keeps writers spinning their wheels instead of building sustainable careers.

Every episode, we're going to dig into what actually works versus what we're told should work. No sugar-coating, no feel-good platitudes, just honest talk about the realities of creative work from someone who's survived spectacular failures and built something that pays the bills.

Today, we're starting with my own journey because it's a perfect example of how everything you think you know about writing careers is probably wrong. And if you're struggling with your writing, wondering if you're cut out for this, or feeling like you're spinning your wheels—this one's for you.

I’m an original gangster in self-publishing, dating back to 2007. So you could say… I’ve seen some things and have watched this industry evolve and grow.

Writing careers often don't follow neat trajectories, and mine is proof. Sixteen years ago, I published my first fiction title to complete silence. I was newly single from a divorce (no kids, he was a Republican—need I say more?), and was free to unleash my 28-year-old self into the Carrie Bradshaw kind of life.

I still worked a corporate job (sucked balls), and to get a promotion, I signed a non-compete (terrible idea) with a bridal stationer. I would write at night and sometimes during scheduled “meetings” with myself during the workday. I hated my job.

I started writing in 2005 as an outlet while I was traveling a lot for work. It was often lonely, sitting in hotel rooms and airports for extended periods of time. Writing kept me entertained. Who knew it would eventually lead to where I am now?

Let’s just say I’ve had a wild ride in publishing. We’ll get to that.

A humble beginning. Nothing amounting to overnight success or an outlier. Years later fast forward to today, I run nine pen names across fiction and nonfiction plus my own name (nonfiction) that generate consistent income.

So there’s hope for you!

What happened in between taught me everything about what actually works in this business versus what we're told should work.

Here's what I wish someone had told me when I was starting out, and what I've learned from both spectacular failures and unexpected wins.

Your First Book Will Probably Suck (And That's Fine)

By 2007, I had spent two years writing my first novel with nothing but technical writing experience and dangerous levels of romance book intake. No budget, no understanding of structured storytelling or how to properly outline a romance novel; just pure determination and delusion.

The result? Silence. Complete, devastating silence when I published in June 2007.

Here's what I learned: Your first book failing doesn't mean you can't write. It usually means you picked the wrong format for your particular skills, or you haven't found your voice yet. It could also mean you didn’t spend enough time editing, or didn’t hire an editor that works well for you. It could be that you didn’t have the right level of marketing budget, as well. Don't let one failure define your entire writing identity. It isn’t the end of the world.

I had bartered for editing with an English major from college I was still in contact with. Designed my own cover. I had zero cash investment in that book. It didn’t suck; it just wasn’t “market” great.

And I certainly didn’t have access to “GoFundMe” type crowdsourcing options. Which is why I’m so adamant with people these days that having these huge launch budgets simply isn’t necessary (or ideal). If the book performs well, you can always add things later like paperback, hardcover, sprayed edges… whatever. I see way too many newbie authors trying to do these huge launches when they’re nowhere near ready for the market. But we’ll get to that in another episode.

Let’s get back to the story.

Being financially responsible and single, I didn’t spend a dime on marketing because I was still paying off school loans, and just bought a 5-bedroom house with a $2200+ mortgage, because I had single woman money, liked the neighborhood, and did what I wanted to. (I had good income and credit, okay?)

Although I learned about ad runs from a design perspective in college, launching an ad campaign for my silly little romance book seemed reckless at the time given my attire requirements of professional $400 suits and $200 heels for work, and student loan debt. Damn, I looked good. Some days when I look in the mirror at my messy bun, graying red hair, and yoga pants and tank top as my uniform, I miss the old me. But then I remember I get to write random words from my weird thoughts, and shrug it off.

But anyway, looking back, I’m glad I didn’t waste a single dime on that book. Never begged my family or friends at the time to read it.

I was a no-name pen name. And thank goodness for that, because I didn’t have any hype into it and could easily crawl back into my cave of introvertism and begin again if I found my guts again.

Instead of quitting entirely, I shifted to what I called "musings"—just writing thoughts and observations without the pressure of crafting perfect narratives. This kept my writing muscles active during the recovery period while I soothed my bruised heart from lofty ambitions of a Carrie Bradshaw life.

The takeaway: Treat your first book as an education, not career validation. Keep writing through the disappointment, and move on to the next book. Work on craft. Find three things you wish you would have done better from the last book you wrote. This is how you grow.

The Wilderness Years Aren't Wasted Time

Between 2009 and 2015, life happened.

A new marriage, kids, the chaos of being a functioning adult while trying to maintain creative ambitions. Writing became background noise while I learned even more software, programming, and design, and spent my days doing research on a niche topic.

I thought I was losing valuable writing years. Having left my corporate job to raise babies at home while my husband heavy-hauled equipment on his semi-truck, I was worried that I was no longer contributing financially.

But what I was actually doing was building the expertise that would later fuel my success. Those technical skills became the foundation for nonfiction books that actually sold.

Corporate work started feeling like a waste of time compared to income streams that lived entirely in my head. But I was determined.

And then in May 2012, I had to leave my job (and live with my non-compete clause) and take care of our first-born son. It was a relief but at the same time, the scariest most financially reckless thing I had done in my whole life.

The lesson: Your "writing career" includes everything you learn, not just the words you put on paper. That day job teaching you project management? That's writing material. The software you learned for work? Future book topic. Your detours often become your destinations.

That time is not wasted *not writing* if you use it well.

Write What You Know

This would be the lesson I would gain serious money from. Although I loved to read and surround myself with romance novels, I didn’t *know* them. I hadn’t studied enough on structure, development, or even learn about writing cliques, groups, or involve myself into writer circles that offered critique. I was a total newb.

But I had uncanny knowledge into a nonfiction topic; expert-level experience that was often sought out in my professional circles. It was ancillary to a profession, but not something core, and essential to learn. So I took everything I knew, including on-the-job training, workshops I was sent to, and my own research and documented my knowledge into a non-fiction novel.

It would be the first book of its subject and kind.

All the while, I was building an email list under a pen name brand, trading snippets of my knowledge and what was inside the book for email addresses. I grew that list to around 8,000 by the time I was in final draft stages.

This was the one thing I did completely right.

I wrote it under a pen name, just in case I made a fool of myself. And it was such a rush to hit “publish” in late August 2015.

Build the email list. I started this practice a long time ago, and understood early the value of domain rank, owning data, and how powerful email conversion is compared to social media.

The Money Changes Everything

October 30, 2015: $989.68 direct deposit from my first serious nonfiction book.

I had sold around 89 copies (if I remember right) at roughly $11.21 royalty per copy for an 8.5 x 11 black and white interior book.

That moment shifted everything. Not because I was suddenly *rich*, but because my skills in writing technical non-fiction had proven it could generate real revenue.

By this time, we had 4 kids already, and little did I know, I was already pregnant with twins having just had my 4th in April 2015.

My husband's skepticism turned into support. Could I write more books like this? Would I be able to find other topics to write on? We started looking into possibilities, which led me eventually to start writing under my own name in 2017.

Here's what that taught me about the psychological shift: You can't treat writing like a business until it starts paying like one. You shouldn’t get yourself into a ton of debt, beg people to buy your book, or enlist family to support you. You have to give the right audience a reason to care about your book. And I did that with the email list growth right off the bat.

That first real check transforms you from hobbyist or aspiring to professional in ways that can't be faked or rushed. Good writing sometimes takes time; marketing and building takes just as much.

I initially had a 1.1% conversion rate from sales to email list. Reviews started to come in, and that only converted to more sales (even more than the first month) for months and months after. After the book matured, I had estimated about a 18% conversion from sales to email list, but it’s hard to tell after it’s been published on Amazon.

Not bad for my first professional non-fiction title.

Earning money for words and knowledge that lived in my head was a rush. Never let that feeling die, even when your royalties aren’t as much as you hoped they would be. Just keep going, keep writing, and work on building your email list.

Don't feel guilty about caring about money. Writing that pays is writing that has found its audience and proven its value. Chase the money—it's usually pointing toward what people actually want to read. And invest it back into your future books.

Multiple Pen Names Are Strategic

By 2020, I was generating $5,000 monthly across multiple pen names. Each identity targets different genres and audiences—some fiction, some nonfiction, each one a focused slice of my personality and expertise.

It was strategic market positioning. Each pen name could speak and cater directly to its audience without diluting the others.

The practical benefits: If one pen name gets caught in drama or writes something controversial, the others keep generating income. You're not putting all your eggs in one reputation basket.

The creative benefits: You can experiment with different voices and genres without confusing your existing readers or damaging your main brand.

Consider pen names not as hiding from your work, but as focused marketing. Each identity becomes a specialized conversation with a specific audience.

Having the variety of pen names and projects to work on will help keep your creative well full. You’ll have a variety of different topics and storylines to work on. So if you get stuck with one, even with all the outlining you’ve done, you can always switch gears and move on to another project in need of your time.

Infrastructure Beats Inspiration Every Time

Most writers romanticize the struggling artist aesthetic. I weaponized comfort instead. Good keyboards, an ultrawide monitor, a stream deck, iPad 12, design software for covers, Vellum for formatting, Scrivener to keep everything organized, candles, gadgets, apps—tools that made writing feel less like work and more like play.

The ritual became as important as the writing. Sitting down at my specific setup with my specific tools created the psychological trigger that it was time to work.

The ritual became as important as the writing. Sitting down at my specific setup with my specific tools created the psychological trigger that it was time to work. Your brain starts associating the physical environment with creative output, making it easier to slip into writing mode.

The ritual creates the mindset. I start every writing session the same way: specific playlist, yogurt or bagel, specific drink (usually coffee), check my notes from the previous session, document my task list in my journal first and then in Notion, then dive in. This routine tells my brain it's time to shift gears from regular life to creative work.

Here's what I've learned about creating the right environment: First, eliminate friction wherever possible. If your laptop takes five minutes to boot up, those five minutes give your brain time to find excuses not to write. If your chair hurts your back after an hour, you'll unconsciously avoid longer writing sessions.

Temperature matters more than you think. I keep my office slightly cool because it keeps me alert. A warm room makes me sleepy and less focused. Find your optimal temperature and maintain it.

Lighting affects everything. Harsh overhead lighting gives me headaches. I use multiple soft light sources—a desk lamp, some ambient lighting, maybe a window if the natural light is good. Your eyes shouldn't strain to see your screen or notes.

Sound environment is crucial. Some writers need dead silence, others need background noise. I use noise-canceling headphones even when I'm not playing music because they signal to my brain that it's focus time. Find what works for you and make it consistent.

Comfort isn't laziness—it's efficiency. When you're comfortable, you can focus on the work instead of being distracted by physical discomfort, technical problems, or environmental annoyances.

And here's the truth about inspiration: it shows up at 6 AM when you're brushing your teeth and random moments when you’re busy doing other things, not when you need to meet deadlines. Process and good habits keep you productive when inspiration decides to take vacation.

Invest in making your writing environment as pleasant as possible. Good tools and desk surroundings aren't indulgences—they're productivity multipliers. Start with the basics: a chair that doesn't hurt, a screen at the right height, a keyboard that feels good under your fingers. Build from there.

Guard Your Pen Names Like State Secrets

One of my hardest-learned lessons: Keep your pen name identities separate and secret. Share with NO ONE. You can’t trust ANYONE in this industry. Not even your editors (so I’ve heard). Insist on NDAs, and keep your pen names separate with various different editors.

All it takes is one angry BookToker, Bookstagrammer, an editor with an axe to grind over professional opinions, or jealous author to put you on blast, and suddenly your brand is associated with drama you didn't start.

Even when they got the story wrong. You can’t unring a bell.

I’ve seen it all dating all the way back to 2007. Like I said, I’m an original gangster.

Multiple pseudonyms are insurance. If one catches fire from controversy, the others continue generating income while that identity goes into witness protection. I wish more authors knew this, because we often become targets for political opinions (because books are political), author clique bullying, viewpoints on disclosures and genre rules, em dashes, the Oxford comma (Oxford comma forever), fights over software (ridiculous I know), etc. And now we get to argue over AI. It never ends.

The indie publishing world is smaller than you think, and drama spreads faster than good reviews. Protect your brands accordingly.

Process Over Passion

After sixteen years, what keeps me writing isn't inspiration or artistic calling—it's good habits and systems that work whether I feel like writing or not.

I focus internally on process and ritual while keeping my ear to external industry changes. I learn the unwritten rules, the algorithm shifts, the career landmines to avoid. But I don't let external chaos disrupt internal methodology.

But, I do love some indie author drama. Especially when it touches on a topic of my expertise.

Create rituals around your work. My stream deck is a time saver, my monitor transforms into a writing portal where Scrivener takes up the entire space with focused writing against an art background. Writing becomes your identity when practiced consistently at the intersection of tools, time, and intention.

Process beats passion because process can be summoned on command. Passion shows up when it wants to, usually at the worst possible moments.

Remember this when you get a great idea while at a work meeting, and finding yourself fighting the urge to quit your job.

What Actually Matters After All These Years

The platforms keep changing—BookSurge became CreateSpace became KDP. The industry shifts constantly. New drama erupts weekly. We live for this shit.

But the fundamental equation stays the same: arrange words with precision and purpose, solve problems people actually have, write original and epic stories, surround yourself with talented professionals, and money follows.

I’m still a “nobody” in the grand scheme of things. All I managed to do was keep writing books that were specific to niche interests and topics or types people loved.

I was lucky to start when indie publishing was still figuring itself out, when every success felt meaningful because we were all learning together. Now self-publishing has a broad array of who is uploading files every day, which means lower barriers to entry but fiercer competition.

While some may say that KDP has become a cesspool of low quality books (and I can agree in some respects), largely what I see are opportunities for those authors to learn and grow.

My Advice to You

Start where you are with what you know. Don't wait for inspiration, perfect conditions, or the right moment. Just start writing, keep learning, and prepare to pivot when your first attempt fails.

Because it probably will fail. Mine did.

Focus on solving real problems for real people, whether through fiction that entertains or nonfiction that educates. The market will tell you what works faster than any critique group or writing guru.

And remember: every writer you admire started exactly where you are now—staring at a blank page, wondering if they're cut out for this. The only difference between published and unpublished writers is that published writers kept going despite the failures.

Your writing career doesn't need to follow anyone else's blueprint. It just needs to work for you, your life, and yes—your bank account. Everything else is creative mythology.

The words are waiting. Go arrange them into something valuable.

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Remember that raw, unfiltered collection of writerly wisdom and what-the-actual-fuck moments I poured into "What is This Fuckery"? Yeah, that one. The book that captures the beautiful disaster of being a writer, from the sacred morning ritual of mainlining coffee from my battle-worn Yeti to the existential crisis of finding the last orange slice gone missing during a crucial editing session.

Well, guess what? It's yours. Free. Gratis. A digital high-five to every paid subscriber who's been riding shotgun on this ink-stained journey through What is This Fuckery on Substack.

But wait, because timing is everything, and the universe has a twisted sense of humor—next month I'm dropping "Whiskey & Writing." Yes, a whole-ass book dedicated to the dual muses in my life: the amber liquid that fuels late-night editing sessions where Nerys reappears for an encore, the furry dictator who shares its name. It's cosmic poetry, really.

For the uninitiated wondering what fresh literary chaos you're missing, imagine a collection that takes you behind the laptop screen where the magic (and occasional meltdown) happens. We're talking everything from the sacred art of proper fuckery usage to the advanced physics of procrastination. There's a whole chapter on emotional support snacks, for fuck's sake. Because let's be honest—sometimes the only thing standing between you and a complete manuscript is a bag of gummy bears and sheer spite.

Why subscribe to What is This Fuckery? Because where else are you going to find a community that understands your obsession with notebooks you'll never write in, validates your relationship with caffeine, and celebrates the fine art of telling imposter syndrome to go fuck itself? This isn't just another writing blog—it's a digital speakeasy where we trade war stories about battling blank pages, share secret recipes for creativity-inducing cocktails, and occasionally solve the mysteries of the universe (or at least figure out why Track Changes is being such a dick today).

Plus, with chapters like "Wereotters and Book Dragons" and "The Dudes and Other Characters," you know you're not getting the same recycled writing advice that's been circulating since Hemingway first grumbled about adjectives.

Become a paid subscriber now, and join a tribe of literary misfits who understand that sometimes the best writing comes from the spaces between the chaos—usually around 2 AM, probably involving whiskey, and definitely with a cat plotting world domination in the background.

Because let's face it: we need a space where we can be unapologetically human, gloriously imperfect, and occasionally inappropriate. Welcome to the fuckery. I've been expecting you.

Reviews

“To me, this is the ultimate guide and journal of the trials and tribulations of being a writer. Kerrie’s similes and metaphors are not only original, but hilarious. Her use of sarcasm and wit are refreshing to read. She brings in her family interruptions and finds humor in them, then continues about Camera-Blender Head in reaction to her young son’s drawing. Her use of vocabulary and figures of speech to describe the simplest situations, such as choosing a notebook or beginning the writing process are impressive, especially how she expounds on the magic notebook. All in all, I loved this book. Bravo Kerrie. You leave me envious of your writing talents.”

Are you a writer? Do you need a cheerleader? Then this book is for you.
That's a simple characterization of WITF, but if you could use a boost to your ego, or a spark for your creativity, Kerrie Legend is there for you. She's got your back, but will talk turkey to you if you need it too. Legend's advice is from the trenches, not from lofty perches. You will be able to relate to her doubts and frustrations because she's been there. She's at her best when relating personal tidbits of weird neighbors and plagiaristic Threads followers, but her advice is sound without being dogmatic - she wants you to write like you, not her.
This is a book that can be sipped, and also gulped. It helped when I was struggling with my latest book, and it might help you as well. Enjoy.

Receive a free copy of my book, “What is This Fuckery”, when you become a paid subscriber! (And thank you!) Copy will be available in .epub, and will be below the paywall on this very post.

Thank you for supporting my writing!

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“Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it’s the only thing that ever has.” —Margaret Mead

The writing of future fuckery is on the wall, and it's spelling out a disturbing future for writers/authors and consumers alike.

When tech giants Tim Cook and Jeff Bezos made their pilgrimage to Trump, offerin…

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