Episode Description:
Many authors are doing everything right—publishing consistently, running promotions, chasing algorithms, investing in tools—and still can’t seem to get ahead financially. The books break even. The sales spike and disappear. The stress never really lets up.
In this episode of What If? For Authors, Claire Taylor addresses a painful but essential question: What if struggling to get ahead isn’t a personal failure—but the predictable result of broken systems?
Using the Enneagram as a framework for liberation (not self-blame), Claire explores why productivity hacks, discipline fixes, virality, and AI tools often function as promising distractions rather than real solutions. She unpacks how dominant cultural narratives—bootstrapping, meritocracy, savior myths, and algorithmic “neutrality”—keep authors exhausted, isolated, and blaming themselves instead of questioning the systems designed to extract their time, money, and attention.
This episode is not about giving up. It’s about reclaiming agency, and choosing paths that reduce suffering, build solidarity, and support sustainable creative lives—on human terms.
In this episode, you’ll learn:
Why struggling financially as an author is not a moral or personal failure
How the Enneagram helps distinguish inner work from systemic harm
What “promising distractions” are—and how they keep authors trapped
Why algorithms, ads, and platforms are not neutral or merit-based
How savior-seeking keeps people exploitable and disempowered
The hidden cost of tying hope to virality, productivity, or being “chosen”
How internalized cultural narratives quietly sabotage creativity and wellbeing
What genuine agency, community, and non-extractive alternatives can look like
Why stepping back from writing (temporarily or permanently) is not shameful
Key Takeaways:
You are not broken—and you were never failing
Many author systems are designed to extract, not sustain
Optimization does not equal liberation
Hope does not come from being saved—it comes from collective agency
Building community is a radical act in an extractive industry
Anger can be alchemized into clarity, solidarity, and action
Resources & Links:
Learn more about Claire’s coaching, courses, and books: liberatedwriter.com
Write Iconic Characters: books2read.com/WIC
Happy writing!
TRANSCRIPT:
Claire: [00:00:00] Welcome back to another episode of What If For Authors. I'm glad you're here. My name's Claire Taylor and I'm an Enneagram certified coach for authors as well as a humor and mystery writer. All my services, courses and books for authors can be found@liberatedwriter.com. Go check it out. If you're curious about how you can build a more sustainable author career in uncertain times.
I also have a new book out called Write Iconic Characters, all about using the Enneagram to develop realistic and relatable characters that live rent free in the reader's head. You can find that on most major retailers or go to books to read.com/wic, and that's books two as in the number read.com.
There's a sentiment I've heard from the authors I work with more and more frequently over the last couple of years, which is that they feel like no matter what they try, they just can't get ahead. Maybe they see a pop of sales around a release, but it has almost no tail. So their [00:01:00] books break even, but aren't delivering much more money than that.
Maybe they have a couple of really good sales months where they can pay off some of their debt, but then their sales take a downturn and they're back in the red. Maybe they've only been paying themselves a thousand bucks a month for years and feel sick to their stomach when they think about what that comes out to.
Hourly. Maybe they've tried every promotion possible, done all the things sales gurus tell them to do, and they're still waiting for breakout success. That takes some of the stress off.
Now, this doesn't describe everybody in our industry, so if you're like, no, I'm fine, my income is steady enough and I feel secure with how much I'm making, then this episode isn't for you. But for those who relate to one or more of the scenarios I just laid out, keep listening. Authors who are stuck in this struggle come to me asking how the Enneagram can help them be more productive, more disciplined, more likable, stronger, smarter, more prepared, less of a [00:02:00] burden.
I applaud the desire to self-improve. Certainly, I wish more people would demonstrate that introspection behind the impulse. The problem behind this struggle, almost assuredly isn't that the author isn't productive, disciplined, or smart enough, they are enough. The underlying problem when you can't get ahead is usually something else entirely as a layout for you in this episode where I ask, what if I just can't get ahead?
Money is unfortunately a resource that we need to survive and we need more and more of it lately. If you're the sole source of income for your family, you need a lot of money today to keep the wheels from falling off the bus more than most people have available to them. It's really gotten outta hand how expensive it is to pay all the bills, let alone how much you need to feel some relief from the stress of counting every dollar.
[00:03:00] Authors aren't exempt from this stress and full-time authors usually have it worse than most people because our income can fluctuate so much from month to month. Not only that, but the fluctuations can be unpredictable and totally out of our control. Meanwhile, we're just supposed to spit out creative brilliance as fast as we can.
Sure, Jan. Now, I'm not surprised that authors show up to my coaching calls. Looking like they're about to melt out of their chair from exhaustion. If this describes you on our last call, hey, I'm just glad you made it. I feel like I'm gonna melt outta my chair some days too. What I specialize in with the Enneagram framework is helping authors liberate themselves from shoulds, misaligned expectations and fear.
What I don't do is tell people how to improve themselves. It's a subtle difference, but boy is it an important one.
The Enneagram is a tool for liberation. Liberation means letting go, connecting with yourself [00:04:00] more deeply and learning to feel more connected to the world around you. Liberation is not a process designed to improve you. It's a process designed to improve your experience of your life. There's nothing inherently wrong with you that needs to be fixed and there's nothing missing. But if you're tired of certain thinking, feeling, and behavioral patterns you've been carrying around, I can help you either set those down or appreciate what they're doing for you so that they don't continue to make you miserable and damage your creativity in relationships.
In other words, I don't show you how to be more productive. I help you understand why it feels so life or death that you be as productive as you possibly can be. That allows you to decide if you want to keep on that path of wring yourself dry, or if you wanna try a new approach.
I also don't show you how to be more disciplined. I help you examine your attitudes about discipline so you can identify and appreciate the [00:05:00] ways you're already disciplined and question if being more disciplined would actually get you what you want or just make you miserable.
Similarly, in this episode, I'm not going to tell you how to make more money in your author career. I'm going to help you understand that struggling to make money is not a personal failing, but rather a result of a tangle of interconnected systems that were not designed to make you sufficient money as an author.
While the Enneagram can show us paths towards growth and the inner work we can do to liberate ourselves, what it doesn't do, and this is important to hear, is place all the blame and responsibility for every issue we face squarely on our shoulders. This is super important for us to understand, especially those of us raised in the US or any other country that pushes the narrative of bootstrapping and rugged individualism.
Personal responsibility is great, but it's often [00:06:00] used to blame people for their own victimization as if we deserve all that comes our way, both good and bad, in which case, fuck right off with that. It's just not true. Enneagram work. No matter how much you commit yourself to, it cannot liberate you from poverty and systems that are designed to keep you poor, tired, distracted, and traumatized.
What the Enneagram is really good at doing, however, is helping you see that the poverty you or others might be experiencing is not a sign of moral failure, weakness, lack of deserving unintelligence, ordinariness, laziness, or any other personal factor. And this is why groups and institutions that rely on ideas or processes like natural hierarchy, extraction of resources and exploitation, they don't generally take kindly to the Enneagram.
The more we liberate ourselves, the more we'll desire to help liberate others, which can be [00:07:00] bad for business. If your whole scheme requires people to adhere to your control and silently assume their spot low down on the pyramid.
What I'm getting at here is that it's absolutely essential to our wellbeing that we don't internalize and personalize struggles that are a result of systems that are not designed for our success. Some people's attention flows more naturally toward systems thinking than others. So if you don't tend to think in terms of systems and focus more individually in your thinking, no worries. But this new perspective will be especially important for you to hear and spend some time thinking about. Social subtypes of the Enneagram tend to focus more on systems, and as a social type one, I can tell you what's fucked up in every system around, what can I say?
It's a gift. So what exactly do I mean when I talk about systems? It's easy for this word to feel overly general. So what I'm looking at for the purpose of this, this [00:08:00] discussion are invisible systems, constructed of common beliefs like shared cultural, religious, economic, and political narratives. So these would be beliefs.
Like if you work hard, you'll get ahead. Handouts, make people lazy. God created men to be the head of the family, and we live in a meritocracy.
You can see how these four beliefs when woven together favor men in positions of power. It's natural for them. After all, convince people that the men in those positions got their based on merit and hard work, and that those who are not in those positions really only have themselves to blame.
Now, obviously I think all that's bullshit. But the common beliefs of a society underpin how we design laws, who we shame and shun, and for what, how we distribute wealth, and who is deserving of basic things like safety, shelter, and a fucking vacation once in a while. [00:09:00] So the systems of beliefs, which tend to look like spiderwebs with a bunch of attitudes and beliefs being woven into a single system, they inform how we create more tangible systems like highways, the criminal justice system, welfare and tax codes.
Depending on where you were born, the color of your skin and your gender, you may already have a visceral understanding of how dominant belief systems translate into tangible systems that make it difficult or impossible for certain groups to get ahead.
Meanwhile, you get to listen to people who aren't facing those same obstacles. Patronizingly tell you, if you just work hard, you can have what I have.
Even when we suspect this is wrong, we are very likely to internalize dominant cultural narratives and start blaming ourselves for struggling to get ahead. This is why I do what I do with my coaching. Each of us [00:10:00] carry around many internalized narratives that are not designed for our liberation. Even when we don't internalize the dominant narratives that convince others, we're less than.
We have to deal with a bunch of people who do believe them. That's exhausting.
So what does it look like when we internalize narratives that aren't designed for our liberation? This may look like the author who's struggling to focus on her writing because she's also a mother and assumes most of the child rearing responsibilities out of an internalized narrative. That the only way to be a good mother is to take on an unfair amount of labor without complaining, but she's also a daughter to an aging parent, and she doesn't think twice about taking on the caretaking responsibilities, rarely stopping to ask why her brothers aren't bothering to step up at all.
In this case, she's likely internalized a narrative that women are naturally better at [00:11:00] caretaking roles, and that to be a good mother or daughter, you must care for everyone and be sure not to bother the men folk with it. This narrative is making it difficult for her to write books. It's also, I'd argue, an untrue story perpetuated to benefit men and disadvantaged women.
What does it look like when we haven't internalized the dominant cultural narrative, but those around us have? That's also a problem. It might look like the author who has to choose between embracing his identity and increasing his chances of making livable money because he has a West African last name and suspects that using that for publishing will put him at a disadvantage to white authors in his genre.
Bye. Running off white readers, but hiding behind a more European name feels like a betrayal of something he cares about, but he really needs to make money from this series. That's understandable and it's also a shitty choice created by the systems, namely white supremacy in this [00:12:00] case, under which we live.
There are author specific systems that we're up against too. Think about sales and social media algorithms. For one, those are just a bunch of codified narratives sealed in a black box. What books does Amazon prioritize? How does it categorize books to establish who you're competing against in category pay-per-click ads? What books are deprioritized based on content? Machine learning is a reflection of cultural prioritization that shows up in consumer habits, and it's people who have internalized the dominant cultural narratives who are writing the code.
They're making the original decisions of how it should work based on their idea of what would be the most effective. These decisions are influenced by the larger systems in which these coders live, so you better believe that those narratives are being reflected in the supposedly neutral [00:13:00] algorithm.
And what about TikTok, the last social media bastion of organic discovery? As of recording this, at least what metrics in a video earn it? Prioritization and organic discovery. What amount of melanin in the face of the content creator is served to what amount of melanin in the faces of the possible viewers. If the algorithm is learning based on viewer data, how is the racism baked into our society?
Poisoning that data and teaching the algorithm not to serve videos of black creators to as many viewers. Algorithms don't function on the meritocracy. Many like to believe they do, or rather, the merits are based off deep biases. We may think, well, they rely on lots of hard data, so they must be prioritizing what consumers most engage with.
But take a step back. Firstly, how do we even know that? How do we know what's in the black box of the algorithms code? What is it coded to do and who made those [00:14:00] decisions? Some authors, particularly those having success via the algorithms may say, stop crying and learn to play the game. But what if the game is designed so that you will never be a winner? Why on earth would you wanna play that game?
And this is an important question for us to consider when we're wondering, what if I just can't get ahead? Who is designed to be the winner of the systems you're interacting with?
There are authors who fall within certain demographics who have benefited from systems that are explicitly designed to make them winners their whole life, even if they're only mediocre at what they do. Those people probably stop listening to this episode already because it's incredibly painful for the ego to hear someone say some of your success is not yours to claim full credit for.
It's very hard to hear that. You know what's harder though? Being in a demographic that's always designed to lose. [00:15:00] So I'm probably going to get slandered as a Marxist for this entire episode, but I invite anyone to convincingly spot, or I've been wrong so far. There is so much data backing this up. So many studies, examining the effects of dominant cultural beliefs on the outcomes of people within particular demographics.
I'm not pulling this outta my ass. I read a lot of books on this because I wanna make sure I'm not causing harm in my coaching practice. I'm not a Marxist by the way, but that sure is a convenient label to slap on anyone who tries to point out that the game is rigged in favor of some and against others.
Now, what I'm not saying here is that none of us have room for optimization growth or adjustment that can increase our odds of financial success. I'm not telling you to give up here. The Enneagram helps us see what growth looks like for us and what suffering is and is not within our ability to influence.
It helps us wake up from the narratives we may have [00:16:00] ingested that trigger our core fear and keep us in a box. It helps us wake up to the box we're in. And make decisions that allow us to live a full and colorful life in community with others. And as far as optimization, I think there's room for that too, especially through stuff like strengths work that Becca Simon, her coaches do it right, that are faster.
What I like so much about strengths work is that it encourages self-acceptance and individuation. It shows you that your best process may not look like another person, and that's okay. And what Becca makes very clear is that optimizing your process is not a guarantee of financial success, and it doesn't negate the larger systems that are designed to keep you struggling.
So what can we do in the face of this? Is all hope lost? No, not at all. There is still work we can do to better our situation and decrease our suffering, but it can be painful work. The first step [00:17:00] is to ask yourself where you've been taking responsibility for perceived failures or shortcomings that are actually a result of broader systems working against you, for example.
Have I subconsciously blame myself for my ads not working? Maybe reinforcing a narrative that I'm not good with numbers, rather than wondering if maybe just maybe Facebook ads are not designed to maximize my profit so much as to maximize Metas profit, and maybe the two aims are not as aligned as I believed.
This is the case. By the way. Meta wants to make as much money off ads as they can, so all they need to do along the way is make sure the system hits a minimum effectiveness that keeps advertisers hope alive. Anything above that that people make is purely accidental in the design.
There are two more things I wanna bring some attention to that keep us blaming ourselves for not getting ahead, rather than recognizing and pushing back against the [00:18:00] systems that are perpetuating that situation. The first is what I call promising distractions. Here's a hypothetical to imagine. Let's say that you've designed a machine that extracts wealth from everyone in your town and funnels it straight to you.
How might you keep them from banding together to come after you with pitchforks and a guillotine to take back their wealth? One smart thing to do would be to convince them that the extraction process is just the first step on their own path toward riches. You could do that by dangling the promise of hitting it big in front of them.
Hey, look, now that all the wealth is in one place, it'll be easier for you to get more of it than you had to start out with. You'll also want to deny that your extraction machine is the source of their current poverty, and instead you market it as a wealth generation machine. Then you dole out a small portion of the wealth you've extracted to a few of the towns folk, and hold them up as [00:19:00] examples of the possibility of striking it rich now that the wealth generation machine is in town.
Maybe you also attribute their riches to them rather than your king making saying they worked hard and it paid off. And anyone who works as hard or is as smart as them can also make the same money. Sure. This might be a slightly cynical thought experiment, but hopefully it illustrates the point I'm making about promising distractions.
Those who are benefiting greatly from an unfair system sell those who are harmed by the system, a promise of relief from the suffering they're experiencing. The people who are benefiting also hold up their hands and say, listen, I didn't design this system, so don't blame me.
Often, they'll even go so far as to blame some other victim of the system for the suffering that the system causes. You're poor because immigrants are taking your jobs, for instance. It's important that we learn to spot this shifty maneuver and to recognize a promising distraction when it's being dangled in [00:20:00] front of us.
Unfortunately, once we learn this skill, we may realize that much of what we once thought could be our ticket out of struggle. V is yet another promising distraction. Of the system. What are some promising distractions for authors? You may wonder. Going viral online is a promising distraction. Y'all remember Hawk Tua?
Good for you if you don't, but she's an example of how online virality can become a cash windfall. She went viral, accidentally, then pulled all the levers available to a pretty young, white blonde woman with a wild streak to extract what she could from the opportunity. I am pretty sure she's under investigation at this point.
, but her example remains a promise for many others fighting for scraps from the table of online attention. Keep trying to go viral and you just might make it out,
but so long as we're focusing our attention on that goal, we're unlikely to [00:21:00] step back and go. Why the hell should someone have to go viral to make enough money to live?
The promising distraction keeps us from questioning the bullshit of it, and our attention doesn't shift toward changing things. I do believe that the vast majority of AI tools for authors fall under this category of promising distraction, and I've seen more and more authors for figuring this out too.
The tools like LLMs and Workflow Solutions, they promise authors that by using them effectively, we can get more done. The implication here is that our lack of productivity is what's been keeping us from being able to get ahead. But if we can write twice as fast and create a workflow that blasts content out to every channel at 10 times the rate we have been before, then maybe we'll finally break through.
And while we're desperately tinkering with AI productivity hacks, we're not seeing that our [00:22:00] data attention, innermost thoughts are being extracted and massed to generate gluttonous wealth for like 10 people. We're so sure that if we can just figure this all out, AI will be the ticket to finally get ahead and then we don't stop to ask why should I have to be able to produce this much writing and content to feed myself?
In our scramble to optimize the tools and ride them to the top, we're able to overlook or even justify the massive data centers that are poisoning the air and soil, largely in already disadvantaged areas, sucking up all our water and leaving our electric grids on the brink of collapse because maybe just maybe we'll start writing and marketing enough to reach escape velocity.
We forget to ask if the AI systems were becoming dependent on are even designed for our success at all, or if they're just another extraction machine that we [00:23:00] are on the wrong end of.
This is not a fun thing to think about. I know it might feel like I'm trying to take away your favorite toys here. When I talk about this sort of thing, I'm usually met with anger, disgust, or even despair. Now that doesn't make what I'm saying untrue, but it does mean that I don't expect you to be okay.
As you're listening to this. Those emotions are to be expected when we're struggling and someone tells us the approach we're taking may not get us the results we're hoping for. It can be demoralizing. You may be thinking, okay, what the fuck else am I supposed to do, Claire? I'll get to that in a bit.
Don't worry. And you're of course welcome to not believe me or to decide you want to try to become one of the lucky ones who breaks through to keep all the other people believing it's possible. That's okay. You're welcome to do that. But I just hope you understand the mechanisms at play here. And remember that if you don't get picked, it's not a matter of personal failure.
So that's enough about promising distractions. [00:24:00] Let's talk about the next important concept that we can use the Enneagram to more closely examine in the context of feeling like we can't get ahead, and that's hope for a savior. I do not blame any tired, downtrodden, or desperate person for buying a lottery ticket, praying to be plucked from obscurity or hoping for rescue.
That's the nature of tired, downtrodden, and desperate people, and we've all been there. So I really hope you know, I'm not blaming you for any of this that you've experienced or are experiencing. I'm still having to do a lot of work around examining these patterns myself. At the same time, we do ourselves a favor by exploring how our dream of being saved by a benevolent authority may be contributing to harm.
Let me start by saying that it is in the best interest of the people profiting off unfair and unjust systems of extraction to train those who are being exploited. To sit around looking for a [00:25:00] savior while hoping for a savior is a very human thing to do. It's also a sign of lacking agency and it's easily exploited to keep you from calling out the people who are extracting all your resources of time, energy, money, and attention.
Many of the problems we're facing on a global level today are allowed to continue unabated as a result of people searching for a savior within the very system they need saving from in the us. This may look like searching for a democratic politician that will finally stand up to Trump and his cronies.
It may also look like turning to Trump to keep you safe from the dreaded deep state. Either way, you're hoping that someone deeply entrenched in and benefiting from the system that's harming you will save you from the system. Man, I've got some really bad news for you.
Elon Musk doesn't care about you. He probably wouldn't even like you. Jeff Bezos doesn't care about you. He wouldn't even like you. [00:26:00] Hillary Clinton doesn't care about you. Donald Trump certainly doesn't care about you. What they do care about is making sure you believe they will save you from the problems in your life.
That's how they keep everyone who they've been exploiting for their personal gain from rising up through collective action. It's crucial for us to root out this childish impulse within ourselves for an adult to show up and make everything better.
They're not coming to save us. We must accept that and the terror that may accompany it to access our agency on the other side.
Okay, so we've covered promising distractions and savior seeking. Those are things we benefit from letting go. What do we build in its place with all this new agency? First, we rebuild some healthy connection with ourselves. Then we build mutually beneficial networks with the many others who are not beneficiaries of the dominant systems in which we live.
We build communities on [00:27:00] equal footing rather than constructed around hierarchies. We do the shadow work to root out our own predatory tendency to extract from others rather than to live in community only taking what we need. We increase our capacity to work with people who annoy us, which is a necessary skill for community and solidarity. We build author cooperatives, community spaces, both online and off for readers to gather.
We build support circles with other authors. We let others know what we have to offer and practice asking for the help we need. We stop treating readers as conversion stats and start treating them as our fellow humans, but most of all, we remind ourselves and each other that if we're struggling to get ahead in our author career, blaming ourselves is not productive or even an accurate reflection of reality.
We look for non exploitative financial opportunities and the tangled web of the systems we live in, and we also [00:28:00] opt out of the squid game and work with others to expose the game for the rigged competition. It is one that we were never designed to win.
I'll wrap this up by offering one final, but important thought. If you've been struggling to get ahead in your writing career and you're exhausted from trying. You're allowed to take a step back from writing temporarily or forever to go create security for yourself in some other way. There is no shame in that, and if there is, the shame doesn't belong with you.
It belongs with those who are benefiting from systems that are designed to drain you dry when all you want to do is tell stories and have enough money to pay your bills and maybe retire someday. You're not asking for too much. By wanting to be able to pay your bills and maybe retire someday. And you're not a failure if you haven't made that happen yet through your writing.
And if you don't wanna try anymore, I hope you understand that now you can always write as a [00:29:00] hobby or not. It doesn't actually impact your value as a human one way or another.
So if you're wondering. What if I just can't get ahead? I'll tell you that it's probably not your fault. Don't internalize the struggle as a personal failure because there are so many systems designed to keep you too busy struggling that you become isolated, distracted, and unable to challenge the dominant systems of resource extraction.
Ask yourself where your energy is being sucked into promising distractions offered to authors, and ask tough questions about your patterns of searching for a savior and how that leaves you open to further exploitation. Once you've divested your energy from those things, you'll have more to spend on building networks with other authors, attending to the readers you have, and creating solidarity in the industry.
These things will build the genuine security that your creative mind needs to find paths forward that don't rely on being deemed worthy by a benevolent [00:30:00] person in power or saved by some wealthy altruist. Both things that may never come for you, and if they do, it may only be to use you as a carrot to dangle in front of others to keep them distracted by empty promise.
I'd like to end these episodes on a hopeful note. So while underscoring the dominance of the systems in which we live on, our outcomes might seem discouraging, that's only the first step of this process. That's the waking up part. And yeah, the waking up part can be an unpleasant jolt. But once you're awake, you can do something. You, me, other authors, our readers, we can do something about this if we choose.
We are the adults. We can cause hell, if we want to, we can decide that we don't wanna play the stupid games for stupid prizes today so that authors tomorrow don't have to spend so much time struggling and begging for scraps. I find that an extremely hopeful possibility, and I find it heartening to remember that if you or I are [00:31:00] working 40 hours a week and can't afford basic necessities, let alone a savings in retirement, that's not a failing on our part.
If a disabled writer who can only work 10 hours a week is on the brink of being homeless, that's not a moral failing on their part. That's a fucking broken system. A lot of them stacked on top of each other even. It's okay to get mad here. It's okay to get riled up about this. If you feel like it's not, ask yourself who told you that and what they had to gain by making you believe it.
Please, please stop turning your anger and frustration on yourself and start alchemizing it into action that makes things better for the masses, not just a few greedy bastards at the top. That's it for this episode of What If for authors. Thanks for listening if this episode inspired you, please leave a review wherever you listen or share it with a friend. I'm Claire Taylor, your reformer in residence, and I hope you'll join me next time.
Happy writing.