Can’t Bear to Hurt Your Characters?

I’ve been writing novels – or at least trying to write novels, with varying degrees of success – for about ten years. In general, I’m a very good writer, but I have a chronic habit of not finishing novels in particular. I begin stories, get a quarter or halfway through, and never finish them. Sometimes the story stopped being interesting and I forgot about it, but more often, I had no idea where to go next.

From the reader’s perspective, this writing looked like a bunch of elegant prose and interesting characters just sort of aimlessly drifting with no purpose. Any one chapter, or even a short string of chapters, might be interesting, but after an extended period of reading, you would be left confused. I was just as confused writing these driftwood stories.

Only recently did I realize what I was doing wrong, and I realized it by accident.

A few months ago, I decided to start on a novel – not an uncommon whim for me, to be sure – but the way I came at it was different. Instead of imagining an interesting scenario, or world, or set of characters, I wanted to tell a story about something. It had a moral, a plot, a purpose. (I wanted to write about three things: our relationships with others, our relationships with ourselves, and the relative importance of each.)

For the first time, I shaped the characters and the world around the story, not the other way around. Oddly, I wasn’t comfortable writing beyond chapter 1 without a very clear idea of all the major plot beats, especially the ending. I had never done that before: known the ending before writing much of anything.

Besides helping me gain a clear roadmap for where I wanted my story to go, this mindset also helped me to get over what I had known for a long time was my biggest flaw as a novelist: my inability to hurt my characters. I hadn’t known before how to fix that problem, but all of a sudden with this mindset shift, I stopped having a mental hangup about killing or hurting characters. It confused me at first.

After a short time, I realized a fundamental distinction between the way I’d been writing before and the way I wrote this new story. Before, I had been writing wish fulfillment. I started with characters or situations or worlds that I enjoyed imagining things about, and I wanted to share those imaginings with the world, so I wrote them down. It was never about telling a story, it was about sharing a cute scenario or a cool world or a neat character. And because it was about those things, I would be extremely reluctant to sacrifice the real purpose of the writing for the sake of a “plot”.

On the other hand, when the goal was to tell a story, I didn’t get too attached to any one story component, because the only reason those components existed the way they did was because the story required it; if the story had required something else, I would have come up with something else.

If you can’t bring yourself to hurt or kill your characters, ask yourself why they’re so precious to you. Is your writing shaped around a story you’re trying to tell, or is it simple wish fulfillment? There’s nothing wrong with writing wish fulfillment, by the way – but if you’re writing that type of fiction, it’s often best to know it. That way, you don’t feel compelled to add a plot to what should really be a fluffy one-shot.

Intuition Is Adaptable

Or, why “X is counterintuitive” is just a way of saying “I haven’t seen any sufficiently intuitive explanations of X”.


As a kid, I was a huge science nerd. In particular, I loved Stephen Hawking’s work. He had a TV show at some point, which I watched whenever I got the chance. One of the first books I remember reading was “A Brief History of Time”.

The main reason I loved reading his writing is that it didn’t seem very complicated to me. Not in the way Richard Feynman’s work seems un-complicated—Feynman just seems like he’s dicking around all the time and happens to love dicking around in physics specifically, so much so that he got a Nobel Prize in it. (I’m aware this isn’t remotely what happened, but that’s the sense you get from reading his writing.) Instead, I found Stephen Hawking’s writing to be un-complicated in the way that I later found Eliezer Yudkowsky’s and Daniel Kahneman’s writings to be un-complicated: it just makes sense.

The best physical example of Stephen Hawking’s influence on kid-me is a sheet of sticky paper that’s still stuck to the wall of the library in my parents’ house, on which I wrote an explanation of the Many Worlds interpretation of quantum mechanics.

You’d think I was joking, but…

The easy way to explain this is just to say that I was a genius, or if you don’t feel like giving me that much credit, you can say that I was able to do a lot of book-learning because I had no social life. (This assessment isn’t wrong, by the way.)

But I’m actually going to give myself even less credit than that. I don’t think I’m a genius, and I also don’t think that the extra time I gained by skipping recess to read the encyclopedia (I already told you I was a nerd, get off my back) actually contributed in any meaningful way to my comprehension of “A Brief History of Time”. I don’t think it had anything to do with me at all; rather, it was almost entirely a property of the authors.

Which authors are particularly poignant to you has a decent amount to do with you: I know a girl who thinks that Jen Sincero’s book You Are A Badass is the best book on the planet; I read the first paragraph and immediately put it back down again. But all other things being equal, a human brain is a human brain, and an intuitive explanation is an intuitive explanation.

Assuming you’ve got some very basic algebra, Eliezer Yudkowsky’s An Intuitive Explanation of Bayes’s Theorem will almost certainly make sense to you. (Whether or not you care is a function of your preferences in reading material, separate from whether or not you could understand it if you did care.) Even if you suck at math. I know, because at the time that I read the Explanation, I sucked at math. (I’ve since gotten much better through deliberate effort.) There are books in every discipline that make things make sense to people, that clarify cloudy issues, that provide intuitive explanations.

This is very good news for those of us who think we are just bad at something, and we have no way to get better. I grew up thinking I was bad at math, since I hate algebra and I hate trig and I’d always give up before I finished a problem and it was generally just the dullest drek on the planet. And yet, I have no difficulty calculating conditional probabilities with Bayes Theorem. All I had to do was read a good enough explanation. If you think you’re irreparably bad at something, don’t give up on it, just keep reading.

This is moderately poor news for those of us who are in the habit of writing explanations, though, because we can’t blame our readers’ lack of comprehension on the difficulty of the subject matter. It may partially be about the subject matter—neither all subjects nor all readers are created equal—but there is always some way that we could be better writers, better explainers, and thus have our explanations make more sense.

Personally, I choose to take this as a challenge. If no subject is imperceptibly counterintuitive, no subject is outside my domain, if I’m good enough. I just need to get stronger.

How to Write a Value Proposition

How much do you like getting things you want for free? Probably a lot.

A value proposition makes a business owner want to hire you by giving them something they want for free.

It’s really that simple. And it’s the best way of getting a job, because it’s the best way of getting an employer to like you.

Most people don’t write value props because they’re not willing to put in the necessary work. But there are still some people who are willing to put in the work, but since they don’t write good value props, they don’t get to.

I really can’t fix the former problem—that’s a self-motivation issue—but I can help fix the latter. So here goes.

A good value prop is clear and concise. Most value propositions are emailed, and busy business owners or hiring managers have negative eleven minutes to answer email. Make answering yours easy. Write short sentences and short paragraphs. Don’t include too many parentheticals. Be specific and direct, and don’t use the passive voice.

And for the sake of all that is beautiful in the universe, don’t make typos. Typos in any professional email don’t say “I’m not a writer.” They say “I don’t give a shit about you.” The Grammarly app is good at catching most spelling and grammar mistakes (though I’ve noticed it has a bit of a hard time recognizing the grammatical correctness of general nouns).

On top of making your writing style clear, make your actual points just as clear. You want a job, right? Say so. After you’re done making your value prop, say something like Charlie Hoehn did: “In exchange for these things, I hope that you’d consider taking me on as an intern (real-world or virtual). I would love to help you out on future projects. Let me know what you think, and I look forward to hearing from you.” Be this clear and direct about everything you say.

It doesn’t make the recipient feel defensive. One of the key principles of sales is that you never want your prospect to feel Not-OK in any way. So when you write a value prop, never say that their existing product sucks (even if it objectively does). It could have been designed by the owner’s son. Instead of saying it sucks, say it could be better.

Overall, your attitude about your recipient should be positive, and that includes your attitude toward their current product.

It has a clear demonstration of, well, value. Say exactly what you’re going to do for them. “You’re not utilizing Facebook ads for marketing, I can run an ad campaign.” “You’re not marketing on Craigslist, I can do that for you.” “You don’t have a personalized website, I can code it for you.” Whatever it is that you can do for them, spell it out.

It shows projects, not credentials. For them to take you seriously, you’re going to need to demonstrate that you can do what you say you can. But tell me, if you’re a business owner and you want to know whether I can really code a good website for you, which of these would you prefer to see?

“I have many years of experience with web programming (including detailed knowledge of the inner workings of HTML, CSS, PHP, JavaScript, and SQL) as well as web design, and I’ve both designed and built a number of websites previously, including a website for a non-profit called Speset.”

“I built the Speset website using PHP and CSS. The mailing list I added using MailChimp currently has over 100 subscribers, with no marketing besides the existence of the website.”

The former tells you what I can do. The latter shows you. It is always better to show instead of telling. They say a picture is worth a thousand words, and in the same way, a project is worth a thousand sentences.

You should only tell them something if they can’t feasibly know it just by looking at the project. (Ex. my details about the number of subs to the mailing list and the languages I used to program the website.)

It has a very small and specific ask. Remember, these people are crazy busy. Don’t ask them to think of ways they could use your help. Come up with ways you could help them, then tell them about those ways.

Overall, a good value prop makes it easy for the recipient to say yes. When you’re writing anything, says Isaac Morehouse, founder of Praxis, “you want to make it as easy as possible for your readers to do what you want them to do. Whether it’s understanding an idea, whether it’s taking a specific action, whether it’s emailing you back, make it easy for them.”

Value Proposition Example

Here’s a value prop I wrote to the board of directors at my local skating club (the Pittsburgh Figure Skating Club, or PFSC). Their website is pretty atrocious, so I wrote about how I could improve it.

Dear Pittsburgh Figure Skating Club Board members,

My family and I have been members of the PFSC for many years, and I frequent your website for information about club news and events. I’ve noticed two ways in which your website could be improved to better provide its services.

First, your current WordPress theme isn’t optimal for your website. The PFSC color scheme is black and gold, as anyone can see if they go to Skate Pittsburgh, but the website’s color scheme is primarily mint green and dark blue.

I would fix this by either modifying your existing WordPress blog or by creating a brand-new website for you from scratch. I’ve created several blogs using WordPress, including the one on my personal website. Additionally, I’ve designed and developed several websites, such as Speset and Ellis Wyatt.

Second, while the site contains a wide variety of interesting and useful content, it could be better organized. For example, the landing page contains information about the club’s history, recent news, and congratulations.

I would rewrite and/or reorganize your content so your visitors could navigate your site better. For example, I would reorganize the content on your landing page into several separate pages, then write a cohesive introduction for your landing page that welcomes both potential and current club members.

Throughout this process, I would involve you in my design decisions so I can make sure you end up with a website you love.

Lastly, I would be happy to provide you with a significant discount on my normal rates, since I’d like to help the club.

Let me know! I look forward to hearing from you.

– Jenya Lestina

This may not be the perfect value prop, but that’s the point. It’s not perfect, but it’s good. And once it is good, put it out there. One published sentence is worth ten novels sitting on your hard drive.

How to Not Write Academically

I’ve discussed before that English classes and tests through high school and college don’t measure how good you are at real writing. They measure how good you are at academic writing. As such, if your only experience with writing comes from English classes, your writing is probably very academic. Unless you’re looking to be a professor or researcher, you probably don’t want that, because you probably know that academic writing is generally boring to write and to read. Still, it’s hard to know what the hallmarks of academic writing are, or how to stop.

Today I’ll be telling you what academic writing looks like in detail, as well as how to stop doing the academic thing and start doing the real writing thing. I’ll also give some general writing tips and ways to “find your voice”, or, find your own unique and interesting way of writing.

One of the most common things I’ve seen from people who were taught to write academically is that they never use contractions. Things like “I’ve”, “don’t”, “it’s”, etc. Not using contractions is an easy way to add extra words and sound more formal, and given the word count minimums in many English classes, plus the formal tone of most academic writing, it can be easy for students to fall into this trap. The grammarians are up in the air as to whether or not contractions should be used in formal writing, but the agreement is that for informal writing (blog posts, for example), it’s completely fine.

Here’s another one: excessively complicated sentences, or passive voice. I group these together since they often combine to create a monster of incomprehensibility. When you’re trying to convey complex thoughts, it can be easy to let your sentences become complex as well, but for the sake of your reader, try to write as simply as you can. There are two simple hacks for this: use the passive voice as little as possible, and break your sentences when you can.

For example, let’s take what I wrote above: “try to write as simply as you can”. It’s in the active voice, it’s simple, and it says exactly what you should do. In a sentence that’s already pretty long, the simple phrase wraps it up. By contrast, if I’d said, “writing as simply as possible is important”, is in the passive voice, it’s complicated, and it’s not immediately actionable.

Here’s yet another one: academic writers don’t start sentences with conjunctions. Overall, a lot of people have the mistaken impression that using words like “and”, “but”, “so”, etc. at the beginnings of sentences is poor grammar, but actually, all major style guides say otherwise. The only reason almost everyone thinks it’s wrong is because we were taught so in school: evidently sometime in the 19th century, “some schoolteachers took against the practice of beginning a sentence with a word like but or and, presumably because they noticed the way young children overused them in their writing. But instead of gently weaning the children away from overuse, they banned the usage altogether! Generations of children were taught they should ‘never’ begin a sentence with a conjunction. Some still are.” (source)

Those four things are, I’ve found, the most common ways that people write academically by accident. Even so, there are a huge number of others, and which ones you in particular tend to use depends on who taught you English and how you learned. How do you get completely out of the academic writing mindset if you’re not sure exactly what you’re doing wrong?

I’ve got a simple trick for you that not only will help you stop writing academically, it will also help you find your voice (your unique way of writing). First, write something on a topic you know well. Then wait a while, probably a day or so, until you forget the specific words and phrases you used. Then, record yourself talking about the same topic and transcribe the audio. Finally, compare the two. How is your spoken word different from your written one?

You’ll probably find some obvious differences, like when you talk, you stutter and say “um” a lot more. But you’ll probably also find a lot of non-obvious differences. Maybe your writing sounds verbose and stuffy since you use words you never use when you talk. Maybe there are colloquialisms you use when you talk that you don’t use in writing. Maybe there’s something else entirely. Whatever it is, you’ll find out, and then you can use your own judgement as to how much of your speaking style you want to add to your writing.

For further reading, John T. Reed makes a lot of the same points in his book, Succeeding.

A lot of people accidentally fall into the trap of writing academically, since that’s almost exclusively what our public school system teaches. But if you can realize when you’re doing it and if you know how to stop, you can break the habit, and find your own unique style. Write for your reader, not for your high school English teacher who neither matters nor cares anymore.

English Classes Don’t Teach Writing, or, Why I’m Proud of My 3 on the AP English

I love to write. This is pretty obvious to anyone who knows me at all: the first paid work I did for someone outside my family was writing articles for SEO, I met my high school English requirements before I started 9th grade, and still I continued to write and read profusely and extensively throughout high school and college.

Writing for me has taken many forms. For long periods of time, I kept a daily journal. I wrote posts on many different blogs over time. I wrote long essays in the comments sections of YouTube videos, arguing with strangers. I’ve written everything from letters to politicians to novels.

I just write by virtue of existing. If I’ve got thoughts, they either come out of my mouth into the air or they come out of my fingers onto a keyboard. For the dramatic most part, I took no formal writing classes. I just read interesting stuff and I wrote what I thought, and I analyzed my writing in light of what I’d read to find ways to make it better.

And it was with that background that I signed up for the AP English Language and Composition. I was excited! I got to be in a class with tons of great writers, who loved to write just like I did! The syllabus included weekly the writing of a 2-3 page essay and the reading of 1-3 novellas! Honestly, it looked like a dream come true. If all writing classes are this awesome, why hadn’t I taken one sooner?

This enthusiasm continued throughout the first few weeks. At the time, I was also taking two other classes through the same online program, so I only took about two days to do the work. One day to read, and a second to write. I got good grades, and I was happy. My only minor quip was the fact that on our class homepage, my teacher posted the best essays for any given assignment. My essays were never on there.

I was a little bit bummed, but I figured, there had to be somebody better than me. And yet, when I downloaded their essays to try and learn from them, I noticed something very strange. Their essays all seemed to be clones of each other. They all followed basically the same formula, and it wasn’t even that interesting a formula. Besides their names printed at the top, there was no way for me to tell who’d written which essay. When I read books, I felt like the author was speaking to me in their own unique voice, conveying information that was important enough to them to have written a book about it. When I read my classmates’ essays, I just saw words.

I’d like to say I was completely disillusioned to the falseness of accomplishment in academic writing, and I went on to join such great writers as Stephen King and Kurt Vonnegut in saying so. I wasn’t, and I didn’t. I was just confused.

The realization that getting good grades in an English class and being a good writer were totally different things didn’t come for me until many months later. In the meantime, I’d already begun to question what everyone in my life had been telling me for years: that I was a good writer. Over the course of the class, I didn’t just never get on the “best essays” list. I also got steadily worse grades. My literary analyses got bad marks. I occasionally got Bs on assignments. (Shut up, it was devastating at the time.)

As I do, I responded to all of this by buckling down and working harder. My two easy days for English class became three hard ones as I tried (and failed) to understand why my writing wasn’t good enough. My mental state was shot. I didn’t know what to think about myself. At the same time that my English class was telling me I was average at best, others continued to tell me that my writing was great. I started correcting them, because of course your English teacher knows more about good writing than your prospective audience. Who cares if it’s interesting, it got a B, so there must be something wrong with it.

But the class ended, and a few months passed. I kept writing, because that’s what I do, and I showed it to various people. Just like they’d been saying the whole time, they said it was great. And outside the environment of the class, I started to consider the concept that maybe the class wasn’t as important as I’d thought. After all, in real life, if you can captivate your audience with interesting work, what else is there? I got my final score on the AP test (think of it as a comprehensive final, and the only grade that matters; it’s scored on a bell curve from 1 at the lowest to 5 at the highest), and I got a 3. I wasn’t too surprised, but I also wasn’t too hurt.

At the time, I figured that I was just awful at rhetorical analysis, and that was the reason my score was low. It was a good reason for some time. But I’ve since realized that there’s a deeper problem going on here, and that is that good academic writing is not good writing.

Good academic writing feels impersonal, mostly because it’s wordy. Not in the sense that academics have a broader vocabulary, though most of them do; their sentences are just way too long for the thoughts they convey. Academic writing goes “During the upcoming period, this project will be continued”. Normal writing goes “This week I’ll continue my project”. The academic version has 1.5x the word count for the same thought, it’s in the passive voice, and it’s boring overall.

The purpose of all those words, so far as I can tell, is twofold. For one, it completely snuffs out the author’s individual voice and replaces it with the simple meaning of the words. And for another, it makes the writing super formal, because it overuses a construction that English-speakers use to make something more polite. For example: A rude apology is “Sorry.” A polite apology is “I’m so sorry, I wasn’t trying to hurt your feelings.” More words = more effort = more polite.

Plain old good writing, on the other hand, conveys a lot more about both the author and the subject. When an author lets themself write sentences like “I was excited!”, “Meh, it wasn’t a big deal”, “I was just confused”, and “Can you believe that?!”, it makes it way more obvious what the author is feeling. It makes it obvious that the essay didn’t just apparate into existence, somebody had to write it.

The main problem with using AP English as a gauge of my writing wasn’t that it isn’t a good gauge; it’s fine. It’s just a gauge of the wrong thing. AP English is designed to prepare students for academic writing (because the classes are designed by academics, so their subject matter is disproportionately biased towards things that would be useful for academics; but that’s a topic for another day). If you just want to be a good writer, you don’t take AP English. If you want to be a good writer, you do what I’d unknowingly been doing all along: read good writing, write what you care about, and fix your writing based on what you’ve read. So, since I do want to be a good writer, I suppose that’s what I’ll keep doing. See you again tomorrow!