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.

Having It All Figured Out Is Overrated

I’ve pretty much known my purpose in life since I can remember.

So far as I can tell, I just had a really strange reaction to the concept of death. I first heard about it and I basically thought, wow, this is a problem, this really sucks, someone should do something about it. But as a kid, I just thought the grownups would take care of it, just the same way they would take care of my skinned knee.

As I got a little older, though, being very vocal as I’ve always been about my thoughts on death, I realized the grownups weren’t going to fix it. In fact, they seemed pretty damn complacent about the regularly-occurring permanent destruction of human consciousness. And so, being the egomaniac I am, I decided to personally fix this problem.

As I started high school (and college), my first classes were in lab sciences. After all, mortality is a biological problem and would likely have a primarily biological solution. But as I soon learned, much to my dismay, I suck at lab sciences.

Frustratingly, knowing your purpose doesn’t mean you’ll be good at it.

I immediately changed my focus from biology to computer science. The basic idea was very vague – I think it went something like, “since I’m no good at the science, I’ll make a ton of money and pay somebody else to do the science”.

But I went after it for four years, taking every computer science class my college offered. By the end of that, my new goal had developed into something slightly more cogent: I would create a series of technology-focused startups and become a billionaire, then use the money to fund a nonprofit research company. As soon as the nonprofit produced something promising, it could spin off into its own for-profit startup and start selling it.

I didn’t worry too much about not having any grand ideas for tech startups. I knew I would first have to become the kind of person who could actually execute successfully against a great startup idea if it fell in her lap. So, I made a list of stuff I would need to know to create and run a successful business, from programming to finance to business law, and set to work on ticking items off the list.

By the end of high school and college (which I completed simultaneously for efficiency), I headed across the country in lieu of completing my four-year degree, content with an Associate’s in Computer Information Systems. Toward the end of my schooling, I’d worked full-time at a sales firm for six months, and now I was headed to work in marketing for another six months.

I can’t elaborate past this point, since I’m still living it.

This all probably makes me sound very cool, but that’s only because I conveniently left out all the bad bits. I left out the part where I sobbed into my sister’s arms over the B in chemistry that I squeaked out with all my effort. I left out the part where I had a three-week-long existential crisis over my decision to not attend a four-year college. And I left out the fact that I have absolutely no clue what I’m doing a lot of the time.

It matters how you spin things.

Knowing your purpose is useful, but it’s hardly the be-all-end-all. It doesn’t magic away your insecurities or your problems. It doesn’t make you a good person. Heck, it doesn’t even mean you actually know your purpose: you might just think you do.

Becoming a sociable, mature, capable, hardworking, understanding, responsible, reasonable, rational, good person has not been any easier just because I’ve known my life’s purpose since I was 3. In fact, being a socially awkward egomaniac with a really weird impossible goal has made some of that stuff harder. And knowing my purpose hasn’t made any of those things less important, either: it’s made a lot of them more important.

There is no amount of awesomeness that makes you immune to insecurity. People I’ve met around here, with more raw talent and chutzpah than I’ve ever mustered for anything, are still insecure. It’s common to every human. And at least in my opinion, there’s solidarity in that.

On Letting Down Your 10-Year-Old Self

I have a friend who’s a mechanical engineer. The startup he was CTO of recently fell apart, so he’s been looking for a new job, and was discussing with me yesterday the idea of working for Amazon doing something involving data centers. It would be a fine job and would pay well, but he didn’t want to do it – for a number of reasons, one of which stood out to me.

He said to me, “If I went back in time and talked to my 10-year-old self, and was like ‘Yo, you’re going to grow up to be a Senior Data Center Engineer II for Amazon’ I think myself would slap me. Just, that’s fucking lame.”

I asked, “What would your 10 year old self want you to be doing?” and he replied, “Building spaceships.”

This is where most people would have said something about how we’re destined to disappoint our younger selves, because we had ambitions and dreams unchecked by reality, so we should console ourselves with the Deep Wisdom that having a good life is what really matters, after all, and stop feeling so bad about it.

That’s not the advice I gave my friend, and that’s not what I’m going to write here, because I don’t believe that. If you want that advice, you can read it from a million other sources. But I, personally, am a big believer in being cool by 10-year-old-you’s standards – and this comes from someone who, at the age of 10, wanted to take over the world.

Even so, I am going to say that you need to appreciate how hard it was for you to get where you are. In my friend’s case, he grew up poor, to the extent that he told me writing emails as a part of his job makes him “bourgeoisie”. And yet now, in his late twenties, he’s living in SF and was just working as CTO for a startup that died through no fault of his. I mean, I don’t know about the rest of y’all, but I would call that a hell of a success.

Still, I can sympathize with the thought of “this isn’t want I wanted to grow up to be, I’ve failed myself”. I think if I grew up to just work for Amazon – if that was actually the best I would ever do with my life – my 10-year-old self would also think I was lame. But that’s the point. Your life isn’t over yet. What you do in your 20s, 30s, 40s… that’s not “what you grew up to be”. Until and unless you decide your career is over, it’s not over.

If you were one of those kids with a dream like “be President” or “be an astronaut” or “build spaceships” or “cure mortality”, fulfilling your dream will be really hard. But if you do choose to do something your 10-year-old self would approve of, put in the effort and make it happen. Don’t give up on it, and don’t give up on yourself.

I’m a great believer in luck. And I find that the harder I work, the more I have of it.