Is it even possible to be a writer AND happy at the same time?

This article analyzes the marketing concepts that make writers miserable when misunderstood and gives cold, hard numbers about audience building, sales, and marketing that might otherwise make your head spin. This is a deep dive into the data that makes author businesses work, and you will hopefully leave with at least a better understanding of them. If you are a paid subscriber, I recommend reading the writing rollercoaster to learn more about my publishing journey, five steps to writing freedom to get a quick guide to how to build your writing career, and 10 things I know for sure about being an author to help round out this article.

If you are not a paid member, you can read everything with a 7-day free trial, or give us a one-time tip.

I was hanging out at LA Festival of Books with my friend who wrote a choose-your-own-adventure book called You are a Filmmaker. He’s a professor of film whose been working in the industry as long as I’ve known him, and the book has over 100 endings.

After somebody left our booth with the book, I joked with him that I was thinking about writing a book called You are an Author, but it would be wholly depressing because every ending would be “…and you are miserable.”

“You’ve sold a million books…and you are miserable”, “You’re working at a coffee shop writing your book in the dead of night…and you are miserable”, and so on.

I’ve talked before about how I have big feelings about happiness, but I also don’t want to be miserable.

While it certainly seems like the vast majority of my writer friends have been flirting with misery most of their careers, we don’t actually have to be miserable to write, do we?

The concept that the best art comes from tragedy is ridiculous, after all. Lord of the Rings was written by a father telling a story to his son, and it was revolutionary. Whether it is even ethical to profit from tragedy is a conversation I will keep to another day, but there’s no doubt that the general scholarship on the topic states that we write better when we are sad. In fact, when I typed “can you be happy to write”, this was the first article that popped up, titled Why You Can’t Write When You’re Happy. 

At the beginning of my career, I was definitely fueled by sadness and tragedy. However, since getting on meds and improving my outlook a few years ago I’ve had to change my relationship with my work in order to continue with it.

Turns out that it’s really hard to revisit past work you wrote while suffering suicidal ideation without spiraling again, and that kind of sucks. On top of that, there are few jobs that tell you “in order to be really good at this, we need you to be miserable”.

Even if you are miserable working at big box store #3426, their training manual probably has a section about happiness or averting depression. My plan is to continue doing this work until I die, and constant misery is just not something I can tolerate for the next (hopefully) 40+ years.

So, I did a deep dive into the things that were making me unhappy, and it turns out that it’s capitalism, silly. I’ve written a very long post about how to exist as a writer in a hypercapitalist hellscape, but even with close to 7,000 words I didn’t even come close to scraping the surface of the problem. This has been the work of my whole career. 

Since I live at the intersection of craft and commerce, I wanted to share with you some of the concepts that inform our relationship to making money with our art, how they influence our mindset, and how we can spin them to our advantage when advantageous.

Will that make you happy as a writer? I don’t know. I don’t even think happiness should be the goal, but I hope it will make you less miserable and move the needle closer to neutral.

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One of the best and most dangerous concepts about making money on your writing is Kevin Kelly’s 1,000 true fans. It is the idea that if you can find 1,000 people willing to give you $100 a year, then you have a six-figure business.

It literally sparked a creative revolution, and I use it all the time as a framing device, but there is a pernicious piece of the concept that people forget. Namely, you have to talk to a massive amount of people to find 1,000 people who love your work.

In order to properly understand why this is true, you need to understand the concept of a sales funnel.

The idea behind a sales funnel is that some amount of people who you interact with will like you, some percentage of those people will trust you, some percentage of those people will buy from you, and some percentage of those people will fall in love with your work.

However, writers in general seem to hear 1,000 true fans, see they have 800 Facebook friends, and think they are 80% of the way there. The cold hard truth is that only 1-2% of the people that like you have a realistic possibility of buying from you, let alone becoming true fans.  

That means in order to find 1,000 buyers for your work, you have to talk to at least 50,000-100,000 potential fans. However, not everyone is a possible fan, which means you probably need to spread your message to 10x more than that in order to attract enough people to make these numbers work. That’s between 500,000 and 1,000,000 people just to find 1,000 buyers.

Unfortunately, not all buyers are true fans. In my own business, it seems like 30-50% of buyers will buy again and 10% of buyers will become superfans. That means now I need to find 10,000 buyers to find 1,000 superfans and, thus, talk to 5-10 million people.

We haven’t even included your churn rate in that number, which is the number of people who leave your audience in any given year, which can be 10% or higher. The average churn rate for a SAAS company is 3-8%, which means even in the best companies laser-focused on retention, some people are leaving their ecosystem every month whose revenue needs to be replaced.

There is good news here, though, because this is just a math problem now. Every time you wonder why you’re not doing better, you can just ask yourself if you’re message has been seen by 5-10 million people. If not, then you just have to chip away at that number a little at a time.

I had a conversation with a creator a while ago. What we talked about has gnawed at me. It’s something I hear all the time. It impedes so many creatives from moving to the next level.

He was bitter because nobody he knew wanted to buy his book.

He went to his audience hat in hand and couldn’t get anybody to take a chance on what he had to offer. He didn’t understand why his family would forsake him while they bought whatever celebrities told them to buy.

“It’s not personal,” I told him.

“But why?” he asked me. “They are my family. They should be supporting me more than some celebrity.”

I only had one reply. “Guilt can’t scale.”

You can’t guilt people into buying something. It makes them bitter and resentful. They see your panhandling as an obligation they want to get rid of as soon as possible. They won’t become long-term customers. Even if you somehow get their money, all you’ve done is make yourself a nuisance. You haven’t made a customer for life.

Make no mistake, that’s what you are after in the end. One of the biggest predictors of overall success is customer lifetime value. Obligation does not build a happy customer and is never appreciated. Think about the things you are obligated to do. You are obligated to pay your mortgage. You are obligated to do chores. You are obligated to take your dog to the vet.

All those things suck.

Nobody willingly takes on an obligation with a smile. You can only force an obligation on somebody. And you don’t want to force anybody into buying your product. You want them to buy it happily. You want them to buy all your products because it fits a need in their life, even if that need is just edifying their soul.

I have 20,000 people on my email list, and in the past year, I’ve made far fewer than 2,000 sales. That means at least 90% of the people on my email list haven’t bought from me in over a year.

I could be mad about that. I could sulk. I could cry. I could pound my fist in the air. I could yell at the people who didn’t back.

But what will that get me?

It won’t get more people to back my projects. It won’t make me more money. All it will do is ruin friendships and destroy family ties. On top of all that, it would make me an angry, spiteful, vindictive man. That’s no way to go through life.

So, I leave the 90% alone and focus my products on the ones who do buy. Those are the people who like my sense of humor. They are the ones who resonate with my message. Those people want to buy my products. They have the highest customer lifetime value. They are my target audience. That’s no different than every other company. This is how all companies succeed. They focus their message on the small sliver of the marketplace that resonates with their message.

There are multiple ways to increase your profit, but focusing your attention on who isn’t buying from you isn’t one of them.

You don’t want people to buy things out of obligation or guilt anyway. You want them to buy because they want to buy. Those are the people who are in your ideal market. Those are the people you can build a business around. You will never convince somebody your product is cool if they don’t see a need for it.

Maybe, along the way, you’ll guilt a couple of people into buying from you. But those people are only short-term gain. They aren’t going to buy every one of your products. They aren’t in for the long haul. They aren’t going to support your entire career.

You will do well to remember that and become okay with it. In the short term, it hurts when your family doesn’t buy from you, especially when you are just getting started. In the beginning, you are clawing for every dollar, but that’s why strategic planning is so important. That’s why you can’t focus on the short term. You have to focus on the long term.

And in the long term, understanding that it’s not personal is one of the most important skills you can learn for your business and your sanity. After all, guilt can’t scale.

Now that we’ve broken down how to nurture the bottom of your sales funnel, let’s talk about how to build the juicy middle of it with casual fans. The good news here is that while you’re building up your superfans, you will also be making money on casual fans.

I’ve been a six-figure author since 2017, and I’m not even sure I have 1,000 true fans yet.

Maybe you don’t need $100,000 to lead a happy life. Even though previous scholarship has said that happiness caps out at $75,000 and recent studies dispute those findings, maybe you can live on much less than that amount. Let’s say you would like to make $50,000 as a writer in order to lead a happy life. The latest survey of working writers found they make an average of $12,000, so that would put you at the high end of earners.

Let us also stipulate that this is after expenses, which include editorial, marketing, and everything else needed to run your business. In this scenario, $50,000 is what goes into your personal bank account at the end of the year.

If you are lucky, you can run your business at a 50% profit margin. If you’re a non-fiction author you’re probably laughing behind your 80% profit margin, but for most of my life I’ve run a 22% profit margin, so this is more than double my average.

That means for every $1 you spend, $.50 is pure profit after expenses. If you want to make $50,000, that means you need to make $100,000 because an additional $50,000 will be expenses for your business. It's really important to understand that every business has expenses, and the more you make the more you will spend.

Also, if you are planning on landing a book deal, then you can use this calculator to figure out how many sales it will take to make the earn out of your advance with a publisher. Many people think I am anti-publisher, but I’ve signed over 50 publishing deals in my life. I just think you need to use them strategically when it is mutually beneficial to both of you. Still, admittedly this example is mostly for self-publishers.

So, you have a $100,000 goal for your business so that you can keep $50,000 for yourself.

An ebook generally sells for $3.99-$4.99. For the sake of this argument, though, I'm going to say $5, because it's easy to math. Most vendors only give you 70% of the total sale price, keeping 30% for themselves.

That means on a $5 ebook, you will see $3.50.

At that price, you will need to sell 28,571 copies of a book to make $100,000 in revenue. Now, most people write more than one book a year, so let us assume you write an average of 4 books a year; one every 90 days to stay ahead of the Amazon cliff.

If you release four books a year, then you will need each book to sell 7,142 copies, at least, to make $100,000.

If you release 10 books a year, you will only have to sell 2,872 books in order to make the same amount of money (though releasing more books eats into your profits). Let's stick with 4 books though, since that's what most people can comfortably maintain.

The nice thing about books is that once you have a good back catalog, you can make as much as 50% of your income from back catalog books alone. That means you only need to make 50% of your income from new releases. The more fans your meet, the more you chip away at that number.

It might sound daunting, but it's very doable through marketing and advertising. If you know the numbers, you can work toward them. Otherwise, you are just going to keep being adrift in an ocean of uncertainty.

If you’ve made it this far into a very data-nerdy article on building a writing business, then you are now ready to understand my favorite statistical concept; the Bell Curve.

I have a degree in demographic sociology, so I am intimately familiar with the Bell Curve, as I have worked with it since I was 18.

The general idea of the Bell Curve is that if given enough of the correct data on almost any subject, then the data distribution will look like a bell with a big, fat middle that tapers off on the edges. You can really get into the weeds about whether this is the correct distribution for every population, but since I look at audience building and sales from the sociological perspective of how large groups behave, it is apt for this discussion.

Why is this important in sales?

Because almost everyone gives up on accumulating data before their distribution fits into a Bell Curve.

What do I mean by that?

Let us say that at a convention, every 100 people you talk to will lead to $100 in sales. Once you talk to 100 people, you can reliably predict you will make that amount of money almost every time.

The reason that is predictable is that you have found the normal distribution of your data.

However, if you give up and only talk to 50 people, you will not reliably make $50 in sales.

Why is that?

Because you have not spoken to enough people to normalize your curve.

You see, if you talk to 100 people, you might make that $100 from the first two people, or the last two people, or somewhere in the middle.

But by skewing your metrics, you no longer have a Bell Curve, which makes your curve more erratic and less reliable.

You might make $300 from talking to 10 people or $0 from talking to 70 people, but it's impossible to predict because you have not collected enough data.

The graph of data eventually normalizes into a Bell Curve because there is enough data, a robust data set, to create such a curve.

This can't be overstated enough. If you gather enough data, then your data will, 100% of the time, result in a curve that looks like a bell.

There are ways to correct for a less-than-normal distribution curve, but it's still partially a guess.

The Bell Curve is the foundational metric of statistics. It's how we can poll 1,000 people and make assertions about a whole population.

There is another factor working here, though, because to get a Bell Curve, you need your data collection to be random.

For instance, you can't pick and choose who you talk to at a convention because that is no longer random. I can’t tell you how many sales I’ve made from people outside my target demographic simply because I talked to them.

So, if you only look for people who look like your perfect customer, your standard distribution falls apart.

This doesn't mean you should go everywhere and talk to everyone, even at a supermarket or swap meet, unless they have a high propensity for being filled with your ideal clients.

For instance, if you want to study voting patterns in Texas, you wouldn't poll people in Oklahoma, right? So, you need to find the random distribution in whatever population you choose, like a specific convention. 

However, it does mean when you decide to do a marketing/sales push, you need to get a robust data set. Otherwise, your numbers will vary wildly.

This concept is a foundational component of all sales. It's how you can predict the ROI of your ad spend, choose what conventions to go to, and how much money you will make next year.

People ask how I can so accurately predict my sales numbers, and it starts with having a robust data set.

When I go into a new situation, what scares me most is that I don't have enough data to properly assess the situation, and I don't trust anyone else's data without replicating it personally.

So, how do you use this? Learn your numbers and talk to more people when you do a promotion.

Send more emails. Run more ads. Talk to more podcasts. DO MORE THINGS so that you can better predict your next launch and the next steps.

Your numbers might vary wildly from mine, but you'll be unstoppable once you know what it takes to get normal distribution for your launches.

What if you don’t even care about books and you make all your money on Substack? Well, unfortunately, the way Substack focused their newest software releases is going to make it much harder for you to collect those superfans moving forward.

With the introduction of Notes, there was an enormous surge of people signing up for lots of emails, and now they are realizing they can’t possibly read them all.

Like most platforms, the way audiences split their attention is not evenly distributed. Notes grew newsletter subscriptions horizontally across their already existing users, splitting user attention exponentially among more people, instead of expanding into new markets to bring in new readers.

This means there are roughly the same number of users but exponentially more creators to follow between them. If a user only has $20 to spend on creators, and only follows four Substacks, the choice is clear where to spend their money. If they subscribe to a hundred, it’s much harder.

That attention continues to split with every new person that the user finds, and we have to continue working to earn their loyalty with each post even harder than before.

In the “pre-Notes” days, it seemed like roughly 1 in 10 people who followed a Substack eventually transitioned into a paid subscriber, but after Notes debuted, it seems to have been closer to 1 in 20.

Substack’s own indicates that their ideal metric is that 10% of users will eventually “go paid”. That made sense when everything was highly siloed and finding new publications was hard, but when you expose that same network to more and more creators, that number has nowhere to go down but down.

How much? I don’t know, but I wouldn’t be surprised it if ended up closer to the 1 in 100 number I discussed earlier, and more people choosing not to stick around for the long haul.

Good branding is going to be essential to pull people to your publication in the near future. When a platform is young, a lot of writers succeed with mediocre work and poor branding because there is more demand than supply.

When more people come to the platform, and attention splits, the ones who write the best prose and the ones who are the best marketers tend to win.

So, it is not just about winning the loyalty of people, it’s also about maintaining that loyalty, and also understanding the value that people derive from following you.

I found a little niche at the intersection of craft and commerce. I explore questions about how can we make great work and share it with the world without losing our souls in the process.

My business partner is a publishing analyst. Her value is she is always at the vanguard of the publishing conversation, and synthesizing where the industry is going. People follow her because if she’s not talking about it, they probably don’t have to worry about it, either.

Both of us have overlapping but very different niches in the publishing space and tackle things in different ways, which draws readers to us for different, though complementary, reasons.

What if you fail at doing all of this hard stuff? You likely will, at least with some of this stuff, and that’s okay. Success is built on failure. There are many points of failure that could cause a project to seem like a failure, but it doesn't mean the project itself is a failure.

Let us look at marketing a book, for example. Yes, it is possible that the book is just horrible. However, if you are running an ad for a book, there are so many pieces that could lead to failure, even if the book is great.

For instance, on the ad level:

• The ad copy might not be right

• The targeting could not be right

• You could be targeting the wrong audience

• You could have launched at the wrong time of day

• You could have launched on the wrong day of the week

• You could be targeting the right audience but your ad isn't being served to the right people

• The audience you chose might not be big enough

• The imagery you are using might be wrong

• The competition for ads might be higher than normal

• A more popular book might be targeting the same audience and pulling their attention.

Additionally:

• Ad costs might be higher because of the time of year, like at Christmas time when companies blow their remaining ad budget for the year.

• People might be away from their computers more because it is summer and they are with their families

• A world event might be diverting attention from your advertisements

Not to mention that if you can get a great ad that gets people to click, the fun doesn't stop there.

• The copy on your page might not be strong enough

• Your tagline might not be compelling

• Your cover image might be weak

• Your cover image might not be aimed at the right market

• Your blurb might be aimed at the wrong market

And then, even if you can get somebody to read your book:

• Maybe the first page isn't amazing and they put it down, even though the rest of the book is great

• Maybe the book isn't written to market

• Maybe you have written a book into an oversaturated market

• Maybe trends have shifted

• Maybe you haven't created good enough hooks at the end of each chapter

• Maybe you haven't written a long enough series to earn out your marketing costs.

Those are just some of the things that could happen with a single book that might prevent it to be successful, and, if all of those things go perfectly, then maybe you will have a hit, but maybe you won't, because some unknown unknown that you didn't even know about went wrong.

The good news is that you can tweak any and all of these things and relaunch your book, or any product, again and again, until it's right and you find the perfect audience for it. Most projects aren't failures. It's the marketing that is a failure.

I don’t watch a lot of sports but I really liked this answer by Giannis Antetokounmpo after he was asked if the whole season was a failure because the Bucks were eliminated from the playoffs in the first round.

Being somebody who has failed does not make you a failure, even if all you have known is being unsuccessful.

Screwing up does not mean you are a screw-up, even if you never seem to get it right.

Current states can be changed and often change quickly and without warning.

You are not one thing. You are many things and have the potential to be anything.

I’ve been interviewed hundreds of times in my career. In every one, they ask me how I became a writer. I've answered a lot of different ways, but the one I keep coming back to is that I never knew that wasn't what you were supposed to do.

When I was young, everybody was going to be a director, or a writer, or an actor.

I just assumed that when I hit 40 everybody would have done that thing. It didn't cross my mind for one second that wouldn't happen.

I was intimidated, frankly, because there was so much talent around me.

Then, life happened, and I looked back 20 years later and realized that just because you wanted to do something didn't mean that wasn't what happened.

I tell people that the great separator is time and effort.

When you're at the starting line, there are millions of people around you, but as you keep doing work, people fall off, until you're one of a very few, a select group, that has kept the creative spark.

You have no idea how rare that gift is until you sit back 20 years after high school and think about all the people who wanted to do something creative with their lives, and how few actually ended up doing it.

There are lots of other aspiring creatives, but so few make it to the mountaintop with their spark intact that it's almost a miracle it ever happens at all.

I'm not saying they aren't happy. Many of my friends who stopped doing creative work are very happy, but they aren't doing the creative thing they set out to do when we were wee babies.

They aren't doing the thing that intimidated me about them for so long.

People more talented than you will fall away. People who boast more will go away. People who you think are guaranteed to win will go off and do something else. Hotshot creators will burn bright, burn fast, and burn away. I've seen it all while I've been slowly doing the work day after day.

My work has never been perfect. Far from it, but I've learned from it every step of the way, and kept going. Showing up and doing the best work you're capable of is really the secret to the whole game. It's not one or the other. Making one great product doesn't give you a career. Showing up without making something doesn't make a career. Showing up and doing great work consistently makes a career, especially if you can keep showing it to more and more people.

At the end of the day, you will be alone on a mountain, and you'll look around at other mountains and see the other people who climbed the summit, and you will bond with them instantly, because they were the survivors.

In this work, most of it is about surviving with the creative spark still inside you, protecting it fiercely, and outlasting other people.

At the end of the day, being a writer is work, and work often sucks. Historically, I have not been a happy person. I suffer from both anxiety and depression. I fight every day against my relentless negativity. However, recently I set out to change that as much as I could. I decided my new motto was "chase the joy".

I think understanding all of these concepts allows you to chase joy better in your career. If you know you have to reach 10 million people to realistically build a successful business, then you treasure those people who do resonate with your message.

If you know that it’s incredibly hard to do this work, then when it shows itself to be incredibly hard, you won’t beat yourself up over it too much.

There is joy in the work, though. I didn’t know that at first. Everything I did was filled with misery. However, soon enough, I found that interlaced with my misery were moments where the dopamine hit me.

It was only for a moment, but like a ping in a great ocean, I used it as a guide. Every time I felt that dopamine hit, I would try to analyze why I was so happy in that one brief moment.

Over time, I was able to put together a list of things that made me happy, and even though I was still mostly miserable, I started to chase those moments, whether it was the thrill of a sale or a great review.

I found the things that I really loved doing, the shows that resonated with me, and the parts of my job that I enjoyed...and I tried to do them as much as possible. I assumed my revenue would go down as I cut out the miserable tasks I hated, but I made more money this year than I did last year.

And I did it in ways that mostly brought me joy.

Not always, of course. Honestly, there are still a lot of days that suck. There are things in business you need to do which just aren't fun. There are moments, even in the fun part, that are miserable.

However, for the most part, I could stretch those moments of joy into whole hours or even days. For me, that's a huge accomplishment.

And it all started with a simple three-word motto.

"Chase the joy."

If you got something out of this article, I hope you’ll consider subscribing to hear more from us. All our articles are free upon release and for a few weeks afterward. If you are a paid subscriber, I recommend reading the writing rollercoaster to learn more about my publishing journey, five steps to writing freedom to get a quick guide to how to build your writing career, and 10 things I know for sure about being an author to help round out this article.

If you are not a paid member, you can read everything with a 7-day free trial, or give us a one-time tip.