Category: Writing Life

Read this next time your newsletter feels like a chore…

On March 31, 2024

Most of the time, when a writer starts to feel bored, it’s because they’re writing what they think they should write, rather than what they’re actually interested in.

Led by obligation, rather than curiosity.

We got some experience with this at Trends. People paid $300 per year for the newsletter, and we felt pressure to deliver the same kind of newsletter every week. But you can’t pull business opportunities out of thin air just to fill space.

So over time, we developed a rule: If we’re struggling to fill a segment, cut it, and see if people scream.

It’s a concept I got from Andy Rachleff, the man who coined the term ‘product-market fit.’

“At the end of your free trial, you should pull the trial,” he said. “If the customer doesn’t scream, you don’t have PMF.”

If we were struggling to fill a segment we thought needed to be there, we’d cut the segment entirely, and see if readers screamed.

If they did – if they wrote in asking where such-and-such was – we would put it back the following week, and make sure to prioritize it in the future. That’s how you know you’re making something people care about.

But often, they didn’t complain at all. Because cutting a “meh” segment gave us time to focus on stories we actually cared about, and made the newsletter better overall.

Your readers don’t need you to deliver the same format every week. They need you to deliver the same feeling. Your authentic voice will typically do that better than something you feel obligated to write, even if it ends up being much shorter.

My favorite example of this comes from The Hustle…

A daily writer once called out sick, and all of a sudden, Sam needed to get the newsletter shipped on his own.

What did he do? Cancel all his meetings, and draft a perfect email?

Not quite.

This is what he sent that day…

That’s it. That’s the whole thing.

People loved it.

It’s honest, in a surprising way. Because the truth is that he was busy and he needed to get back to work on other things. But more importantly, he didn’t try to fake interest in a bunch of random news stories and force himself to write a typical email.

He took an authentic emotion, and turned it into something he could share with his audience.

I think of this often.

My newsletter always feels like work. That’s because writing’s hard. It should feel like work, in the same way that going to the gym feels like work. Work you enjoy.

But if it ever feels too much like an obligation, I take that as a signal that there’s a gap between what I’m writing and what I actually care about at the time.

To close the gap, I’ll sometimes spend a few minutes free-writing. Either I’ll write about what’s making me mad right now (no stopping, no edits) or I’ll just set a timer and write non-stop for ten or fifteen minutes about whatever goes through my mind.

Usually, one of those gives me a thread I can pull. It’s hard to write for ten minutes straight without tripping over a thought you’re genuinely interested in.

“Excited curiosity [is] both the engine and the rudder of great work,” Paul Graham once wrote. “It will not only drive you, but if you let it have its way, will also show you what to work on.”

So if your newsletter’s feeling like a chore, rather than something you can sit down and enjoy making, stop for a second and ask yourself what you’re actually excited or curious (or mad) about these days.

Write about that.

To hell with your typical format. Just make sure you’re in it.

How to Stay Relevant

By Ethan

On February 25, 2024

In Writing Life

Here’s something that no one’s going to tell you when you first get started writing or creating things on the internet…

Someday, a new generation of creators will come up behind you, and they’re going to be better than you in a lot of ways.

Sometimes, their work will be better than yours. Other times, it will be worse, but they’ll be better at getting attention, and so eclipse you that way. A few will be both. Others will be better at tapping into the new thing people care about – the thing you think is pointless.

The list goes on…

When this happens – and it will happen to you – you have two choices about how to go forward: You can be small, and defensive; guard the secrets of your trade, and try to deny newcomers the admiration they’re earning with their work. Or you can go the opposite way, and decide that you’ll always do your best to help them succeed.

As you can probably guess, the first path offers nothing for you in the long run, except maybe a little comfort for your ego as you slowly slide into irrelevance. It’s the second path we want.

The second path is tougher, because it forces you to grow as a creative person. It forces you to look at your work, and the work being done around you, and to ask (possibly for the first time in years) what you actually bring to the table that’s unique these days.

It forces you to acknowledge that other people can do some of the things that made you special years ago. It forces you to confront and maybe even kill off parts of your ego.

But if you can do it, you’ll be much better off for it. Because above all, this approach forces you to abandon any kind of scarcity mindset, and when you do that, your work gets better, and you, your peers, and your readers all benefit.

Two people have really helped form my thinking on this.

The first is Tim Ferriss. I’ve been a fan of his for almost two decades, since the publication of his first book, The 4-Hour Workweek. His work inspired entire generations of other writers to talk about solopreneurship, remote work, lifestyle design (a term he coined), and more. And yet, he’s stayed relevant through it all.

I think there are two key factors.

First, he doesn’t hold back information. A lot of writers are scared that if they share everything they know, their audience won’t need them anymore. So consciously or not, they hold back or try to drip ideas out slowly in order to hold onto attention.

But what this really is is a fear that if you say the one big truth you know, you won’t have anything else to say.

I’ve done this. It’s a mistake. It keeps you from writing at the edge of your ability, and what you don’t realize is that by holding back, you’re just being less helpful to readers, which opens the door for someone else who’s willing to tell-all to come in and scoop them up.

Tim tries to write the definitive book on each topic. He doesn’t hold back. As a result, people continue to follow him because they know that he’ll teach them everything he learns along the way.

Your readers are always running into new problems – new issues every damn day. If they think of you as someone who always teaches the maximum they can, they’ll continue to look to you for help with each new issue they face.

That brings me to the other aspect of Tim Ferriss’ long-term relevance, which is his focus. He doesn’t chase trends. Instead, he’s focused on solving the problems he’s encountering in his own life. Then he writes about that, trusting that some segment of his audience will benefit.

So those two things – teaching everything you can, and focusing on the things you’re facing in your own life, rather than chasing trends – those are two good ways to stay relevant for a long time, even as other great writers come onto the scene.

I think they speak mostly to the craft itself; to keeping your work relevant to the audience.

The other person who’s really formed my thinking on this is Joe Rogan, because of how he treats other creators.

Whether it’s podcasting or comedy (both areas in which he’s a dominant player) he’s not just accepting of others coming into the craft, but he actively tries to promote them and make them as successful as possible.

He’s typically pretty subtle about this publicly, but finally shared his thoughts in a recent conversation with Cameron Hanes and Steven Rinella (starts at 2:15:04)

“I don’t think of comics ever as competitors,” he said. “I try the best I can to get them more famous. I want them to be huge.”

What a great mindset.

I wanted that for my career, and frankly, for my day-to-day life. To be free from that useless anxiety over competition, and instead start from this place of abundance. So I chose that, and cultivate it regularly.

These two guys helped.

I also found it helpful just observing my interaction with their work as a reader or listener. In almost two decades, no one has replaced Ferriss in my mind, even though I’ve read and admire many other writers who’ve come up in his wake. No one’s replaced Rogan.

You’re not competing for mind-space in the way that you think you might be.

The only thing that makes you irrelevant are the bad decisions that come from fearing irrelevance. So put that out of your mind, and get back to work.

Do It Anyways

By Ethan

On January 21, 2024

In Writing Life

If you read too much you may come to the startling realization that, “Oh my god, everything I want to say is already being said by someone else.”

You’re right. But write anyways.

Hell, even the three main religions of the world basically repeat on another on the big points.

Hemingway’s Kudu and Quitting Your Day Job

By Ethan

On August 18, 2019

In Writing, Writing Life

Always as a writer there is the question of whether to keep your day job. Successful writers for generations have been telling aspiring writers to keep their jobs and do their writing on the side. Aspiring writers, myself included, have spent generations ignoring this wisdom.

And then there is Hemingway, who found a sneaky way to give new advice on this, then buried it in the pages of an unlikely source: his 1935 safari tale, The Green Hills of Africa. In it, he says…

Now it is pleasant to hunt something that you want very much over a long period of time, being outwitted, outmaneuvered, and failing at the end of each day, but having the hunt and knowing every time you are out that, sooner or later, your luck will change and that you will get the chance that you are seeking. But it is not pleasant to have a time limit by which you must get your kudu or perhaps never get it, nor even see one.

It is not the way hunting should be… The way to hunt is for as long as you live against as long as there is such and such an animal; just as the way to paint is as long as there is you and colors and canvas, and the way to write as long as you can live and there is pencil or paper or ink or any machine to do it with, or anything you care to write about, and you feel a fool, and you are a fool, to do it any other way. But here we were, now, caught by time, by the season, and by the running out of our money so that what should have been as much fun to do each day whether you killed or not was being forced into that most exciting perversion of life; the necessity of accomplishing something in less time than should truly be allowed for its doing.

-Ernest Hemingway, The Green Hills of Africa

It’s tempting to believe that your day job is what’s keeping you from your writing. That quitting it would offer the long open stretches of time you crave to be creative. Depending on your means, it may.

But when you leave a job behind, you turn over an hour-glass. The grains of sand counting down the days before your work needs to begin paying for itself.

It’s impossible to say for certain whether any particular writer should or should not have a day job, or whether they do or don’t stand a chance of making it. But we can comfortably say that no writer should ever do their work in less time than it ought to take.

Most of the time, when we talk about quitting our day jobs in order to pursue writing full-time, the question at hand is “How quickly can I make money at this?”

But another question, the one Hemingway offers, is “How long should this project take, and can I still afford to give it that if I walk away from my paycheck?”

On the Difficulty of Writing

By Ethan

On February 23, 2019

In Writing, Writing Life

The most difficult thing about writing is writing something that’s true. I think that if you can write something that’s true, it will always be good, even if it’s not enjoyable. The truth is not always enjoyable. But reading a truth that you recognize has a certain redeeming quality so that even if the story is unpleasant it sticks, because you see your own experience reflected back at you.

Writing the truth is hard because it forces you to be vulnerable, and also requires that you don’t believe your own bullshit. The bullshit I speak of is not comprised of overt lies. Rather, it is the collection of little half-truths we tell ourselves in order to get through each day. I’m not that lonely. There’s still time. The spinach is tasty.

These half-truths are needed to keep from going crazy in a world where the good guys don’t always win, and bad things happen to all sorts of people, and the rules are different depending on how many zeroes there are on your bank balance. They help you to put two feet on the floor each morning, shave, and wear pants when you might prefer to grow your mane long, flip the table, and donkey-kick the guy who’s texting when he should be paying attention to the traffic light.

The half-truths help you to live a civilized life. Hell, they may even help you live a good life, help you hang on long enough to cut yourself a better slice of the pie. But they will not help you to write.

That is why writing is so hard. Because the mindset needed to write honestly is fundamentally different from the one needed to be a card-carrying member of the civilized world. So writers tend to be recluses, the good ones at least. And the better you’ve done at society’s game, the more difficult it is to recognize truths and put them on the page.

That doesn’t mean your writing has to be unpleasant. There is a beauty to truth. When Hemingway writes about winters in Schruns, about skiing in the high mountain country, and about the hillside farms and the warm farm houses with their great stoves and huge wood piles in the snow, it is beauty itself; words of a true admirer, written by someone who knows.

Hemingway’s truth will not be the same as Neil Gaiman’s truth. For Gaiman, the world is full of ghosts and gargoyles, witches and warlocks. Magic exists, and it finds its way onto every page. Hemingway finds magic in an elk hunt at sunrise, but stays well away (certainly outside shooting distance) of anything mystical.

If you don’t believe in dragons, you will not be able to write about them convincingly, no matter how attractive the market-size for fantasy thrillers. So you must know the true truth of the world, as well as the truth of the world as you see it, and you must avoid believing your own lies, and if you can do all that and clear a few hours a day to put words to paper, maybe then you can write something worth reading.