Right Time To Start A Newsletter, Best Writing Advice, And Fear Of AI?! - Espresso Hour Q&A E3

Boom. Welcome to another episode of the Espresso Hour, where the running joke is, this is going to be much shorter than an hour because we are again, hyped up on caffeine. Let's dive right into the first question Jenny asks. What's something you used to think was true about writing that you now know to be untrue? So, Cole, how would you start with this one?

I think the biggest fallacy I got taught in college because my degree is in fiction writing, is that the best work wins. Brilliant work just rises to the top. If it's amazing, the world will notice it. There's that great quote, oh, my gosh, I'm blanking on the movie. But it's the Build it and they will come. You know, the same thing is true for writing. People think, oh, if I just write a masterpiece, the readers are going to show up. And what you end up learning is that readers value things that they are taught to value. So you need to be the one to educate the world on why your writing is valuable and why it's valuable to someone else. Just because you think it's great doesn't mean that it's great. Or just because you think it's great doesn't mean readers are just gonna magically show up, you know, and especially it's never been easier to write and publish something. You need to be the one going out into the world and hustling your writing like you're slinging mixtapes out of the trunk of your car. You know, if you're not doing that, no one's gonna give you their attention. So that. That was a big unlearning that had to happen.

For me, it's definitely a place of ego where a lot of writers think, oh, all I have to do is put out good writing, and the rest takes care of itself. I don't need to worry about distribution or worry about headlines or worry about formatting. Right? I could. Whatever I end up writing. And I think it's more, what if you did all those things on top of having really good writing?

Right?

How would that magnify everything you were doing? So that's always some advice. One thing I thought was true, that I now realize is untrue is that writing doesn't just happen all at once. You don't sit down, stare at a blank page, and then write something, start to finish, and go from, you know, idea in your head to finished product.

And that.

I made a video on this, but after reading the book, I'm blanking on the name, but it's like the creative routines of hundreds of artists and writers. My big takeaway was that the best writing is not a result, it's a byproduct. Which means the way that these writers, and really how I live now, is doing things outside of writing, that makes writing easy. So 90% of my writing now happens on walks. It happens in conversation. The last 10% where I actually sit down and type. I always have a full outline that I generated either on a walk or just talking to someone or that I've been kind of working on over time. And so my number one thing that was untrue was that writing doesn't just happen, right? It's a byproduct of all the other things you're doing. And that was very freeing because my first nine months writing on the Internet, I was just sit down on Sunday and say, all right, time to crank out a newsletter or time to crank out a blog post. And that would take hours. It wasn't high quality because I wasn't doing the work outside of it to kind of let the idea marinate, which is where all the good thinking actually ends up happening. And so that's it. Writing is not a result, it's a byproduct.

That's a great one. That makes me. Another one that definitely stands out is. I totally agree. Used to think that to write you needed to like sit down and have this perfect writing environment. And in reality, most writing, because life is busy, it has to get done in unconventional places. Some of the best things I've ever written have been on my phone in the bathroom of a restaurant after like three glasses of wine. The whole point of carrying around a smartphone is your ability to capture ideas. And ideas don't happen when you're just sitting at a desk staring out the window going, oh, okay, now is the time to come up with an idea.

Right?

Ideas are always happening. And so you want to give yourself that flexibility to think of writing as something that can always happen, doesn't just have to happen at your desk.

That's why I got this second cell phone where I have nothing. I took one of my old iPhones, took everything off it. All it has is a note taking app. So now when I go on long walks, I can get all the benefits of a smartphone without the toxic everything else. Twitter, Instagram, TikTok, whatever it is that's on there. That's been a big game changer for me. I put that in one of my last videos too. Alright, next question. Jimmy asks, is there ever a right Time to start a newsletter. I'll start with just one take I have on this is I actually started all of my writing journey with just a newsletter. I didn't have a Twitter account. I thought I was going to have a blog and I was going to have a newsletter. Looking back, my original commitment was to write and publish a newsletter every week for 52 weeks. I ended up doing that, and it definitely had its benefits, but the benefits were not specific to the newsletter. It was just specific to me putting ideas out there and hitting publish. So if I was looking back, I would say instead of writing a newsletter every week for 52 weeks, I would publish a tweet every single day for a year. That would be my minimum bar. To start writing on the Internet right now would be all you have to do is commit to putting out one tweet every day because your first 30 will suck. And my first 30 newsletters sucked. But if you can tighten that feedback loop down to something on a daily basis, it's gonna be much better.

Yeah. I'm always surprised when people ask the question of should I be writing on Twitter or should I start a newsletter, you know, or should I be writing on LinkedIn or should I start a newsletter? Because I view them in two completely different categories. And the way I like thinking about it is any digital business has three components. You have your attention engine, which is social media. You have your, we'll call it retention engine, which is your newsletter or, or email system. And then you have your monetization engine, which is. And ultimately, what's the product? It could be a book, it could be an ebook, it could be a course, it could be a community, it could be whatever. And so the right time to start a newsletter is when you have an attention engine, right? Because a newsletter is a closed loop. It doesn't introduce you to net new readers unless for some reason they decide to take your newsletter and go, I'm going to go share this with someone else. And so to me, the path follows that sequence. You first want to write on social platforms, Twitter, LinkedIn, Medium, Quora. You know, even if you're writing on Facebook somewhere where there's already users, you're building your niche there. You have this attention. And now you want to more deeply engage people in typically longer form material. You want to retain them and their attention longer. That would be your newsletter. So the attention engine is, here's the short form version. Hey, if you like this, you want the longer form version, which is my newsletter. And hey, if you want the even longer and more valuable version than that, here's my book or paid product or course, or whatever it is. So I really discourage people from starting newsletters day one, because again, Dickie, to your point, the feedback loop is just too slow. You're not exposing your work to net new readers.

I will follow up all of this with one kind of framework that goes beyond just writing a newsletter. But anytime you're asking, when should I start something? The answer is usually right when you start asking that question. Because if you're pondering like, oh, should I start this? Should I not? You're going to figure out the answer to that question the second you actually go and start it and then put it out there for 10 weeks, you'll have better intel on should I keep doing it? So I think the better question to ask is not should I start? But okay, I'm asking the question, should I start? That means I should start, do it for 10 weeks, and then start asking, should I keep doing this?

That's a great point. Yeah. Underscoring that, if you're asking that question, go start the newsletter and notice what friction you run into. And that will reveal the next logical step.

Right.

It's like when people ask, what time of day should I post? I always say the second before you started asking that question.

Right.

You should just be posting, it does not matter. It does not matter exactly when. So great question. Thanks for asking that, Jimmy. All right, another good question from mournflake33. How concerned are you about AI tech taking over? So, Cole, I know you have some thoughts on this one. I saw you write a thread on it, too.

Yeah, the interesting thing, so I am not in the camp of, oh, AI is going to replace all our jobs, and I guess we're just going to be hooked up to tubes watching Netflix for 24 hours a day.

Right?

AI will automate maybe the bottom 10, maybe 20% of jobs in the sense of, take a newsroom, for example. You have a lot of writers that get paid to just write the factual news. Like I. My first major in college was journalism. And one of the things that they trained you on was writing just very objectively. Man walked down the street, man got robbed by other man. This happened at 3:42pm, right. Just super objective. And the reality is, a lot of that objective speech can be automated with AI, and that's fine. And that's where the efficiency is going to come in. But AI isn't going to automate away most writing jobs. What it's going to do is it's going to augment them. So something Dickie, you and I talk about all the time in ship 30 and where we've created all of these templates and everything, right? The purpose of creating a template isn't to remove the writing. The purpose is to remove the most boring and most repeatable part of the writing so that you can focus on the highest value part of the writing. A template isn't replacing you. A template is allowing you to do what you do faster and more efficiently and of higher quality, more consistently. So in my mind, the future of AI and writing is that it unlocks even more speed, creative freedom, efficiency for writers. It becomes a tool that writers use, just like today. Like if a graphic designer said, oh, no, no, no, I don't use Photoshop, I do everything by hand, you'd be like, why? That's such a great tool there for you to use, right? So Photoshop didn't automate away graphic designers. It lowered the barrier to entry. It allowed more people to become graphic designers. It allowed them to increase their efficiencies, it allowed them to scale their work, right? The same thing is going to be true with AI.

It'll be.

It'll be a tool that you'll be shocked if you talk to a writer and you're like, you don't use AI, what are you doing?

It's the surgeon in the room framework, right? So if anyone's unfamiliar, mentor mine, Tim Francis taught me this. And if you think about a surgeon, there's like 17 things that go on when someone does a surgery. Now, how many of those the surgeon themselves actually do is make the incision, do the actual surgery, and then sew things back up, right? Every other, the anesthesia, the pre check, the post check, all of that is very automatable and doesn't have to be done by the surgeon. So applying that to writing, right? This is really a delegation framework. But if you apply that to writing, what are the parts that a writer actually does? It's coming up with the idea and all the other parts of how do you format that idea, or how do you plug that idea into a consumable way, or how you do. How do you templatize that for readability or for virality, whatever that is, is going to be automated or AI'd, right? But the thinking itself will continue to be done by humans, which is just going to accelerate things. So all it's going to do is replace the easily repeatable or filler content, which, to be honest, a lot of writing on the Internet already kind of resembles AI it's people taking an idea that does it need to be expanded and figuring out a way to expand it.

Right.

So it's adding fluff for the most part. That's my take, though. It's going to, just like you said, increase efficiency.

Yeah. Here's two easy examples. So one is we create all These assets for Ship 30, our email newsletter, tweets, landing pages, all this stuff. So every time I go to write a newsletter, we use this framework that we talked about called prepping the page. You know, you go through, you kind of divide the page into sections. You show yourself where these subheads are going to go. Maybe you kind of outline the list. Every time I write a newsletter, I have to do that, and I have to do that by hand. And I've written thousands and thousands and thousands of articles and newsletters on the Internet at this point. And when I sit down and I have to prep the page for those seven minutes, my skin crawls because I'm like, my brain already know. I just want it to be done. I know exactly what needs to be done. I just want it to be done. But I have to go through and I have to click buttons in order to do that. What's AI gonna do? AI is gonna allow me to click one button and it's gonna save me seven minutes of time, and it's just going to prep the page for me. Now I can just move on to do what I do.

Right.

Same thing with hooks. Every time you sit down to write something, a tweet, a newsletter, that first intro, that hook, the thing that you grab the reader's attention. Well, in my head, I've got 50 hooks, I've got a hundred hooks that I use over and over and over again. Well, it takes a lot of mental bandwidth for me to sit there and cycle through all the hooks manually in my head and go, which one should I use? AI is going to allow me to just click a button and it's going to randomly present me with one, and I can just shuffle through and go up. You know what? That's the one I want. So what's that doing? It's reducing my cognitive load. It's increasing my efficiency, and it's moving me from the, oh, I gotta get through this boring sludge part of the writing to let me just get on with the writing. So AI as a tool is like, us as writers should see that as a tremendous lever and mechanism for our own work. Whereas the lemmings are always like, oh, AI is going to seal My job. Here's the brutal truth. If AI was going to steal your job, you weren't doing very high quality writing in the first place.

Right?

And your job as a writer is to move out of being paid to write words to being paid to think. And all AI is going to do is remove the jobs where people just sit down and go, I get paid to write 75 words and increase the efficiency and leverage of people who get paid to think. All right, Artist Voyage asks, what was the best writing advice you got? And kind of, what was the result? What's your answer to this, Dickie?

So this actually wasn't a writing framework. It was more a life framework that I then applied to writing. And I think that's a good way to go about things. Very few things are writing specific. I think they're more life specific. And this was, no one cares what you do. They care what you can do for them. And so instead of my first nine months, every blog post was very much from like a me, me, me perspective. And I didn't one time think about the reader. And then I read that quote and was like, okay, that means every single thing I'm writing, I need to approach from a place of empathy. So I think about this as empathetic writing, which is putting myself in the reader's shoes and saying, what value am I providing to the reader by putting this out there? Every single thing I write at the moment, I. I start with the very first question is, what problem am I solving and whose problem am I solving? So right away, I know exactly the problem and the person who has that problem, which one, makes it much easier because I can write directly to them. And two, it immediately starts that frame of providing value in some way. So I'm not writing from a place of ego, like, I think this or I think that it's someone out there is reading this, is experiencing a problem, but my writing is going to solve it. So this goes for copywriting, this goes for Twitter thread writing, goes for YouTube videos. If you are creating from a place of me, me, me, here's what I have to think and not instead putting yourself in the consumer shoes, you're not going to see the results that you're hoping for.

I love that phrase. And my answer is, I probably. It's essentially the same thing just said differently, which is you are not the main character of your story. The reader is the main character. And what that means, it's echoing the same thing, Dicky, that you were explaining, which is just, it's not about you. Even if the story is about you, it's not about you. And a good way of thinking about this is if you're telling a story, especially about something that you experienced, the story or the experience is the context to the lesson that you want the reader to take away. It's the example. So it's not you talking about yourself, it's you talking about yourself. To reveal a lesson or to reveal a takeaway or to reveal something that's or an answer to a question that matters to the reader. And that's a very important nuance. And a lot of times beginner or aspiring writers think about writing as a me exercise. I got to sit down and it's all about me. I got to say all about me. This is what I think. This is, this blah, blah, blah, blah, blah. And it takes a really long time to unhook yourself out of that and operate from a place of who do I want to reach? Who do I want to help? What's their name? Where do they live? How old are they? What are their wants, needs, hopes, dreams, and aspirations? What are they struggling with? What questions do they have? You are in service of the reader. The reader is not in service of you.

Boom.

That does it for this episode of the Digital Writing Espresso Hour. If you want your questions answered, you can reply to our tweet every single Monday. We're asking questions to our Twitter audience, but you can also reply to this YouTube video within the first hour of it being posted, and we guarantee we'll answer your question. That's it for this episode. Make sure you hit. Like, make sure you hit subscribe so you don't miss out on future ones, and we will see you at the next Espresso Hour.