Why I Haven’t Written Anything This Year

Wait… what?

You read that right. I haven't sat down and written a newsletter post from scratch all year.

Not one.

Oh, I've published plenty and I stand behind all of it, but none of it started with me at a keyboard and a blank screen—which is how I did it for the first twenty-one years of this publication.

Nowadays, that kind of feels like writing in script using a fountain pen the way I did back in Our Lady of Guadalupe elementary school.

Is this an admission that I’ve been AI slopping you, my loyal readers, this whole time?

Not at all… but what I am doing, I’ll leave it up to you to decide what to call it.

It makes me think of my friend Amanda McGrory. Amanda is a 7x Paralympic medalist that uses a wheelchair, but I’ve heard her say “Let’s walk over there.” I know what she means, obviously… I’ll be walking my slow ass next to her as she valiantly resists the temptation not to just leave me in the dust. The result is what anyone traveling next to her would expect, but she’s using an aide to participate.

The difference here in my “writing” is that you can’t see the aide I’m using to produce this writing—but more and more, you’re probably assuming it’s in there somewhere. For the record, I’ve manually typed all of the em dashes that have appeared in this post up to this point. I’ve been using them for over 20 years and I don’t plan to stop now.

My challenge is that I don’t have a ton of time to write, but I’d like to do more of it, while still making sure what I produce is authentic. I've been writing this newsletter since 2004. There's no fund brand or book brand or coaching brand sitting on top of me. It's just Charlie, and the business of Charlie, no matter who was signing the checks at the time, has run on people recognizing my voice when they see it.

That’s why I produce these posts in a very particular way that I’d like to share with you. I go into it more deeply with the cohort members of my Visible Work thought leadership class and we’ve got a group forming for September, but I’ll just share the post process for now.

First off, writing isn't one thing. It's a stack.

You pick a subject, you figure out what you actually think about it, you get your thoughts in an order that works for the point you’re trying to make and for the reader’s understanding. You turn that into sentences, and then you edit.

Those are different skills and I don't have an edge on all of them. Turning thoughts into sentences is just transcription—and that’s a commodity. I don't transcribe any better than Claude does.

Where people go wrong is where they turn a topic into sentences using AI, attempting to skip a step by outsourcing the thinking and insight. “Give me a post about X” versus, “Here’s what I think about X… it’s a function of A, B, and C, and I don’t think C matters anymore. Help me turn that into a draft.”

In fact, not only do I not skip out on the thinking these days, I double down on it through voice conversation. I used to have to sit down to write—and my sit down time didn’t always come at a time when I had the most energy or enough bandwidth to push my thinking. Sometimes, because it was 2AM, I just pushed through.

Or, it just didn’t get done at all—and the worst post is the one you didn’t write.

Now, I have lots of time to write because I run voice conversations and “Claude interviews” when I’m at the gym or doing other things—like this morning when I was making my daughter’s lunch for camp. The most useful thing AI does for me isn't composition or insight or research. It's that it time-shifts my voice into the hours where I've actually got something to say. I’ll outline something I’m thinking about or a topic and ask Claude to interview me. I’ll specifically tell it to use as “as many of my own words as possible” when it turns the interview into a draft.

That works for me because of how I already think. I speak the words in my head. I sit on a lot of panels and go on a lot of podcasts. I'm often writing what I've said and speaking what I wrote. Talking was never the workaround. It's where the voice—how I write and my style—lived the whole time.

Typing was just the step where I did my own transcription.

Figuring out what I think is different. That's a step where I do have an edge (hopefully).

It's got a second use case I took a while to appreciate, so I wasn’t good at it for a while. My writing could and should be transactional. Monday, I wanted to let my audience know I’m going to a comedy event tonight where I’m on a panel. In this post, I’m letting you know that I’ve got this cohort opening. These are effectively marketing leads that my business needs to generate. I haven’t always tied my writing into these needs very well, but when it works, it works really well. If I can thread the needle through being both informative, interesting, inspiring, AND if I can drive some clicks, everyone wins.

That’s where tying my calendar, tasks, projects and goals into my writing planning using AI has helped a lot. It gives me a sense of my “marketing needs” for the next week or do so I’m not completely starting from scratch on what to write about.

Professional writing should have a job. Done poorly, it sounds salesy and self-promotional. Done right and it can entertain and accomplish a revenue goal. It can get me a VC coaching client, get me noticed for teaching, and it used to put me in front of founders to invest in. If you think of yourself as a company (the company of you, with lead gen demands and a sales funnel) then a lot of what you write is transactional whether you admit it or not. It's hard to sit inside your own head and work out what somebody else would find interesting about you. Most people are bad at that question and a machine is actually pretty decent at it. Asking what your ICP would actually care about can be a game changer.

I won’t say it’s gone perfectly. A friend recently called me out and told me a post didn't sound like me.

What he caught was the language because I didn't do my normal passes—line by line edits where I read it in my head and decide whether I could say that and sound not just human, but Charlie-like.

Why didn’t I do that? Interestingly, it was because the insight I shared wasn't mine to start with. I'd asked a bunch of questions about whether a startup's market size narrative had anything to do with the history of home pregnancy testing, and the through-lines that came back weren't ones I'd have drawn.

Pointing Claude at that product go to market was my idea, but the analysis was largely Claude’s. Perhaps unconsciously, I didn’t do the language pass because it would have felt like stealing ideas that weren’t mine. I was just the muse.

Most of the time, I start with an interview, so the raw material is me before any editing happens.

Here’s how the editing works, like in yesterday’s post about pitching, when I orchestrate a narrative but not all of it is interview driven:

The first draft came back competent, which is the problem with competent. Nothing in it was wrong. I just wouldn't have published a word of it as written.

Initially, it had me sitting in a pitch meeting nodding along "because I'm a professional and also because I'm a little bit of a coward."

Huh? I'm not a coward. Saying it to your face is the entire thing I'm known for as a VC, and it's most of the reason founders take the meeting in the first place. The machine reached for a self-deprecating aside because self-deprecating asides test well I guess, and to get there it made a claim about my character that's the opposite of true.

Once I flipped it, that correction turned into the premise of the whole post. I say it out loud, most VCs won't, and “here's what they're not telling you”.

A few lines later: "I will say a version of it out loud." Nobody talks like that. I don't say "a version of it." That's the sound of a sentence that's been sanded down. I sent it back and asked for a pass on the whole piece, and the AI tell turned out to be sitting in the verbs the entire time. I am not concluding. It is being ranked. You have built a beautiful deck. Every one of those is one contraction away from sounding like a person you know. There was also a paragraph where ninety seconds "holds" three things, and then holds them again, and then holds them a third time.

“Holds” is not a word I have used out loud in my life other than in fantasy baseball.

The bigger pattern took a few rounds to see. It builds up to jokes and I start at them. It wrote "you're brilliant, you're standing in front of me being brilliant, that's not in question" as a cushion before getting to the part where you're going to hire idiots.

Cut.

It wrote a careful escalation, some of your hires will be very good, some will be fine, some of them will be, and I say this with love, absolute idiots, one sentence after I'd already said most people are idiots.

Cut.

Every soft landing it laid down in front of a punchline came out.

It describes jokes instead of telling them, too. Its version of the competitive landscape slide was "four quadrants and you're in the upper right one, which is my favorite quadrant." That's accurate. That's not funny. Mine runs the horizontal axis from Hard like a fork in the eye to easy like Sunday morning, the vertical from Awesome down to shitty, and puts Brad up in the corner with all eight of his checkmarks.

Same observation. One of them is my writing, even though it’s not me writing. Also, no one is ever writing. We’re all typing anyway, but saying I “typed” a newsletter post sounds just as weird as it would for Amanda to say anything other than walking.

Here's the lesson, and it's not the one people expect from a post like this. The draft is not a thing you edit into shape. It's a thing you argue with, and you only get to argue with it if it's specific enough to be wrong.

The best argument in that whole post isn't in the draft anywhere. I read the section on making revenue sound easy, and I typed one sentence back: anything that sounds hard falls out of my top five opportunities out of two thousand in the funnel. That's the actual mechanism. That's why difficulty kills you, and it's not because anybody sat down and decided your business was too hard. It came out of me because there was something in front of me specific enough to react to.

A vague draft gets you nothing. A confident, wrong, specific draft gets you your own opinion in about four seconds.

Claude then wrote my sentence up into four paragraphs and I cut three of them.

I don't have a word for what that is. It isn't writing the way I did it in 2004, and calling it editing undersells the part where the argument comes out of my mouth first. Prompting is the word people use and it covers about four percent of it.

Whatever it is, it's mine when I've fought with it and it isn't when I haven't. The one time I skipped the fight, somebody caught it immediately.

I’ll stick with “writing” for now. After all, it’s taking me the same amount of time.

I’m just not sitting for most of it.

P.S. Here’s that thought leadership cohort again. Hopefully you’ve learned something or enjoyed this post enough where it doesn’t come off as too transactional to share.