The Shame of Not Updating Your Website

How hard is it to fix simple things? Pretty hard, actually.

Hi friends! I’ve been a little quiet lately, but I’ll be back soon and look forward to sharing more with you. In the meantime:

• NeuroDiversion 26 is coming up in March, and it’s going to sell out! There are currently less than 50 tickets remaining. I’d love to see you there, so if you’re interested, don’t hesitate to sign up.

• I’m also hosting an online event for the New York Public Library on the topic of neurodivergent entrepreneurship. It’s free and anyone can join.

Last but not least, I’m working on updating some long-ago projects. Here are a few thoughts on that process. 🙂

Live view of the author not updating his websites. 📷

Quick show of hands: who has a website that they haven’t updated in forever? Yeah, me too. Except I have twelve of them.

Some of them don’t matter—nobody goes there—but others do. Every day, a decent number of people follow links or search for phrases that lead them to one of my online homes. And then they have a poor experience or don’t find what they’re looking for, because everything’s outdated and nothing works.

Why, you might wonder, do I have so many inactive websites? (Why is the sky blue? I might respond.) I’m not claiming it’s the greatest way to live, though at the time I make each one, the idea seems logical enough.

• I have a new book coming out, so we need a mini-site to capture interest

• I’m going on a tour, so we need a process for people to sign up in 20 different cities

• I have a crazy idea that will end up being brilliant or terrible, but either way it’s gonna need an online home of its own

And then of course there are the main portfolio sites I build and maintain for years, before starting to … build and maintain something else. The bottom line is that I am simply hard-wired to work on multiple projects, and not be one of those “one thing” people.

(I greatly admire the author Percival Everett, who’s had a lot of breakout success lately, but struggled with low sales of some of his books for years. In one of my favorite interviews of him, he said something to the effect of “My agent told me I’d make more money if I kept writing the same book over and over, but I don’t want to do that.” Me too!)

no doubt this guy is secretly stressed about not updating his website 📷

The Problems Are Obvious (Which Somehow Makes It Worse)

I’m in a few groups with friends where we meet to critique each other’s sites and businesses. I enjoy being helpful! And I strongly dislike being the one in the hot seat, because I already know many of the things that are wrong.

The bio is from three years ago. The links go to dead pages. There’s a pop-up promoting something that ended in 2022. The design looks like it was made with tools that no longer exist—because it was. (Sadly, for many sites I’ve made, this list is greatly abridged.)

If you have your own version of this problem, you probably know the feeling. It’s not that you don’t know what to fix. It’s that knowing makes it worse. You carry around this low-grade awareness that something out there with your name on it isn’t representing you well—and every day you don’t fix it, the shame compounds a little more.

Am I satisfied with such mediocrity? Absolutely not—that’s why I feel shame over it. It bothers me often.

It’s Not Writer’s Block, It’s Maintenance Block

I’m not one of those authors who hates the act of writing but loves “having written.” I actually like writing! The process itself is fun, at least much of the time. In fifteen years of book-writing, I’ve only been “stuck” on a book once or twice.

But when it comes to revisiting anything from the past—I have a great level of resistance.

I suspect this is familiar to many readers. Making something new lights up every reward center we have. Maintaining something old activates approximately none of them.

For those of us with ADHD, it’s basically our calling card. Novelty is fuel, while maintenance is the opposite of novelty. And so the old things sit there, gathering dust, while we’re off chasing the next shiny object.

Why “Just Fix It” Doesn’t Work

Sometimes, not having a clear first step is the problem. Everything feels interconnected and overwhelming. You sit down to update one page and realize it’s connected to a template that’s connected to a plugin that hasn’t been supported in five years. Now you’re troubleshooting infrastructure when you just wanted to change a paragraph.

After a long process of getting psyched up to actually fix the problem, you’re right back where you started—only now you’re more discouraged than before.

Other times, the sheer number of decisions is the problem. Which thing do I fix first? Do I consolidate? Delete something entirely? Redesign from scratch or patch what’s there? Each question spawns three more, and before long you’ve spent forty minutes thinking about it and done nothing.

And then there’s the version of stuck that’s the hardest to explain: the strange comfort of familiar defeat. You know your website—or something else—is bad. You’ve accepted this state of being. There’s something almost stable about the situation—and the idea of partially fixing it feels worse than just leaving it alone. After all, at least right now, the shame is evenly distributed.

A lot of the work I’m doing these days is about why simple things are hard. Not “simple” in the sense of unimportant, but simple in the sense of you’d think it would be easy, and yet here we are. This might be a topic of my next book, but we’ll see how it goes. Just don’t ask me to update the website for it.

Do you feel shame about not updating your website—or anything else that “should” be simple? What’s your version of maintenance block?