Why I moved from Wordpress to Substack (And what it all means)

I have moved my writing from Wordpress to Substack. Like all good decisions about technology, it had to do with deeply felt questions of identity, purpose, and whether I really believe in myself.

Wait. Let me explain.

A few days ago, Bluehost kindly informed me that renewing my hosting account for the next three years would cost $395. If I wanted to keep Wordpress, I needed to keep Bluehost. If you work that out, it means hosting my personal blog at russellmaxsimon.com was costing me around $11/month. Not too bad at all.

But it did raise the question: what exactly was I doing on that site? I hadn’t published anything since my alarmist, cautionary climate announcement back in January. (For the record, I am still alarmed, and everyone should still take caution. It’s only getting worse.)

But readers have not exactly been knocking down my door. Google analytics tells me so. Now, that may have something to do with my complete lack of self-promotion, exemplified by my decision to digital detox and stop telling everyone online what I’m doing and writing all the time.

It may also have to do with my lack of output. For months, I have been reassessing why I write, what I want to write about, and what measures of success in writing matter to me, if any. No matter how I pose this question to myself, it’s always a tough one to think through.

“I just write for myself”

If you are the kind of person who goes around telling people, “Oh, I just write for myself,” I can only assume that means that you write a diary. Offline. Where no one can read it.

Good on ya.

I am not that kind of person. I started as a journalist. But even before that, as long as I can remember, I have written to be read. If no one reads it, what’s the point? If a tree falls in the woods… a poet should be there to paint the picture for the rest of us.

But what kind of readership was I looking for? Did I just want my grandmother (hi Lynne!) and my family and friends to read me? In that case, perhaps I should keep doing what I was doing and pay the $395.

Or, did I want to try to make some kind of income off my personal writing? Or - and this was the real choice - did I want to simply reach as wide a readership as possible, money be damned? Was I looking for fame and influence, or to make a living?

David Perell, whose work I’ve been following for a while, has grappled with this question too.

What About Medium?

Basically, I was trying to decide whether I should move my writing to Medium. On Medium, after all, they give you readers. They put your stuff in front of other people. If it’s good, it gets in front of more people.

Here’s what Perell had to say about that in a great post called The Ultimate Guide to Writing Online:

But David, what about Medium?

Don’t write on Medium.

Look, I get it. Writing on Medium is an easy way to pick up readers and increases your chances of going viral. But the costs exceed the benefits. Medium is terrible for SEO. You don’t own your content and the platform makes it difficult to turn one-time readers into loyal ones.

The more you can use platforms you own, the better. Rather than writing on Medium, do the work to build a personal blog. That way, you can have a central place to point people to.

So I took part of his advice and disregarded the other part. I decided not to post on Medium. Medium is where you go to get readers to the exclusion of all other goals. That’s why politicians post their big ideas there. They want the most possible number of people to read it.

But I was also sick of building a personal blog. Not much building was going on in any case, and now I had a $395 bill coming up for my trouble.

The model that appealed to me most was a combination of what Ben Thompson does at Stratechery and what Azeem Azhar does with his Exponential View newsletter. And, for that matter, what David Perell does with his his newsletter, called Monday Musings. The model is some free content plus paid subscriptions for readers who want more, focusing on email for distribution.


I wondered what technology Azhar and Perell were using for their newsletters, and before long I found the answer: Substack. I started researching their shtick, and here’s the passage the won me over, from one of Substack’s recent blog posts:

We started Substack because we wanted to build a better future for readers and writers. Today’s media environment is built on warped incentives, with writers and publishers forced to compete for people’s attention. Many who succeed under the current model are the ones willing to hunt for clicks by fomenting outrage or catering to the lowest common denominator. Many writers and outlets have become convinced that the only path to success is through reaching an audience of millions. It can be hard to see a way out. 

I do not want to foment outrage, nor do I want to cater to the lowest common denominator. That way lies the hallowing out of your soul, not to mention our democracy and our world order.

Substack is keeping it simple, and aligning its business model with the interests of its writers. Rather than my paying $395 and then making a go of it for the next three years, I could pay nothing, and then Substack makes money if and when I make money. I like that kind of alignment.

The only question I had left to answer was: did I believe in myself?

Do you believe in yourself?

Haha, jk lol.

People who know me know that I think everything about that question and that advice is bullshit. Americans seem to be particularly inured to the idea that if you only believe in yourself, you will gain all your wildest dreams. Maybe it’s something about our capacity for optimism or magical thinking, or just our capacity for refusing to accept our own shortcomings, or maybe it’s our capacity for sticking our head in the sand, or maybe it’s our naive belief in our own exceptionalism or maybe it’s…. I could go on.

But in all seriousness, I needed to ask myself a pretty serious question about my writing: did I want to professionalize it, or just keep it casual and low-stakes? And if I wanted to professionalize it, what was I willing to do to make that work, and what was my metric for success?

I had to answer those questions before I could decided what to do about that $395. They are big questions. Are you just writing for yourself? Then go buy a Moleskin and grab a pen.

For me, once I decided what my purpose and goals were, the choice of technology became clear. I was going to shut down the Wordpress blog. I was not going to Medium. I was going to write more regularly, and use Substack to set up a subscription service, a la Perell and Azhar.

And I was going to write about the thing I always think about anyway: what really matters. What really matters in life, in work, in politics, in everything. I had my purpose. I had my goals. And so I had my technology platform.