is author of The Honest Broker on Substack, a frank and opinionated guide to music, books, media, and culture. He is author of 12 books, and previously served on the faculty at Stanford.
1. Why Substack?
I started cutting off my ties to mainstream publishing more than 15 years ago. I quit using an agent, and gradually stopped pitching article ideas to editors. Instead I voluntarily made self-publishing my main focus.
I’ve worked successfully inside the system—publishing a dozen or so books and writing for major periodicals—but the system started to feel inflexible and constraining. I wanted freedom to write on my own terms, even if that meant taking a financial hit.
I took the initial step in August 2007, and self-published an article online for the first time. It was a marvelous experience. The article went viral and got linked on other websites and forums. Within 24 hours I’d received dozens of emails from readers all over the world. That direct contact with my reader had never happened before, even when I wrote something for the New York Times or another major outlet.
In those instances, readers write letters to the editor—not the writer. That’s even what they called the process of responding to an article: a letter to the editor. That now seems strange to me. Isn’t it much better when a reader enters into dialogue with the actual writer?
So I started self-publishing with a vengeance. Over a ten-year period, I set up five different homemade websites, and published more than 400 essays that way.
I didn’t get paid for any of them, but that was okay with me. I still did some paid writing back then, and I have other marketable skills. I can always do side gigs outside of writing to pay my bills. That’s why I never solicited advertising or even sought a sponsor.
I pursued these writing projects for just two reasons—for the joy it brought me, and to have a positive impact on the culture.
All this happened before Substack even existed.
So when Substack came along, I was ready for it. Substack gave me the tools to do what I was already doing, but made it much easier.
I’m happy as a clam on Substack—assuming that clams are happy. I prefer operating as an independent force in the culture, without obligation to advertisers and overseers.
As a result, I’ve turned down every freelancing opportunity that has come my way in the last 3-4 years. In a few instances I’ve spoken with high-powered people in the publishing business who have asked me to write for them. But after having all this freedom on Substack, it’s hard to give it up.
That said, I’d like to see some of my Substack writings appear eventually in book form. So maybe I’ll find a way back to the mainstream publishing business. But my main responsibility won’t change: I’m an independent operator in the microculture - which (as I’ve written about) is where all the action is now.
2. How long did it take you to find your groove?
Even after joining Substack, I still wrote in the old way for a while.
But my sentences soon started to change. There’s something different about my relationship to the reader on Substack - it’s more informal, more personal, less constrained by journalistic conventions.
At first I didn’t even notice. But I soon saw that my prose was less like writing, and more like conversation. I spoke to the reader the same way I’d talk to a friend over dinner after the second glass of wine. That’s when the truth-telling begins.
This felt right, so I kept doing it.
Sometimes I look at things I’ve written, and it feels strange to see such a huge change in my writing style after so many years and so many books. But I’ve always believed that writing must adapt to the circumstances, and I’ve always adjusted the sentences in my books based on the subject matter. So what I’m doing on Substack is not entirely different from my past approach - only more extreme.
3. How has it changed you?
I feel more comfortable writing in this way. I deal directly with the reader, and no longer think about editors or gatekeepers. Sometimes I laugh about this - because I know that no legacy media outlet would dare publish most of the stuff I put out on The Honest Broker.
My strangest articles are sometimes the most popular ones. Not long ago, I wouldn’t even consider writing them. It’s such a drag fighting with editors when you try to do something a little different - they are so risk averse nowadays.
It helps that I’ve been embraced so warmly by readers. But it makes me wonder why editors today are so hostile to risk-taking. It’s revealing that my audience has grown so much after I broke away from their rules and regulations.
But I’ve seen this elsewhere. Mainstream publishing continues to operate as if the vibrant, fast-growing microculture doesn’t exist. They should learn from the rule-breakers who are prospering in the indie world. But they don’t.
4. What mistakes have you made?
I probably still make mistakes. I make almost every decision about my writing based on feeling and instinct - without a lot of thinking. That’s the lasting curse of my upbringing as a jazz musician. I always improvise, even when careful planning might be better.
So I don’t pretend to have all the answers. Not long ago, I met some other successful Substack writers - and every one of us was doing things differently. I realized that my strategies for successful writing are just things I’ve stumbled on by chance. They might not work for other people, and maybe aren’t even the best for me.
On a more specific matter, my biggest mistake is not doing more on other platforms. If I were younger, I’d make a serious commitment to videos and podcasts. I could do a lot with these formats. In some ways my conversational style is even better suited to speaking in front of a mic or camera than it is to writing.
But I’m really not that ambitious. I do all this for fun and happiness and the sheer joy of sharing positive ways of living with others. So I constantly see obvious ways of building my career, and still I just walk away from them.
5. To pay or not to pay?
Recently I’ve been doing around three articles every week. Two of them are usually free, and one is behind a paywall. But even the paywalled articles have a little bit of free stuff at the start.
So every subscriber has a positive experience, but paying customers get special treatment.
I might change this approach in the future, but right now it feels right.
I absolutely believe that writers deserve to be paid. I always advise other writers to charge for their work. I have no qualms about getting paid for my own. But I also want to have a positive impact with my writing, and I can reach more people with articles that everybody can access.
It’s a balancing act.
But the bottom line is that indie writing on Substack can’t function without paid subscriptions - so I encourage readers to be generous. This is a key way that they can support quality journalism in a time when we need it more than ever.
6. What artistic and technical choices have you made?
I think less about those things nowadays. There was a time when I worried about the technique of writing - and that helped me develop my craft. But my main focus now is speaking honestly and forthrightly.
There’s so much spin and gaslighting in journalism today. I actually made a list of all the reasons why writers tell lies.
I came up with 21 reasons - and probably could have added many more.
Here they are:
Writers sometimes lie…
1. To make an article more sensational.
2. To please an editor.
3. To avoid upsetting advertisers.
4. To return a favor.
5. To punish an enemy.
6. To surpass a rival.
7. To get tenure or a promotion.
8. To help a friend or ally.
9. To tell readers what they want to hear.
10. To fit in with a peer group.
11. To increase clicks and views.
12. To influence an election.
13. To get access to informants.
14. To support an ideology.
15. To avoid controversy.
16. To protect a source.
17. To win a grant or some award.
18. To curry favor with government officials.
19. To look cool.
20. To enhance their reputation with other writers.
21. To get laid.
This is why so many people distrust media.
The single biggest contribution I can make as a writer is to serve as a trustworthy guide. I strive for total candor, and treat the reader as a friend or member of my family. That’s why the name of my Substack is The Honest Broker.
7. What has been the effect on your writing?
I described above how my prose style became more informal and conversational on Substack. But there were other changes as well.
When I stopped thinking in terms of printed media, a whole world of opportunities emerged. When I write about music, the ability to embed YouTube links or entire Bandcamp albums is a game changer. But I now also include many other bits and bobs in my articles - social media posts, screenshots of emails, homemade graphics, tables, spreadsheets, and plenty of links.
This feels liberating. I can’t do this when I write for the New York Times or the Wall Street Journal. This is a huge advantage to writing on Substack, and I love the freedom it gives me.
Some of the most popular things I’ve published on Substack are just homemade graphics. For example, a simple conceptual chart I inserted in my “State of the Culture 2024” article went viral, and reached millions of people.
If I had been writing for a legacy media outlet, I wouldn’t even have considered including it - just imagine telling an editor that I want to illustrate my own articles. The graphics department would have a meltdown. But these kinds of quirky choices are possible on Substack - and readers are very receptive to them.
8. In it for the long haul?
I’m older than most Substack writers. So I see my writing today more as the culmination of the long haul.
Things that I did decades ago, mostly for intrinsic reasons, now serve as the building blocks for my writing vocation today - for example, my intensive study of music and career as a jazz performer, or my lifetime reading project, or my world travels, or my varied workaday experiences.
These got me to where I am, and give me the opportunity to help others on their own personal long haul. That’s my main motivation right now - I’ve reached a happy place in my life, as a writer and just as a human being. I’m now blessed with a large audience on Substack, and this is my chance to give back. That will be my top priority going forward.
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I agree this was a great interview. Ted Gioia is always paving the way.. His essay about the literary publishing world taking the same road as the music world was one of the first things I read on Substack and have loved reading him ever since.
“But my sentences soon started to change.” - This may be what fascinates me most on Substack: writers allowing their styles and forms to change for the medium. When enough people do this, we’ll have new forms or genres. As the rise of the magazine made short stories possible, so I like to speculate about what we’re cooking slowly here.
Wonderful interview!