Should you start a Substack?

TLDR: For most of you, no, starting a Substack is not the best way to build a financially sustainable long-term writing project. You should definitely build an email list, but you should do it with a free newsletter you run alongside a website/blog that you own. Especially for people like me, who write and speak mostly about abstract intellectual topics that are not directly useful, writing should be the way you build your audience and not the way you monetize your audience. After you’ve built an email list through consistently publishing your writing for free, you can monetize in other ways that make more sense for our kind of work and will earn you more money in the long-run.

A few people have asked me this, and we’ve discussed it a couple times in IndieThinkers.org, so I figured I’d set down my take on this.

If you don’t know, Substack is a platform that makes it quick and easy for authors to launch paid newsletters.

Substack is a good model for you if you meet at least one of the following two criteria:

  1. You already have a sizable audience on some other platform
  2. You have authority and expertise on something that’s useful

If neither of these describe you, you probably should not start a Substack.

In all other cases, you are better off starting a free newsletter through a blog.

It is true that Substack lets you build a free newsletter just as well as a paid newsletter, but for reasons I outline below, it’s not the best way to go. Substack’s specialty is paid newsletters and that’s what they’re going to be developing the product for over time.

Substack is particularly unattractive if your work is like mine—or what I call the indie thinker model. If your main focus is on relatively disinterested truth-seeking domains such as philosophy, science, literature, or personal creative writing of any kind (i.e. work that can be great and gain huge audiences, but is not obviously useful). If this sounds like you, then Substack—or any paid newsletter for that matter—is unlikely to be the right option for you.

Why a free newsletter is better for indie thinkers

There are a few reasons why most of you will be better off building a free newsletter, by publishing free content, on your own internet property.

If you’re not super famous, then one of your top goals is growing your audience, and the best way to do that is by constantly creating awesome free content.

A paid newsletter might get you some recurring revenue, but you won’t be publishing as much free stuff, so your audience growth will be significantly hampered.

Super famous writers can get away with this because they don’t need to grow their audience to make a good living, and they have other ways of growing their audience (like guesting on top podcasts, etc.).

For indie thinkers, if you’re content is not directly useful, the fact is that not many people will want to pay for your writing alone. But if people like your work and style, they will gladly sign up for free email updates from you, and this lets you earn money later in a variety of ways that make more sense for indie thinkers.

Examples include books, courses, premium communities, merch (if you build a brand), affiliate commissions, or mentoring (in the biz world they call this ‘coaching’).

These offerings are more sensible value propositions for your audience than asking them to pay for your recurring words. Your words don’t feel monetarily valuable so not many people will want to give money for them. But creating and facilitating a 6-week experience for your readers to think, write, and discuss some of the themes you write about? That’s a genuinely edifying and potentially transformative experience that people can easily justify paying a few hundred dollars for.

And you’re not shutting down your audience growth by paywalling the very thing that should be attracting new people into your orbit. Every time you launch a new paid offering, you can reasonably expect to make more than you made the last time.

If all your most loyal readers pay you a decent subscription fee monthly or annually, it’s a bit harder to launch other offerings later. You risk being overly transactional. By building and maintaining an audience of loyal readers by consistently publishing free work, you’re also building a reserve of good will. If four times a year, you simply let them know you’re offering a paid course, or a book, or whatever, people who choose to pay will be all the more happy to throw you some money, and people who aren’t interested will at least never call you rapacious. If you’re paywalling your main everyday writing, and later you develop paid offerings, you’ll probably have fewer buyers (“I’m already giving this person money”) and might even ruffle some feathers (“All this person cares about is money.”)

A few other things

Substack takes a pretty hefty fee of 10%.

Eventually you’re going to want more sophistication from your email service provider and Substack is currently very, very basic. This is why I use Convertkit, a fully-featured email provider made for writers and creators. You’ll eventually want to build automated email sequences, for instance, to thank someone after they buy one of your books, and stuff like that. Convertkit has a nice free plan to get started. There are a few other options out there, too.

Substack does not let you use a custom domain, which means Substack technically owns any traffic you drive to your posts. This might not seem significant, but if you’re in this for the long-term, then you really want to own every piece of what you build.

One exception

Perhaps one exception would be if you’re truly very bad with even simple technology and you have no longer-term goals to make a living from your writing; you just want to starting writing consistently, for fun, and start building a modest email list for your writings immediately. In this case, starting a Substack with no paywall is not a bad way to go.


The overwhelming majority of writers and content creators should focus on publishing free content and driving your readers to opt-in for free email updates. Offering a free weekly newsletter is a fine way to do this, but you can also just offer content updates (send an email every time you publish a new blog, or every time you publish a new podcast, or every time you publish a new video).

There are many great platforms for blogging and most of them will integrate just fine with email service providers like Convertkit. If you don’t have strong opinions on the kind of platform you want, I generally tell people that a self-hosted WordPress installation on a host like Siteground is probably the cheapest way to start a fully-featured website you have complete control over (~$35/year). Then start a free trial on Convertkit, which gives you 1k subscribers (with limited functionality). Integrate Convertkit with Siteground until you hit 1k subscribers, then start launching paid experiments, which will pay the bill for Convertkit.

In the IndieThinkers.org Library, I have a three-part screencast tutorial on how to do all of this. It will take you less than a couple hours if you follow my walk-through. A little more work than starting a Substack, but for the average indie thinker at the beginning of a longer-term vision, your chances of building something financially sustainable are much greater.

This approach gives you the foundation for almost any kind of monetization model you could possibly want to develop later (including a full-fledged business of any kind). And if you want to get off WordPress for something a bit hotter but more expensive, like Webflow or Ghost or whatever, you can do that later without too much trouble.

How many readers do you need? Kierkegaard only hoped for one

From Copenhagen on his 30th birthday (May 5, 1843), Kierkegaard wrote the following in the Preface for his first book, Two Upbuilding Discourses:

Although this little book… only wishes to be what it is, something of a superfluity, and only desires to remain in secret, as it came into existence in secret, I still have not said farewell to it without an almost fantastic hope. Insofar as it, by being published, is, figuratively speaking, starting out on a kind of journey, I let my eye follow it a little while. I saw, then, how it set out on its solitary way, or solitary set out along the highway. After one and another little misapprehension, when it was deceived by a fleeting resemblance, it finally met that individual whom with joy and gratitude I call my reader, that individual whom it seeks, toward whom, as it were, it stretches out its arms; that individual who is benevolent enough to let himself be found, benevolent enough to receive it, whether in the moment of meeting it found him happy and confident, or "melancholy and thoughtful." On the other hand, insofar as, by being published, it in a stricter sense remains quiet without leaving the place, I let my eye rest on it for a little while. It stood there, then, like an insignificant little blossom in its hiding place in the great forest, sought for neither for its showiness nor its fragrance nor its food value. But I saw also, or believed that I saw, how the bird whom I call my reader, suddenly fixed his eye upon it, flew down to it, plucked it off, and took it to himself. And when I had seen this, I saw nothing more.

Two Upbuilding Discourses

If one person reads your blog, that should be enough to keep you going.

If ten people read your blog, you should feel privileged and extremely motivated to give them better and better work.

If a few hundred people read your blog, this might seem like a trivially small audience relative to social media celebrities but it’s a large audience relative to many great thinkers in history! As I wrote about in Lessons from Nietzsche’s Awful Publishing Results, his book Human, All Too Human only sold 120 copies in the first year.

The Second Golden Age of Blogging

Many people say that “blogging is dead,” but dead for whom? Blogging remains powerful, just not for the same type of person who found it powerful in the “golden age of blogging” (roughly 2003-2009). In that period, blog-based intellectual freedom coincided with professional career tracks. Tyler Cowen, Crooked Timber, Instapundit, etc. — most of these people were already successful, institutionalized professionals, and the blog was a new way for them to think and talk in public, having fun while parlaying their professional status into increased public reach. When people say “blogging is dead,” what they really mean is that this type of blogging is dead.

Blogging was then diffused into social media, but now social media is so tribal and algo-regulated that anybody with a real message today needs their own property. At the same time, professional institutions are increasingly suffocated by older, rent-seeking incumbents and politically-correct upstarts using moralism as a career strategy. In such a context, blogging — if it is intelligent, courageous, and consistent — is currently one of the most reliable methods for intellectually sophisticated individuals to accrue social and cultural capital outside of institutions. (Youtube for the videographic, Instagram for the photographic, podcasting for the loquacious, but writing and therefore blogging for the most intellectually sophisticated.)

Those who think blogs are irrelevant today — usually Gen-Xers or older — typically underestimate the degree to which real power has evacuated traditional institutions such as academia and New York publishing houses. Such people think, because they don’t know many institutionalized professionals who still blog, that blogging must be dead. What they don’t realize is that the credibility premium historically enjoyed by professional institutions is plummeting toward zero. This fact is so obvious to younger Millenials and Zoomers that it goes unremarked, undebated, because it is already baked-in to their reading/watching behaviors.

If the First Golden Age of Blogging saw the blog as a public amplifier of creative, intellectual talent ensconced in professional careers, today we are living through a Second Golden Age of Blogging, where the blog is now a vehicle for starting and exiting careers. Starting a career might mean building an audience that later becomes a customer-base for some kind of independent entrepreneurship, or it might mean winning the attention and interest of employers in a target industry. Exiting a career might mean blogging pseudonymously (exiting careerist constraints), to make intellectual progress and impact for its own sake. Or exiting could mean building a bridge into a new, different career track. This blog is certainly one example, but I’m not just generalizing from my own experience. There are countless examples of individuals who have successfully navigated all of these pathways, in recent years, with their personal blog as a primary source of leverage. In fact, there are so many examples that no individual case seems interesting enough to be newsworthy. Blogging isn’t dead, it’s so alive that it’s imperceptible.

You can’t be smarter than you are

This might sound obvious, but it’s not: You are only as smart as you are. People get stuck because they aspire to be smarter than they are. People refuse to produce until they are as smart as they want to be, but the only way to become as smart as one wants to be, is to start producing work at one’s current stupidity level. If you feel that you are dumber than you wish to be, the only way to become smarter is to produce smarter work, but the only way to do that is to start now producing whatever you are currently capable of producing. The reason is that you have to become possessed by a real, living, breathing, passionate agenda. It’s a trajectory, a process, where one idea or question or puzzle is what propels you into the next.

Writing an honest, unpretentious, and stupid blog post today at your current, actual stupidity level will give you something to beat with a slightly less stupid blog post the day after. Writing two stupid blog posts, two days in a row, will boost your internal sense of production potential enough that you’ll allow yourself to generate 5 new blog post ideas, whereas yesterday you never even allowed yourself to have new blog post ideas because you saw yourself as not-yet-smart-enough to even deserve your own blog post ideas! Of those 5 new ideas, 4 will be really stupid but 1 of them will turn out noticeably smarter than both of your first two blog posts. The 4 really dumb blog posts will be ignored and forgotten, but that strong post will get more reads and shares than all of the previous ones combined. And so on… Fast forward 6 months, and the “stupid” version of you who dared to be honestly stupid is now 3x smarter than the version of you who chose to postpone working until you’re finally smart enough.

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