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Blogging is an endurance sport. It takes a while to hit your stride, but as Deep Dish’s 4th birthday approaches, and with it, a million views and a thousand comments, I think I have a decent sense of whether it’s all been worth it.¹ Is blogging really that rewarding? Did I waste my time on this thing? Should you start a blog?

My upcoming book is about cheap options for attracting serendipity into your life—the kind of decisions that have a small or fixed downside, and open up exposure to unlimited potential upside.

UPDATE: My book, Optionality: How to Survive and Thrive in a Volatile World is available now!

Blogging is an example of this kind of positive asymmetry. The downside costs are capped (you can get started with all of $50) while the upside is essentially unlimited. It’s a big old Internet out there, and the rewards are highly attractive—but perhaps not in the way that most people might expect.

So I’m going to talk about whether blogging has been worth it for me, with outcomes ranging from ‘meh’, to ‘nice to have’, to ‘holy shit, life will never be the same’.

• Blogging to Get Filthy Rich
• Blogging as a Forcing Function for Writing Practice
• Blogging as a Source of Meaning
• Blogging as Extended Phenotype for Attracting Mates and Allies
• Reasons NOT to Start a Blog

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Making Money from Blogging

Starting with the least-appealing outcome: I don’t know exactly how much money I’ve made from blogging, but I guess it’s pretty close to zero dollars. I try to remember to add referral links to Amazon etc, but this is a relatively trivial income stream that roughly covers my expenses (email software + hosting grows in line with the audience).

Two important notes: my blog is a minnow in the grand scheme of things—a good day brings in 1000 views, and 10,000 is exceptional—and I’ve made no real effort to monetise it. There are no ads or ‘sponsored’ posts, and my Patreon experiment was short-lived. I could use this platform to market stuff directly to y’all, which I’ll do for the first time later this year, but a ten dollar book is about as ambitious as it gets.

In other words, I’ve done everything in my power to make sure I don’t make a cent from this thing, mostly out of pride and some kind of hangup around moral purity.

The fact that I suck at making money from blogging obviously doesn’t mean it’s not possible (Nat’s post has an interesting breakdown, with his Roam course causing a huge spike in income). But I do recommend against starting a blog if this is your main motivation.

It’s not just that there are so many better ways to make money. It’s that a ‘commercial’ personal blog is fundamentally just a weird proposition: unless you have a direct patronage model, your interests are not aligned with your readers. No-one likes ads, or sponsored posts, or sneaky affiliate schemes, or clickbait, or SEO-optimised posts which cram in keywords with all the subtlety of a bulldozer. If you set out with the motivation to make money, you will definitely end up doing something shady.

The related problem is that it mixes up business and pleasure, and possibly sours both of them. From Derek Sivers, in the barbell strategy post:

How nice to not expect your job to fulfill all your emotional needs. How nice to not taint something you love with the need to make money from it.

If you do go down this path, my only suggestion would be to try to bring a unique perspective. There’s nothing new under the sun, but you have to either add a fresh angle or synthesis, or at least say the old thing in a more entertaining way.

I mentioned in the last post that I don’t read many early retirement blogs, because as far as I can tell, no-one has ever done it better than Mr Money Mustache (although by all means hit me with recommendations). It’s no coincidence that MMM’s blog now pulls in some astonishing profit, even though it wasn’t originally intended to be a money-making venture, while the legions of bloggers following in his footsteps do not.²

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Blogging as a Forcing Function for Writing Practice

OK, yes, I lied through my teeth when I told you my schedule was ‘usually every second Friday’. But I do feel a strong pressure to deliver, and on average I’ve managed a new post every ~2.5 weeks for the last four years. I know that no-one is sitting by their mailbox hitting refresh in the hopes of seeing my name pop up, but I still feel a mild sense of shame as weeks go by with no new post, and this feeling is useful to me.

So: if you want to get better at writing, you should absolutely start a blog. It will force you to not only write regularly, but crucially, to ship regularly.³

The second great benefit is that if you are writing regularly, almost by extension, you’re also being forced to think carefully about whatever it is you think you know. From How to Take Smart Notes:

Richard Feynman once had a visitor in his office, a historian who wanted to interview him. When he spotted Feynman’s notebooks, he said how delighted he was to see such “wonderful records of Feynman’s thinking.”

“No, no!” Feynman protested. “They aren’t a record of my thinking process. They are my thinking process. I actually did the work on the paper.”

“Well,” the historian said, “the work was done in your head, but the record of it is still here.”

“No, it’s not a record, not really. It’s working. You have to work on paper, and this is the paper. OK?”

It’s easy to fudge a coherent worldview in your head, or while talking shit at the bar. It’s only when you sit down and have to pin the ideas to the page, with clear arguments linking the various claims, that you realise how fuzzy and vague your model of the world really is. Writing is not just a way of ‘capturing’ your thoughts. Writing is thinking.

These days I mostly do this through my Roam/Zettelkasten practice, which means that converting my thoughts into finished prose is more of a formality. But I always learn something in the final assembly, and there is an extra special benefit that comes from writing in public.

When you make claims that might be seen by anyone on the whole wide Internet, you’re going to want to have thought carefully about what you’re saying. I often end up being wrong about things, but I’m never just running my mouth with a stream-of-consciousness directly to my keyboard.

And of course, the best way to get the right answer on the Internet is not to ask a question, but to post the wrong answer. I have learned a lot from comments and emails either pushing back on my views, or building upon them in some useful way.

So: if you want to be forced to think more clearly about the world, and be challenged on your views, you should absolutely start a blog.

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Blogging as Meaning-Making

Every now and then people send me very nice emails and messages about something I’ve written. Without this kind of feedback, there’s no way I would have kept going this long.

I won’t say more about this except that I find it endlessly trippy and bizarre, in the best possible sense, that people benefit from my work in some small way, and occasionally in larger ways. This seems like a pretty great reason to start a blog.

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Blogging as Extended Phenotype

A friend suggested that blogs are part of our extended phenotype, and the image of a digital peacock’s tail that suggestively swooshes through cyberspace has stuck in my mind.

Over the years, Deep Dish has served as a fine-grained selection filter for drawing like-minded folks into my orbit. Anyone who gets in touch has already read my intimate thoughts and interests, and not only not clicked away in horror, but found something to connect with.

The blog expands my surface area for serendipity far beyond what I could achieve in real life: it’s like permanently being at a party, meeting interesting people from all around the world.

Here’s some of the random cool stuff that has arisen out of blogging:

• Making some of my closest friends (and several pen-pals)
• Meeting dozens of readers in real life
• Writing a book
• Helping to design a backpack
• Personal recommendations for books, products, ideas
• Going on dates, including meeting my girlfriend
• Getting syndicated in major publications
• Podcast appearances and media interviews

None of this happened by design, except insofar as I’ve mentioned my inbox is open. I have no idea what will happen next, but I’m pretty sure it’ll be something good.

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Reasons NOT to Start a Blog

An option is attractive when it has a small or fixed downside cost, which buys you exposure to potentially unlimited upside. But these are long shots: there’s no guarantee any individual option will ever pay off, and more likely than not, it won’t. That means you have to take a portfolio approach, and be prepared for failure.

I got unusually lucky, in that my first two posts went semi-viral. That means I got to skip the ‘labouring in obscurity’ step and go straight to having a small audience, without the uncertainty of knowing whether it would pay off. So my outcome is not representative, and neither is any other pro-blogging article you come across: by definition, we only ever hear from the survivors.⁴

The modal outcome of blogging is that you pour your heart out, and get nothing but crickets in return. Now, that doesn’t matter so long as you’re running a cheap experiment with limited downside: buy a domain, fire up the default WordPress theme or whatever, and see if you get any traction. As Nat Eliason puts it, “if you spend more than 4-6 hours setting up the V1 of your site you’ve overthought it.”

But it does matter if you rack up dozens of hours writing posts that disappear into the void, or waste time on a custom design, or spend money on fancy software. Now the downside is no longer cheap or capped: it’s a large and ongoing cost, in exchange for highly uncertain benefits.

I know this from bitter experience. I typically spend 10-20 hours on each post, and sometimes longer. This is a pretty stupid trade-off to make, especially considering my modest readership: some of my effort-posts get a couple thousand clicks and then more or less disappear into obscurity forever. I know I would be better off doing shorter/less polished posts, and not bothering with images and all the other time-consuming fiddling on the margin. For whatever reason I can’t bring myself to do this, so I’m more or less resigned to the fact that the market for my personal labour has some glaring inefficiencies.

If I had no audience, and I didn’t gain any other benefits from the act of writing, the asymmetry would tilt in the wrong direction: it would be a whole lot of pointless work, with essentially no upside.

The fact is that most blogs don’t last more than a few months, and don’t start out with a following. That’s why it’s crucial for the process itself to be intrinsically rewarding: it might take a long time to get to the point where you’re making money/meaning/serendipity, so you have to find some other motivation to soldier through.

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The Blogging Renaissance

In my book, I talk about ways to get exposure to serendipity that are more attractive than starting a blog. But I don’t buy the idea that blogging is ‘dead’, and if anything, my guess is that we’re going to see a big resurgence.

The media landscape is increasingly fractured, and trust in institutions is (deservedly) low. It’s much easier to build trust and rapport with individual writers than it is with large publications, which seem to be doing everything they can to destroy their own credibility. There are lots of journalists doing important work, for which I am very grateful, but most of my favourite writers are subject-matter experts or talented dilettantes going their own way: a practicing psychiatrist, a historian writing epic eight-part series on e.g. the Battle of Helm’s Deep, a former Goldman guy on all things finance, a twenty-something independent researcher from Russia busting the claims of popular science books, etc.

Most of these people blog for non-financial reasons. But new funding models like Patreon and Substack are encouraging top talent to go solo, and it’s increasingly viable to make a living as a writer without doing any of the shady stuff mentioned above.

This works because even though there are 4.5 billion people online, we’re still in the ‘early days’ of the Internet. Most people, myself included, have not yet internalised the full implications of this. There are opportunities for every niche interest you can imagine, there are many friends and collaborators to be found, and there is somehow still a dearth of great content (hit me with your blog recommendations, or if you’re a blogger, introduce yourself in the comments!).

So even after all the caveats mentioned above, I would encourage more people to blog. This has already paid off for me, even with ~80 posts and a relatively small audience.

I have no clue what will come my way in future, but as long as the blog is floating around in cyberspace, I know I’m maximising my surface area for serendipity to strike.

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Notes:

1. Nat Eliason kind of sniped me on this one with his excellent recent post. His blog is at least an order of magnitude bigger than mine, so it might be interesting as a point of comparison.
2. As Peter Thiel would say, every successful business is a monopoly of one. You have to create a new category and then dominate it, rather than copy what everyone else is doing.
3. The only better training I can think of would be to get a job in journalism, because it forces you to deliver the goods every single day, with a firm deadline, and a focus on clear communication over stylistic flourishes. Lots of famous authors (including my all-time favourite, Terry Pratchett) developed their chops as newspaper reporters.
4. On the other hand, I’m also unusually bad at publicising my work, being active on social media and the relevant forums, posting links to reddit, and all the other things I really ought to be doing in order to build an audience. For someone who is willing to put in this kind of effort, it probably ends up as a wash.