When I teach my “How to get started as a freelancer” class — which I really should teach again, the last time I ran the course was in October 2020 — I often ask students what kind of freelance writer they’re interested in becoming.

Inevitably, I get the same answer — travel writer.

Why wouldn’t you want to travel and write about your experiences and get paid for it? There is literally nothing wrong with wanting that — except that the value equation tends to go one-way.

Travel (either as a business expense or on someone else’s dime) —>

Write about experiences (a process that may only require minimal outside research, since you are your own primary source) —>

Get paid.

All of the benefits, in this case, flow towards the freelancer.

Where is the value to the reader — and where is the value to the client paying for the assignment?

Yes, you could end up writing the kind of travel essay that continues to provide value to readers (and publishers) long after its initial publication. David Foster Wallace’s A Supposedly Fun Thing I’ll Never Do Again is the obvious example, as are books like John Hodgman’s Vacationland. But Wallace and Hodgman had already created significant value for a lot of people, publishers, clients, and corporations — including a collection of readers who had already bought in (pun intended) to whatever it was they were going to publish next.

In those cases, it could be travel writing.

In your case, it might have to be something else first — although it is possible to publish travel articles early in your career if you can pitch them in a way that demonstrates the value you think they’ll provide to a publication and its audience.

It’s also possible to publish travel articles early in your career if you go the other way around — if you sign up with a travel site like the Matador Network and grab one of its available assignments, for example.

In both of these examples, the value equation becomes a little more balanced. If you are a writer who has already road-tripped from Las Vegas to Zion National Park, for example — if you have already done the work — the Matador team is ready to exchange a portion of the value of your experience for a portion of the value they have as a paying publication.

Likewise, if you can craft a pitch explaining why your travel experience can benefit someone else, you might be able to get an essay published even if you are a relatively new freelancer.

(Ask me how I know.)

But you’ll make a lot more money, long-term, if you write about stuff that isn’t travel. Travel articles are typically lower-paying assignments, in part because so much of the value has already been used up in your taking the trip. You already did something fun! Now you get to write about it! Compare that to the article I wrote last week explaining which credit cards allow co-signers, which involved contacting each of the major credit card companies and asking them about their co-signing policies. I generated new value for Bankrate by reaching out to credit card issuers and updating old (outdated) information, and I got paid accordingly.

I was thinking about all of this last week, when I was scrolling through Substack Discover to see how my blog stacked up (pun intended) against everyone else’s.

The first thing I noticed was that Substack subdivides the blogs you can discover into two categories: Paid and All.

You are more likely to be found on Substack Discover if you put at least part of your blog behind a paywall — and as more people continue to find your blog through Substack Discover, there’s more opportunity for you to gain new paying subscribers.

Since Substack takes 10 percent of your total subscription revenue, this means —

wait for it —

You make money on Substack when you help Substack make money.

This isn’t a 1:1 correlation, and there must be some free Substack publications that have a significant subscriber base (Zeynep Tufekci’s The Insight is currently free, although there was a paid subscription option at one point), but the connection is so obvious that I can’t believe I didn’t think of it earlier.

If I want my Substack to increase in value, I have to increase my value to Substack.

This makes me wonder whether I should be doing something to help Substack make money.

My primary goal — both with this blog and, if you want to put it this way, my life — is to become excellent at writing, music, and teaching.

My secondary goal is to use the current best practices (re: cognition, learning, habits) to codify a method by which one can become excellent at things.

My tertiary goal is to get other people excited about becoming excellent at things.

My quaternary goal (YES, IT’S A WORD) is to earn money from all of this.

I’m already earning plenty of money from my writing, in part because I’ve already devoted a decade to becoming the kind of writer who can create a lot of value for clients and readers. This is why I can currently place “earning money” as a less-than-top-level goal — although I know enough about money to understand that if there is value to be extracted that I am not currently extracting, I am perhaps being less than excellent at pursuing this goal.

(There’s also an argument that you can’t really become excellent at something until your excellence provides significant value to a significant number of people — which is why I consider myself an excellent freelancer and a very good teacher but not yet an excellent musician.)

So — if I front-loaded the fourth goal by actively working to make Substack money, then Substack would be more likely to promote my ‘stack to more people, which might get more people excited about becoming excellent at things.

If this happens in conjunction with my becoming excellent at things and my developing/disseminating an effective method that can lead towards excellence, then all four goals are achieved.

Win-win-chick-din.

How can I help Substack make money?

The obvious answer is that I have to make part of my blog subscriber-only.

I’m a little disappointed that it has to come down to this, because I believe that you should think carefully about where you spend your accumulated value-transfer points, and I’m not at all sure that I want to ask you to transfer value to me when I am already earning enough value-transfer points to meet my needs (and then some) by providing value to freelance clients.

Why do I need you to give me $5 every month?

(Or wait, is it $7 per month these days? When did it become $7?)

Because I want Substack to promote my blog to more people — and I don’t think that will happen unless I can demonstrably prove that my blog provides value to Substack. (Right now, the only real value that my blog offers Substack is the value of “getting more people used to reading and subscribing to Substack blogs.”)

Are there other ways to increase my readership? Is there a non-obvious answer I’m not thinking of, that could make Showing My Work a loss-leader of sorts in the greater Substack enterprise?

There’s the slow way of doing it, where I teach a bunch of classes over the next year and get one or two new subscribers per class.

There’s the crossposting method, although I’m not sure I’m gaining enough new Twitter followers to increase my subscriber base simply by crossposting my blogs to Twitter — and I am very sure that Twitter isn’t doing much to promote my crossposts because they don’t add much value to the greater Twitter enterprise.

Here’s a sample metric from my most recent crosspost, if you’re curious. I have 4,285 Twitter followers, and only 162 of them even saw this tweet:

Note that Twitter will help you make more money — at least in theory — if you pay Twitter money. The value equation tends to tilt in favor of the entity that can offer the most value, and in this case, it ain’t me.

Where was I?

Right.

Making a portion of Showing My Work subscriber-only.

One option, which I have been thinking about for a while, is to run The Biographies of Ordinary People as a paid serial novel. The best time to have launched this was the day I turned 40, of course — but the second best time could be tomorrow, if you were interested in that.

The other option is to follow the typical Substack model where you make 80 percent of the posts free, paywall the comments, and put out a weekly (or daily, if you post more than once per day) subscribers-only post.

The third option is the one I haven’t thought of yet.

Here’s the thing of the thing:

I want to create value for you —

and I have extra value to share —

but I could potentially bring more value to more people if I helped Substack increase in value, which would in turn increase the value that flows towards me.

This would require you to exchange some of your accumulated value for some of mine, which means that whatever value I’m creating for you had better be worth it.

Wow, it looks like I found another thing to try to be excellent at — or, if we want to be a bit more grammatically correct, another way of pursuing excellence.

Because I don’t want to be the entry-level freelancer who says “you should pay me because I want to travel.”

I want to be the magician-level writer (and musician and teacher) who says “I’ve already done the work — and here’s what I’ve learned.” ❤️

UPDATE:

THAT LAST SENTENCE REALLY SHOULD BE

“I’VE ALREADY DONE THE WORK — AND HERE’S HOW YOU CAN DO IT TOO.”

THAT’S WHERE THE VALUE IS.

THAT KIND OF COMMUNICATION IS WHAT I NEED TO WORK ON,

IN ADDITION TO THE DOING-ITSELF OF THE WORK-ITSELF,

THE CREATION OF TECHNOLOGY-EQUIVALENT-TO-MAGIC,

AND THE EXTRACTION OF COMMUNICABLE, SHAREABLE TECHNOLOGICAL TECHNIQUES.