How To Start A Substack
Or, what a book from the 1700's tells us about how to live.
So You Want To Start A Substack?
Let’s break it down into 5 easy steps.
Step 1: Annoy Your Friends Until They Tell You To Start A Blog
Spend the first thirty years of your life being told you should start a blog by friends, family, loose acquaintances, third cousins, and the occasional airplane seat mate.
Achieve this by saving up all of your interesting thoughts and unloading them on your friends after ordering the third round of drinks. Your captive audience will listen politely and suggest—no, insist—that you start a blog, because they would absolutely read it, if only you would shut up there and then. Realize in that moment that blogs were invented by people with know-it-all friends to get a moment’s quiet at dinner.
Step 2: Take Zero Action To Start Your Blog
Maintain this cycle of oversharing, receiving encouragement to start, and enduring hangovers for at least a decade. Experiment with WordPress. Consider buying a domain. Lament that the breeding habits of your Irish-Catholic ancestors ensured that there are some 30 million people on Earth with your name and propensity to sunburn, so if you want to buy something remotely close to your name you’ll need Bezos bucks. Conclude that without the right domain there's no point to starting the blog.
Step 3: Decide To Start A Substack Instead Of A Blog
Watch from the sidelines in the early-2020’s as the world of blogs gives way to a new and exciting technology called email Substack. Decide that becoming an early adopter will provide a unique opportunity to establish a profile and build an audience. Then persist in taking no action whatsoever.
Step 4: Do Everything For Your Substack Except Starting It
Enter your late twenties and tear your life down brick by brick before rebuilding it halfway across the country. Then conclude on a slightly manic Tuesday in late October 2024 that you will finally start that blog Substack that you always talked about starting. Enjoy a eureka moment and come up with a name you like on the spot. Find an appropriately defaced Roman statue in the public domain as a profile picture. Dedicate several hours to the things that make or break a writing project like font choice and color palette. Once you’ve done all that, you’re ready!
To do just a little more nothing.
Come up with ideas for what you would write and scribble them down on little pieces of paper. Make mental notes when a point lands particularly well in conversation with friends to later identify if it was your genius or the third gin martini that had them laughing so hard. Maybe choose to set up a robust file infrastructure on Google Drive because the key to writing well is properly named folders. Continue not writing.
Step 5: Start Your Substack
Eventually reach a place chronic procrastinators know well, Too-Painful-Not-To-Take-Action Mountain. It’s a geographic feature commonly found at the intersection of ambition, panic, and self-loathing. Now—and only now—you may begin to write.
Congratulations! You’ve started your Substack. I hope it was an enjoyable process for you, although it sounds like you probably have some other things to work through.
Ask And You Shall Receive
Of course, while anyone can use the process above to create a project of their own, this specific one is mine. And its name is Pound Foolish.
Before there was ChatGPT there was Google. Before there was Google there was Dear Abby. Before Dear Abby you would ask a local priest to sacrifice an animal and discern your future from its entrails. No matter your preferred methodology, all of these tools, at their essence, are trying to help us get answers for our questions.
Human beings are questionful creatures.1 We’re obsessed with asking ourselves things like “how can I be handsome and smart?” or “how do I know where to plant my crops?” or “how bad is it to pair a black belt with brown shoes?” Anyone who has spent more than five minutes with a toddler knows that the questions start early and keep coming well into our twilight years. It’s simply in our DNA to ask things.
Regardless of the diversity of topics one might ask about, Pound Foolish contends each question is really just a reflection of the underlying question how do I live my life? After all, each of us enjoys this mortal coil but briefly, and what to do with ourselves while we’re here must surely be our chief concern. Unfortunately, it’s far too easy to lose ourselves in the muck of the day-to-day and completely miss out on the bigger picture as the years go by.
I’m no exception to this. Actually, I’m something of an expert on getting the small things right while getting the big things wrong. This Substack is my attempt to share from the mistakes I’ve made along the way and the lessons I’ve learned from them. You can think of it as a collection of self-serious thoughts on cultivating a life whose little artful touches are consistent with living abundantly in line with our greater values.
What’s In A Name
Why call it Pound Foolish? I’m sure you’ve heard the words before. In fact, the phrase “penny wise, pound foolish” first showed up in the 17th century book, The Anatomy of Melancholy, by Englishman Robert Burton.2 Since then, we’ve used it to mean going to great lengths to save pennies while failing to manage the much larger expenditures that are counted in pounds (or dollars, yen, lira, doubloons—take your pick).
But I think the phrase works well beyond the merely pecuniary—it captures everything this Substack is about—struggling to connect the small things to the big things and subsequently failing to cultivate the life you want because of it.
I also love that Melancholy, which focuses on what we would call depression today, is a text that attempts to explore serious topics with a comedic tone by an author who struggled with the very illness he was warning against.3 Famously, Burton confessed in his book that “I write of melancholy, by being busy to avoid melancholy.” Whether it’s 1621 or 2025, the matters we struggle with are the things we’re interested in reading and talking about. “Physician,” the Man said, “heal thyself.”
The first real piece will arrive in your inbox this coming Tuesday. It’s about the subtle art of having a guy for that, whatever that may be. I trust that the eight real people and two bots currently subscribed will be giddy with anticipation until then. If you’re somehow reading this, not subscribed, and would like to be, the button is right here:
Pound Foolish is—like all of us—a work in progress. Ultimately, I just hope something in it will be valuable for you on the journey.4
Wiktionary says it’s a word and I like the sound of it. Besides, people can make up words. Shakespeare came up with ones like alligator and gossip and—unfortunately—skim milk.
Available in full thanks to our friends at Project Gutenberg.
My 11th grade history teacher isn’t here to stop me, so I’m fully within my rights as an American to cite the excellent Wikipedia article.
Remember that picture of the clown from the very beginning? That’s a painting of Stańczyk—the most famous Polish court jester of all. The full title of the 1862 painting by Jan Matejko is Stańczyk during a ball at the court of Queen Bona in the face of the loss of Smolensk. It’s the unofficial painting of Pound Foolish.