Lines To Take

Lines To Take

Now We Are One

Lessons from a year on Substack

Jack Kessler's avatar
Jack Kessler
Mar 05, 2026
∙ Paid

1. This is harder than I anticipated

I may have been just starting out on Substack, but I didn’t arrive by way of a turnip truck. I’d written a daily newsletter, West End Final, for more than four years and close to a thousand editions. It won awards1, grew to 100,000 subscribers… and yet, it was nothing like this.

Of those five newsletters a week, perhaps one or two were a précis of an important local or national news event. Think a grim stabbing in London or some Covid-19 vaccine update. Whereas at Lines To Take, the ambition is to produce a column every day. You’ll know better than most that I don’t always pull it off. But the intent is there.

Worse still, back then I had the readymade excuse of an employer paying me to send something. But Lines To Take somehow needs to justify itself. No one is forcing me to do this.

2. Ideas, ideas, ideas

Forget the greenback, stable coins or crypto, the only currency that matters is ideas. The difference between having one and not is wider than a mile. I keep a rolling iPhone Notes app in which I jot down little thoughts, often after ingesting several jolts of caffeine. They always seem inspired at the time. The problem only arises when I actually refer to them, at which point I realise they are completely unusable.

Variety is always front of mind. I don’t want to write five newsletters a week on British politics, and I assume no one wants to read it either (or, at least, not from me). But I physically recoil at writing about subjects I know little about and where I can’t possibly add value. At the same time, I don’t want to limit this newsletter to my three areas of genuine expertise: Roger Federer’s 2004-2007 seasons, Tony Blair quotes and fuel duty revenues.

3. Promotion anxiety

Ralph Waldo Emerson is credited with saying: “If a man can write a better book, preach a better sermon, or make a better mousetrap than his neighbour, though he builds his house in the woods the world will make a beaten path to his door.”

Yeah, no. ‘If you build it, they will come’ is a business model about as successful as Kevin Costner’s movie career post-1993. Growing a business has never been about the product alone — people have to know about it and to learn for themselves why they’ll love it. I mean, no one drinks Red Bull because it tastes great.

I haven’t asked anyone out on a date in about a decade. Instead, I get my fill of potential humiliation every weekday, when I promote the newsletter on social media. The audience — mostly on Bluesky — is quite different to those already subscribing, which adds a further level of discomfort and complexity.

Crafting social media promotion — posts, threads, zingers — takes time. And all too often, I’m asking the intern2 to distil a newsletter that is really very difficult to define into 180 characters. Like, how would you have promoted this piece to a bunch of cynical, mostly lefty strangers online?

Lines To Take is a reader-supported publication. Please consider becoming a free or paid subscriber. Thanks, Jack

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