I sent my first daily email in June 2022.

That email was all about my experience on the cult UK TV quiz show Countdown (a niche topic if ever there was one).

4 years later and I’ve certainly picked up a few tips, tricks and lessons on the craft of newsletters, the writing process, creating content and the mental side of daily emails.

To mark this momentous milestone, this week I’m sharing four lessons from my four years of writing and sending daily emails.

First up:

Pleasing other people is not the goal.

When I started writing these emails, I bent over backwards to never say anything which someone else might disagree with. Hence months of emails which, looking back, were about as exciting as a ham sandwich.

Around then, an email floated into my inbox from a reader telling me he’d unsubscribed. 

Turned out he enjoyed the emails but he’d unsubscribed for a very different reason:

“I’ve unsubscribed from your newsletter. They were good. But you were sending the emails every day. And I don’t want to get an email from you every day”

Writing daily (or “week-daily”, as I do) was my plan from the start. It was a non-negotiable for me. 

Yet here was a reader telling me that he’d unsubscribed BECAUSE the emails were daily.

And that’s when the penny dropped:

It’s literally impossible to write a newsletter which no-one disagrees with. There will always be someone who’d prefer this newsletter to be sent less often, with more actionable tips, with less selling, less stories from suburban Sheffield and even less Dad jokes. I’m sure there’s also people who shake their head in despair when I write “we make our lives harder than we need to” or “your workload isn’t causing your stress”.

Which means the only way to send a newsletter which readers don’t disagree with…

Is to never send a newsletter in the first place!

I think this is why I decided “fuck it, I’m not going to write what other people won’t disagree with. I’m just going to write what I want, when I want, in the way I want”.

So that’s what I do.

And guess what?

This is why I enjoy writing my newsletter so much. It’s why these emails energise me rather than tire me out. It’s why I rarely second-guess myself when I send an email. And it’s why I get genuine and heartfelt replies to these emails each and every week.

Which isn’t a bad place to be.

As it turns out, there’s actually another benefit to trying not to please everyone which is even juicier. A benefit which deserves an email of its own.

That’s teed us up nicely for tomorrow.

Back then with lesson #2.

To fulfilment,

Tom