(if you’re not interested in newsletters or writing, you might want to close this email and come back tomorrow)

Today I’m celebrating TWO special anniversaries.

As this email gets fired into hungry inboxes all across the world, Lauren and I are enjoying our five year anniversary.

That’s right.  It’s five years to the day since I took Lauren to the Lady Mildmay pub for a pint and a pork pie.

And the rest, as they say, is history.

That’s special anniversary number one.

Special anniversary number two?

Today marks my 500^th daily email.

When I sat down just over 2 years ago to put finger to keyboard and write about 5 lessons from my appearance on the cult UK TV show Countdown, I had no clue whatsoever about daily emails.

499 emails later and having studied & worked directly with some of the biggest names in the daily email space, I’m a lot more clued up.

That’s not to say I’m sending perfect emails each day.

But in the last 2 years I’ve learnt a hell of a lot about writing, the writing process, creating content, the craft of newsletters, the mental side of daily emails and even the tech side of things. 

Plus I’ve learnt a whole bunch of stuff I didn’t know I needed to know which has allowed me to dial-in my writing and have people opening, responding, forwarding, clicking and buying from my emails.

So I've come a long way since I sent that Countdown email to my first 7 subscribers.

If you’re curious, here’s some of what I’ve learnt sending 500 daily emails in the last 2 years:

*** How to get over the curse of perfection.  If I wrote my daily emails the way I used to write a credit report at work, I’d still be tweaking & improving that Countdown email today (2 years later!).  Sure, that email would be much better for it.  But the other 499 emails would be wisps in the wind and from a newsletter perspective, the last 2 years would’ve been a write-off

*** The pros & cons of sending emails daily vs weekly vs irregularly and which frequency to pick depending on what you’re trying to achieve

*** 4 “tricks” I use to write daily emails on the rare occasions the words aren’t flowing and that day’s email feels like squeezing blood from a stone.  These reliable tricks have allowed me to ping out an email even when I’m feeling tired, uninspired or not in the mood to write (funnily enough, some of these emails have got some of my best reader reactions)

*** How to promote coaching via writing and why the “modality” I coach from (The Inside-Out Understanding) lends itself so well to emails, LinkedIn posts, newsletters, blogs and so on

*** How I went from writing emails in three or four HOURS to now regularly penning emails from scratch in 15 or 20 minutes.  I’m not saying I write all my emails this quickly (I don’t – some still take much longer than I’d like) but my writing time is increasingly getting quicker and there’s no reason to suspect this won’t stop

*** The only aim I have when I write my daily email.  This aim isn’t “teach”, “sell”, “educate”, “add value”, “inform” or anything similar. But I think it’s why I can send emails every day which people don't just read but look forward to reading (if my readers’ feedback is to be believed)

*** How to deal with the rough patches of writing a newsletter, including unsubscribes, responses from trolls, feeling like emails are disappearing into a black hole and wondering if readers are judging, nitpicking & criticising the emails, let alone enjoying them

*** The approach to take when writing a LinkedIn post vs a personality-based daily email vs a theoretical weekly newsletter vs a Substack essay-style newsletter.  Truth is, writing a daily email in essay style (for instance) or a LinkedIn post in daily email style (another example) is no different to serving soup on a plate.  You can do it, but you’re making life tough for yourself

*** Where I find an endless supply of email ideas.  Nowadays I don’t sit at my laptop screen and ask “what on earth will I write about today?”. Instead, it’s a question of “what idea will I pick today?”

*** How I kept going. I think I’ve skipped less than 20 days of daily emails in the last 2 years.  Even today, it would still be easy to change my mind and go from writing daily to weekly.  But this would probably lead to emailing fortnightly, then monthly, then once every six months and then not emailing at all, which would defeat the whole point of having a newsletter in the first place

Anyway, this email is a bit of a diversion from the norm.

And I suspect a chunk of people reading this email won’t be all that interested in this topic.

But then again, perhaps I’m wrong.  Perhaps there are a few plucky souls reading this email who have their own newsletter. Or a few other plucky souls thinking about starting their own newsletter or making a few posts on LinkedIn.

There’s only one way to find out.

Here’s the deal:

I’m thinking of running a webinar where I dive into the ins & outs of the bullet points above, then open things up for questions and keep going for as long as the questions keep coming.

The webinar won’t be free, but it won’t be expensive either.

But I’ll only set up the webinar if there’s enough interest.

Time’s precious after all.

So if you’re potentially interested in downloading what I’ve learnt about newsletters and digital writing in the last 2 years into your brain (and avoid scrabbling around trying to piece everything together like I did), hit reply and let me know.

Replying doesn’t commit you to anything, but it does tell me “Tom, I might be interested”.

If there’s enough interest, I’ll set the webinar up.

If there’s not, I won’t.

This is the only email I’ll be sending about this webinar.  As I said before, I don’t think most of you want to be reading about this stuff on a regular basis.

Which means if you’re interested in joining the webinar, the only way to get the details is to hit reply to this email.

That’s it for today.

Onto other matters tomorrow.

 - Tom