It’s time for the next phase. I’m going to be posting newsletters much less from now on.

I’m not going away completely, I’m thinking of taking some of my best emails and turning them into an autoresponder sequence people can sign up for if they want. And I’m pondering turning the recent workshop I did on using AI for newsletters into a mini course.

And I’ve got a couple of fun side-projects on the go too.

But overall, you’ll be hearing from me a lot less. And I won’t be taking on any client work or starting any big new projects.

I’ve really enjoyed writing emails over the years and hearing back from people they’ve helped or amused. It’s been a wonderful way to make a living.

But I kind of enjoy drinking beer in the sun, reading, watching football and hanging around with friends just that little bit more. So that’s what I’ll be doing more of from now :)

I hope you’ve found my ideas and information useful over the years. And a special thank you to everyone who’s bought something from me. If you’ve got my Unsnooze Your Inbox course on writing emails or my Email template packs I’ll be continuing to support them as ever (and they’re still available for sale for anyone who hasn’t got them yet).

I wish you every success and you never know, I might see you on a beach somewhere or at a Newcastle match :)

- Ian

But there are a handful of things that would improve my enjoyment of quite a few of the newsletters I read - and I believe make them more effective.

1. Stop Being So Serious

   Obviously one reason for writing a newsletter is to establish your authority and expertise. But that doesn’t mean you have to write in deadly serious professorial tone all the time.
   
   You’ve got to remember most of your readers, most of the time, will be reading your stuff as a bit of light relief. They don’t want it to be hard work. A little bit of humour and a lighter touch makes it a lot more likely they’ll keep opening and reading your emails.
   
   And unless they’re opening and reading your emails you won’t be establishing any kind of authority or expertise.
   
   And, frankly, writing in a professorial tone can come across as a bit condescending. No one wants that in their inbox. Much better to be the friendly colleague sharing experiences and ideas without trying to come across as better or smarter.
   
   Most of my early emails hit that professorial tone. And most of my best results came when I lightened up and started writing to people as equals, not students.
   

2. Stop Being So Angry

   I get it. You want to change the world. You know a better way and the staus quo is just so wrong. And there are so many charlatans out there teaching and implementing bad ideas.
   
   But again, you’ve got to think of your readers. Most of us don’t want angry shouty emails in our inbox. And most of us don’t want to work with angry shouty people.
   
   We want a bit of positivity. A bit of hope. Anger is just so…well…so tiring.
   
   It’s OK to rail against bad practices every now and then. But focus more on the positive. The beacons of good practice. Great new ideas. People doing things the right way.
   
   Inspire us, don’t just berate us.
   

3. Stop Being So Confident. So Sure of Yourself. So Black & White.

   This is a very personal one. And one I’m ironically not so confident in.
   
   We know from studies that people who talk with absolute confidence and certainty tend to be believed more than those who mention doubts and shades of grey.

   
   But I’ve found over the years that the most experienced people with the most expertise are the ones who can see the alternatives. The different scenarios. The shades of grey.
   
   Someone who tells you with absolute certainty that something will work has probably only tried it 3 or 4 times and it happens to have worked every time. Survivorship bias is a powerful thing.
   
   Someone who’s done something 20 or 30 times will have seen the exceptions. The pitfalls. The watch-outs.
   
   They’re the people I want on my side.
   
   Maybe mentioning the caveats and the shades of grey hurts you when it comes to selling to the newbies and the naïve. But for me at least, it helps when selling to people who’ve been around the block a bit.
   
   And those more experienced clients - I believe - tend to be the best ones.

It probably won’t have escaped your attention by now that I’ve fallen into all these bad habits over the years. I’m sure you will too every now and then.

But thinking about who I want to be in my emails helps me avoid them. It certainly isn’t someone who’s arrogant, angry and cocksure.

So just reading back my emails before I send them and thinking “is this me?” helps.

It might help you too.

- Ian

One of them has a sideline in icebreakers you can use at events and parties.

It’s an excellent newsletter overall, but it never ceases to amaze me how unlikely it would be I would ever use or hear any of them.

Whole different planet unlikely.

They’re of the “If a sixteenth-century painter was at your service today, what would be your still-life painting defining your life at the moment?” or “If the story of your life is 300 pages long — what’s on page 283?” variety.

I assume they work for the regular readers of the newsletter and that I’m the outlier.

In my case I don’t even do events or dinner parties - just friends in the pub or curry house. And what we talk about tends to be our recent holidays, football and what weird thing Conor’s relatives have done now.

Asking someone about what a sixteenth centry painter would draw about them would result in a swift clip round the ears and an f-off.

We’re more Brassic than Frasier really.

But it does go to show what a huge variety of interests and styles and ways of doing things there are.

Each can work in their place with the right audience.

It’s the same with your emails.

Don’t feel shy about your sense of humour or what interests you or your points of view and opinions on what matters to you. Some people will click with it, others will hate it.

But you’re far more likely to end up with people buying from that smaller group who really click with you than if you stay grey and generic to everyone.

- Ian

The conversation reminded me of a bit of an epiphany I had when talking to a client nearly 30 years ago.

It was one of those “shooting the breeze” conversations over coffee and he was having a bit of a grumble about how busy he was.

“You know, I used to invite guys like you in all the time to tell me about your latest products and services so I had a handle on what was available on the market. Now I just don’t have time for any of that”.

From his perspective, his lack of time meant he was getting out of touch with what useful services were out there he could call on when he had the need.

From my perspective, I realised it had much worse implications for us.

Because those discussions we used to have with potential clients did a lot more than keep them in touch with what we had to offer.

They built relationships.

And those relationships were crucial to the client feeling comfortable buying from us.

When a need arose for the kind of thing we did, even if they quickly found out we had a relevant service, without the relationship those chats would have built up they just wouldn’t feel OK about hiring us. They’d go with a supplier they knew, even if their services were less of a fit for what they were looking for.

Over time I came to realise that the key to winning consulting work wasn’t just to have the best service for the client. It was to be top of mind and a known quantity when a need arose.

And to get there you absolutely needed to be having regular interactions with potential clients *when they weren’t yet ready to buy*.

Sure, there were exceptions. Brand new services no other consultants (yet) offered. Cases where someone was unequivocally the best by miles, even if they didn’t have a relationship.

But 80% of the time the work went to someone with a good service that had a good relationship. You needed both.

The key to establishing that relationship was to be in regular contact.

And the key to be in regular contact in a world where clients are just way too busy to meet with you just to see what you have for sale was to have something else of value that made meeting with you useful to them.

Something interesting and useful even when they’re not ready to buy. But that gets you talking to them and building a relationship to put you in pole position for when they are ready.

In the sector I worked in we started using a regular research program to identify new trends and issues that affected our clients and new technologies and approaches that could help them.

Clients were more than happy to have us come in to present the results of that research (and often to participate in the research themselves).

They found the insights valuable. Sometimes it directly led to discussions about working in the area of the research. But often it just helped to position us as insightful and trusted partners so when we bid for other work we were seen as a preferred option.

The company my son is talking to face the exact same problem today. Except it’s even more extreme as clients can find out all the factual info they need from a quick Google without needing to call suppliers in.

Their natural opportunities to interact and build relationships are limited.

So they need to create some.

They need to find some way of clients valuing a meeting or call or discussion with them long before they’re ready to buy - so that they’re in pole position when the time is right.

I don’t know what that thing is. Maybe it’s research or benchmarking or an innovative point of view they can share like we used to. Maybe it’s organising industry events or facilitating valuable discussions. Might even be a regular newsletter.

There are many ways of doing it - the only given is that you need to do *something* to keep in regular contact with potential clients before they’re ready to buy.

What’s your approach?

- Ian

“Good to Great” is brilliant marketing.

Telling someone they’re rubbish and need to improve tends to trigger defensiveness. Telling them they’re good but there are a few things they need to do if they want to be great tends to go down a bit better.

But I have to tell you that the biggest impacts and the biggest financial gains I’ve seen in most everything to do with marketing don’t come from going from good to great.

They don’t even come from going from bad to good.

They come from going from doing nothing to doing something half decent.

Most of the advice you’ll read about marketing is of the “good to great” variety.

It’s sexier. It’s more fun for experts to write and they get to flex their expertise and position themselves in the go-to bucket.

And it’s more fun to read too because it’s often new and clever information. Or if you already know it you can nod and get a self-satisfied glow that you’re up on the latest trends.

But in truth, there are exponentially more people out there who know about good marketing than there are actually doing it.

And I think to a large degree, constantly talking about great marketing actually puts people off doing it because it seems too difficult.

You’ve probably heard a lot of email experts, for example, bang on about how you should be emailing daily. About how it unequivocably gets better results and blah blah blah.

And while that all might be true, it’s just not realistic for most people.

So they end up doing nothing.

And I can promise you, the leap from sending no emails at all to sending one a month or one a week gives you much bigger jump in performance than going from weekly to daily.

And it’s doable.

Same goes for almost any marketing you might be thinking of. Nothing to half-decent is the big win.

Next time you find yourself holding back from something in your marketing because it seems to hard or too time-consuming, ask yourself whether you’re focusing too much on the great version when a half-decent version will work fine.

You can always get to great later. Though I find it’s rarely needed.

- Ian

Including me - too often.

The easiest way to know what to write about in your newsletter is to ask your readers (or potential readers).

You can run a survey to your email list or on social media. You can ask a handful of people informally face to face, over the phone or via email or socials.

I did a mini survey once about topics by messaging contacts on Linkedin and got some great and very thoughtful answers.

It was really helpful. And almost anyone can do the same thing.

But typically we don’t.

Sometimes it’s because we assume we already know the answers.

We don’t.

Sometimes we’re afraid to ask, worrying that people will think we’re not really an expert in our field if we have to ask them what they want to hear about.

They won’t.

Sometimes it’s because we believe BS like “Steve Jobs said he never relied on market research”.

Yeah. Jobs said that. But when sued, Apple were forced to disclose a bunch of documents that showed they had done more market research than any other tech company.

And sometimes we get lost in the debate about the accuracy of surveys and all the potential biases and problems you can encounter.

Which might all be true. But I can promise you, when it comes to picking a topic for your newsletter, even flawed research is better than not asking.

Because if nothing else it gets you moving. Unstuck.

It gets you writing about something. Anything.

And from there you get feedback. You can see what clicks and what doesn’t.

And the momentum of writing builds and builds until it becomes a habit.

So if you’re stuck starting or continuing with your newsletter because you’re not sure what the best thing to write about is…know this…

—> You don’t have to write about the “best thing”. Just something useful.

—> If you ask, you’ll find out something useful, and people will be grateful you asked

It’s a real case of “just do it”.

- Ian

At that point you’ll pretty quickly realise it’s a good idea to write about your client’s problems and goals. That’s what they’re interested in.

The next step is cottoning on that writing about topics you’re not interested in is pretty much impossible. At this point you’ll probably stumble onto advice like this:

Which seems pretty sensible. Ideas expressed in Venn diagrams always seem more insightful.

The trouble is, it doesn’t really work. Not from a practical perspective. It only narrows down the range of things you could write about from close to infinite to a few million. Not much help.

So next you’ll probably hear advice that you should go really narrow. “An inch wide and a mile deep”.

That gives you a little niche where you’re saying something different to everyone else.

The problem is it often narrows your writing way beyond the services you might want to offer. And frankly, you end up running out of new ideas after a while and your writing begins to feel a bit repetitive. If not to your audience then certainly to you.

The answer?

It might be different for you, but what’s worked pretty well for me is to write about three different areas and to mix them up a bit over time.

1. I write about my area of expertise generally. In my case for the last few years it’s been email marketing/newsletters. In the past it’s been “marketing for consultants, coaches and trainers”. These are broad enough topics that I have plenty to go at to keep the emails valuable and varied. And it establishes me as someone with broad enough knowledge in that area to be able to help with a wide range of problems.

2. I also write about one specific area within my field of expertise. This allows me to differentiate from what others are saying and mark myself out as a deep expert and the “go to” person for that specific topic. When I was writing about marketing for consultants, coaches and trainers my “deep dives” were into online marketing/email marketing. Now I focus only on email marketing my deep dives have been into using AI to aid your writing.

Mixing between these two levels roughly 50:50 allows me to establish myself as a broad and deep expert in my field. It means I’m the go to person (or at least one of them) for anyone wanting help in a narrow area like using AI to help with writing emails, but I’m also well in the mix for the much larger range of clients who want more general support with their newsletters.

And it means my writing is varied and interesting for my whole audience. Not everyone wants to hear about a single narrow topic all the time. And even if it’s your main focus of interest, just like with music or TV or films, we all like a bit of variety.

Hold on Ian, you said three different areas…

OK, so the final area I write about - maybe 5% of emails - is…

…anything I fancy

I suggest you reserve 5% for something similar too.

If writing about something completely off-topic makes you happy, or you really need to say something about a specific topic: do it.

If you’ve built a good relationship with your readers they’ll indulge you.

It’ll also help build a more rounded, more human perception of you.

They might well find it valuable or interesting or inspiring too (first rule of email: as long as your emails are interesting and your readers keep coming back for more, you win).

Of course, if you stray massively from the reason people signed up for your emails too often, you’ll eventually lose them. They won’t feel you’re relevant any more. That’s why I say make it at most 5% of your emails.

But doing something different every now and then is good for the soul. And it’s good for your emails.

- Ian

That may sound a bit weird coming from someone whose emails largely consist of teaching you how to do things…

…but the thing is that I sell online training.

People who buy my stuff want to know how to do things. That why they buy.

But if you’re a consultant, or a coach, or you sell done-for-you services, that’s *not* what your clients are looking for or why they buy.

Back when I did consulting, my clients wanted to know what their problem was. What the real root cause of the issue was. What they should do to fix it.

And they wanted to know that I knew how to fix it.

But they didn’t need to know or want to know how to fix it themselves.

Back then I did that initial problem diagnosis and solution recommendation live with them as part of the sales process.

If I was in consulting today I’d use an email newsletter, but I wouldn’t fill it with content teaching potential clients how to solve their problems.

Because if someone wants to know how to solve a problem it usually means they want to try to solve it themselves. Which means they’re unlikely to hire a consultant to do it for them.

People who want to hire consultants want to know other things. What’s the real problem? What should my priorities be? What are the best types of solution? What criteria should I use to select someone to help me? How can I make sure the project is a success? How can I monitor progress?

I’d focus my content on those questions.

There’d be a bit of “how to” - but mainly to prove I knew how to solve the problem rather than to give them something they would do themselves.

Buyers of coaching have a different set of questions they’re interested in, as do buyers of products.

Now as it happens, most of the people teaching others how to write emails and newsletters are like me: they sell online training. So the emails we write tend to have lots of “how to” in them.

But that doesn’t mean yours should have. You need to think more deeply about what your buyers would actually value hearing about. What would be useful for them.

It might be “how to”. But it might well be something different.

Make sure you’re emailing them what’s really valuable, not just what everyone else seems to be emailing.

- Ian

We simplify. We omit. And most of the time it’s not a problem. It makes communication more efficient.

But sometimes it can trick us and bamboozle us.

And it often does that in marketing.

Read about email subject lines and you’ll often hear “The purpose of the subject line is to get people to open your email”.

But that’s not right.

Or rather, it’s a linguistic simplification.

What we really should be saying is “The purpose of the subject line is to get *your ideal clients* to open your email”.

Not just “people”. Not just anyone. Your ideal clients.

In the same vein, the purpose of a lead magnet isn’t to get people to opt in to get your emails. It’s to get your ideal clients to opt in to get your emails. The purpose of a call to action in an email isn’t to get people to click through to your offer, it’s to get your ideal clients to click through to your offer.

Surely I’m being pedantic. When we say “people” in this context then of course we mean the right people. Right?

The trouble is that when we simplify our language, then over time, we simplify our thinking.

When we repeatedly say “people” instead of “ideal client”, we begin to forget what we should really be focused on.

Instead of asking ourselves “what does my ideal client care about? What would get them to open this email?” we fall back on “what would get people to open this email?”.

We lose the specificity and the focus on *our* people. We start creating clickbait subject lines designed to maximise open rates instead of appealing to our perfect customers.

I’m sure you’ve often heard that a lead magnet needs to be easy to consume and give instant gratification.

But does it?

Maybe it does. After all, we have to compete for attention with a million other things.

But maybe it doesn’t. Maybe that’s not what *your* ideal client is looking for. Maybe it’ll attract exactly the wrong sort of person.

Asking yourself “what can I offer that will get lots of people to sign up for my email list?” could well end up with you getting lots of the wrong people signing up who are never going to turn into paying clients.

But just changing a few words and asking yourself “what can I offer that will get *my ideal clients* to sign up for my email list?” forces you to think a bit deeper. And you’re much more likely to come up with ideas that actually attract the right people for you.

It’s a simple linguistic trick you can play on yourself. But it’s a powerful one.

Whenever you catch yourself using the word “people”, replace it with something more specific like “my ideal clients”.

I guarantee it will give you much better answers.

- Ian

It certainly seems that way if you listen to the experts with fancy products to sell you on winning with emails.

But really there are only a few things you need to do to succeed.

One is to make an offer. Because if you never actually make an offer in your emails, there’s no real reason to have an email list at all.

Well, I suppose people could buy spontaneously without an offer. They could be so impressed by the expertise you show in your emails that they reach out to you and ask if they could work with you.

It does happen. It’s happened to me.

Just not often enough to keep the lights on.

So making offers or linking to them is important. But you don’t need to do it in every email.

Because as long as people keep reading your emails, they’ll be there when you do make your offer in the next one, or the next.

The other thing it’s important to do to succeed with email is to influence. To move your readers closer to being ready to buy.

When readers first join your list they’ll be at various stages of readiness. A small number will already be on the verge of buying, but most won’t.

There’ll be a handful of things holding them back. The issue isn’t urgent enough, they don’t see the full benefit, they’re not convinced your solution will work yet, they’re unsure they’ll have the time to be able to implement it.

These are things they’ll need to be convinced of over time before they’ll be ready.

But you don’t need to convince in every email.

Because as long as people keep reading your emails, they’ll be there when you do show them how important this is, or you prove your credibility, or you show them that others just like them have been able to do this.

And often, time itself is on your side. This issue gets more urgent. They decide they need to do something about it. And they turn to whoever springs to mind that could help.

And as long as they keep reading your emails, you’ll be up there top of mind when that happens.

You’ve probably guessed already what the only thing you need to do in every email is by now.

“Because as long as people keep reading your emails” is the clue.

As long as they keep reading, they’ll see your offers. Your little drips of persuasion will take effect. You’ll be top of mind when the time is right.

As long as your emails are fun enough, interesting enough or valuable enough that people keep on reading them, you’ll win in the end.

- Ian

The original application came from business networking. Something I just never enjoyed but forced myself to get half-decent at because early in my business it was pretty necessary.

Strategically Ruthless as applied to networking means being very targeted about which events you go to. It means applying “WIIFM” and only going to events where there’s a very good chance of meeting potential clients or a good number of people who could refer you to one.

Now, of course, there are plenty of examples of people who go to weird events and happen to bump into someone who knows someone who knows someone who turned into a huge client for them.

But there are plenty of examples of people winning the lottery too. That doesn’t make buying a lottery ticket a +EV strategy. Stick to events with a high density of clients or referrers.

Tactically Generous means that once you walk into that room, you throw “WIIFM” out of the window and focus on being of service. On being helpful and valuable to everyone you meet.

You often see people being Tactically Ruthless at networking events and it’s a big mistake. They focus only on the people who could be useful to them. The minute they realise you’re not a potential client they’re looking over your shoulder to find their next victim.

In theory, it mean they spend more time with the people who could be potential clients or referrers. In practice, they get a reputation for being rude and self-interested. And at networking events, reputation gets around.

Being Tactically Generous sounds like you might end up “wasting” your time helping people who can’t help you much in return. But in practice, it helps your reputation. It’s also rather more pleasant.

And because you’ve been Strategically Ruthless and focused on events with a high density of potential clients and referrers, the reality is that most of the people you’re helpful to could well return the favour anyway. The difference is you don’t have to be a jerk about it. You help everyone and because you’re in the right room with the right people it works itself out.

Not something that helps much with writing emails of course, but I though you might find it a useful principle to thing about nonetheless.

- Ian

And I’ve talked about how these techniques can work from a business perspective: building a bond with your readers, making the other side of an argument look ridiculous, highlighting your strengths.

But as I was writing those articles something struck me. And with an utter lack of humility I’ve called it “ the first rule of humour in business writing”.

You see, the thing about those business benefits of humour is they only happen if the humour lands. If your readers smile, snigger or chuckle.

And yet the surest way to kill any chance of your humour landing is to focus on those business benefits. To start by thinking “I’ll add a bit of self-deprecation here, it’ll help me bond with my reader” or “If I over-exaggerate here it will help me win the argument”.

The best - nah, the only - way to make humour work is to focus on the humour. To only add your aside or your comic triple or your self-deprecation if you feel it’s funny.

Not because of the business benefit. Not because of how you think it’ll make people see you.

Just if it feels funny to you.

If you start from the perspective of “hah, if I put this here it’ll be funny” you’ll get the business benefit that comes from humour.

If you start from the perspective of “I should add something funny here to get [business benefit]” it won’t work. it’ll feel forced.

It’s an example of what I call being Strategically Ruthless but Tactically Generous.

In this case, Strategically Ruthless means that in the cold light of day I take the decision to add humour to my writing for the business benefits. And I learn some of the techniques.

Tactically Generous means that when it comes to the actual writing, I wipe all thoughts of the business benefits from my mind and just focus on doing the best I can to add a bit of humour to my writing to make my readers smile.

If I hadn’t been Strategically Ruthless I wouldn’t be thinking about humour and I wouldn’t have done the reading and thinking beforehand to allow me to actually add the techniques. It puts me in the right place at the right time with the right skills.

Being Tactically Generous means I have the right mindset in the moment to make that preparation work. If I was Tactically Ruthless and was thinking “what’s in it for me” as I wrote, then the humour would be forced and uncomfortable. My motivations would be obvious. But by focusing instead on “is this actually funny?” more often than not I can get it right.

Strategically Ruthless, Tactically Generous is a a principle I’ve used again and again. It’s something I discovered (maybe even invented) when I figured out how to make networking work for me even though I really didn’t enjoy it.

I’ll share that example next time as the principle is really powerful and worth understanding.

- Ian

Today’s bit of humour you can add to your emails and newsletters is…self-deprecation.

Self-deprecation is, of course, where you poke fun at yourself in an amusing way. For example:

Self-deprecation is a handy technique. When you write emails with tips and ideas there’s a risk you can come across as a bit full of yourself. A bit over-confident (and frankly, a lot of people who write marketing newsletters really are overconfident - at least the ones I seem to end up reading).

A bit of self-deprecation here and there takes the edge off that. It says you don’t take yourself too seriously. You’re just a normal person who happens to have some great ideas.

Now you have to be careful with self-deprecation. Constant self-deprecation can come across as a bit nervous, needy or even rather manipulative (see my newly discovered “first rule of humour in business writing” next time).

And you don’t want to be constantly undercutting your own expertise.

But if done right, self-deprecation can actually boost perception of your expertise.

A while back I heard Drayton Bird use the line “I'm an absolute duffer at everything else in life, but what I am good at is marketing”.

I’m pretty sure Drayton isn’t really a complete duffer at everything else (I can attest to his drinking abilities). But that line allows him to show off about his marketing expertise without it feeling like he’s showing off.

In fact it makes his marketing expertise sound like a superpower because all his talents are concentrated in that one area.

Another way of using self-deprecation to enhance the perception of your abilities is to make fun of your own obsessiveness or interest in the obscure.

If you’re an expert in your field the chances are you’re pretty obsessive about it. And you’ll most likely know a lot about some weird and wonderful little areas: that’s what makes your expertise unusual and valuable.

By making fun of that you subtly highlight it.

For example, an SEO expert could say something like:

I spent a happy 9 hours yesterday researching the latest tweaks Google have made to the RankBrain algorithm.

Yikes…that sounds a teensy bit obsessive! Mea Culpa.

Being super obsessive about your area of expertise is quite funny, but also rather reassuring for clients to hear. I’d rather have some numbers-obsessed robo-nerd advising me on conversion optimisation than a well-adjusted person who’s more interested in sports and their social life. Which is perhaps why Flint McGlaughlin of Meclabs talks like he does.

Calling out your own obsessiveness is easy to do.

When you’re going to explain a new idea or advanced technique, just mention how you came across it and highlight the extraordinary lengths you went to. Then use an aside to reflect on how weird that level of obsession must sound.

Then resume with your explanation.

Easy,

- Ian

OK, maybe I’m, er, exaggerating a bit.

But exaggeration is a simple way to add a bit of fun into your writing.

Here’s a recent example:

That’s an example of using exaggeration sarcastically to make a point - my preferred method.

Using exaggeration like this works well for a couple of reasons:

1. It’s probably how you’d talk in real life. It’s definitely how I’d talk. It’s the more articulate version of “yeah right”.

2. The humour fits naturally into the writing. It serves a purpose. You’re not having to shoehorn something in just to be funny: the exaggeration highlights the ridiculousness of the thing you’re arguing against.

3. In many ways, it’s a more effective riposte than just saying something is wrong. I’m not 100% sure why: maybe people like to side with others who are funny. Maybe using humour doesn’t sound so aggressive. Maybe it sneaks under people’s critical faculties. Whatever the reason, it seems to work better.

The key to making this type of exaggeration work is to take the thing you’re arguing against (in this case the idea that writing shouldn’t be helped by tools) and finding analogies where the same idea (not using “tools”) would be ridiculous (I picked hammering a nail and driving a car). The more visual those analogies the better.

The other option is to draw an exaggerated comparison with the person giving the advice.

For example, I could have said:

“A professional copywriter with decades of experience and a full-time focus on writing telling a busy small business owner they shouldn’t use AI tools to help them is a bit like Heston Blumenthal telling me I shouldn’t buy my food at the supermarket and instead I should grow it all myself before spending hours a day cooking it.”

So next time you’re making an argument against something, rather than purely relying on logic, think about whether a bit of humorous exaggeration would serve you better.

If nothing else, it’ll make your writing a bit more fun.

And often, that means your message will get across better.

Not to mention the fact more people will read your next one.

- Ian

One is through technique. I gave an example of this - the use of asides - last time.

If you’ve read much PG Wodehouse or Jane Austen you’ll know that the particular combination and pacing of words they use is just - well - amusing. It makes you smile.

Wodehouse could write a shopping list and I’d probably end up laughing if I read it.

Most of us don’t have that talent. Though I do think it can be improved by reading more fun stuff rather than all those earnest-but-deathly-dull posts on Linkedin we seem to feel it’s our duty to wade through.

But there is an easier way to make your writing a more fun read.

It’s simply to write about more fun stuff.

I was trawling through some of my older newsletters and noticed just how many times I reference popular culture to illustrate a point.

Dr Who. Only Fools & Horses. Scooby Doo.

Only the highbrow stuff from me, obvs.

You can’t do it every email, but if you can find a way to make your point using a popular TV show or film or music as an example then people who like those shows, films or songs will smile. It’ll bring back good memories for them and you get to hang on the coattails of those good memories.

It also makes it easier to get your point across quickly since you won’t have to give an in-depth explanation. They’ll have half the story in their head already. And because you’re attaching your point to a strong existing memory, it’s more likely to be remembered too.

How do you make those connections?

Watch the shows. Or read about them. Don’t just spend your time reading “important” business stuff.

My Dr Who link came from noticing it was Tom Baker’s birthday and then diving in a bit and finding out he’d nearly been fired after just a couple of episodes based on initially negative feedback from viewers.

That led to what I think was a really useful post about persevering through change.

And it was my willingness to dive into the “irrelevant” weeds that led to that post.

We all have interests outside of business. Give yourself permission to include them in your writing.

For those who share those interests or who remember similar things, it’ll build a closer bond.

But it works even for those who don’t as it provides some levity and shows that you’re not just a boring old faceless expert who knows about nothing but their topic.

And perhaps most important of all, it’ll be fun for you too.

- Ian

Obviously your main goal is to send something useful. If every email is just fluff your readers will eventually drift away.

But that doesn’t mean you have to ram an encyclopedia down their throats every email. They already have access to tons of useful information and often they’re reading your emails as a pleasant break from the pressures of the day.

So a winning email is one that gives your readers a useful idea or practical tip - but that also makes them smile, snigger, or just not have to fight to keep their eyes open as they read it.

And the good news is that the bar isn’t all that high.

The reason I sent my Molesworth takeover email on Sunday was that I’d had my fill of uber-serious po-faced emails dropping in my inbox. Almost every expert these days seems to feel the need to present their stuff like they’re some kind of omniscient sage without a shred of self-doubt (or self-awareness, it seems).

I long to get something useful but lighter instead.

I’m sure a lot of your audience does too.

And it turns out that some of the techniques for lightening up your writing are surprisingly easy. For example, the Aside.

An aside is where you briefly break from your main narrative to make a side comment or observation (like this, except funnier).

Asides are often written in parentheses - or sometimes after dashes like this.

Sometimes I’ll do them on a separate line in italics.

Like this.

You can use asides to clarify or expand on your points. But I mainly like to use them to say something a bit tongue-in-cheek or snarky.

I sometimes compare it to a game of football (that would be soccer to you heathens).

Or

(Quick aside: has anyone *ever* learned how to be a better manager at business school rather than just becoming consultants or bankers?)

How do you come up with asides?

Surprisingly easily.

Often when you write something or read it back, you’ll find the aside just naturally jumps into your head. The trick is to be brave enough to write it down for public consumption.

For example, when I wrote “omniscient sage without a shred of self-doubt” I immediately thought “or self-awareness” and smiled to myself. The same happened when I was writing about how I went to business school to learn to be a better manager and remembered that I came out as a consultant instead.

When you find your writing triggers a thought that makes you smile, write it down. It’ll usually make your readers smile too.

Other good ways to use asides for comic effect are:

Exaggeration: for example “It was the worst sales meeting I'd ever had (I'm pretty sure I saw the customer's wallet sprouting legs and running for the hills halfway through my pitch.)"

Self-deprecation: “It was the worst sales meeting I’d ever had (which is saying something given I once had a meeting where the potential client only uttered 4 words in total)”.

A pop culture reference: “It was the worst sales meeting I'd ever had. (I felt like I was trying to sell a Krusty Burger to Lisa Simpson during one of her vegetarian fads.)”

Irony: “It was the worst sales meeting I'd ever had. (Naturally, it was right after I finished reading 'How to Win Friends and Influence People' for the third time.)”

You have to pick what fits with your style. The examples of exaggeration and self-deprecation would work well for me I think. The Krusty Burger and Dale Carnegie ones less so.

And don’t overuse them. One or two per email is enough. Any more and your readers lose the flow of what you’re trying to say.

And as I say, the main thing is just being brave enough to try one. Of realising you don’t have to be deadly serious for people to take you seriously.

- Ian

Kathy got half-way through and gave up. Possibly offended by the spelling. I’m rethinking my marriage now :)

PJ on the other hand corresponded with me for the rest of the day in Molesworth-ese.

What was the clever marketing behind the email? The subtle psychology and influence strategies?

Er…none.

Honestly, I’d just read a handful of emails from “marketing experts” and found myself so bored by them.

So serious. So sure they were right.

The content could have been great for all I know, but they just didn’t connect. At least not with me.

So I thought I’d write an email about how it’s OK to have a bit of fun in your marketing. And if you’re having fun with something you’re more likely to do it.

And then I thought “well, obvs I should have some fun with this email”.

And then I got carried away.

Was that email going to make anyone more likely to buy something from me? Unlikely.

But I enjoyed it.

And it did get me thinking that maybe it would be useful to send a few emails with ideas on how to inject a bit of fun into your newsletter and marketing (while still getting results).

I’m quite looking forward to it :)

- Ian

PS obviously you can’t just write for your own amusement every time - that would be self-indulgent and a surefire route to zero subscribers and income. But one of the joys of running your own business is that you don’t have to maximise the heck out of everything commercially.

And maybe, just maybe, you can do both.

as any fule kno writing is DEAD DULL and worse than latin with old greybeard fizzing at you. but lo! sum swot has found out why. it is becos we are all TOO SERIOSE about it like we are at speech day or prize-giving (which i never get invited to as i am not a girly swot like you-kno-who).

even the beaks who teach us this DISMAL ART seem to have swallowed a DICTIONARY and speak like they hav stiff collars all the time.

but listen, o suffering pupils of the world, if you are not larfing while scribbling your DEATHLESS PROSE you will end up like peason - a sad sack who only writes about geograhy and the imports of Venezuela (uterly wet).

i kno the masters sa we must IMPROVE OURSELVES and "DO TODAY wot other CHUMPS wont so TOMORROW we can do wot they JOLLY WELL CANT (and they will be UTERLY JELUS)".

but i sa to you - stuff and nonsense! how long can you keep that up? about as long as molesworth 2 can resist stealing my tuck, which is to sa not very.

and think of the poor chumps who hav to READ this stuff. if you are BORED STIFF writing it, they will be FAST ASLEEP reading it. they will drop like flies in scripture lesson.

so be a brick and make it FUN. tell a joke about grabber or how you avoided the head's study. write something CHEEKY in the margin. talk about SPACE BUGS from mars (v. intresting).

just make it GOOD and NOT DULL. that is all any fule need to kno about writing.

yrs, etc. n. molesworth (curse of st. custard's)1

I’ve been waxing lyrical about how much time AI can save you with your writing, and how the output can often be more thorough and better written than you’d come up with yourself.

Obviously there are some downsides too. Ones we’ve bumped into more than a few times.

And if you’re feeling a bit overwhelmed by this whole AI thing they may make you chuckle and reassure you that sometimes our AI friends aren’t quite as clever as they might think they are.

So here, with all the dogmatism of brevity, are my top 5 AI blunders:

1. "When Numbers Go Haywire"

Your AI confidently declares your product has a 1000% satisfaction rate. Impressive. But…

Unless you've cracked the code to parallel universe customer service, something's a bit... off.

It’s not always going to be as obvious as that. It’s more likely to be a quote about a 57% improvement some company saw or £1.2m of savings or another vaguely plausible number that conveniently backs up your point.

Our finding is that AI is very reliable when there’s lots of data available. But when there’s a numbers vacuum it tends to panic and make things up.

Tip: Double-check those stats with good old-fashioned Google. In fact often just asking your AI to double-check its figures will result in it ‘fessing up.

2. "The Case of the Imaginary Expert"

Ever heard of Dr. Fakey McFakeface, the world-renowned expert in... everything? No? That's because your AI might have just invented them to back up a claim. The same goes for referencing.

We wrote a couple of dozen AI-assisted articles with detailed referencing (in APA 7th Edition style no less) and Claude nailed them perfectly. Then all of a sudden, out of nowhere, it got about half of them wrong on the next article.

As with point #1 it was most likely because there were plenty of available references for the first articles but we veered into more obscure territory with our later one.

Tip: Always cross-check at least a sample of your references or expert quotes. Ideally all of them.

3. "The Jekyll and Hyde Newsletter"

Does your newsletter start sounding like a formal academic paper and end like a text from your teenage nephew? You might be experiencing a case of AI personality disorder.

This happens particularly when writing a long article via multiple prompts in a chat. As you fill up your AI’s “context window” (working memory) it seems to forget things from earlier in your chat. We’ve had it lose the writing style, or even forget the main topic of the article and start writing a section completely out of context.

Tip: Repeat the main style parameters you’re looking for in every prompt (e.g. “please use my writing style as you analysed earlier” or “please write in a minimalistic journalistic style at Flesch-Kincaid Grade Level: 9-11”). And use phrases like “Remember to keep it in the context of [umbrella topic]” to avoid your AI disappearing off down a rabbit hole.

4. "The 'Oops, Wrong Audience' Blunder"

Nothing says "we value you as a customer" quite like explaining basic industry terms to your expert audience, or peppering your newsletter with Gen Z slang when writing to retirees. Fr.

Tip: Make sure your AI knows your audience as well as you do. Give it a clear picture of who's reading, and it'll be less likely to make your readers go "Huh?". Our early years articles always include an audience definition along the lines of “You’re writing for an audience of early years professionals and practitioners who work in nurseries and kindergartens and are looking to develop their professional skills and provide the best support to the children in their care”.

5. "The Clickbait Catastrophe"

"You Won't BELIEVE What This Newsletter Says (Number 4 Will SHOCK You!)" If your subject lines are starting to sound like they belong in a late-night infomercial, your AI might be going a bit overboard.

It’s not just headlines. When you ask an AI to write a promotional email or post it has a tendency to go a bit over the top. In our case every interview Kathy has done is apparently game-changing or revolutionary.

Tip: if your AI comes back with something over the top you can tell it to try again and be less clickbaity. For our emails we add prompts like “Avoid hyperbolic phrases like ‘game-changing’ and ‘transformative’”.

So there we are: five AI blunders that might be lurking in your newsletters.

But don't worry – with a bit of oversight and a good sense of humour, you and your AI can create newsletters that inform, engage, and occasionally make your readers smile for all the right reasons.

Until next time, keep it real (even when your writing buddy isn't)!

- Ian

PS: This newsletter was written with the help of an AI. Any unintended blunders are purely the fault of Claude, not me. Obvs.

But what I haven’t done is talked about how to get started.

A bit of an oversight really given that most people have probably had a little try, but haven’t really got going or had much success using AI to help their writing.

Maybe that’s where you’re at. Or maybe you’re still in the “thinking about it, but it all seems a bit complicated” phase.

If so, here are my top 3 tips for getting started with AI-assisted writing without getting overwhelmed:

1. Start small with brainstorming

Your first step shouldn't be asking AI to write your magnum opus. Instead, use it as a brainstorming buddy.

Next time you're stuck for ideas, try asking an AI tool like ChatGPT or Claude to suggest some topics or angles on your chosen subject. For example:

"Give me 10 ideas for blog posts about productivity for small business owners"

You'll likely get a mix of decent ideas, rubbish ones, and a few gems you hadn't considered. The key is to treat it as a jumping-off point, not the final word.

Bonus tip: after generating an initial list, say:

“Great. Come up with some additional topics which are a bit left field, weird or unusual - ones that small business owners would want to read even just out of curiosity” (obviously replace “small business owners” with your particular client types.

2. Use AI for research, not regurgitation

Once you've got your topic, AI can be brilliant for quickly gathering information and examples.

Let's say you're writing about time management techniques. You could ask:

"What are 5 popular time management techniques, and what are the pros and cons of each? Please tailor your answer to the perspective of a [your client type]"

This gives you a solid foundation of knowledge to work from. But - and this is crucial - don't just copy and paste the AI's response. Use it as a starting point for your own research and thinking.

Remember: your readers didn’t sign up for regurgitated AI content. They signed up for your unique insights and experience.

3. Edit ruthlessly (and add your own flavour)

If you do use AI to generate any actual content, treat it as a first draft.

AI writing often lacks personality and can be a bit... well, boring. So your job is to inject your own voice, add relevant examples from your experience, and make sure it actually makes sense.

Read it aloud. Does it sound like you? If not, rewrite until it does.

You can use the prompts I recently shared to get the first draft written in a style close to your own. But even then it’ll never be perfect - you’ll need to tweak it to get it to sound right.

And make sure you fact-check. Especially references and quotes.

Don’t get complacent. We wrote a couple of dozen articles for students recently with a lot of references in them using Claude. It did the first 23 flawlessly - every reference was correct. But on number 24 it made most of them up.

I’m still not 100% sure why, but I’m sure glad we double-checked and fixed them.

The bottom line? AI writing tools can be useful allies in your writing process. But they're not magic wands, and they're certainly not replacements for your expertise and personality.

Use them wisely, and they can help you beat “blank page syndrome” and write much faster. Use them badly, and you'll end up with bland, generic content that does nothing for your business.

Start small, experiment, and try to keep your own voice front and centre. That way, you'll harness the power of AI without losing what makes your writing uniquely valuable.

- Ian