Email is f🙊cking hard! How do you make it good?

This email was originally sent to subscribers on April 17, 2024. If you want to receive epic emails like these you should subscribe!

A rant… kind of.

We’ve been developing Groundhogg for 6 years, and our sister company MailHawk for 3 years. That’s a combined total of 9 years of first-hand, hands-on, in-the-trenches good email experience.

You wanna know what I learned from those 9 combined years of first-hand email experience?


Excuse my language…

The honest truth is that email, or at least the business of sending email to leads and customers, has been getting progressively more difficult. And it will likely continue to get more difficult.


The short answer is over-saturation sprinkled with a bit of bad behavior.

I want to dive deep with you. Let’s talk about it.

Part 1.

If email had audio, you’d go deaf.

~Me, just now. I’m going to get that on a shirt.

When I asked ChatGPT, the average person receives 70-120 emails per day. I don’t know if that’s totally accurate or not, but it sounds right, and has the added benefit of making my point.

Anecdotally, I receive ~100+ emails a day across 3 inboxes.


That’s a lot of email. It’s a lot of reading. Reading takes time. Time is money. Do you see where I’m going with this?

And not all of that is good email. Likely, most of it is bad email, ignored email.

We know recipients are very discerning about which emails they open and take the time to read. By the way, thanks for reading this far.

We fight for scraps of attention with catchy and inflammatory clickbait subject lines. It’s actually exhausting trying to write engaging emails. I have yet to get a satisfactory email to come out of ChatGPT, but I see a bunch of people daily on X saying it’s possible.

There are really only 3 types of email.

  • Personal correspondence: Cat photos from your mum
  • Corporate correspondence: Credit card notices and password resets
  • Everything else is really just Marketing

And if I were to arbitrarily assign a percentage of how much time I spend on each per day it would look something like this.


How much time do you spend voluntarily looking at marketing emails every day? Probably not much.

If you’re an outlier and you love to read marketing emails don’t call me out, okay?

We’re fighting for 5% of peoples’ short attention. It’s a tough gig. People are stressed outstrung out, and stretched thin.

I’m not saying this to demoralize anyone, but I’m trying to add context. Why is email getting harder? Why are click rates going down? Why are people not engaging?

Because the inbox is too over-saturated with garbage. With stuff people don’t care about. With emails that don’t relate to their situation. People are turned off by our sh💩tty empathy-lacking emails.

How does that make you feel?

My best-performing email of the last 6 years was our April Fools joke about switching Groundhogg to a SaaS model.

This email…

  • Did not Include a call to action
  • Didn’t have an offer or discount
  • Did not provide education or anything helpful
  • Did not add value really in any way

But, I got a lot of responses and engagement! I received dozens of replies, and from them, I discovered a recurring theme.

“Got me! I just about crapped my pants… luckily I read the entire email. The email had me hook, line and sinker.”


First, my subscriber saw the subject line “Groundhogg is going SaaS,” and felt immediate panic/urgency/fear. Something they loved and relied on was changing.

Second, they read the email introduction, which starts out very official sounding, compounding their fear.

Third, as they get deeper into the email, the absurdity of the situation starts to set in. It creates confusion, doubt? “Is this email for real?”

Lastly, and on cue, the “April Fools!” is delivered just before the pieces click together. Creating a sense of relief, and tickling the recipient’s funny bone. They’ve been had!

So, what’s the takeaway? Why did a silly prank outperform every email I sent for the last 6 years?

Because it made people feel.

In one email we made people feel fear, urgency, joy, anger, laughter, confusion, and many more emotions.

An aside: Maybe the best way to solicit feelings from your customers isn’t to rage-bait them. I wouldn’t send that email every day, but maybe sometimes?

As a society, we used to write letters. Letters conveyed feelings and emotions. When we read them we’d cry and laugh. We’d feel.

What makes people feeeeeeel?

The most successful brands moving forward will be able to consistently make people feel. By extension, the most successful email marketers will be able to elicit feelings via email.

So, the question becomes: “How do we write an email that elicits emotion?”

While I’m still working on an exact formula on how to write an email that elicits feeling (I’ll probably come back to this in the future) I went back to all the great emails I’ve ever read and I’ve identified several common themes.

1) I care (really care) about the subject.

This seems obvious. But let’s be honest, do the people you’re emailing care about what you’re sending them? If a subscriber just stopped receiving your emails, would they even notice?

If the answer is that they don’t care, we should ask, “what do they care about?” If you don’t know that, maybe ask yourself what you care about.

One of the things I care about is economics, and I’ve been following our situation closely. One of my favorite newsletters is No Mercy / No Malice.

I usually find his content highly engaging. Either because I think he’s absolutely right pointing out the level of incompetence demonstrated by others is magnificent and *the topic *riles me up, or because I disagree with his take and he gets me going.

2) The outcome is consequential.

Either directly or indirectly, the outcome of the topic within the email can affect me positively or negatively in some way. If this, then that. Something is happening.

As an example, a consequential topic might be “Gmail’s bulk sender policy is changing, and you could be at risk!” A bit sensational, but being up to date on those details is necessary and could impact future performance.

The health conscious might respond to a topic like, “Common household items that are leaching microplastics into your water.”

Whatever the topic, it must matter and have real-world implications for the reader.

3) It relates to my current situation.

While I read the email, it makes me think of me.

Marketing psychology tells us that people place themselves in the situations they read and witness. While reading a book, we often think about what we would do in similar situations. When we watch TV we shout at the screen in vain at the characters to not open the door hiding a chainsaw serial killer. Looking into the best adverts is like looking into a mirror that shows us the us we want to see.

Why should it be any different for email?

So, how do you make an email relatable? Based on my research I have a few suggestions.

  • Use stories. They don’t have to be long, but personal experience is often very relatable. If you don’t have your own story, use someone else’s.
  • Know your subscribers. Knowing what your subscribers are dealing with will make it much easier to craft messaging they can identify with.
  • Practice empathy.

4) It challenges previously held ideas or beliefs.

Being challenged immediately gets the gears turning, and elicits engagement. That’s why subject lines like, “You’re doing email wrong.” work. Your first response would be, “No, I don’t.” Then, you’ll read the email to prove to yourself that you’re right.

You don’t always have to be so opaque. There are more subtle ways to challenge your subscribers. Here are some I’ve seen…

  • Offer opposing perspectives and ask which they agree with and why
  • Ask hard questions. The human impulse is to answer.
  • Make (evidence-backed) assertions that challenge the status quo.

Personally, I love reading stuff that challenges me. The mental effort of defending a position is stimulating, win or lose.

5) It’s entertaining.

Entertainment is one of the biggest economic drivers on the planet. According to the very official-looking website Statista, the value of the entertainment industry was $2.3 trillion in 2022 and is projected to grow to $2.53 trillion this year.

Chart is from Statista

As I mentioned earlier, people are bogged down with the day-to-day. If you can bring reprieve, joy, and laughter to the inbox, you’ll win.

That’s easier said than done of course. So here are some suggestions to add entertainment value to your emails.

  • Add opinion. There’s a reason shows like The View are still around (for better or worse).
  • Use language. Use language that might shock your audience out of their deep sleep.
  • Be unpredictable. Predictability breeds boredom. If you’re married you already know that.
  • Be funny. Hot take, comedy is alive and well. So many companies are worried about optics and sensitivity, not wanting to offend. You can be different simply by sending the joke you already thought of.
  • Be energetic. If you were to give a presentation on low energy, nobody would listen. So why would you write an email with low energy?

All that sounds hard.

Probably because it is hard. At the time of writing this sentence, I’m on day 3 of trying to piece together coherent arguments for why your email is not performing as well as it could be.

I guess that’s why they say, “good things take time.”

I believe that people can *feel *the effort that you put into something. With AI saturating content, I predict more and more people will be drawn to high-effort content.

This does not mean you should delete all your email sequences, re-write all your other emails, and start over. Low-effort emails still have their place. You still need to send cart abandonment emails, offers, and check-ins. Otherwise, how would people know how and when to buy?

But high-effort feel emails will elevate the effectiveness of all your emails.

So sit down, take the time, and write about something you care about and send that to your audience. See what happens.

Picture of Adrian Tobey

Adrian Tobey

Adrian is the founder and lead developer of Groundhogg. He believes that marketing automation should be simple and accessible so any business can use it to grow.

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