13 Creative, Smart, and Unconventional Ways to Overcome Email Writer’s Block

I want to share something that’s not going to be a secret anymore:

I often get stuck when it comes to writing my email newsletters. Sometimes I enjoy writing these emails, but sometimes I don’t. It’s a matter of timing.

I knew I needed to come up with a solution to overcome “email writer’s block” that didn’t feel like such a burden. 

I’ve been working on this, and documenting my progress. 

I figured that if you are reading this, it may be a similar challenge for you as well.  That’s why I wrote this blog, which features 13 of my favorite nerdy, “no fluff” ways to overcome email writer’s block.  Some are ordinary, but some are not often heard of and even a little unconventional.

And now, honestly, I only write newsletters when I’m in the “flow,” and this makes my work SO much easier. 

In a few of my previous blogs, I introduced some of the “why and how” of email marketing.  If you still aren’t sure if email marketing is worth your time, and/or you are exhausted and overwhelmed from focusing only on social media or word of mouth marketing, read this article first. 

For an even deeper dive into how email can help you get more clients, this “no fluff” article may help.

Even though email is generally more of a “one-way” channel than social media, it’s still considered to be a more intimate way of keeping in touch.

The reason: We need to be invited into someone’s inbox, or it’s spam. End of story.

This sounds great, until the time comes to actually sit down and write an email.

This is where I can help.

What I’ll be covering:

Knowing Your Niche and Ideal Client
Answering Questions and Dispelling Myths
Setting Up a Repeatable Structure
The Starbucks Test
Micro Stories
Point of View
Repurposing Your Content
Capturing Random Inspiration
Using Promotions in Your Newsletter
AI Prompts
Consistency
Make It Easy On Yourself: 3 Tips
Mindset: Overcoming Fear

Let’s get started right away!

1. Knowing your Niche and Ideal Client

This is where you must start. Ignoring this step pretty much guarantees writer’s block due to lack of clarity.

An email newsletter isn’t a personal journal, and it’s not just another task to hand completely over to AI.

It’s about building a relationship with your subscribers. And just like with any other relationship, if you are not sure what makes a good match yet, how can you possibly know what to focus on, or what to write when you sit down and think:  “Ok, time to write an email to my audience, and I’m STUCK.”

Make it easy on yourself and start with this step.  Make it even easier and even more fun by starting with this branding archetype quiz.

2. Answering questions and dispelling myths

Once you really are SUPER clear about your niche and ideal client, you can start gathering a list of database of common questions they ask, things they complain about, and myths they may be subscribing to that can undermine their desire to get from their own “point A” to “point B.”   

Examples might be:

• 7 common mistakes people make when..
• 9 myths about..
• How to avoid..

You can even use ChatGPT or other AI tools to help you with this (more on this in a moment)

I DO recommend doing your research on this. Amazon book reviews, Facebook Groups, and Pinterest are great places to do some sleuthing.  Note: This may take some time but just get started. I promise it’s worth it!

3. Structure: Setting Up A Repeatable System

I firmly believe that creativity is difficult without some kind of structure to define it and contain it, and to automate it.

Without this structure, you’ll be expending more energy and wasting a lot of time.

I’m not talking about the freedom to draw outside the lines. I’m all for those inspired moments. 

In fact, rather than fight against the way creativity works, I almost always prefer to take advantage of these moments and get everything I can out of my head and onto a screen (or paper) so that I can draw on this “bank of ideas” later.

Since I’m not a professional writer, I have the luxury of focusing on other tasks when I’m not feeling blessed by the writing inspiration fairy.

Creativity is a wonderful thing, and it works at its own pace.

However..

Content marketing needs to happen consistently. For example, if your audience knows that they’ll get a new podcast or email from you on Thursdays, you want to keep this up and not just post when you feel like it, sporadically, otherwise you’ll be forgotten. Seriously.

This does NOT mean you need to sit down and make yourself write when you don’t feel like it (If you are not a professional writer)

It DOES mean having scheduled times to either write, record, schedule, or create the containers and structure for your content.

If this means that every Tuesday or the first Tuesday of each month (or even quarter) you schedule time to get on a roll with writing and formatting blogs, recording podcasts, and writing and scheduling emails, stick to it.

I teach this in depth in the Future Proof Your Business. Academy.

A large part of automating your business has nothing to do with technology, but how well you make use of habits, templates, and repeatable processes. You can find out more about these concepts in this article. 

4. The Starbucks Test: Conversational emails are more engaging

One way to overcome writer’s block is just to imagine yourself having a conversation with a friend over coffee. When speaking this way, you come across as simply and authentically wanting to share what you do. 

Many, including myself, recommend that the vast majority of your emails have this tone.

The concept of the “Starbucks test” came about (I can’t take credit for it, besides, I live in an area of Europe that has no Starbucks.. we do cafes, with ceramic cups.. but it’s the same general idea.)

How it works: Pretend that you are about to meet a friend for coffee in the place pictured above. You are just shooting the shit, talking about life in general, maybe telling a story, supporting each other, maybe asking for or giving advice. Even when the goal is to cut to the chase, the tone will be conversational, not formal.

This is hard to fake or copy, and AI can’t do all of this for you.

Some of the best copy I’ve seen flows naturally and sounds like it comes from a human with a real personality. What often gets in the way of this is overthinking and trying to “sound” a certain way.

Remember, you aren’t writing a cover letter for a job interview or emailing a prospective employer or trying to close a deal. In fact, this tone, for this purpose, is quite stiff, awkward, suspect, and generally off-putting.

That’s why I started out with the Starbucks test.

Start with this. Actually speaking into a microphone or (with permission) recording a conversation with a friend about what you do may also be helpful. 

The next step is a great way to continue..

5. Micro Stories: A great way to begin your email  

One way to not just SOUND natural, but to feel and BE natural and authentic, is to tell a micro story.

I don’t do this because it’s a “thing” but because people tend to remember stories better than facts or bullet points. 22x more, in fact. That’s a LOT!

It’s ok to tell a story about yourself if it’s something your audience can relate to. We all have difficult weeks, insights, and favorite moments to share, such as a nice relaxing day in the garden or going on a hike with the dogs.

It’s not only OK.. but encouraged.

Share these things. Share those moments behind the scenes of your brand.

Depending on your brand archetype, this could also include your direct experience with cool new books, podcasts, or other resources, geek insights, adventures, jokes, food porn, travels, uplifting stories, moments of truth, case studies, or tales of badassery. Or a unique combination.

Being that my brand is a combination of a nerdy Sage and the Explorer, it’s almost effortless for me to share nerdery, my idea of time and location independence, and tales of my travels and residence in SE Europe.

What I don’t do well is trying to be “cool” on camera. I’m also (gasp) not really a classic “people person.” I prefer sharing ideas with like-minded people. I’m ok at storytelling and it’s something I want to cultivate. 

None of this is supposed to be “right” or “wrong.” When you tell your own story, the way you go about it will be as unique as you are. You also DO want to share your opinion, or point of view. (More on this in a moment)

Remember, your newsletters are not corporate emails.  Even corporations today don’t want to sound “corporate” when communicating with their audience.

Giving to your community (your list) isn’t about delivering info that anyone can find anywhere online, so don’t completely rely on AI. (More on this in a moment)

That would be like telling a personal assistant to write everything for you, instead of sharing your own point of view.

Your own experience, expertise, story, and voice can be woven in to make those emails much more intriguing.

We tend to think that people don’t care about this.. But they do. 

 I6. Point of View: Don’t be afraid to express your opinion 

One of the foundations of marketing is developing your unique point of view. I’m talking about that thing that you may have been told others don’t want to hear: Your OPINION.

Toss the notion that you need to water down your point of view. This is BS.

By this I don’t mean purposefully looking for hot button issues and taking an abrasive stance just for the sake of stirring things up. What I mean is that if you present yourself as someone who just wants to make sure nobody gets offended and everyone is happy, you’re not going to be an interesting brand, and nobody is going to get excited about what you do.

I have a strong POV about email, for example, and about social media. I think that too many people focus on social media and creating content that disappears within hours, and that this strategy is a waste of time. Social media, in my opinion, is an important tool, but the way it’s being used (and hyped in some ways) isn’t sustainable for most of us.

Don’t get me started on dancing on TikTok, for example.

Recently I shared a post on Facebook featuring a short video of woman doing the “Dance and Point.” I said something nice about how this tactic probably works for her ideal clients, and then stated a clear and concise POV: It’s not for me.

(I’m also in the good company of quite a few marketing experts as well)

It was a strategic comment, not a random one, that positions me as someone who obviously doesn’t focus on this tactic. For the record, I’m not against short form video at all.

One woman commented: “Do what makes you happy.” This is a valid comment. However, I was wondering in the back of my mind if I offended her, more from a perspective of curiosity than worrying about if I did or not.

On the other hand, this post got a lot of likes and positive comments from my ideal clients who are also tired of this trend. They don’t want to be pressured into doing it, and are likely glad that someone spoke up about it. They were not just saying “Do what makes you happy.” They were saying “Hell, no” or “If I did that I would feel ridiculous, and my audience would think I lost my mind.”

BOTH are ok! But I want to attract the kinds of people who are thinking “There HAS to be a better way than this.” (And I DO offer an alternative)

And THIS, my friend, is why we get to know our ideal clients and what they are REALLY thinking, not just what we think they SHOULD be thinking.

I spent a few hours getting inside the head of my ideal client, and that’s exactly why I wrote that post.

I also recommend a good rant from time to time. If you are reading this, I’m going to assume that you know how to do this artfully. I’m also going to invite you to do this intentionally and strategically.

When we hold back for fear of “rocking the boat,” what we are actually doing is watering down our message, and this is a loss for those who maybe want or need to hear it.

As long as it’s not a personal attack on anyone or does any harm, and you know what the hell you are talking about. (I assume you do) Again, this is an art. And at a certain stage of our evolution as individuals and entrepreneurs, come on.. we’re “allowed” to take a stand.

What if nobody did this? Can you imagine a world like this? It’s not one I would want to live in.

POV marketing is often underused, and I can see how content might become even more bland and homogenized with the advent of AI.. or at least at FIRST. (Again I’m not against AI.. we’ll get to that in just a moment)

Then people will start to notice what’s missing.

Smart entrepreneurs will not only incorporate their POV, but continue to cultivate it. This is one excellent way to stand out from the crowd, not to get temporary attention, but to become known for something you’re actually proud of.

For more on this topic, I really like Tad Hargrave’s (Marketing for Hippies) approach to POV marketing. 

7. Repurposing your content isn’t cheating!

This concept fits in nicely with my POV about social media and not spending hours on creating content that either nobody sees, doesn’t last long, is done with hopes of “going viral,” or takes hours and hours to produce. This tactic commonly leads to burnout and not having the time to do all the other things we need to do as entrepreneurs.

Back to email.

It’s easy to begin to think that every single email needs to be an original masterpiece, and that this is something we have to sit down and do once a week.

If you are thinking that you don’t have time for that, I would agree.

Consider this as well.. Some people love to write, and can’t wait to sit down with a cup of tea or glass of wine to do just that. Others do not, and there’s nothing wrong with that.

Your emails can be repurposed from:

• Video transcripts or podcast show notes
• A longer blog. You can break it down into chunks and focus on one of them in your email. You can even create a little suspense by ending with: “Stay tuned.. I’m going to talk more about _____next week!
• Older emails. I go through a complete cycle of content each year. This month’s focus is on email. A lot of the content is the same (which is nice, in my industry everything changes SO fast) so I can share it again.
• An excerpt, chapter, sample, or key concept you talk about with your clients or in an online course or membership. I like to say:
  “I teach this in depth in my Future Proof Academy.” or something to this effect.
• Case Studies. If you are already documenting case studies, why not use them in your emails?
• Testimonials and reviews: Take one positive thing someone has said about you and create a short email around it, relating it back to your audience.
• A social media post. Ever started to write a novel in your Facebook group? Download all your Facebook info.. You may find a goldmine there.

Sometimes my best ideas flow from a single Facebook post or live video stream. If this is you, it makes sense to repurpose them for emails.

A few things to keep in mind:

1. Repurposing does NOT mean simply copying and pasting old or existing content.

2. If someone is subscribed to your list, they are giving you permission to enter their inbox. Because of this, it makes sense to go a little further and give a little more than you would to just a social media follower who isn’t really that invested in hearing from you.

It is possible to do this without creating a lot more work for yourself via repurposing, while still delivering value, such as exclusive content, tips, invitations, special offers, discounts, etc.

3. You’ll want to keep your old content organized so you can easily retrieve it. You’ll also need to do some planning, because when this is done randomly it gets chaotic and time-consuming, much in the way working in a cluttered environment would be. (I’m a slide deck and spreadsheet nerd, but you can use whatever organizational system works for you)

Yes, I know this sounds like MORE work instead of less, but a little bit of front-end work will make your life a lot easier down the road, and save you a LOT of time. 

I also don’t want to be flippant about this and just leave you hanging and thinking “Great, now how do I do that?” 

Yes, I do teach this in my courses and in particular I focus on this topic around the end of the summer. 

That’s because this is a good time to focus on how to make life and business a little “lighter” by getting rid of what we don’t need, prioritizing, and also making room for the new, just in time for fall. 

A few quick tips:

1. Don’t just jot stuff down in a notebook. As your content library grows, and if you hire a team, you’ll want a better way to document processes and share them. 

I have a slide deck with every step and every screenshot.. it’s a checklist that takes me from blog concept to Pinterest pin to email copy.  Because even I am not gonna remember all that shit, nor do I want to, when all I want to do is make some coffee and follow a checklist. 

2. Spreadsheets sound boring, but start keeping track of email newsletters, including the date, subject line, main purpose, and content of the email. (Later you’ll want to keep track of keywords, cta, and other data, such as click through rates)

3. Start naming your files very specifically. You don’t want to be hunting for a files with vague titles like “spring workshop” or “blog posts” or anything that you, 3 years from now, will likely be confused by. Be very specific and think like a librarian with naming conventions: 

Summer 2023 Workshop: How to Organize Your Email Marketing System Slide deck Student Version. 

Also don’t forget to toss old, redundant files or file them in a different folder. 

This is a start.. because the best time to get into good habits with organizing content when there still isn’t a lot of it is now. 

8. Random inspiration for your email newsletter: The Idea Bucket

Some call this an idea bank. The thing is, random ideas will strike at times when you are unable to turn them into anything. Quickly put your ideas in a place where you can easily return to them later.

I like using Trello cards for this. Others may prefer a spreadsheet, or a simple document, or even a voice recording. Get in the habit of having one centralized “Idea bucket.”

Inspiration can come from anywhere. 

Do you have a favorite podcast you like to listen to?

A TV show?

Books from your favorite author? A blog?

Do you go on Pinterest to find new recipes and craft ideas?

Ideas often happen not just from without, but from within.

Some of my best ideas come in the early morning hours when I’m still in a dream state.

Or sometimes I’m walking the dogs or doing some other chores, and an idea hits me.

This ideas may be dismissed, because they seem mundane. However, life is about learning, and there are so many parallels and connections between our everyday lives and our businesses, as entrepreneurs.

Write a list of “conversation openers” or just start typing at the conversation plays in your head. Once again, you can imagine yourself sitting with a friend over coffee. You might say, in real life, “I never thought I would say this, but…” or “I had this interesting thought today about_______.  or maybe a question, like “Do you ever feel that __________?

For me, what works is imagining myself in this scenario, and just let the “conversational” words flow.

Put them in your “Idea Bucket.”

You may be surprised to discover that within days, you may have enough topics for the next 90 days or even an entire year!

Your own life experiences are also PERFECT material for your emails. Pay attention to those moments and thoughts.

9. Promotions in your newsletter

Eventually, after building a relationship, yes, then of COURSE you want to present your offer.

There’s no hard and fast rule about how often to promote and what to include in promotional emails. This will be determined by your current offerings, your niche, ideal client, brand voice, the seasonality or cycles of your business, and your own personal preferences.

Most of the time, this is about giving a lot of value. 

However…

I will say again that it’s kind of weird to never make an offer. It even looks a little suspect. Of course you are going to have offerings that might be a perfect next step for your audience, and this is done respectfully, strategically, and in a way that feels good for YOU.

This is also where the Starbucks Test comes in handy. Likely, if we wanted to offer something to a friend or group of friends over coffee, we would confidently say: “I’ve got this thing that I think would be perfect for you and solve _________ that you mentioned earlier. It seems like the next logical step. I can tell you more, if you like.”

Except for the fact that you are speaking to more than one person, you can present your offer pretty much like this.

Heck, this can even be what your conversational tone sounds like in an email. When I read some of the messages from  marketing experts I admire, it’s usually very low key and conversational. Not in an apologetic way, but in a confident “I want to tell you what I have, then you can decide if it’s something you want.” That’s it.

Others have a different brand voice. I’m a bit of a nerd. Others are great storytellers. Some like to push the boundaries of convention. Do what works for YOU.

However, don’t be shy about making it EASY to buy. If links or buttons are hard to find for those who want to buy, it’s annoying for them to have to jump through hoops.

This IS a good time to ask for an action, and DO be direct about it: Buy Now, Learn More, etc. 

And what about UNsubscribes? These will happen. It’s normal in the world of marketing. Besides, if someone subscribes just for the freebies but never, ever plans on doing anything more, it’s better to let them go since they will end up costing you anyway, because we’re paying for the size of our list (getting rid of the dead weight is a good idea from time to time) and lack of engagement has a negative effect on deliverability rates.

In the end it comes down to this:

If it lands in the “sweet spot” you’re good, and yes, people who are outside this sweet spot may unsubscribe. Let them.. it’s healthy for everyone, and for your business.

10. AI Prompts: No more writer’s block

Many today seem to be loving AI to help them create content, and I’m one of them.

I’ve been meaning to write a blog exclusively about how to use prompts to do everything from creating content to code to ways to streamline workflow. For now, I’m going to focus on writing emails

I admit, I tend to avoid writing emails. Even though they tend to be more conversational in nature, it always feels like a big project, especially if I don’t batch and schedule.

One way to get past this is to get some momentum going, with a little help from AI.

You can use ChatGPT or a subscription to a tool like Jasper.

Many email marketing services, like Active Campaign, also have a built-in AI tool, which I think is ok, but at the moment I still mostly use ChatGPT as my “one stop” content generation assistant.

You can experiment with different options to see what works for you, and your workflow.

Remember, the more specific the prompt, the better the result.

It’s much like asking a personal assistant to help you write it. You wouldn’t ask them to read your mind. (Although sadly, some bosses actually do)

How the heck can we ask it to write something effective, if we don’t even have the right information to prompt it? Yep, this usually means going back to step 1: Nailing your niche, ideal client, message, voice, and story.

This is the reason I don’t BEGIN with AI, and I didn’t lead with the topic of AI in this blog.

I believe in starting with our own experiences, stories, and ideas first, and THEN using AI to develop those ideas further. From there, we can edit and make it our own. 

Here’s a list of prompts that I recently used for my own business, which I hope may be helpful for yours: 

ROLE: Marketing strategist who helps service-based entrepreneurs. My ideal client is a service-based solo entrepreneur who has an intermediate knowledge of marketing and has some basic skills using ChatGPT to create content. She’s overwhelmed.

She’s also a GenXer who understands technology, but wants it to work FOR her. She doesn’t want to be a slave to technology and she doesn’t want to spend a lot of time on social media.

Give me 5 ideas to write about in my newsletter about email marketing and how it can help service-based entrepreneurs get more clients.

I wanted something more specific, so I added:

Give me 5 ideas to write about in my newsletter about how to grow an email list.

Avoid ideas geared towards absolute beginners or that are very advanced.  Avoid using corporate jargon.  

The results I got were a good start, but needed some editing.

The SEGUE

Remember when I talked about writing a story to begin your email? 

Well, what comes next, you might be wondering? How do I relate my story to the actual message I want to get across, or the gifts or insights I want to share? Great question!

Sometimes I get stuck on how to make it relate to the main message and the Call to Action. So let’s play with it..

The prompt:

Write a short story for my newsletter about my recent move across town with the dogs (story here). Relate it to how you can be proactive about stressful times in your life so that your business can still run without you there, 24/7. Write it to [idea client avatar] in a warm, authoritative tone of voice.

Result: It totally made up its own “moving with your dogs” story that was way off.. But to be fair, I didn’t tell it that the trip involved moving 2 huge doghouses and riding in the back of a truck with 3 dogs who had no idea what was happening.

Which is why we need to be very specific.

To be fair, it did a fairly good job with the segue.

I’m still working on getting ChatGPT to speak like I naturally would. As a Sage/Explorer brand archetype that sometimes adds a bit of dry wit, I find that AI tends to generated a lot of corny, cheesy humor that I do see a lot of female entrepreneurs use, but is way off brand for me.

Now for the next prompt:

Add a Call to Action at the bottom for my Future Proof Your PracticeToolkit, which is.. (add more details)

It actually did a pretty good job with this one. I’ll still need to tweak it, but not by much.

This next prompt is SUPER important for email marketing:  

Write a subject line and preheader for my email message. It should be intriguing enough to get someone to notice it in their inbox and choose to open it to learn more about what is inside. The subject line and preheader should each be no longer than 50 characters. The email is: [add your email content]

Notice how I used AI. It wasn’t random. I included a microstory, a CTA, and other information that will help AI help me come up with avenues I may not have thought of. 

I can also ask it to write a short introductory paragraph:

Write a short introductory paragraph for my email about email marketing that will hook my readers so they keep reading. Write it to [add target audience] in a [add tone of voice] tone of voice. The paragraph should introduce this email: [add your email content]

So far, I’ve got at LEAST a month’s worth of emails I can send for this month’s theme: Email. Next month I’ll do the same with the topic of time, prioritization, “productivity” and quality of life, and in the fall I’ll do the same with marketing strategies and funnels.

I’m sure there’s a LOT more I can do with AI and train it to really dial in what I need from it. I’m still at the beginning stages of all of this.

There may seem to be a lot of work when you first start out, but after the first few times this work pays off and it saves a ton of time.

11. Consistency in your email marketing

It’s also important to be consistent about your message. Once a week is a good starting point.  It’s like a first date: It’s not about trying SO hard to impress that people won’t recognize you without a ton of makeup and nice clothes and being “on” all the time.

It’s about showing them some of your best stuff, but in an approachable, conversational manner, like a letter to a friend, or a meeting over coffee.  More great things will flow if they hang out with you, trust that.

And don’t promise to be there, and then not show up! This is almost as inconsiderate as spam.

Hopefully this blog showed you some ways to make the entire process a lot easier.

One of my favorite ways to remain consistent is by batching and scheduling. (See #3)

You can create a month or more of emails in advance. Because realistically, ideas don’t flow in a steady stream on a daily basis. There are plenty of days when I don’t feel inspired to write at ALL, and those days are every bit as productive as the days I set aside for getting into a writing “flow state.”

Of course, you’ll want to get more and more strategic about the promotions your emails lead up to, but that’s something else I teach in depth in some of my courses and in my coaching.

For now, just get started.. and keep going. Not everything is going to be refined all at once, and that’s ok!

12. How to make it even EASIER on yourself

I’ve got a few more tips for you:

1. You CAN borrow ideas from other emails you receive. Of course you don’t want to copy word for word.. but a lot of opening phrases aren’t copyrighted any more than a conversational sentence would be.  We all get inspired from each other, and I don’t think this makes us less original, especially as we gain more experience and really develop our own POV.

Of course, you’ll need to have a way to store and retrieve emails or the messages you want to keep for later inspiration.. from a few select brands or people you admire. (Keep this to a minimum or it will become cumbersome)

2. Your emails don’t have to be long. Some even type a short and sweet note, with a link to a blog or podcast or video that does the talking.

In other words, It’s not always the email itself that is usually offering entertainment, education, or enlightenment, but what is IN the email itself. A link to something nice and juicy. .

Think of it as the intersection where your great content.. and what your ideal client or patient wants to hear about.. meet.

3. You can start documenting everything you do. NOW is the best time to start streamlining your workflows and systems so that you don’t have to sit down every day and waste mental energy trying to produce content from scratch. When you have a document or a checklist to follow, you’ll thank yourself later.

This is something I teach in more detail in the Future Proof Your Practice Academy.

13. Mindset

The Take-Home

The hardest part about email marketing is usually getting started.  (This blog will help you if you are still putting it off) 

The next hardest part is remaining consistent, and usually the problem with this comes from what may appear to be writer’s block, but is often a lack of clarity about our niche, ideal client, mission, and story.

This is something I also teach in depth, but here’s a resource for you to help you get you started on REALLY nailing it when it comes to your brand.