#01: Thanks, Dad

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Reach deep inside and ask yourself:

• What's happening behind-the-scenes in my business that my readers could find interesting?

Hints (only if you need 'em)

1. You have at least one interesting thing happening in your business right now — you've just started or re-committed to sending an email each day — but there are probably more

2. Position whatever you choose to write about as benefiting your reader ("I'll give you a behind-the-scenes peek")

3. Position whatever you choose to write about so it builds up your status ("I have lots of valuable stuff to share with you"), rather than hurts your status ("Right now, I'm unsuccessfully looking for work")

#02: You had one job

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

How might you address this common insecurity:

• "Other people are doing much better than I am, even those who started after me."

Hints (only if you need 'em):

1. Think of personal experiences where you felt insecure about this, and think of the advice you'd give yourself then

2. Wrap up your advice in a personal anecdote, an analogy, a pop culture reference, etc.

3. Even if you have to tell people the hard truth, end on an inspiring or positive note

#03: Relationship status

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Inhale, exhale, and ask yourself:

• What small bit of industry news can I break for my reader today?

Hints (only if you need 'em):

1. Think (or look) back to email threads, social media conversations, questions you've seen in the past few days to one week.

2. What new patterns or trends or occurrences can you spot, which haven't already been discussed to death?

3. It's ok if what you spot is small, borderline trivial, as long as it's new.

#04: See you later

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your puzzle today can be easy if you let it, and it's to answer:

• What real-world scene have I've witnessed lately that could interest my readers or make them smile?

Hints (only if you need 'em):

1. Think of today, yesterday, or at most, the past two days. You will have at least a dozen possible answers if you only sit for a moment and allow them to surface from memory.

2. The key is "real-world scene," not something you read online, and not something from a book.

3. If it made you smile or say, "Hmm," there's a good chance it will make your readers do the same.

4. Think about things that happened in your family, on the street, at the park, at the office. Think of people, animals, or nature.

5. Tie in the scene or observation as best you can to the general topic of your newsletter and your offer today, but don't worry about it too much. Call out the fact it doesn't tie in perfectly, but say it's your newsletter, and you wanted to write about it.

#05: Love/hate

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Ask yourself:

• What movie character, scene, or reference can I base today's email around?

Hints (only if you need 'em):

1. It can be a movie you saw recently, or one of your all-time favorites.

2. Think small. No need to retell the whole movie. Focus on one specific scene, line, or funny/interesting/unique aspect of the movie.

3. If your movie is not mainstream, "sell" it to your audience, and give them context so they can ride along even if they haven't seen it.

4. Work yourself into the email — your reactions, your background, your attitudes. Ultimately this email is about you, not about a movie.

#06: Am I indecisive or not?

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The grass is not always greener on the other side, so ask yourself:

• What cliche can I challenge, negate, or turn inside out for my reader today?

Hints (only if you need 'em):

1. It can be a cliche in your industry. For example, with marketing:

• The fortune is in the follow-up
• The headline is 80% of the ad
• Long copy beats short copy

2. It can be a general cliche:

• If it ain't broke, don't fix it
• Don't put all your eggs in one basket
• Practice makes perfect

3. Choose something you can congruently argue against, and make your point serve your reader's interest.

#07: Bedtime story

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

A simple prompt to help your readers identify with you. Ask yourself:

• What personal story can I share that features... my mom?​

Hints (only if you need 'em):

1. If you're having trouble coming up with a story idea, it's because you're trying to be creative and critical at the same time.

The solution is to come up with 10 possible ideas. Don't worry about making them any good or fleshing them out. Simply write 10 possible story ideas, and you'll have multiple that are good enough to use.

2. Make the story as trivial or profound as you want.

3. No need to share anything that you feel uncomfortable sharing.

4. No need to tell a huge, 3-volume, family saga. A single snapshot is perfectly good.

5. As usual, tell your story, and then connect it to a conclusion or point that the reader can benefit from or be inspired by.

#08: No autographs

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Look over the testimonials you've gotten, and ask yourself:

• "How can I extract a lesson from a testimonial that I've gotten, which will be valuable to my reader?"​

Hints (only if you need 'em):

1. Ideally, share a testimonial that says something great about you or what you're offering... and that you also can extract some lesson or insight or joke from.

2. The testimonial could be for you personally, for your emails/content, or for your offer.

3. What if you don't have ANY testimonials? You still have lots of options. Here are a few:

• Use some other element of your subscriber list as social proof (list size, engagement rates, the profile of the people who are on it, etc.)
• Use a testimonial for the solution/approach you are promoting, rather than yourself or your specific offer (eg. a testimonial for daily emails as a practice, rather than for Daily Email Habit)
• Use today's email to ask for a testimonial — be forthright, and ask for a favor

#09: Risk takers

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

How might you challenge the following assumption in your readers:

• "There's some fundamental flaw with me or my business."​

Hints (only if you need 'em):

1. You can challenge this assumption directly, as it manifests in your readers' heads.

For example, if I want people to email their list daily, then one specific "fundamental flaw" that gets in the way is, "The people on my list are just not buyers."

2. You can also challenge this assumption indirectly by challenging the meta-assumption, "My situation is unique."

3. Whenever you're challenging assumptions that people hold dear, it makes sense to use an analogy, third-person cautionary tale, or your own personal story to make your point... rather than judging, accusing, or haranguing your reader.

#10: Barroom brawls

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

You don't always have something to say. Today, ask yourself:

• What idea or story have I read in a blog post/newsletter over past week or two, which could be interesting to my readers?​

Hints (only if you need 'em):

1. You'll have an easier time if you restrict yourself to blogs/newsletters that are are relevant to your readers, rather than your own out-of-left-field obsession.

2. That said, if you find something interesting... there's a good chance your readers will find it interesting, too. Particularly if you explain why you find it interesting.

3. As usual, inject yourself, your attitudes, and your experiences into this whole topic. Ultimately, this is your newsletter, and it's about you, even when you're seemingly just curating others' ideas.

#11: Don't forget to subscribe

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Today's puzzle theme is "inspiration." Ask yourself:

• How can I recast what my reader is doing into a fight for the greater good?​

Hints (only if you need 'em):

1. We're all forced to do lots of mundane things every day. This is your opportunity to remind or even enlighten your reader — there is a greater good to it all, beyond simple self-interest.

2. Possible greater goods that your reader might actually be fighting for: freedom, creativity, helping the needy and deserving, justice, preserving the established moral order, beauty, etc.

3. You have lots of tools to get your point across — a case study, a logical argument, a list of arguments (a listicle email), a pop culture illustration, ...

#12: Puzzle

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Readers ask the darnedest things. So ask yourself:

• Which reader question can I answer today, in a way that ties into my offer?​

Hints (only if you need 'em):

1. If you don't have any reader questions, you can always pull a question from a Facebook group or a subreddit made up of people in your niche. And in your email, simply say, "Here's a quirky question I came upon today..."

2. You can use your email to directly solicit more questions.

3. You are not simply an advice column writer. Use this email as 1) an opportunity to flex a bit (your knowledge, your audience, the fact people come to you with questions) and 2) to naturally tie into your offer.

#13: Chaos therapy

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Today's puzzle is about calling some of your readers out. Ask yourself:

• What's an obsessive, unconstructive behavior that a good number of my readers engage in?​

Hints (only if you need 'em):

1. You can find such behaviors referenced between the lines in interactions you've had with your audience... or in yourself if you are a part of your own market... or by checking forums, subreddits, or Facebook groups.

2. For bonus points, give this behavior a funny or mocking name (eg. constant checking for unsubscribes or new subscribers => "daily email nail biting").

3. As usual, it's best if you don't make your reader feel directly attacked. To avoid this, you can use yourself as case study, or a third-person cautionary tale, or an analogy.

4. Position your approach or your offer as a more constructive alternative to what your reader is now doing.

#14: Big brain

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Today is your opportunity to genuinely teach. Ask yourself:

• What's an actual, practical tip I've learned lately in my domain that I can share with my readers?​

Hints (only if you need 'em):

1. Think back to recent stuff that's made you say, "Oh that's a good idea." It can come from your personal experience... a newsletter... a book... a podcast... a conversation you've had.

2. If you have proprietary info that you sell, or plan to sell, keep it behind the paywall. This is an invitation to give your reader something small, valuable, and surprising, not a call to cannibalize your sales.

3. If you cannot think of any recent tip that you've learned, then think of something evergreen. And when you present it, frame it by saying something like, "Yes, you've probably heard this before, but it's been so valuable to me that it bears repeating, and repeating often..."

4. Teaching is good and all, but don't forget to make your email fun or lighthearted, by including a story, an analogy, or just a little bit of wordplay.

#15: Heartbreak

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all fail much more than we succeed. So ask yourself:

• What's a personal story of disappointment that I can share with my readers?​

Hints (only if you need 'em):

1. Your story of disappointment can be something new, or something old. It can be a big disappointment, or a trivial one.

2. One way or another, end on a positive, determined note. Ultimately, you are a resilient, resourceful person, and you want resilient, resourceful people on your email list.

3. If you're having trouble coming up with this personal story, do the usual. Come up with 10 personal instances of disappointment, without judging them based on whether or not they are suitable for an email. At least 2-3 that will be a good fit.

#16: She must be very self-actualized

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Ultimately, people decide to trust you, bond with you, buy from you, based on shared values. So ask yourself:

• What's one thing I believe about time, which I can share with my audience today?​

Hints (only if you need 'em):

1. Your philosophy about anything — time, money, work — is likely to consist of various beliefs and values. For this email, pick just one.

2. Don't worry about pandering to your audience, and saying something they will agree with. Say what you really believe, and let the right people come to you.

3. If you're having trouble finding even one belief you hold on a topic (such as time), it's because you are being critical while trying to be creative. Come up with 10 possible beliefs, then choose one of them.

4. Wrap up this core belief in some kind of infotainment — a story, a reader question, a joke, a funny thing that happened on the way to the dentist.

#17: For sale

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

From time to time, it's good to stop the infotainment and just sell. So ask yourself:

• What's one unique aspect of the deliverables in my offer that I can highlight today?​

Hints (only if you need 'em):

1. Use this email to remind people of your offer. Be explicit and spell out what it is, who it's for, who it's not for, what's inside.

2. In addition, focus on one aspect of the actual product/service/deliverables buyers get for their money. Explain what it is, why it's unique, and why it's good for the buyer.

3. It's fine to sneak in some humor, a testimonial, an analogy, etc. But don't bury the lead — today's email is about selling what you've got.

#18: Wouldiwas

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your best customers are readers. So ask yourself:

• What's a lesson from a book I'm reading or have read recently that I can share in my email today?​

Hints (only if you need 'em):

1. Pick something that caught your attention then, or that sticks with you now, even after some time has passed.

2. Work yourself into the email. Why are you reading this book? What do you think of it? What else does it make you think of? Or simply, where were you when you read the lesson you are now sharing?

3. If you have not read a book recently... start reading. It gives you new ideas, makes you better at writing, and immediately separates you from others who are only commenting on tweets and the day's news.

#19: Either is fine

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

It's Friday the 13th today, and that currency matters. So ask yourself:

• Which current event can I tie into my email today?​

Hints (only if you need 'em):

1. If you read the news, you can talk about something that's actually on your mind, that has shocked you, that you have opinions about.

2. If you don't read the news, do what I do: go to sites like theguardian.com, nypost.com, news.ycombinator.com, and see what catches your attention.

A few I had to click on just now (feel free to use any of these):

• ​Certain names make ChatGPT grind to a halt, and we know why​
• ​Girl, 11, rescued off Italian coast after three days clinging to tyre tubes​
• ​New Jersey drone cluster sightings prompt call for ‘state of emergency’​

3. If you do click on a story like the above, it's worth reading to the end. You will often hit upon a unique detail in the article that sparks the idea for your email.

#20: Inside or outside

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all secretly think we can predict the future. So ask yourself, how you can challenge the following assumption in your reader's mind:

• "It didn't work before, and so it won't work this time either"​

Hints (only if you need 'em):

1. The "it" in this assumption is what you are asking your reader to do — write daily emails, lose weight, prospect for new clients.

2. You can also challenge this assumption indirectly, by challenging the meta-assumption, "I can tell the future!"

3. Whenever you're challenging assumptions that people hold dear, it makes sense to use an analogy, third-person cautionary tale, or your own personal story to make your point... rather than judging, accusing, or haranguing your reader.

#21: Something is very wrong

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We're more likely to buy something if we feel it's customized to us. Even if it just feels like that. So ask yourself:

• What tool are a good number of my readers using, which I can call out in my email?​

Hints (only if you need 'em):

1. A tool can be something physical (eg. a model of guitar amplifier) or it can be virtual (eg. a brand of email software, like ConvertKit).

2. Call this tool out, preferably in your subject line, to draw in people who are using it.

3. If you can give a coherent reason why your offer is particularly relevant to users of that tool, you will double or triple or quintuple your odds of a sale.

#22: I hope this finds you well

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We bond over common frustrations, so ask yourself:

• What recent business frustration or failure can I share with my readers?​

Hints (only if you need 'em):

1. Even a small, trivial frustration can be exaggerated or dramatized to become funny, interesting, or relatable.

2. If you're not running a business, then share a frustration or failure around running your newsletter.

3. Don't leave people feeling riled up with nowhere to go — give them a way out via your offer.

#23: No, try again

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all want to hear about people, particularly people we know about. So ask yourself:

• Who is somebody well-known in my industry who has fallen or disappeared, and what lesson can I draw from that?​

Hints (only if you need 'em):

1. If you're having trouble of thinking of people in your industry, try "chunking up" and broadening what you think you do:

• email marketing => marketing
• marketing => business
• business => negotiation, communication, problem-solving

2. An alternative is to "chunk sideways," and focus on a sister industry:

• email marketing => newsletter businesses
• newsletter businesses => YouTube creators
• YouTube creators => TV stations or channels

3. If you don't want to get too polarizing, don't name the person, or give them an alias. But you're likely to get the best results if you throw somebody under the bus without remorse.

#24: Notice

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

All of us have to work, somehow, somewhere. That's an opportunity to connect with your readers. So ask yourself:

• What's a personal story I can share about working from home/from the office?​

Hints (only if you need 'em):

1. Choose one: working from home, or working from the office, whichever gets you more emotionally riled up right now.

2. Your "story" can be a simple snapshot, rather than a there-and-back-again hero's journey. In other words, your story can be a single-panel comic, rather than a three-panel comic, or a full-blown comic book.

#25: It's now Adam West

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Sometimes it's good to force yourself to mix in a new format. So ask yourself:

• How can I write today's email in the form of a pre-flight safety demonstration video?​

Hints (only if you need 'em):

1. If you have never been on a plane, or if you've never paid attention to one of those videos, check out this quick breakdown of the format.

2. You can focus your email on explaining the safety features of your newsletter as a whole... or the emergency exits of one specific offer you make.

3. Don't stress about the unlikely event of a water landing. Just write your email in this format, send it out, and see what happens.

#26: Please help

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Sometimes you gotta take the focus off yourself and onto your readers. So ask yourself:

• How can I call out and help readers who face the problem, "What's worked for me before is not working any longer"?​

Hints (only if you need 'em):

1. "What's worked before" will depend on your audience. It could be a way of making money... practicing or progressing in their profession or area of interest... dealing with people they have to deal with.

2. Ideally, name this problem and call it out in your subject line, to telegraph to the right segment what your email is about.

3. Calling out a symptom ("Lost your ability to fly?") rather than a problem ("Kryptonite poisoning?") can be even more powerful.

4. Pick a problem you can really solve with your offer.

#27: A perfect date

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

People who read your emails want to trust you beyond just your industry-specific expertise. So ask yourself:

• What reader question can I answer today, which has nothing to do with my products or offers?​

Hints (only if you need 'em):

1. If you have readers reaching out and asking for advice or opinions beyond your strict expertise, use one of those questions.

2. If you don't have any such reader questions, pick something from the AskReddit subreddit, and just say, "I came across an interesting discussion online today..."

3. Resist the temptation to pick a question that's on the usual topic of your newsletter. Use this email as a vehicle to share your ideas, values, or personal story.

#28: Holiday valley

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your copy is secondary to your status. So ask yourself:

• What impressive-sounding invitation has somebody made me recently, which I can talk about to boost my status a little?​

Hints (only if you need 'em):

1. This invitation can be a job offer, an invitation to speak or present, or any kind of opportunity that's not available to everyone.

2. This invitation doesn't have to have turned into reality or have become anything. It's simply enough that somebody brought it up as a possibility.

3. If you cannot think of anything, then start a STATUS file. Whenever any even small status-building thing happens, add it to your STATUS file, and you will never go wanting again.

As for today's email, you can write about how you've been invited inside a private, members-only community of business owners and marketers, called Daily Email House.

#29: The parchment is hairy

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Expose your readers to something new today. Ask yourself:

• What interesting story from a book I've read can I share with my readers?​

Hints (only if you need 'em):

1. The story can come from a fiction book or a nonfiction book.

2. The story can be about your newsletter topic, or you can work to tie it into your topic.

3. You're more likely to think of a story if you think of books you've read recently, say, in 2024.

4. As usual, squeeze yourself into this story, or in front of it, or after it. Share why you read this book, or why you liked it, or why you hated it.

#30: Is there any other kind?

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

If it's good enough for Ogilvy and Bencivenga... you get the idea. So ask yourself:

• What are the reasons why my offer is priced as it is?​

Hints (only if you need 'em):

1. A high price is ok, a low price is ok. What matters is that you explain why your price is what it is.

2. Think of the real reasons first, including nonsensical, thoughtless, or selfish ones. Then think of how those reasons work in your customer's favor.

#31: Merry Christmas

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Today is Christmas, at least according to the new calendar. So ask yourself::

• How can I work Christmas into my email today?​

Hints (only if you need 'em):

1. Yes, today's prompt is that simple. No need to overthink it.

2. If you celebrate Christmas, then you have plenty of stories and memories and experiences you can use. Come up with 10, pick just one.

3. If you don't celebrate Christmas, then you have reasons why you don't celebrate, and what you do instead on today's date.

#32: Exciting future

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

It's the holiday season. Many people are spending it with family — or not. So ask yourself:

• What prediction can I make about the future of family and family relations?​

Hints (only if you need 'em):

1. You don't have to be right.

2. The more certainty you communicate, the more interesting your prediction becomes.

3. The more novel your prediction, the more interesting it is. It can even make sense to take a popular, widely accepted prediction and argue the opposite.

4. Yes, it's ok to make a prediction (or write an email) that has nothing to do with your narrow industry or niche.

#34: Have you seen him?

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Curation is one purpose of a good email newsletter. So ask yourself:

• What interesting blog post/newsletter/magazine article about my industry have I read recently?​

Hints (only if you need 'em):

1. There are lots of yearly roundup posts and emails going around right now. Many have interest insights about what's worked well and what hasn't.

2. Pick one interesting point you want to share from what you've read, rather than three or five.

3. As usual, work yourself and your attitudes, experiences, and quirks into this curation email.

#34: Should have been you

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all compare ourselves to others. So ask yourself how you can address the following question roiling around your reader's head:

• "How are all these idiots, who know less than me and who can't provide as valuable product/service as I can, succeeding so much better than I am?"​

Hints (only if you need 'em):

1. You can ease into this question with a case study, a comment from a reader, an analogy, etc.

2. You can comfort and reassure your reader, or challenge and call your reader to account, or both.

3. It's the end of the year — a good time to talk about making 2025 something better.

#35: Suspicious

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We're still neck deep inside the holiday season. So ask yourself:

• What personal story can I share that involves the holidays?​

Hints (only if you need 'em):

1. It can be something that just happened, or something that happened years ago.

2. It can be profound or trivial.

3. As usual, a "story" in an email doesn't need a beginning, a middle, and an end. Often, a single snapshot will do.

#36: Not easy to explain this to women

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Who's on your list? You want the right people there. So ask yourself:

• What reader question or comment can I lambast today, because it's so contrary to the kind of audience I want?​

Hints (only if you need 'em):

1. You can use a reader question, comment, or even a testimonial.

2. You can be brutal about it or you can be polite. But the less you pull your punches, the more effective your email is likely to be.

3. If you don't have any good questions or comments to lambast, seek them out in subreddits that are relevant to your audience.

#37: Conincidence or conspiracy?

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Last day of the year. A good time to inspire people to make a change. So ask yourself:

• How can I write an email on the theme of, "In 2025, some will get left behind, while others will thrive. Which group will you be in?"

Hints (only if you need 'em):

1. You can explicitly come up with two groups, the haves and the have-nots, and invite your readers to join the right group.

2. You can also be more subtle about it, and make a prediction of what it will take to be successful in 2025.

3. You can get serious or heavy with this... but you don't have to.

4. Coming up with a new name is a good way to get a grip on a vague or unwieldy concept. I call this the "Luggage Handle" principle.

#38: My people

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Happy New Year. And since it's January 1st, ask yourself:

• How can I sum up my 2024, and what plans can I share for 2025?

Hints (only if you need 'em):

1. You can share personal stuff, or business stuff, or both.

2. You don't have to share anything you don't want to.

3. If you really have a LOT of stuff to share, it can make sense to pick just one cool thing for today, and cover the rest in subsequent emails.

#39: Tasteless

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Time to call out a segment of your audience that's particularly ready to buy. Ask yourself:

• What change from black to white, or from white to black, has a segment of my audience experienced lately?

Hints (only if you need 'em):

1. It can be a business change. Made a lot of money, lost a lot of money money, fired somebody, got fired, got hired, got promoted, etc.

2. It can be a personal change. Marriage, divorce, a baby, death in the family, a new towns, hitting a milestone age like 40.

3. Call out your audience, preferably in the subject line.

4. For bonus points, give them a credible reason why your offer is particularly relevant to them, since they've experienced that change recently.

#40: A lot of you have asked

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

People enjoy a peek behind the curtains of the people they follow online. So think about your own newsletter, and ask yourself:

• What am I doing to grow my reach, influence, and audience?

Hints (only if you need 'em):

1. Pick one thing to share, not a dozen

2. Pick something you're ok sharing, because it's not your proprietary secret

3. Pick something that makes you sound resourceful, successful, or smart, as opposed to... not

4. If you're not doing anything right now to grow your reach, influence, and audience, then make a plan today, and write about that

#41: ACME

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Can talking about problems be fun? Let's see. Ask yourself:

• What pop-culture villain or monster can I use as an analogy for a problem my reader is facing?

Hints (only if you need 'em):

1. Pick a problem first, then think of the villain or monster to represent it

2. If that doesn't work, try it the other way around

3. It can be a specific, named character, eg. Ben Settle's use of Gollum from The Lord Of The Rings to represent phone addiction

4. It can also be a type, eg. Dan Kennedy's "time vampires" who suck out not your blood but your time

#42: Customer service

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all work. That's an opportunity to connect with your readers. So ask yourself:

• What's a personal story I can share about a career move I've made?

Hints (only if you need 'em):

1. You can talk about an incident that triggered the move.

2. You can talk about an experience from the actual career move — before, during, or after.

3. As usual, don't use an email to recount your entire career history. Pick one specific snapshot, give enough context for it to be meaningful, and then tie it into your offer.

#43: Recommended reading

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Curating content outside your narrow niche makes you appear like an all-knowing wizard. So ask yourself:

• What interesting blog post/newsletter/magazine article have I read recently that has nothing to do with my industry?

Hints (only if you need 'em):

1. When you talk about stuff that isn't directly relevant to your audience, it becomes doubly important to highlight why this is relevant to them.

2. If you sometimes simply link to outside resources, resist the temptation to do it today. (See hint 1 as to why.) Instead, use this to promote one of your own offers.

3. Don't be vague or general. Instead, dig into the article and find one specific point/fact/quote that you can build your email around. ​

#44: Good news, bad news

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

There are two kinds of people — those who believe in black-and-white dichotomies of the world, those who don't, and those aren't sure. So ask yourself:

• What's my attitude to the idea that there's always a right and a wrong, black and white, in every situation?

Hints (only if you need 'em):

1. Think about it first, and get clear on what your attitude is.

2. It's ok whatever you decide.

3. As usual, the more certain you are in your position, the more people will resonate with you.

4. Wrap this up inside a story, reader question, case study, animal parable...

#45: It's not so bad

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The more you feature reader questions and comments, the more engagement you will get. And engagement is valuable. So ask yourself:

• What's a question or comment I got, which I can use to inspire my readers?

Hints (only if you need 'em):

1. The "inspire" part can be inherent in the question, eg. "How do I pull myself up my bootstraps?"

2. Alternately, it can be in your response. "This reminds me of the time I pulled myself up by my bootstraps."

3. If you don't have any questions or comments that fit the bill, pay a quick visit to a subreddit or forum or group related to your industry, and pick something that appeared there.

#46: Quick save

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

It's time to talk front-and-center about your offer. So ask yourself:

• "How can I get an authority/celebrity endorsement for my offer today?"

1. In case your blood pressure just shot up, first, take a deep breath.

2. If you don't have an actual authority or celebrity to endorse your offer directly, and today, then get creative:

• Maybe somebody has endorsed the approach or mechanism underlying your offer?
• Or they've endorsed some small aspect of what you're offering (your way of handling refunds, your way of delivering content, an ingredient in your supplement bottle)?
• Or they've endorsed a similar offer, even if it's not exactly like yours, which you can then riff off?

3. Resist the temptation to bury this at the end of an email that's really about something else. Think how to make this the core of your email today.

#47: Countries are run by...

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Entrepreneurs, coaches, copywriters, and those in other professions like to see themselves addressed directly in print. So ask yourself:

• What segment of my audience can I call out by profession?

1. Call out a profession because it's a sizable part of your audience, or...

2. Call out a profession because it's a particularly lucrative part of your audience

3. Ideally, call them out in your subject line as well as the body copy

4. If you can, make an argument for why your offer is particularly relevant to people in their profession

#48: A honse is not a home

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

People often judge a book by its cover. So ask yourself:

• How can I take a contrary position on some commonplace or cliche my reader has heard a million times?

1. The commonplace can be something particular to your industry or to the topic of your newsletter

2. The commonplace can also be a general saying or cliche:

• A penny saved is a penny earned
• Rome wasn't built in a day
• Actions speak louder than words

3. This is an opportunity to stretch yourself, and to think or say things you might not think or say otherwise.

#49: Collections tip

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

From time to time, it's good to drip out actual "how to" advice. So ask yourself:

• What's a small, surprising, practical tip I can share with my readers?

1. Your tip can be about your newsletter topic or not ("life hacks" are always game, regardless of what your newsletter is about).

2. If your tip is related to the topic of your newsletter, don't share stuff that you sell now or want to sell in the future.

3. You can wrap this tip inside some personal context (where you are now as you write, what time it is, what's around you, where you found this tip, etc.) and be done with it.

#50: Playing the long game

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The cost of an offer is the price + everything you have to do after you buy. So ask yourself:

• How long will it take my customers or clients to get the results I'm promising if they buy?

1. You can talk about the worst case, best case, average case, or all three.

2. If you're offering a service or something else done-for-you, you can talk about the (short) time people will have to invest before you take care of everything else.

3. Whatever the reality is (short, long, indeterminate time), explain it in a way that 1) your prospects can feel good or inspired by it, and 2) you come across as the honest and trustworthy business person that you are.

#51: Leeds

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We bond over common frustrations, particularly with those who seem distant or more successful than us. So ask yourself:

• What's a recent frustration I had with a prospect, customer, or client?

1. It can be a small or a big frustration, a legitimate gripe or completely inside your head.

2. Lean into however you reacted. If you didn't get bothered or were amused, great. Explain why. If you did get genuinely upset or fired up, also great. Explain why.

3. End on a positive or inspiring note. It's fine to get people riled up, but give them a way out.

#52: Owls ain't cash

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Gary Bencivenga says: being a consumer advocate is a form of proof. So ask yourself:

• What can I warn my readers to stay away from?

Hints (only if you need 'em):

1. Think of what you don't like in the competition or in alternatives to what you offer.

2. Give a credible reason why, so you don't sound bitter or self-serving.

3. You can also warn your readers about things that have nothing to do with your industry.

4. Tie this up in an occasion. In other words, wrap wrap it up in a recent reader question, current event, or your own current personal situation, so it's clear why you're talking about this now.

#53: Dry spell

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Many times, people will only make a change when they've really had enough. So ask yourself:

• What are the signs of a setback or plateau my readers may be experiencing now?

Hints (only if you need 'em):

1. These can be external, measurable signs (eg. stagnant sales, no second dates).

2. They can be internal, wooly signs (eg. frustration, malaise).

3. You can use your existing knowledge of your audience, or read between the lines in your communication with readers, or dig into a subreddit or Facebook group where your people hang out.

4. Ideally, focus on one such sign or symptom, and develop it — paint a picture around it, give it a name, dimensionalize it.

#54: I'm much, much more than that

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

People remember others based on a few unique characteristics. So ask yourself:

• How did I pick up my quirky and unique habit, attribute, or mannerism?

Hints (only if you need 'em):

1. Think of fictional characters for inspiration when it comes to quirks:

• Sherlock Holmes smokes a pipe
• James Bond drinks martinis, but only shaken, not stirred
• Holly Golightly eats a yogurt each morning in front of Tiffany's

2. Your unique quirk can be small and frivolous. in fact it's probably better that way.

3. Tell the story of how this quirk came to be. And make it into A STORY, something that sucks people in, even if the reality was it just kinda happened.

#55: 2x2

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The last "format remix" puzzle was a big hit. So ask yourself:

• How can I write today's email in the format of a 2x2 matrix?​

Hints (only if you need 'em):

1. If you don't know the 2x2 matrix format, you can find a breakdown of it here.

2. In a nutshell, you're looking for a topic that you can reduce to two independent yes/no questions. This gives you four options or categories or outcomes to describe.

3. You don't need to create a graphic. Just writing about it will do.

4. You can take this seriously, or you can turn it into a joke.

#56: Paranormal

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

It's engagement time. So ask yourself:

• What recent reader question or comment (not testimonial) can I feature today?

Hints (only if you need 'em):

1. Use the question or comment as an opportunity to say something new, surprising, or funny.

2. Use the question or comment as an opportunity to implicitly promote your offer by:

• Showing there's interest in it, or
• Overcoming an objection to it, or
• Pre-selling the basic approach that underlies your offer

3. If you have no recent questions or comments to feature, take a look inside subreddits or Facebook groups where people in your audience hang out. And simply say, "Here's a question I just saw..."

#57: 1.4 billion lbs of hidden cheese

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

If you regularly tell people something new, you'll get them addicted to reading your emails. So ask yourself:

• What's something new I've learned from a newsletter, blog, or video in the past few days?​

Hints (only if you need 'em):

1. If you're stuck, it's because you're beeing too critical of yourself. Make a list of 10 possible answers to this puzzle, and at least one will delight you.

2. Add in your own commentary, reaction, or simply personality as you share this information.

#104: Hadouken-ing

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Novelty is one of the strongest tools you have to keep your readers reading. So ask yourself:

• What new and fascinating fact or story have I read lately?

Hints (only if you need 'em):

1. Give preference to sources outside the usual circle of blogs or newsletters in your niche.

2. Even a small fact or story can be fascinating if you frame it that way.

3. For bonus points, spell out in words that yours is a newsletter where readers are exposed to new ideas.

4. If you're ever really stumped for fascinating facts or stories, try this.

#58: Seen in Barcelona

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The Internet is feeding on itself. From time to time, it's good to "add a new cookie to the cookie jar." So ask yourself:

• What interesting or cute real-world observation, scene, or snapshot can I share with my reader?​

Hints (only if you need 'em):

1. You don't have to have a full-fledged story or a profound observation.

2. Think of things or scenes inside your home, down your street, at your local coffee shop, at the gym, ...

3. Many uninteresting things become interesting if you look close enough or long enough.

#59: Consumption idea

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all take our cues from others. You can use this to grow your status. So ask yourself:

• What's a time when I got up and commanded the attention of an audience?​

Hints (only if you need 'em):

1. This can be literal — a time you actually got on stage and talked, or stood up in a meeting, or climbed up on a soapbox.

2. It can also be figurative — a Zoom presentation you gave, a discussion group you led, people you advised over email or over a beer, etc.

3. If you draw some takeaway from this experience that's interesting or valuable to your reader, you'll insulate yourself from the risk of sounding like a braggart.

#60: Groucho on TV

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Other people's thoughts are springboards for our own. So ask yourself:

• What's a quote I've read recently that I can riff off?​

Hints (only if you need 'em):

1. The quote can come from a book, newsletter, or news article you've read.

2. It can be profound, infuriating, curious, ...

3. The point here is to give you an opportunity to share your point of view, not to defer to authorities.

4. If you have no quotes to share, you can always find a bunch on any topic here.

#61: "Go big or go home"

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Travis sago says: Get your market to write your marketing for you. So ask yourself:

• What's a specific phrase that I've heard someone in my audience use?​

Hints (only if you need 'em):

1. Look over email responses you've gotten, or other interactions you've had with actual readers. Look for a specific and unique phrase, argument, or fact.

2. The phrase doesn't have to be directly related to your offer — it's a means of calling out a segment of your market

3. if you don't have a good phrase to use from your own subscribers or customers, take a look in subreddits or Facebook groups where your audience hangs out.

#62: Not The Onion

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Linking to current events is one way to get people to read your email today... instead of never. So ask yourself:

• Which current event can I tie into my email today?​

Hints (only if you need 'em):

1. Five minutes of "research" will take you out of the sea of Trump and Musk news that everybody else has already written about.

2. If you don't read the news, go to sites like theguardian.com, nypost.com, wsj.com, news.ycombinator.com, and see what catches your attention.

3. When a story does catch your attention, it's worth reading to the end. You will often hit upon a unique detail in the article that sparks the idea for your email.

#63: The cat's birthday

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

It's got to be more than about just money. So ask yourself:

• What's a time I did what’s right for a customer or reader, even though it was not advantageous for me?

Hints (only if you need 'em):

1. It can be something you did for your audience as a whole.

2. It can be something you did for somebody in your audience/marketplace one-on-one.

3. If you don't have a good personal story that involves your customers or readers, think of stories from life in general. What's a time you did right by someone, even though it was not advantageous for you?

#64: FREE

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

If you enjoy writing for its own sake, you have to be reminded to sell. So ask yourself:

• How can I just sell my offer today?

Hints (only if you need 'em):

1. Don't teach, don't entertain, don't make excuses. Just find a way to sell what you have, directly.

2. Focus on one thing, rather than reiterating the entire sales page for your offer.

3. Possible categories of thing to focus on: the price, the promise, the proof, the problem solved...

#65: Not a fan

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Prospects always have a silent question in the backs of their minds: "Why am I seeing this TODAY?" So ask yourself:

• How can I tie today's email into an event that happened on today's date?

Hints (only if you need 'em):

1. If today's date is personally meaningful to you in some way, you can use that.

2. Otherwise, a quick Wikipedia search will bring up a bunch of events to riff off:

• 1813: Jane Austen publishes Pride & Prejudice
• 1985: USA for Africa records We Are The World
• 1956: Elvis makes his first national TV appearance

3. Use this as an opportunity to entertain and surprise your readers, rather than to beat them over the head with facts.

#66: Bitcoin finally explained

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Q&A emails are easy and even fun to write... and they beget more easy and fun Q&A emails. So ask yourself:

• What's a question I recently got from a reader that I can use to genuinely instruct or teach something?

Hints (only if you need 'em):

1. This is not an invitation to give away hardcore how-to stuff that you normally sell.

2. Do teach people something valuable — by giving them a small tip, a general direction to go in, a direction NOT to go in, or simply a different way of looking at the topic.

3. If you don't have any reader questions that fit the bill, take a look in Facebook groups or subreddits where your audience hangs out.

#67: Double life

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Inspiration time. Ask yourself, how can I write today's email around the core concept of:

• "Each minute you delay costs you down the line."

Hints (only if you need 'em):

1. You can use a third-person "precautionary tale," a rational argument, a personal story, or a historical anecdote to illustrate your point.

2. It's wise not to anger, humiliate, or belittle your prospects. Present facts — and let your prospects draw the conclusions.

3. End on an inspirational note. Preferably, by getting readers to act now in taking you up on your offer, which will pay off big for them down the line.

#68: Baby names

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Time to call out a segment of your audience. So ask yourself:

• What specific new venture, hobby, or goal has a segment of my audience set their mind on?

Hints (only if you need 'em):

1. You might find mention of this new venture, hobby, or goal if you read between the lines of your readers' responses.

2. As usual, if you cannot find anything good in your own audience, look inside a Facebook group or subreddit where people in your audience hang out.

3. If even that doesn't give you anything, then your intuition or a simple guess will do.

4. Make an argument why your offer is particularly relevant to somebody in your reader's current position.

#69: Advance praise

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

You can't start teasing things too early. So ask yourself:

• What offers am I planning to promote in the near future?

Hints (only if you need 'em):

1. You can make a list of upcoming offers and share them all.

2. Or you can focus on just one upcoming offer, and work that into your email.

3. Use this as an opportunity to give people a peek behind the curtains of your newsletter.

4. Do still promote an existing, current offer.

#70: Longest elevator ride

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We're all held back by "knowing" what other people are thinking or will think. So ask yourself, how might you challenge the following assumption in your readers' minds:

• “I can guess what millions of people are thinking”

Hints (only if you need 'em):

1. Start with a list of things that your reader might feel sure others are thinking or will think.

2. You're unlikely to change people's minds by telling them, "That's ridiculous" or "Boy, how wrong you are..."

3. You have a decent shot at changing minds by using a story, an analogy, or a parable.

#71: Just a perfect day

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

All of us either love being where we are... or planning to go where we aren't. So ask yourself:

• What's my stance on travel?

Hints (only if you need 'em):

1. Yes, today's puzzle is about whether you like to travel or not. But this is really an opportunity to share your deeper personal beliefs and values, so that the right people can connect with you.

2. Whatever your stance is, the more you lean into it, the more attention and resonance you will achieve.

3. It's good to tie abstract topics like this to an occasion. In other words, connect it to something specific that happened recently to answer the question, "Why are you talking about this now?"

#72: All natural

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all like gossip, even if it's disguised as rational discussion. So ask yourself:

• What's a hot new offer in my market, and what's my take on it?

Hints (only if you need 'em):

1. You can talk about a specific offer, or a category of offers you are seeing.

2. If you aren't comfortable naming names, you can waffle a bit or anonymize who you're talking about.

3. This is your opportunity to insert yourself and your attitudes into a conversation that might already be going on in your reader's mind.

#73: Beware

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Most people have some experience with pets, often with strong emotions tied up. So as yourself:

• What personal story can I share that involves pets?

Hints (only if you need 'em):

1. You can talk about a pet you have now, or one you had long ago.

2. You can talk about a pet that you always wanted, but never had.

3. You can talk about why you don't like pets, and why you don't understand or really make allowance for other people's obsession with pets.

4. Whatever you choose to talk about, wrap it up inside a personal story.

#74: Let me just finish this

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Time to call out a segment of your market. So ask yourself:

• What's a whack-a-mole situation in my readers' lives?

Hints (only if you need 'em):

1. Look at perennial promises/offers in your market. They are perennial because they address a problem that just won't get solved.

2. You can use this to give your readers a new insight into their problem. Maybe the reason the moles keep popping up is not that the size or make of your reader's mallet. It might be something underground.

3. Pick a whack-a-mole situation that you can address with your offer, either because you have a new solution, or because your solution solves the REAL problem.

4. Ideally, call this whack-a-mole situation out in your subject line.

#75: Took me a while

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

People are always looking for clues that you're a real person, really writing. So ask yourself:

• How can I pick up the thread of an email I wrote earlier this week?

Hints (only if you need 'em):

1. The easiest way is to feature a reader comment or a question that builds off your earlier email.

2. You can also have a Columbo-like "Oh, one last thing" moment, where you write a new email and simply add a new point or illustration to what you wrote earlier.

3. If you want to get cute, you can do this by inserting an inside joke for your best readers, which refers to an earlier story.

#76: It works?

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

There are many kinds of proof, but one kind trumps them all. So ask yourself:

• How can I make a demonstration of my offer?

Hints (only if you need 'em):

1. Some demonstrations are really just illustrations, showing how an offer does its thing. (Think of the famous "it slices, it dices" infomercials.)

2. Another option is to give people a sample of what your offer is about (eg. an excerpt for an info product).

3. If your offer is an info product teaching people things, you can put one of those ideas to use in your email, and demonstrate that way. (You don't have to spell it out if you don't want to give away your teaching for free.)

4. A demonstration works better if it is DRAMATIC.

#77: Pan hacks

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Once every economic cycle, it's good to actually teach your readers something specific and new. So ask yourself:

• What little tip can I share with my readers today?

Hints (only if you need 'em):

1. Think of things you've learned recently. If it was new and valuable to you, chances are it will be new and valuable to your readers.

2. If you've discovered this tip yourself, of if you learned it from someone else but put it to use yourself, your readers will find it more credible and interesting that if you're simply passing on stuff you've read, which has no connection to you.

3. Teaching is great, but it goes down easier if you wrap it up inside a bit of personal context, or an anecdote, or a joke.

#78: Daily emailer at work

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your business is what you make it. So ask yourself:

• Who are the kind of customers/clients I want to work with?

Hints (only if you need 'em):

1. If you don't already have such a list, it might make sense to sit down and make a list of 10+ characteristics of such customers/clients before you write this email.

2. The customers/clients you want to work with are not just anybody who will give you money. If you're honest with yourself, you'll find there's always more that makes for enjoyable and meaningful work.

3. You can wrap this up in a case study, personal story, analogy, Seinfeld reference, ...

#79: Includes assembly

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Time to sell. So ask yourself:

• How can I help my reader "grasp the advantage" of my offer?

Hints (only if you need 'em):

1. Grasping the advantage is often about the "benefit of the benefit." What does having your offer really translates to in the customer's life or business?

2. It can help to think along different dimensions:

• How your prospect will feel
• How people will think of him
• What this will mean in terms of money
• What this will mean in terms of emotional wellbeing
• What unpleasant things he will be able to avoid

3. If you do start thinking along different dimensions, pick just one to write about today, and save the others for other emails.

4. As usual, it's best to wrap this up in something specific and concrete — a personal story, a reader question, an interesting observation, etc.

#80: Make Chile Great Again

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Nothing inspires more than the belief we're part of something big, powerful, and inevitable. So ask yourself:

• How can I appeal to the idea of growth, progress, or destiny?

Hints (only if you need 'em):

1. If you have genuine religious or philosophical beliefs about these ideas, don't be shy about sharing them.

2. If you don't, try zooming out and look at the bigger picture — of your life, of the world in general, of the human race.

3. For bonus points, think up a unique name to get a handle on this vague and abstract belief you're talking about.

#81: Collie pun

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Outside of a dog, a book is man's best friend. Inside of a dog, it's too dark to read. But it's never too dark to tell a joke. So ask yourself:

• What's a joke I could tell my readers?

Hints (only if you need 'em):

1. If you know a good joke, you can make the entire email the telling of it.

2. If you don't know a good joke, you can find a joke (good or not) in about 30 seconds of searching online.

3. Even a one-liner quote (Groucho Marx above, about books and dogs) or a stupid pun (today's disconnected infotainment) can be enough.

4. Use the joke to open up your email. In the words of Dan Kennedy, "Make 'em laugh and take their money."

#82: Size matters

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Human insecurity is just about the only constant through the ages. So ask yourself:

• "What is my reader insecure about with regard to size?"

Hints (only if you need 'em):

1. It could be physical. If you're writing about fitness, sex appeal, or sexual performance, you can address insecurities about the size of specific body parts or the person as a whole.

2. It could be abstract or virtual. An insecurity about the size of their portfolio... the size of their audience... the size of their savings account.

3. Whenever you're touching into somebody's sore spot, it pays to be considerate and even indirect.

#83: Death by Danforth's

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Take a moment, and ask yourself how might you challenge the following assumption in your reader's mind:

• "I don't have the time to do this"

Hints (only if you need 'em):

1. You most probably won't convince people they have time they don't have, particularly if they are adamant they don't have it.

2. Instead, you'll have to give them a shift in perspective:

• Will they be saving time long-term?
• Will they be getting rid of things they are spending time on now?
• Will they be somehow more productive and able to do more in the same amount of time?

3. You can wrap up your answer inside a reader question, an anecdote, inside something interesting you read recently, ...

#84: Generous selling

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

You might not believe it... but testimonials work. So ask yourself:

• What's a recent testimonial I can feature in my email?

Hints (only if you need 'em):

1. The best testimonials talk about a real result.

2. The second-best kind of testimonials are from people who were skeptical or had objections before, but are now convinced.

3. A testimonial can be a valuable lesson in itself. Sometimes, the testimonial-giver writes it out for you. Other times, you have to draw the lesson out.

#85: Ok grandpa

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your readers want glimpses inside your world. So ask yourself:

• Who is a strange character who lives in the outskirts of my life?

Hints (only if you need 'em):

1. It could be a mailman... a local homeless guy... a neighbor you sort of know, sort of don't.

2. Pick somebody who's worth writing about — or make them worth writing about. In other words, highlight or exaggerate one or two of their characteristics or mannerisms to where they become a "character."

3. You don't have to share the whole history of your interactions with this person. A single snapshot will do.

#86: Starter pack

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Time to have a bit of fun. So ask yourself:

• What can I put in my own "starter pack"?

Hints (only if you need 'em):

1. If you're not familiar with what a "starter pack" looks like, take a look at this example from the New Yorker and this entire subreddit devoted to examples.

2. You can create a starter pack for yourself or your newsletter... for your industry (eg. "course creator starter pack"), or even to mock a segment of your industry you want to distance yourself from ("thought leader starter pack")

3. The goal here is to have fun, rather than to overwhelm people with "value"

#87: Sus will be there

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

An easy day today. Simply ask yourself:

• What comment can I make on a recent blog post or newsletter I've read?

Hints (only if you need 'em):

1. If you were surprised, entertained, or made to think by an idea or a new illustration... share that with your readers. There's a good chance it will do the same for them.

2. You ca make this email super short, and simply share a good idea, or link to somebody else's article.

3. On the other hand, you can also take somebody else's blog post or newsletter for a starting point for sharing your own stories and opinions.

#88: Hard to mess up

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Often, the most basic stuff works the best. So ask yourself:

• What specific problem or desire of my readers can I call out today?

Hints (only if you need 'em):

1. Don't be discouraged if you are saying something basic. That's the point today.

2. If you're going to give your readers any hope that their problem or desire can be solved, you'll need to present or at least hint at a new plan.

3. You can either reveal what your plan is, and make that the body of your email... or you can make it a part of your offer.

#89: Fan mail

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We typically look to provide proof for our offers. But there's a big missing piece. So ask yourself:

• What specific proof can I provide for myself, not my offer?

Hints (only if you need 'em):

1. Pick one piece of proof, and write about that.

2. Ultimately you want proof that you are trustworthy... that you can do what you say you can do... and that you care about your audience, beyond just getting their money.

3. Your proof could be a testimonial or endorsement (about you specifically, not about your offer).

4. It could also be an anecdote or story of how you got your magical skills and knowledge.

5. It could even be something about your pedigree. In other words, you can make the argument that you were meant to be where you are today, doing what you are, because of how the stars lined up.

#90: Big idea

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

An analogy is one reliable way to come up with a big idea. So ask yourself:

• How can I work an analogy into today's email?

Hints (only if you need 'em):

1. You can make an analogy for your reader's current situation.

2. You can make an analogy for the underlying problem that's keeping your reader stuck where they are.

3. You can make an analogy for the opportunity or outcome you're promising.

4. You can build your entire email around an analogy, or you can simply use an analogy as part of your bigger argument.

#91: Two unwritten rules

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Something hyped, something bold, something viral, something old. Ask yourself:

• What kind of a listicle can I write today?

Hints (only if you need 'em):

1. Listicles of 7 items or 10 items work the best.

2. If you're having trouble coming up with a topic for your listicle, write a listicle of 10 listicle ideas first.

3. You can have an intro to your listicle, but you don't have to. It's often good to just jump straight from your subject line into your listicle.

#92: Literally

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Sometimes, people need to see a real and present danger up ahead to change their ways. So ask yourself:

• How can I make the claim my reader can't keep going the way he or she has been going?

Hints (only if you need 'em):

1. If you tell people to make a drastic change, you will come up against resistance. One tried-and-true way is to primarily talk about other people, not them.

2. Another option is to talk about yourself, and what you're seeing/doing/planning.

3. Stories, analogies, and current news items are proven ways to bundle up the unpleasant truth that the time to change is here.

#93: Not chicken

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Your personal stories are really there for the reader to identify with. So ask yourself:

• What's a childhood discovery I can tell a personal story about?

Hints (only if you need 'em):

1. If you can't think of a single childhood discovery, think of 10. Don't criticize and critique your ideas. Just write down whatever comes to mind, and make a list of 10.

2. A good way to open a story is to drop people into the middle of the action.

3. Don't be afraid of sharing something that's strange, weird, or embarrassing. Odds are, many people have had similar experiences.

#94: Homer's third epic

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

What book are you reading? Whatever it is, ask yourself:

• What did I read recently in a book that I can share with my readers?

Hints (only if you need 'em):

1. It can be a fascinating new fact.

2. It can be a powerful new perspective.

3. It can be a cool story you hadn't heard before.

4. It can simply be a phrase or analogy that made you smile.

#95: Theft prevention tip

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Since it's the end of a month full of infotaining emails, ask yourself:

• What small, practical tip or technique can I share with my readers?

Hints (only if you need 'em):

1. The key word is small.

2. Sell people on your tip — both applying it could mean to them, and what not applying it could cost.

3. Your tip or technique can have to do with your newsletter topic. It can also simply be a life tip or hack.

4. Tie this tip into you. How you discovered it... how you're using it... what it's done for you personally.

#96: It worked for the cat

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

What is most personal is most general. So ask yourself:

• What's not working in my life?

Hints (only if you need 'em):

1. You don't have to share anything you feel uncomfortable sharing.

2. Even small frustrations, doubts, or woes can make for a good email.

3. This isn't about seeking pity or even a solution. It's about allowing your audience to identify with you.

#97: Press button

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

A huge segment of your audience has a completely mistaken idea of what you offer. So ask yourself:

• What aspect of my offer does my reader think is an orange, when it's in fact an apple?

Hints (only if you need 'em):

1. If you have them, go back to customer conversations, and pull up specific questions or misunderstandings your customers or prospects had.

2. Otherwise, make a list of 10 possible apples/oranges misunderstandings about your offer, and pick one.

3. This misunderstanding can be about your specific offer, or about the general category of solution that you provide.

#98: A tooth for an eye

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

The world is bigger and more complex than ever. We're still hoping for understanding. So ask yourself:

• What's the impact of today's front page-news on my specific industry or audience?

Hints (only if you need 'em):

1. Pick one specific hot news story or trend. If you need ideas, take a look at your favorite (or least favorite) news site, and choose something that's trending today.

2. Make specific predictions about your industry or audience, as opposed to the universe as a whole.

3. The point here isn't to be right. The point is to put your reader's experience into a bigger context.

#99: Free to a good home

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

We all want confirmation that we've made the right decision. So ask yourself:

• What's a product or service my reader may have bought recently?

Hints (only if you need 'em):

1. Call out this product or service in the subject line.

2. Use this product or service as a way of attracting your reader's attention... so you can transition into your sales point.

3. If you make the argument that your offer is particularly good for people who have bought product or service X, you're likely to drive extra sales.

4. If you don't know any products or services your readers may have bought, then look at your own recent purchases.

#100: Name this plant

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

When people come to you with questions, it puts you in the position of the wise man (or woman) on the mountain. So ask yourself:

• What reader question can I answer today?

Hints (only if you need 'em):

1. Don't just answer the question. use it to highlight yourself, your own expertise and experience, and trustworthiness.

2. If you can build up the person who asked the question, you will build yourself up even more.

3. If you have no reader questions to answer, check inside facebook groups or subreddits where your audience hangs out.

#101: Guaranteed to pop

DEPT. OF DISCONNECTED INFOTAINMENT

YOUR DAILY EMAIL PROMPT

Even ridiculous guarantees can help close the sale. So ask yourself:

• What guarantee or warranty do I provide to my customers?

Hints (only if you need 'em):

1. If you already have a guarantee or warranty, say what it is — and sell readers on why it's impressive and sexy.

2. If you don't have a guarantee or warranty, you can decide to come up with one now. Think about the biggest promise you are (un)comfortable guaranteeing... and the offer around it (money-back, double-your-money-back, "I'll eat my hat" etc.)

3. If you neither offer a guarantee/warranty, nor want to offer one, then turn that into a sales point. Why is it ultimately good for your customers that you have this policy?