What Daily Emails Taught Me in 5 Years

Discover how daily email habits built trust, loyalty, and revenue.

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Can Typos Be Overlooked in Daily Emails?

Committing to sending emails daily may require letting go of perfectionism.

'Yes, by emailing more often, I'll tell you now, there were typos in those emails. Absolutely...
But they were sent, and that was the thing I was committed to.'


Takeaway:
• Prioritize consistent communication over perfect grammar.
• Minor mistakes won't hinder engagement if content is valuable.
• Tools like spell-checkers can help, but don't let perfectionism stop you.

How to Set Boundaries in Your Emails

Deciding what personal topics to include in emails maintains professionalism and personal comfort.

'You have to decide what you will and what you will not talk about...
You can put your own boundaries... Don't feel like you have to share everything.'


Takeaway:
• Establish clear boundaries on personal sharing.
• Maintain professionalism while building connections.
• Share what feels comfortable to enhance authenticity.

Do Daily Emails Annoy Subscribers?

While some may unsubscribe, daily emails attract engaged subscribers who value your content.

'Yes, you get people unsubscribing, yes, that is gonna happen. But the people who stick around are the ones who actually want to solve the problem, and they want to hear from you.'


Takeaway:
• Accept that some unsubscribes are natural and healthy.
• Daily emails filter out unengaged subscribers.
• Focus on nurturing engaged readers who appreciate your content.

Is Emailing Daily a Messaging Hack?

Daily emails offer more opportunities to refine messaging and improve conversions.

'If you email more often, which is what I do, I email every day, I'm getting 365 tries a year at figuring out the perfect message...
Every day is a new chance for you to show up and test a new message.'


Takeaway:
• Frequent emailing allows rapid message testing.
• Refine your messaging faster to increase conversions.
• Daily feedback helps optimize your marketing strategies.

How Frequent Emails Aid Re-engagement

Regular emailing improves your ability to re-engage inactive subscribers.

'By sending more regular emails, my ability to re-engage email subscribers is way better than anybody else I know...
So for example, I'm emailing say 30 days in a 30 day month. That means if the person hasn't opened or clicked an email in 30 days, I know they've had at least 30 emails.'


Takeaway:
• Frequent emails help identify disengaged subscribers sooner.
• Early detection allows timely re-engagement strategies.
• Maintaining list health becomes more effective.

Should You Write Emails in Real Time?

Writing emails live adds authenticity and connects more deeply with readers.

'One of the reasons I try and always write my daily emails in real time, that like that day rather than batching them...
It's much more like reality TV... They get to see the different moods you are in.'


Takeaway:
• Real-time emails reflect genuine emotions and experiences.
• They make your communication feel timely and relevant.
• Authenticity fosters stronger connections with your audience.

How Personal Stories Boost Engagement

Sharing personal anecdotes can deepen subscriber connections and enhance engagement.

'And when you're sending that many emails, you'll find that you do start bringing more of yourself into them.
And that means people come up to you and say, oh, I've got a cat too, I really love cats...
And when they do that, what are they proving? They're proving that they know you. They know things about you.'


Takeaway:
• Personal stories make you relatable to subscribers.
• Sharing builds trust and loyalty.
• Real-life anecdotes encourage engagement and interaction.

Why Open Rates Matter Less Than You Think

Focusing on total weekly engagement can be more insightful than individual email open rates.

'What's really interesting about email open rates... So for most people, they'd be happy with an email open rate of, I don't know, 30, 40%. But even if you're getting 40% open rate and you've got a sizable email list, that means that 60% of the email list are not really reading your emails... By emailing more than one a week, every day, I found that across a week, more than 80%... of people on our email list will open an email in a week's period.'


Takeaway:
• Daily emails increase cumulative weekly open rates.
• Frequent emails reach a larger portion of subscribers.
• Focus on overall engagement rather than single email metrics.

How to Gain Permission to Email Daily?

Gaining your subscribers' permission is crucial when increasing email frequency.

'First of all, one of the things you have to do in order to make this work is you have to give yourself permission, and I know it sounds kind of crazy... So there's three things I did to give myself permission. The first thing was, I told people that at the point of signing up, I said, this is what you're gonna be getting.'


Takeaway:
• Inform subscribers upfront about your email frequency.
• Setting expectations reduces complaints and unsubscribes.
• Giving yourself permission empowers consistent emailing.

Should You Email Subscribers Daily?

Consistent daily emailing can significantly enhance engagement, but is it worth the effort?

'Yes, it does sound like a lot, doesn't it? Like, I'm gonna email my list every single day, and I've been doing it for more than 10 years. In fact, I've done it in multiple industries, done it B2B and B2C.'


Takeaway:
• Emailing daily can boost engagement and sales.
• Consistency builds habits for both sender and receiver.
• Daily emails are effective in both B2B and B2C contexts.

Episode Info:

Title:
I Sent An Email Every Day For 5 Years. This Is What Happened...
Episode Link:
Keywords:
email marketing, audience growth, consistency
Episode Air Date:
May 7, 2025

Podcast info:

Show Name:
The Email Marketing Show
Author:
Email Marketing Heroes
Owner:
Email Marketing Heroes
Category:
Business, Marketing

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