10 Things I Learned from Sending an Email Every Day for a Year

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At the end of 2023, I challenged myself to create a new daily non-profit newsletter named Email 366. I promised to send a daily, fresh, actionable email tip all 366 days of 2024 (leap year!) with best practices and expert advice to help subscribers boost their organization’s email efforts.

If you’re a newsletter publisher, you know the challenge of creating content for a monthly or weekly newsletter. But sending something daily? That seemed like the definition of insanity.

It was a long year, but I successfully sent a new email every day, and I learned a lot along the way. It’s not easy to send an email every day — but it’s absolutely possible, and it opened new doors for my business over the course of the year.

Here are 10 lessons from 366 days of consecutive sends. 

1.) Address the readers’ pain point

I’ve been in the non-profit sector for 25 years, and I’ve successfully used email to help organizations grow and thrive. I know that email is a pain point for many charities — they know they need to do more with email, but they’re not always sure where to start or how to improve their existing strategy, and I knew that if the tips were too complicated to implement, teams wouldn’t implement them. Once I understood what my audience needed, I set out to turn this pain point into an opportunity to differentiate my newsletter.

I addressed it by sharing a quick daily tip that was easily digestible and actionable at work.  Every email started with a to-the-point subject line and then a tip that anyone could implement quickly. My goal was for every email to take less than 60 seconds to read.

With so many emails to send, it would’ve been easy to have gotten distracted and sent emails that felt like filler. I wanted to send something truly valuable every day, and the focus on that pain point helped me stay on topic throughout the year.

But even within that focus, there were still opportunities for me to drill down deeper. For instance: the no. 1 email related question I get asked by non-profits is, “What content should we share besides fundraising asks?”

I decided to tackle this head on with a feature I called “Wednesday Where’s the Beef.” On Wednesdays, I shared a content tip that wasn’t a fundraising ask so organizations could beef up their email strategy by sending a variety of different types of content.

Over 52 Wednesdays, readers learned from examples how they could connect and engage readers without asking for a donation.

Email 366 was created to deal with a general pain point. But then I drilled down to solve a specific problem within that area.

2.) Organization is key

I spent a lot of time pre-launch organizing my content. I created a document where I listed all my email tips and divided them into different sections. I used an Excel spreadsheet to list the daily tips. I made sure to share a variety of tips on numerous email topics throughout the year.

Additionally, I wanted to “stay ahead” of the calendar — I never wanted to be in a position where I had to write the email and send it on the same day. All of my emails were prepared 2-6 weeks in advance. In the middle of a month, I’d compose the next month’s posts and add them to Beehiiv, the email platform I used for Email 366. This way, I only had to check individual emails the day before they were sent.

That lessened the stress of sending every day. I knew that with any given day the email was already prepared. I just had to do a final check before hitting “send.”

This also provided me flexibility. If something came up which needed to be addressed right away, I could slide an email to the following month and quickly compose the email for the next day.

3.) 1 out of 3 is good

When my dad was studying to become a rabbi, one of his teachers asked, “What must you remember before going up to the pulpit to deliver a sermon?” Answers included “go to the bathroom” and “make sure you have your notes with you.” The teacher had a slightly different answer.

“A baseball player who hits .333 is going to the Hall of Fame,” he said. “Remember that not every speech will hit the mark. But if one out of three does, you’re doing fine.”

Not everything we post is gonna be a big hit. That’s hard to take as a publisher, but it’s worth remembering. If one out of three daily posts resonated with an individual subscriber, I was doing fine — that would mean I’d publish more than 100 really great posts in a year. More publishing meant more chances to publish something that resonated with my audience and/or potentially led to new business.

4.) Make sure your subject lines stand out

In 2021, I signed up for Rob Hope’s “100 days of landing page tips.” For 100 straight days, a new tip arrived in my inbox. In the subject line of every email Rob sent was a 🔥 and next to it: “Landing Page Hot Tip #.” By day four, as soon as I saw the 🔥, I knew it was an email from him.

I decided to follow his model. From tip 1 my subject lines always included 📨 and next to it “tip #.” (In the inbox, that meant they looked like this: 📨 tip 77: Email + Text = Success.) This was my way of creating inbox visibility and helping my emails stand out in people’s overflowing inboxes.

5.) Find different ways to engage with readers

Emailing every day is a grind, both for me and my subscribers. I tried my best to find ways to engage readers and involve them over the course of the year.

That included:

• Incorporating in-newsletter polls and surveys into newsletters.
• Asking questions and requesting readers email me answers.
• Sharing an email I received from a non-profit and asking subscribers for their feedback.

For that last one, I did something extra: I asked those who responded if I could share their response anonymously. I then created a post on my website with their feedback so my subscribers could read the opinions of their fellow non-profit smarties.

When you can, engage your audience and make readers part of the process. 

6.) Find ways to share new perspectives

Every Sunday of Email 366 was called “Sunday Smahts” — a shoutout to my family’s Boston roots — where I posted a tip shared by a sector expert. The Sunday edition served three purposes:

1. To lessen the writing burden on me.
2. To give readers a break from me. (Hearing from me every day is a lot!)
3. To introduce my audience to experts who they could connect with. 

Over 20 experts provided a few tips that I spread out over the course of 52 Sundays. I also made sure to link to each expert’s LinkedIn profile, website, and newsletter sign-up page so subscribers could connect and continue the conversation.

I also sometimes highlighted specific examples from the non-profits that my readers worked at. When I highlighted specific examples from those non-profits within the newsletter, I also gave a shout-out to the organization featured. That built goodwill among my community — the non-profit’s team would often email me to say how appreciative they were that I included them as an example of good email strategy.

I also incorporated crowdsourced content into my newsletter — asking readers for their own advice or ideas, and then sharing them via the newsletter. (More on this in a moment.) The effect was the same: to bring new voices and perspectives into the mix.

7.) 365 emails is a lot. Make sure you keep your readers entertained

“Friday Funnies” was my way of sharing a tip that came with a smile and sometimes a laugh. 

The non-profit world deals with very serious issues — hunger, homelessness, disease, poverty, and more. It’s a lot of doom and gloom. As I told subscribers, there is a place to share something from time to time that delights their audience and maybe even makes them laugh.

On Fridays, I’d share a funny cartoon, meme, video, or post meant to get readers smiling headed into the weekend. I, of course, included a tip alongside it.

If you’re going to write a daily newsletter, you’ve got to keep readers entertained. This was my way of doing that.

8.) Sign-offs can help build routine

I ended almost every email the same way: “Back at it tomorrow.”

This was my way of committing to my readers that I’d be back in their inbox the next morning with another tip. I was following football coach Bill Belichick’s advice: “No days off.”

Using the same sign-off every day was a little like when a broadcaster or podcaster ends every show with the same phrase. Over the course of the year, it became both my calling card and a nice way to keep readers in a daily routine.

But I did sometimes sign off with a different phrase, and when I did, people often noticed and would email me. That was another way to generate conversation.

9.) Answer questions from subscribers

When subscribers email you, answer them. Create a conversation with an individual reader.

If you’re sending daily, you’re probably going to get a lot more replies over the course of the year than you would if you sent only weekly or monthly. Be ready to commit to replying and engaging your subscribers in conversation.

And yes, that can get a little overwhelming. Some of my posts received no feedback, while others brought in lots of responses. It can be time consuming to reply to all these emails. But no matter what, I answered every email. I enjoyed learning from others, answering their questions and going back and forth on sector topics. And some of these replies even led to consulting work for my business.

10.) When you commit to something…

I was always taught: “Don’t make a promise you can’t keep.” If you commit to something, see it through.

That’s easier said than done, of course. But if you’re going to go the daily route, be prepared to actually do it. Subscribers sign up because they want that daily nugget of wisdom that you can provide. Once I committed to a year’s worth of newsletters, I couldn’t quit on my subscribers halfway through.

But I also only committed to a single year’s worth of emails — not a daily email in perpetuity. That gave me the opportunity to reevaluate my strategy and figure out if I wanted to keep things going in 2025 or make a change.

11.) Give them more than they asked for

Even when you’re writing something every day, it’s important to find ways to surprise and delight your readers. Whenever you can, give them something unexpected.

So with that in mind, I promised 10 lessons, but I’ll share a bonus tip: Make sure you choose the right platform up front.

I published Email 366 on Beehiiv. I had never used Beehiiv before this.

Did it work out in the end? Yes. 

Would I do it again this way? Nope.

I’d used ActiveCampaign, Constant Contact, and Mailchimp before. But for Email 366, I decided to test a new platform and that meant growing pains.

I should’ve thought about it more before I launched. Let’s say Beehiiv wasn’t the right platform for a daily newsletter. Migrating elsewhere mid-year could’ve been a huge mess.

The good news is that I learned to get the most out of Beehiiv and really liked the platform. I’m going to use it again for my newest non-profit newsletter, From Survival to Thrival. But if you’re going to publish a daily, make sure you’re using an email platform you’re comfortable with. (Editor’s note: We’ve got some recommendations for platforms in this post.)

Email 366 was a wonderful experience, and one of the most ambitious projects I’ve ever taken on.

I met a ton of wonderful dedicated non-profiteers who are making their communities — and the world — a much better place. I was forced to come up with new content every single day that would be helpful and implementable. I’ve worked in this space for decades, but this project really pushed me to be creative in a brand new way.

Considering a daily? Make sure you know what you’re getting into. It’s a grind, but there’s definitely an upside to being present every day, no matter what’s going on around you.

And Email 366 reminded me that shaking things up is a good way to make sure I’m delivering real value for my audience. I won’t be writing daily in 2025, but that’s because I’ve launched a new newsletter for the non-profit community. It’s a new opportunity to learn — and to build something exciting — for my readers.

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