Earlier this week I met with an agency leadership team that wants to launch a client-facing newsletter but felt pretty intimidated by the bandwidth their initial concept might require.
Picture this: as an agency sending a monthly email to current and past clients, they thought they’d need to create an original case study for each newsletter.
I’d be intimidated, too.
Especially if the hours to produce that sort of work on top of client work just aren’t there.
They’re not alone.
A majority of the hopeful newsletter creators I coach have this mix of emotions:
I suggested they streamline their ambitions from a new case study each month to a touchpoint each month that may or may not include a case study but ALWAYS includes information their client base will find valuable... and that they figure out a way to add a bit of personality that showcases the ways they think / work to remind clients why they like working with them.
The stress on their faces visibly reduced.
They’d been thinking about the newsletter as needing to feel like a product (“look what we did”) instead of as a means of humanizing themselves and exposing the work culture they tend to hide behind a curtain in customer relations.
We left the meeting with me advising a newsletter with 3 or 4 sections max, starting with a personal introduction, including a mix of original and curated content they know will help their clients, and closing with something quirky / funny the readers might look forward to in each issue.
They’re also rethinking how polished a case study even needs to be for them to share work with clients. Maybe, instead of a formal page on their blog, it’s a short recorded screen share video of how they solved a UX problem for a client.
Will it require a bit of effort to launch? Yes.
But it doesn’t feel so heavy now that they’ve given themselves the grace to mix original and curated content and to only share case studies when they have the time to create them. Plus they’re excited that they can use it as a way to showcase who they are individually.
What they’re doing reminded me of this article the team at Audience Ops published a few months back. It addresses how content can play an important role in customer retention. Disclosure: Audience Ops is a Simple Focus Software company.
I believe the content we create for customers after they convert is just as important as the content we create to help them decide to convert. Newsletters are a natural way to stay in touch with existing customers.
And, if you’re thinking, “But, Ashley, I run a newsletter that I monetize through sponsorships so this really doesn’t apply to me,” my counter is that it’s so close it’s basically the same premise.
It’s just that in the case of a customer newsletter, your brand is the sponsor instead of 3rd party advertisers, which is what you get in this newsletter, right? Curated is the sponsor, but not in an obnoxious way.
How many of your readers do you know by name?
Last week, as I took time off to go metal detecting in England, I was struck by the thought that because the most successful newsletter creators are the ones that truly understand their readers, that a good measurement of progress is how many readers you’ve actually engaged with personally.
As I crept my way across the field, I challenged myself to list off as many reader names as I could.
The list goes on. They’re all people I met because of publishing Opt In Weekly.
Maybe you haven’t had a direct conversation with a reader (why not, though?), but you’ve begun to recognize the people who take time to respond and comment on what you send. Hopefully, you’re responding to these sorts of replies after each issue.
And while it’s great to recognize their names—heck, you could track this in a spreadsheet—I think the more important question is what else do you know about them?
Have you engaged enough to understand what their goals and challenges are?
Do you know if they’ve made a major career change recently?
Do you know what they aspire to become?
Do you know what sort of books they like to read?
Or if they’ve launched a TikTok account?
While this all might sound like data big tech would love to pounce on, gathering this information informally, through conversations or messaging back and forth, is insanely helpful in guiding your content strategy.
Rather than imagining a faceless crowd of strangers reading your work and attempting to guess what they’d find valuable, you’ll be able to settle your mind on one person and think “What would Tina find helpful this week?”
Your newsletter then becomes an ongoing conversation between you and individuals.
And there’s a very high chance that the problems one reader in your audience struggles with are shared by many.
Suddenly, your readers will begin thinking, “How did she know I have this problem and needed a way to solve it?”
If you haven’t yet, reach out to a few of your friendliest readers and try to book a 30-minute call to talk 1:1 with them.
Keep it casual.
Tell them it helps you get to know your readers and understand how you can improve your newsletter.
Ask them questions and let them tell you their stories.
Then, internalize what they’ve told you and use it to fuel your upcoming issues.
Get to know as many as you can.
Not only by name, but by what they need that you can provide.
Do you ever stop to think about what life was like 2,000 years ago?
Like, was it very Game of Thrones minus the magic or more The Croods?
These are the kinds of thoughts I have whenever I’m metal detecting in England… and that’s what I’m doing this week: spending 12 hours a day walking farm fields, swinging a detector, listening for the right kinds of beeps, and digging holes in search of lost objects that hold stories of the past.
So often the targets we dig are the less glamorous parts of the story; little blobs of lead or bits of copper.
But sometimes, they are the more exciting bits:
Things once treasured.
And today (I’m writing this Wednesday so by the time you read it it will technically be yesterday), as I bent down to uncover what I assumed would be another blob of lead, I was surprised by the unmistakable shimmer of gold.
I found my very first Celtic gold coin.
It dates back to sometime between 17 and 35 AD.
And it is tiny.
And more than I expected to uncover when I went out searching.
Are you using the process of creating and publishing your newsletter to do the same?
I’m not talking about metal detecting anymore.
I’m referencing the process of seeking something that holds a story you know your readers will treasure.
Each week, we try to do that with Opt In Weekly’s Newsletter Tips as we scour the web for the latest newsletter advice and insights.
In preparation for my being gone, though, I reached out to some of my favorite newsletter publishers to ask them a question:
What's one thing you've learned from publishing a newsletter?
Their answers (below), are treasures in themselves.
Thank you to Seth and Samantha for holding down the fort with this week’s curated content while I’m seeking other treasures.
Monday morning my 12-year old daughter woke up upset.
She was trying to hide it but I could tell.
I felt like a detective.
She should have been in a decent mood.
Although I had work (from home, as always), they were out of school. They had both Good Friday and Easter Monday off. So the funk she was in—very much an on-the-edge-of-tears existence for a good 15-20 minutes—shook me.
It was more akin to when she’d realized last minute that an assignment was due THAT DAY, a moment I did not want to relive.
So, of course I prodded, assuming that if some big school project needed to be tackled I’d better know.
Or if some personal issue needed extra love and mama coaching.
I needed to know the problem so I could empower her to solve it.
Eventually she spilled:
SHE WAS UPSET THAT IT WASN’T EASTER DAY ANYMORE.
And suddenly I remembered she’d done this after Christmas Day, too.
Y’all, as tough as this girl is (and I say that mostly because her sister is known to be more emotional while she holds it all in), she has a soft spot for the passing of special moments.
We talked about how, in addition to the loss of people, we also mourn times that were special to us.
I don’t always feel this way about holidays just as they’ve ended, but I can relate when it comes to finishing a good book. Saying goodbye to anything that evokes strong feelings can be difficult.
For her, it is especially hard to let go of the excitement of yesterday when yesterday involved family time and candy (I think there’s a correlation there).
This start to my week—the anxiety, then the discovery of what was actually happening, and the mama instincts that told her it was ok to be sad all passed in less than a half hour—but what’s sticking with me is whether we newsletter creators can apply this to our process.
What can we learn from mourning the special moments?
Does hitting send each issue feel like relief, or do we simultaneously miss the build up?
And what does experiencing our newsletters feel like to subscribers?
Should we read each issue thinking, “I’d like the reader to be a little sad when they’re done reading this?” Not because the topic makes them sad, but because the moment you just created for them is over?
I know, one can go back and reread a thing, but it’s never the same as the first time.
If your goal is to stir some sort of emotion and connection, is it also to create something good enough to mourn?
So good, in fact, that with each issue your subscriber remembers the way you made them feel and does not hesitate to open and see if this one also delivers?
Guess what people don’t love to read:
Stories that don’t have CONFLICT.
I intentionally use emojis in the subject line of this newsletter so I can scan the reply-to inbox and see which issues get the most direct responses.
And, no surprise, the ones where there’s actually a bit of plot in the intro get way more replies than the ones without.
Think about it.
You’ll hear people say, “Oh, that was such a good story.”
What they really mean is, “I was emotionally invested in the outcome.”
So it’s easy to understand why when I shared about my family’s struggle to get to our cruise port in time after a canceled flight, I got messages from people saying they’d stopped everything to read about it.
And it’s also easy to understand why a less conflicted story about how gemstone hunting (and the jewelry made from it) is like curating quality content results in less response. It teaches a lesson, but there’s not really anything at stake.
So… what am I getting at?
Should every issue of our newsletters drive intense emotional response?
I don’t think it’s possible.
Think about your favorite television series.
Sometimes it’s full of drama and surprise.
But there are also episodes dedicated to character and plot development, where nothing seems to happen.
They’re episodic in nature, moving the bigger story forward.
Our bigger story here is the universal conflict of being a newsletter creator.
We live in a land of conflict:
What to write about.
When to send.
How to grow an audience genuinely interested in what we create.
How to connect with that audience beyond the inbox.
All the opens and clicks and metrics tied to the unfolding of a narrative between you and the people who subscribe to the thoughts that burst from your brain.
Sometimes you will be on fire, telling an intense story.
Sometimes you will share little bits of yourself that help your readers without tapping into conflict.
And, perhaps, if you talk to them enough, you can bring them on a transformative journey that feels more like a weekly letter from a friend, where it seems like nothing really happened, but, in fact, so much actually did.
This week’s round up of newsletter tips and insights includes an article about owning the conversation (see Marketing). What conversation do you want to own, and are you doing that in your newsletter?
The air is pretty thin at 12,000 feet.
But also exhilarating.
Kind of like when you walk outside in winter just to feel the cold air in your lungs.
Except, you know, at 12,000 feet you’re more likely balanced on the side of a mountain.
At least that’s where I was last time I was in Colorado.
I think it was 2016.
My husband and I were taking a group on an aquamarine adventure on Mount Antero.
Yes. You read that right.
We were literally hunting for aquamarines.
Which meant we spent our days scraping rocks off of rocks, precariously perched on what felt like a glorified gravel pile, watching for little glints of light reflecting off the pale blue, dust-covered crystals.
The view up there, above the treeline (which is where we camped at 10,000 feet) was absolutely stunning.
But while the panoramic scene is incredible, you find aquas looking down, not out.
And if you’re looking extra carefully, you’ll miss the signs.
Those slivers of crystals look like bits of glass, but everything is covered in a brown dust, so you have to train your eyes to seek them.
We found a decent haul that trip.
On the last day, I took my time scaling the climb to a ledge where we’d been working for the past 2 days.
The sun was at a perfect angle for me to see that the mountainside was covered with tiny aquamarines.
I couldn’t pass them by, so I slowed down and collected one after another after another.
Most were tiny.
As I neared the top of my climb, I almost lost my balance and went sliding down when I saw an aquamarine about the circumference of a C battery. It’s 24 carats.
I wouldn’t have found it if I didn’t go so slowly, and it wouldn’t have seemed so massive if I hadn’t been picking up all the tiny ones along the way.
This past weekend, Sal gave me a necklace and earring set made out of a few of our aquamarines and some gold he’d found in Nevada to celebrate a special birthday.
It captures the memory as artwork, and reminds me of our adventure.
The process of finding them is not something most people would endure.
You have to really enjoy the moments of discovery and the moments building up to the next discovery.
Which is very much like curating and creating a newsletter.
There’s a lot to process.
Sometimes an article title or a new thought on a topic feels like it should serve my reader, then I dig deeper and discover the title is the best part.
And sometimes there’s highly relevant content waiting to be found and set into a lovely composition you’ll actually value.
If you’re curating content and contextualizing, get ready to spend some time on the mountainside doing what other people don’t have the patience or energy to do.
The air is thin up there.
3 lessons I’ve learned from newslettering
Note: I define newslettering as not only creating one, but also studying the genre via subscribing to newsletters and interviewing people who regularly hit “send.”
1) The best way to figure out if your plan is going to work is to try it.
I’ve talked to many people who are crippled by anxiety. They want 100% assurance of success before launching. It doesn’t work that way. You come up with an idea and you test it. Then you iterate and you test that. And the best chance you have at success is launching with an intention to help others, not yourself.
2) Consistently reporting on a topic is both a goal and a reward.
Subject matter expertise isn’t something anyone is born with. It takes immersion. Challenging yourself to stay on the pulse of a topic your readers care about makes you their guide. Assessing the value of curated content to their lives (“should this be included or does it fail to meet a quality standard I’m creating on the fly?”) helps you begin to recognize quality, form your own ideas, and become a part of the conversation.
Committing to serving readers is both a personal learning journey and a path to thought leadership.
3) Email newsletters are relationship growers.
Letters have historically been an intimate way of staying connected. From my earliest issues I noticed that the more vulnerable I was—and the more focused on specific audience members I’d personally spoken to (as if writing just to them)—the more my message resonated with all subscribers. Mary Ellen Slayter explained it well in an interview when she said that newsletters take 1:1 and make it 1:many, but that only works if you still write as if it’s 1:1.
And it takes time. Issue after issue of sending little pieces of yourself to all those 1s.
Last week I shared a particularly tense story and encouraged you all to persevere in your newslettering.
This week’s intro is not quite as thrilling, but, I can attest, the more you put into your relationships with subscribers, the more fulfilled you will be by the process.
We set an alarm for 3:15 a.m. so we could get dressed and leave my parents’ house by 4.
That would give us ample time (more than my husband thought we really needed, but he knows I have airport security line dread) to get to the New Orleans airport 1.5 hours away and catch a 7 a.m. flight to Orlando.
From there, we’d Uber to Port Canaveral and board the Carnival Mardi Gras around noon ET, with time to spare before final boarding at 3.
So as my phone beep, beep, beeped I thought a little 9-minute snooze was no biggie.
At 3:24, though, I jolted to reality when Sal announced that at 2:15 the airline sent a text saying our flight was canceled.
No “we’ll get you on the next flight out” offer.
No explanation for the cancellation.
After a quick search for alternative flights, we made what felt like an extremely risky decision:
On the chance that if we arrived between 3 and 4 p.m. ET (yes, after final boarding), that they’d take pity and let us on the ship.
We got the girls out of bed in a frenzy and were on the road at 3:45 a.m. with an ETA of 3 (but that obviously accounted for no stops or traffic… on a spring break Saturday).
We made great early progress.
Quick gas and bathroom stops.
Light traffic in the wee hours.
All good… ish.
Customer support opened at 9 ET, but even calling right at that moment got me on a “higher than expected call volume” loop that eventually became “give us your number and we’ll call you back.”
The call back came an hour later, and even then I was on hold for 20 or 30 minutes before I heard a real person’s voice.
She took my information and said she’d email the people in charge at the port in hopes that they’d make an exception. Our ETA at the time was 3:15 p.m. ET, but we knew we had at least one more gas stop to make.
While she had me on hold, Sal and I heard a low whistling sound that lasted about 10 seconds.
No. No. No.
I muted myself and asked what that meant. I was on hold anyway. Desperate that my only line to the cruise gods was going to reassure us they’d get us on the ship.
Sal was monitoring the slow-but-steady loss of all electrical elements on his SUV.
The SAME SUV whose condition for its age he’d been bragging about the day before.
“They say at 200,000 miles, it’s just getting started.”
Goodbye power steering.
Goodbye air conditioning.
Goodbye clock display.
He was thinking maybe it was the battery and if we just kept it running it would get us there.
20 minutes later it died on the side of Interstate 10, just east of Tallahassee.
And I was STILL on hold.
Sal’s expression said he was ready to give up.
But when I whispered, “Uber?” he nodded, “Yeah.”
I switched the hold over to speaker and tapped the app in hyperspeed.
Someone could be there in 25 minutes.
I went so fast it prompted me to slow down to approve a price first, but I didn’t really want to know.
He was on his way.
And, of course, the customer support rep came back on seconds later.
“They’ll call you as time gets close to leave dock to see how you’re tracking.”
Sal organized roadside pickup for the SUV and we told the girls not to lose hope.
Our 9-year-old took deep breaths and held back tears.
Our 12-year-old helped us all stay positive. “This will work!”
The Uber driver showed up, we packed our bags into his trunk, and we were moving again.
We left a vehicle on the side of an interstate.
This could work. Our driver was intrigued by our story and now committed to the cause.
We hit the Florida Turnpike and several rounds of stop-and-go traffic.
And then, CRASH.
He rear-ended someone in creepy, crawly traffic.
I’ve never seen 2 people settle a fender bender that fast.
They took pictures of the damage and each other’s license plates in what felt like 5 minutes.
Our 9-year-old was losing hope.
I held her hand.
She took even deeper breaths than before.
We passed through Orlando, Sal coordinating SUV repair (turned out the mechanic shop address was wrong and the tow truck driver recommended taking it to a different one) while I figured out that the airline was going to reimburse us up to $600 per person for alternative transportation.
And then we were there, ship in sight, still at the pier, and we rushed up an escalator to an older man who was shaking his head NO.
“Here’s how our day went.”
Cue real tears welling in the eyes of our daughters (maybe some in mine, too).
“Let me check with my supervisor. Do you have your vaccination cards and negative tests?”
They let us on the boat at 4:45.
And we had a blast.
…and a story that is almost painful to tell because I’ve had babies and this day was actually more stressful.
How to improve your newsletter with this story?
Give up and you miss the boat.