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Becoming a Dad Changed the Way I Think About Newsletters

Fatherhood changed the way I ask questions, handle mistakes, and even write alt text. Here’s what I’ve learned that I apply to my work.

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My son, our first child, turned one recently. I expected fatherhood to change just about everything about my life — less sleep, less free time, lots more dirty diapers. But what I didn’t realize was that becoming a dad would change the way I think about work and reframe the way I think about a lot of my daily tasks.

I used to cringe when a favorite songwriter had a kid and then wrote a song about new parenthood. I cringed when I saw some bro on LinkedIn try to turn something their kid did into a lesson about work or when a celebrity wrote a book about how to parent. 

And now I’m doing that here! But I really did learn a few things this year, and I wanted to share them with you. (Because dads like to share wisdom — or whatever they think is wisdom.) Whether or not you’re a parent, I hope you’ll take away a few lessons, too.

(And Ben: Happy birthday!)

Here's a decorative image of three animals: An owl, a flamingo, and a seahorse

Feel free to ask your dumb questions

I was a new dad who’d never changed a diaper when Ben was born. The only thing I knew for certain was that I knew nothing. I just knew I would ask something dumb — eventually, at least. 

It took me 45 seconds to come up with my first dumb question.

Ben arrived, and the doctors called me over to a little scale where they were weighing him. I looked down at his tiny feet. They were black.

I hadn’t remembered reading anything about black feet in any of the parenting books.

So I asked them: Are his feet supposed to be black? Is that normal?

That’s when they held up a piece of paper with his tiny footprint. They’d pressed his feet in black ink to make the footprint.

It was the first of many, many stupid questions.

But getting that first one out of the way really did help! With a baby, new stuff happens all the time, and I quickly became unafraid to ask, even when I knew the answer would be obvious. I didn’t have to preface questions with, “I know this might be a dumb question, but….” I just asked.

I’ve tried to apply that to my work. I’ll often be on a call with a new client, and they’ll use jargon I’m unfamiliar with or refer to a metric that needs clarifying. I have to remind myself: There’s so much I don’t know, and there’s no reason to pretend like I know everything. If anything, the people I talk to appreciate that I want to understand what they’re discussing.

Even when it feels like it might be a stupid question, I now just ask.

Reset your approach to your to-do list

Weekends are different now as a new dad. Before my son was born, I’d typically spend a little time on the weekend catching up on some work. I run a one-person consulting business and also publish this website, but being kid-free meant that I could tackle a few tasks whenever I had a bit of free time. That might mean a little time on a Saturday morning to write and then time on Sunday evening prepping for the week ahead. If I had the time, I might cross a few other items off my to-do list.

But this year, the routine had to change. What I realized is that on a weekend with a baby, I might be able to carve out two or three hours for work. In that window, I’d only get one or two things done.

At first, being so seemingly unproductive on a weekend felt like a failure. I’d find myself feeling stressed on a Sunday night about how little I’d accomplished.

What I needed was a shift in mindset. Getting one or two things done on a weekend wasn’t a failure — I’ve got a kid now! I’ve got other responsibilities! This has helped me redefine what a priority truly is, and also to rethink how I approach the notion of productivity.

At this stage in life, if I get those one or two weekend tasks done, that’s more than enough.

Ben sits on my legs while I sit on our light-colored couch. I'm wearing a black polo shirt and pink-and-black-striped socks. Ben was at the age where he was still small enough to fit comfortably on my lap. (That wouldn't last long.)

Good ideas can come from anyone

A few weeks after my son was born, we hired a photographer to take some pictures of our family. Midway through the photo shoot, Ben got hungry, and I grabbed a bottle to feed him.

When it came time to burp him, I put Ben into the position the nurses showed me at the hospital: his chest on my shoulder while I gently patted his back. But I couldn’t get a burp out, which stressed me out, least of all because it was happening in front of a stranger.

“Would you like me to show you how I do it with my kids?” the photographer asked. She had four children at home, so she had plenty of experience. 

I handed over Ben and watched as she propped him up on her knee, tilted him gently forward, and placed her hand on his back.

Before she could even pat his back, Ben let out a massive belch. (Until then, I’d been unaware that a child that small could make a sound that large!) Naturally, that position became my go-to any time I needed to burp my son.

That day was a reminder: Good advice and ideas can come from anyone. Experts are all around us. You just have to make space and listen.

Little mistakes happen all the time

A few years ago, before Ben was born, I was babysitting for a friend’s kid, who was then about a year old. We were sitting quietly together on the floor when he started pulling himself up onto an ottoman. All of a sudden, he tumbled, cut his lip, and began bleeding everywhere and screaming.

I was able to clean the child up and calm him down — but still, I was mortified. My friend had trusted me to watch their child, and I’d managed to screw things up! There were tears! Blood! I’d broken the child!

When my friend got home, I shamefully explained that I’d screwed everything up, and if they needed to take my first-born child as a replacement, I’d understand.

They laughed it off. Tears? Blood? A bad fall? That happens a few times a month, they told me.

I thought they were just trying to make me feel better, but now I’ve got a kid at about that age, and I watch my son stumble and fall all the time. It happens, and he never seems all that bothered by it. He cries, and then he gets back up and tries to stand again.

When you’re new at something, the little mistakes all seem big. It helps to talk to someone who’s been there and can put things in perspective. That typo you made today in your newsletter? It’s a little thing — we’ve all been there. You don’t need to sweat it.

Write alt text the way you read your child a story

When you include images in an email, remember that not everyone will be able to see them. Some subscribers have images turned off, and others use a screen reader to read aloud the email. But there’s a way to make sure those readers can understand what they’d see if they could see those images: alternative text, also known as alt text.

Anytime you insert an image into your email, your email service provider will allow you to add alt text. Even though using alt text is an accessibility best practice, many writers insert nothing or insert unhelpful copy that doesn’t really describe the image. (“This is a photo of a duck.”)

So let me try to explain how to write alt text the right way.

Every night, I read my son a bedtime story. With a child of this age, reading a story isn’t just about reading the written text. On every page, I also describe what’s happening.

With bedtime approaching, my son and I read along to a copy of “The Watermelon Seed,” by Greg Pizzoli. As I explain the basic concept of the book — a scared crocodile believes that he’s swallowed a watermelon seed and that that seed will grow into a whole watermelon inside his belly — my son points towards the book in his blue, striped pajamas and gives his father false hope that he’s fully understanding the lesson of the story. (He does not; he just likes pointing at things.)

Take one of my son’s favorite books, “The Watermelon Seed,” by Greg Pizzoli. It’s the story of a crocodile who swallows a seed and thinks a watermelon is growing inside him. On one page, the crocodile says, “It’s growing in my guts!” But after I read that, I explain what else is happening on the page: “The crocodile imagines being inside his own stomach, and in there, he imagines looking at an X-ray of his belly. The X-ray shows a big, green watermelon rapidly growing inside him and stretching out his stomach!”

That’s alt text.

The next time you have to write alt text, imagine yourself describing the image, in colorful detail, to a toddler. Do that, and you’ll write great alt text for your readers — and make your newsletter more accessible to all in the process.

Your peers will grow at different rates than you, and that’s fine

Ben spends a lot of time hanging out with four other babies, all of whom were born within a few weeks of each other. Some of his friends have multiple teeth; some have none. Some can talk, and some barely even babble. Ben is nearly 10 pounds heavier than one of his friends, even though she’s two weeks older. (Ben is in the 98th percentile for weight and above the 100th percentile for height, which I didn’t know was possible. I figured 100 was as high as you could go!)

All of this is totally normal since everyone grows at different rates. That doesn’t stop me from worrying half the time. Ben’s friends are starting to walk — why isn’t he?

Then I’ll go to work, and I’ll chat with newsletter operators who are worried that they’re falling behind. They look at other newsletters, many of which started around the same time, and wonder: Why do they have more subscribers? Why do they make more money?

I’ll tell them what my pediatrician has told me a few dozen times this year: Don’t get caught up comparing yourself to others. Some newsletters grow faster than others, and that’s OK. Focus on your next milestone — whenever it happens, it happens. And, as your newsletter (or child) matures, there will be new yardsticks by which to measure them, so try not to get hung up comparing metrics. Just remember that other newsletter operators are just as concerned about their baby’s milestones as you are about yours!

Just try it

A few weeks after Ben was born, we went to visit his grandfather. His apartment building has a heated pool.

So, a week before the trip, we had this conversation with our pediatrician:

Us: Is it safe to take Ben in the water at this age?

Pediatrician: Sure! Just see if he shows interest.

Us: And how would a ten-week-old show interest?

Pediatrician: Put him in the water, and if he starts screaming, he’s not interested.

Honestly, it sounded like our pediatrician was just making this up. But we followed her advice anyway — good advice sometimes sounds a little ridiculous. We put our kid in a suit, placed a floppy hat on his head, and gently cradled him in the shallow end of the pool. Did he show any sign of actually enjoying the pool? Not really. But did he scream? No! And at that stage, for two brand-new parents, that was a pretty big win.

You don’t know what will work until you try it for yourself. So if you hear a great idea that worked for someone else’s newsletter, try it with your newsletter and see what happens. The pediatrician’s advice applies here, too: If your audience freaks out after you try it, that’s your sign to stop.

Other people do things differently (not necessarily better or worse)

The first few times I saw my parents and in-laws babysit my son, I’ll admit: I almost lost it.

I had developed a certain way of doing things with my son. I had my way of holding him, my way of changing him, my way of feeding him.

The grandparents never did things the way I did them.

At first, as I watched them babysit — and do things entirely wrong, at least in my expert opinion — I wanted to correct every little action. Then, my wife and I came to an agreement: If we were going to delegate responsibility to them, we had to delegate fully. If someone else was watching Ben, we told them what they needed to know, offered the chance to ask follow-up questions, and then left the apartment.

The only thing that really mattered when I came back was that my son was OK. I didn’t want to know what happened while they were on the clock. They’d kept the kid alive — that was really all that I cared about.

As Inbox Collective has grown, I’ve brought on some help. Claire edits the stories you read on this site and makes them a lot better. Nataasha — the wonderful assistant I found through a company called Oceans — takes care of a lot of the odds and ends of the business. My job is to delegate, not micromanage, and let them do their thing. They don’t do their jobs exactly how I do them, but they do their jobs wonderfully — and they do the work that needs to be done.

Visually guide your audience

We take Ben to a baby music class a few times a month. The instructors there do a fascinating thing: As they sing, they also use sign language. Between the verbal and visual cues, the idea is that the babies will start to learn certain behaviors a bit faster.

I’ve been thinking a lot about this in the context of some of my favorite newsletters, many of which use both written and visual cues to help readers navigate their newsletters. They might use design elements — numbers, bolding, or icons — to help readers quickly find what they want. They’ll tell readers at the point of sign-up or in a welcome email when to look for the next issue. Or they’ll close an email with a preview of next week’s newsletter as a way to build anticipation.

It’s a nice reminder: Some readers sit down ready to dive into the full text of what you’ve written, while others scan for a bit of information. Adding multiple cues helps each reader get value from your newsletter.

Not everything works all the time

Some days, when we feed Ben, he’s so eager to eat. On other days, he takes his food and flings it everywhere. And then the next day, he’ll eat like he’s never eaten before.

Same baby, same food — completely different reactions. As a parent, seeing your child suddenly reject food can be disorienting and upsetting.

And I’ll see the same thing happen with newsletter audiences. Sometimes, you work hard on a newsletter, and the audience dives in, eager to read and reply. Other times, you do something big and hear crickets.

Every newsletter gets a slightly different reaction. Don’t be too hard on yourself if one email gets an underwhelming response. Chances are, the response to the next newsletter will be better.

The breakthroughs happen when you least expect

A baby goes through a remarkable string of milestones in their first year.

But what’s incredible is how often these milestones sneak up on you, the parent.

I remember one morning a few months ago. I left him in the living room, where he could roll around and play with a few toys. I just needed to grab one thing from the fridge. I wasn’t worried about him going anywhere.

And then I looked down and saw Ben. He’d decided, for the very first time, to crawl all the way from the living room to the kitchen. No notice, no warning — it just happened.

The breakthroughs with your newsletter follow a similar pattern. You’ll try something new, like a new growth tactic or a new way to monetize your newsletter. You’ve done lots of stuff like this over the years. Sometimes it works OK, and sometimes it doesn’t. 

But this time, things are different. The response will be overwhelmingly positive.

You always hope that the good stuff is coming, but it usually doesn’t show up on a regular schedule. There are a lot of forms a milestone can take, so when you have a win, even a small one, take a moment to celebrate.

Through good days and bad, you have to keep doing the work. Sometimes, if you’re really lucky, you get the chance to take an unexpected step — or, I suppose, crawl — forward.

Thanks to our sponsor
The stories you’re reading on inboxcollective.com are made possible thanks to the generous support of our summer sponsor, GetResponse. They’re an email marketing and automation platform with comprehensive, affordable, and easy-to-use tools to grow, engage, and convert your audience. If you’re looking for a platform with powerful automation and monetization tools, give GetResponse a try.

By Dan Oshinsky

Dan runs Inbox Collective, a consultancy that helps news organizations, non-profits, and independent operators get the most out of email. He specializes in helping others build loyal audiences via email and then converting that audience into subscribers, members, or donors.

He previously created Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better email, and worked as the Director of Newsletters at both The New Yorker and BuzzFeed.

He’s been a featured speaker at events like Litmus Live in Boston, Email Summit DK in Odense, and the Email Marketing Summit in Brisbane. He’s also been widely quoted on email strategies, including in publications like The Washington Post, Fortune, and Digiday.