What I Learned From Publishing A Paid Weekly Newsletter for 2 Years

Photo by Nicole Honeywill on Unsplash

Maybe I should have been paying my subscribers instead, for all this insight…

It hurts to admit this, but I’m a longtime “wantrepreneur.” You know the type: someone with an entrepreneurial itch and a few ideas who’d rather buy another online course than actually do the work.

When I quit grad school in 2011, I never seriously considered finding a conventional full-time job. Instead, I cobbled together a grab bag of freelance income streams while I dabbled in tutoring.

None of these things were really going anywhere when I met my husband on OkCupid in 2013. Husband (Byrne Hobart) is the professional yin to my yang: intensely driven with stable goals over a long period of time. I admire that, but it’s not me.

I did eventually land and work 2 full-time startup jobs, one in New York and one during our brief stint in San Francisco, and both of these had lots of room for growth. But I wasn’t 110% bought in, which probably showed.

Instead, I bowed out of the workforce when we moved back to NYC a few months before my first daughter was born. Unlike some other stay-at-home-moms, I never dreamed of this future for myself. It just made sense at the time, and that was good enough for me. (Had we stayed in SF, I would have given working motherhood a try instead — we were on the waiting list for a billion-dollar daycare there).

Stay-at-home-motherhood certainly has its upsides. I’m thankful for the options available to us, living comfortably even on a single income. But I also didn’t envision never earning another dollar in my life. When all of my kids leave home, I’ll probably only be 55 or so!

So I wasn’t surprised when, in the brief window between my first daughter’s 1st birthday and my second daughter’s conception, I got the entrepreneurial itch again. It dawned on me that becoming a mother had given me new options, in terms of target market.

The quick launch

I quietly piloted and launched Just the Facts Mom (JTFM) about 2 years ago, in March 2017 (oops, I didn’t realize that Dragnet’s Joe Friday never actually said that until I went to link something here… ah, Nick at Nite).

Just the Facts Mom (a short email newsletter, sent weekly) was a very quick way for moms to get their news. It focused on health, relationships, and parenting-type material (no politics, fashion, or celebrity nonsense).

Tinkering to get everything up and running was great fun at first, I love teaching myself new stuff. JTFM was run on a simple stack of Mailchimp newsletter + Chargebee subscription processing + Stripe payments + Thrive Themes for the website.

At first, I just tried to get into the flow of producing content. I’d capture links on a Trello board as I stumbled across them during the week, choose links to add to my Mailchimp newsletter template, then write a couple hundred words of summary myself. Add a gif and a subject line… boom, newsletter.

The slow growth … very, very slow…

A pretty good handful of my friends signed up right away, at my low early adopter rate ($2/month). A few more crept in the door over the next month or two at $3/month. I even managed to sell a subscription to a stranger (never did figure out who she was!)

The newsletter’s churn rate was low — nonexistent, really. No one from my small but devoted group of paying subscribers ever unsubscribed. Given the low price of a few bucks per month, perhaps they just didn’t want to hurt my feelings. But the open rate also stayed very high, usually around 70%. Maybe that was all guilt-reading, but I doubt it!

I never added new subscribers with any consistency, though, because my marketing efforts remained extremely spotty. (More on that below). I kept going mostly because I liked writing the newsletter, and I kept telling myself that I’d do more marketing later.

Two years later

I recently pushed pause on JTFM. It seemed like a good time, as my dog and my dad had just died two weeks apart.

I wanted to give some thought to the past and future of the project. So I did. Turns out I’ve learned a lot. Here goes:

Goals are hard to set

On the one hand, I neither need nor want my side projects to turn into full-time employment, as I am already the full-time caregiver to 2 (almost 3) little kids.

At the same time, it’s so easy to fall victim to Parkinson’s Law, and freedom from immediate financial pressures is a double-edged sword. I was almost never late to publish the weekly newsletter, but always pushed the amorphous and less-pleasant marketing tasks to the side.

I intended to set some objective goals for the newsletter so that I could know if and when to quit. I never really did that. If this natural stopping point hadn’t come along, who knows how long I would have dragged it out?

Systems are everything

People who knew about my newsletter often remarked that it was amazing I could find the time to produce it. But, of course, I’d chosen a project that suited my strengths (reading & summarizing). Plus, thanks to some carefully-honed systems, I could produce each weekly newsletter in only about 2 hours of focused work.

The main problem is that operating a business, even a microbusiness like this one, contains many different kinds of tasks. They can be hard to prioritize and inefficient to switch between. So, even a less-than-perfect system for deciding how to do things, and when, can be really valuable.

I didn’t ever really develop any systems or workflow for marketing JTFM, so that part stayed painful. Very painful.

Marketing is hard

Guys, I just don’t like marketing. I’ve spent hundreds of hours in the past 5+ years consuming free and paid educational materials about marketing. I read and read and watch and listen… yet the pain and floundering continue.

I’ve heard all the talking points: marketing is about sharing your special gifts with the world, it’s about forming relationships, it’s about matching with customers in ways that make them delighted to give you money to solve their problems, etc.

I just hate marketing. I avoid even looking at my own sales page. I redid it several times over the past 2 years, with great dread and angst, and I still just hate everything about it.

Whatever you do professionally, if it’s not a conventional job at a company with division of labor to protect you, some degree of marketing-like responsibilities will fall squarely on your shoulders. This is an opportunity, and a challenge.

I don’t have much trouble with self-esteem or other types of self-promotion. I buy things from other people online all the time! But when it comes down to it, setting up a site, on my own behalf, asking people for money just… ugh. Not sure what to do about this.

Marketing content is even harder

There was a big old tension baked right into my business model: if you’re selling busy people content on the basis that it will save them time, how can you pique their interest (with content) without exhausting whatever ability/desire they had for consuming content in the first place?

It’s like giving people who are only a tiny bit hungry a big sandwich as a free appetizer. They’re not going to order much when it comes time to pay.

I didn’t want to publish bad free content as a way to market my (good) paid content. But I also didn’t want to give away all the good stuff.

It was also kind of tricky to differentiate to know when to produce content about news for moms (i.e. why moms need a better news source, i.e. mine) from the first-order news itself.

Paid newsletters work mostly for people who already have an audience

When I launched JTFM, I felt heartened by the emergence of paid email newsletters (and technologies for their dissemination) that I saw happening.

In particular, I had been keeping an eye on Rob Howard | Hiatus’s Hiatus newsletter ever since it was advertised to me on Twitter about a year ago. Hiatus promised weekly news for citizens who wanted to become well-informed by real information, not clickbait and noise. It was basically the general interest version of my mommy newsletter.

Howard seemed to take a real stab at making Hiatus work, he had clearly invested way more money and time than I ever did into his project (trademark, paid advertising, etc). He tinkered with the business model too, starting off Hiatus for free, then offering paid sponsorships, then moving to Patreon.

Hiatus shuttered not long ago (RIP). And I’m forced to admit that most of the thriving newsletters/Patreons out there are the side projects of independently/previously famous-ish and well-audienced creators.

I don’t have no audience, but I don’t have a huge audience. I actually converted a respectable percentage of my existing mom audience to the newsletter. It’s just that 1% of a modest number is… a much smaller number.

It’s hard to deal with slow news days

Once people were paying for my newsletter, I really had to deliver it. But the world didn’t always oblige. Some news weeks were genuinely slow, without much of interest to report.

I would have liked to skip the newsletter on those weeks, or to send a shorter one, because my overarching goal had been not to engage in clickbait and other stupidity. Instead, I sometimes ended up sending links that I wasn’t thrilled to share. Ick.

It feels bad to do bad work

I’ve done bad work (and known it) plenty of times in my life, especially for school. But I really felt extra bad on those days when I sent a less-than-very-good newsletter.

A few entrepreneurs are sociopaths I guess, they just want to take money and run or they eat their seed corn customers. But I believe in the idea that you can (often) find a way to align your strengths with what the market wants, to everyone’s benefit. From this perspective, bad work feels bad! It’s defecting from the deal.

I am not a brand

At first, it felt very official to have separate Facebook and Instagram accounts for my newsletter. I dabbled in Facebook Live, which was actually fun. I really meant to launch a big social media thing in support of JTFM. Every week, I made a few to-dos, to post stuff for marketing purposes.

As time wore on, though, I mostly just felt guilty for neglecting these — while never mustering the motivation to market more in this way. I didn’t really want a big mass social media thing around my content, I didn’t want to moderate comments from randos, I didn’t want any of it.

The truth is that I am not a brand. And I am definitely not a brand with a simple shtick, though I tried to be one for a while. Some individuals pull this off, but I am just a person. An eclectic, sometimes-interesting, trying-to-be-thoughtful person with a lot going on. But just one person.

I would rather interact with the world straightforwardly as myself. So that’s what I’m going to do. Relatedly…

What’s next

Well, it’s a line of work that allows me to interact with clients as myself, and one at a time, instead of en masse through a brand. I’ll announce the details soon, you can sign up here to be the first to know.

I’ll stop publishing JTFM indefinitely, though my commentary on parenting and parenting-related news will remain available everywhere else you find me (Facebook, Twitter, Instagram, Medium).

Thanks for coming on this long, weird journey with me. 🤗