How not to f*ck up your newsletter

Or: how to navigate the increasingly dark and deep sea of 2025 “growth hack” listicles

Hi,

When Erin Shetron emailed me out of the blue to ask if I would host this essay since she didn’t think it fit on her publication, I believe my exact words were “F*ck Yes! I’m in.”

Usually, we don’t go in for all the cursing, mainly because a subset of our audience doesn’t like it, and nobody has unsubscribed from a newsletter because of too much cursing.

I think an exception was warranted in this case. Enjoy!

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To anyone currently bingeing all the "how to hack your newsletter growth in 2025" listicles floating around lately: I see you, I love you, and I’m worried about you.

As someone who’s spent the last two years producing and growing over 60 newsletters (and the previous five years as a marketing director), I deeply understand the slightly sickening but mostly heady, hopeful allure of these articles.

Which is how I also know that, if blindly adopted for your own newsletter, much of the advice in these articles can accidentally fuck your shit up.

So, I present for your consideration (and sanity): Eight recommendations to help you navigate the increasingly dark and deep sea of “hacks,” “tips & tricks,” “takeaways,” and “keys” to growth. If you’re keen to grow your newsletter this year without accidentally fucking it up, this is for you.

1. Practice healthy skepticism, namely about who benefits most from the “how to grow” content you’re consuming. For example, if you are reading an article from a person or group who makes it their whole thing to publish “how to grow” articles, just know that while they absolutely have incentive for creating good, useful content, they have even more incentive for gaining: readers/subscribers, opens, and clicks. Why? Because increasing these kinds of metrics increases the chances to sell subscription upgrades, goods and services, and ad space. Basically, pumping out these types of articles makes money. Like my 7th grade history teacher always said, if you’re curious why anything is playing out the way that it is, follow the money. I’m not here to vilify making money—I, too, require money to live—I’m just suggesting adopting some skepticism when deciding which “growth hacks” to try, especially when they’re written by anyone turning a profit by constantly creating and pushing said hacks.

2. Practice discernment. “This worked for this other person!” Yes, but that other person is selling financial literacy classes and you are trying to paywall your personal essays about life on a ranch. When consuming growth strategy advice, remember to discern the differences between your newsletter (including its goals, topics, purpose, and audience) and that of whatever case study is being presented.

3. If it sounds too easy, it is. I just got an email that was all about “one way to get a 19x ROI.” The tip was to sponsor, AKA run ads, in their newsletter. At first blush, you might think (because they are literally telling you) that all you have to do is buy an ad in this newsletter and you’ll make 19 times whatever you spent on that ad. Upon further investigation, however, you’ll learn that the minimum ad spend is $3k and they are estimating you’ll get 30 qualified leads. Even if they could somehow guarantee a cost of $100 per qualified lead (they can’t), you’d need a 3% conversion rate to turn just one of those leads into a paying customer. Then, to reach that 19x ROI, that one customer would have to pay you $57k. For some businesses that might be reasonable, but for me and basically everyone I know, running $3k worth of ads in a newsletter does not usually drum up enough clients to earn $57k.

4. Consider saturation. Ask yourself, if every single person reading this list took this advice, would the advice still work? This is one of my favorite ways of discerning worthwhile advice from turds in a toilet. Often, if everyone took the same advice, competition would increase, demand would drop, and worst of all (to me), your newsletter would be like everyone else’s.

5. Cultivate an eye and intuition for “right place, right time.” So much of growth strategy, although not many would admit it, is about being in the right place at the right time. When reading through case studies and testimonials, remember that the biggest success stories you’ll see always have a “right place, right time” element to them, though you won’t see it written about. Moreover, anyone who says “I did this specific thing that grew my newsletter, and if you do that exact same thing then you will grow your newsletter to the exact same extent!” doesn’t understand strategy. They are just someone using their “right place, right time” to gain your attention and, you guessed it, make money. And don’t confuse “right place, right time” for luck or happenstance; the more you can develop a knack for putting your work in the right place at the right time, the more you’ll grow.

   1. Some examples of right place: Highly prominent/visible ad placement, especially open/curious audience, highly novel offering, low competition. Ask yourself: is this the best place for my work?

   2. Some examples of right time: You’ve been working on your craft, dialing in your voice, and your branding’s on lock. Your work speaks to a current event, relevant quandary, or topical theme. Your audience has been primed and is eager to receive from you. Ask yourself: Is this the right time for my work?

6. Filter strategies through your values, your goals, and your gut. A good, sustainable strategy will align with your values, help meet specific goals, and spark that “yes, let’s fucking go” from your body. There are so many strategies to try, and the ones that feel right to you will almost always perform better than the ones that feel off. I’m not a mystic so I don’t know why this is true, just that it is. Mystics, sound off in the comments!

7. Keep your dopamine gremlin in check. That gut feeling I just mentioned? Don’t mistake it for the dopamine gremlin inside you that’s currently high off the possibility of growth, productivity, and recognition. We’ve all heard the Edward Abbey quote, “Growth for the sake of growth is the ideology of the cancer cell.” It’s also the ideology of the dopamine-deprived. Regulate your nervous system, get clear on your goals and values, and don’t let that greedy little dopamine gremlin behind the wheel.

8. Adopt a testing mindset. If scouring growth hack articles is your jam, honestly I love that for you. There are so many solid, useful ideas out there! Despite what the articles might say, the only surefire way to know if a growth strategy will work for you is to test it. A testing mindset looks like…

   1. Acknowledging from the outset that the strategy may not work

   2. Tracking the results with non-judgment, curiosity, and discernment

   3. Not panicking and cutting off the experiment too prematurely (before there’s enough information to prove a result)

   4. Not engaging in sunk-cost fallacy and keeping the experiment running even after the results are not what you’d hoped

A few “growth hacks” I like, as a growth strategist and editor:

1. Hone your voice above all else. Yes, work on craft. Sure, publish consistently. Yes, produce work you’d covet if someone else produced it. But before you try pinning down a niche for your newsletter or taking another workshop or setting up another color-coded content calendar (@ me) or reading another “growth hacks” listicle, the single piece of growth advice I can’t overstate is this: Find. Your. Voice. Whether you’re writing how-to articles, conducting interviews, culling pop culture recommendations, or doling out micro-fiction, find your voice. Find your voice so that your writing is unmistakably yours, no matter what you’re writing about. Find your voice so that your narrator and characters and recommendations and observations float off the page. Find your voice so that you can publish anywhere and people will say, “Oh shit, who is the person behind this?”

2. Do it your way! Reinvent the wheel! Make it weird! Seriously, people are inundated. People are trying to cut down on screen time. The more you can get in touch with your creativity to produce a newsletter that’s unique, surprising, and yours, the more people will fall in love with and share your work. Creativity is contagious, and bringing your own unique creativity to your newsletter is an invitation for everyone reading it to engage in their own creativity.

3. Pitch your work audaciously. Getting in front of new, relevant audiences is essential… actually, it’s so essential that it feels a little stupid typing it out, oops. Anyway, pitching your work to writers, interviewers, podcasters, etc. who are new to you/your readers can be extremely advantageous to growth. Even if the newsletter or outlet you’re pitching to seems like a reach, pitch anyway! To me, the most important aspects of a pitch is relevance of the topic and high potential for audience appeal. Take this article as an example: I emailed Russell a pitch for what I thought would be highly relevant and appealing to his audience, and even though I don’t have a high subscriber count, he accepted! And now my unhinged opinions astute recommendations are reaching new folks who’ve probably never heard of me. Hi!

4. Email free subscribers separately. If your goal is to get more of your free subscribers to upgrade, there’s a lot of conflicting opinions out there about how often to paywall, what to paywall, etc. In my experience, I’ve seen the best results by simply remembering to email these folks before a paywalled piece goes live. Keep it simple, keep it friendly, and keep it relevant. Like a press release, there’s gotta be a good reason for writing to them. Your reason is a new banger of a paywalled post that’s about to get published. Every so often, use the filter tool to send an email to free subscribers only. Tell them why they’ll love your upcoming post, invite them to upgrade, and thank them for sticking around even if they don’t upgrade. Then make sure to send them a free preview to the paywalled post.

5. Throw money at the problem. Commerce over capitalism! Spending intentionally! Supporting solopreneurs and small businesses! Feminine economy! If you’re like me, it’s not likely that you’ve got a bunch of extra cash to throw around, so this advice may not be for you. But if your growth goals are on a timeline (maybe you are shopping your book next year or launching a workshop or turning on paid subscriptions), spending some money in the right places can help get you there. Do not rush, do not make this choice out of fear, and do not spend money you don’t have. If you have the budget and you’re already doing the work to grow organically, here are some places to consider spending your money:

   1. Newsletter classifieds. I love how old-school and straightforward these feel, and I love that it’s a surefire way to get in front of new, relevant audiences. The click rates aren’t usually high from my limited testing, so temper your expectations, but still—I’ve definitely seen that the right ad in the right newsletter can send along new readers. (I’m currently working on a private directory of classifieds as another perk for my clients - comment or DM me to add yourself or someone you know to this list!)

   2. Paid social media ads. It’s easy to throw away money on social media ads, so I’m hesitant to share this. But having run a few tests myself, I’m cautiously optimistic that this is a viable way to improve brand awareness and gather leads for digital goods and services like workshops, consultations, and courses. Russell has a whole course on creating profitable FB ads)

   3. Get help placing essays. Writer’s Relief is a company that will create lists of good target magazines for your work based on the length, themes, submission windows, etc. They will also take care of the actual process of submitting for you.

   4. 1:1 Strategic + editorial consulting with an experienced professional (this is what I do). You can be the most together, most genius, most efficient, most creative person at producing your newsletter, but it still doesn’t negate the fact that two brains are always, unless the second brain sucks and is mean, better than one. There is nothing more helpful than having a skilled professional review your writing, your branding, and your strategy. Not because they have the answers, but because together, in joint pursuit of creating something honest, captivating, and remarkable, you start seeing the creative solutions and opportunities you hadn’t seen before.

Before I go, a huge shout-out to Valerie Monroe of How Not to F*ck Up Your Face for the inspiration behind the title of this piece. Valerie is not fucking up her face or her newsletter, please go check her out!

Happy strategizing! See you in the comments!

—Erin

Erin Shetron is a frequent crier and strategist to the (Substack) stars. You might recognize her from her popular interview with Amanda Hinton, her oops-too-personal life updates on Notes, or mentioned in Substack circles as “someone I hired for newsletter guidance because Alex Dobrenko called her a Substack whisperer??” With a background in creative nonfiction and poetry along with years as a marketing director, she now helps writers and entrepreneurs produce their best, most impactful work while honoring their creativity and wellbeing.

Erin enjoys walking her elderly dog, kick-chalking her pool cue, reading fantasy novels, dreaming about the feminine economy, and espousing the benefits of radical, unabashed, loving honesty. A Philadelphia native and proud Temple University alumna, she now lives in Oregon with her boyfriend and dog, who you may hear snoring in the background of your calls (the dog, not the boyfriend).

If you liked that one, I highly recommend Erin’s publication. I feel like she literally works with all the coolest, hippest, most successful Substacks, and she is a great writer, too.

What do you think?

• Do you feel better about your Substack journey now that you’ve shaken off the shackles of growth articles?

• Are you hyped to get back into the Substack saltmine?

Let us know in the comments.

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Photo by insung yoon on Unsplash