Originally published on The Strategic Ampersand Substack · 7/15/26

Years ago - as in pre-pandemic - I attended a newsletter session at a conference that lasted all morning. Having been to numerous email sessions at various conferences over the years, I expected the usual: open rates, subject line formulas, send time optimization charts. <insert yawn>

Instead, the speaker made a clear, human case for why we needed to treat newsletters - subscriptions, email marketing, all of it - with genuine care. Not just technical precision. Care.

For example: A giant snowstorm in the forecast? Create a segmented audience email that not only notes the perfect product from your catalog, but have it be SECONDARY to offering safety reminders and regional warming centers links.

The impact was so great I started focusing more and more on helping clients with their newsletters - and eventually ended up on the other side of the conference room, presenting what I’d learned over the year or so since sitting in that morning session. My talk’s perspective: a great newsletter strategy is no different than dating.

Why dating? When someone subscribes to your newsletter, they’re saying yes to a first date. They liked what they saw. You’ve moved from Instagram handle to actual phone number. They’re willing to give you their time and inbox access; which, if you’ve ever tried to clean out an inbox, you know is not nothing.

What you do next determines whether there’s a second date, a tenth date, or a quiet unmatch - or if a boundary was crossed: “don’t ever contact me again” text… so let’s not go there.

What follows is a distilled version of that talk updated for 2026. While a lot has changed since 2019 (hello Substack, goodbye Tumblr), the fundamentals? Remarkably intact. Buckle up, Buttercup. This will be fun.

Speaking of Substack: there’s a note at the end noting a high-level difference between newsletters and Substack.

CONSENT. CONSENT. CONSENT.
The First Date Only Happens if They Say Yes

1. Authenticate your email. SPF was the standard in 2019. In 2026, the acronym triplets - SPF (Sender Policy Framework) + DKIM (DomainKeys Identified Mail) + DMARC (Domain-based Message Authentication, Reporting, and Conformance) - are the baseline; Google and Yahoo made this mandatory for bulk senders in 2024. If you’re not set up for all three, your newsletters may never reach the inbox regardless of how good they are.

2. Opt-in only, always. No exceptions. Buying a list, scraping contacts, or adding people because you met them once at a networking event is the email equivalent of showing up uninvited to someone’s doorstep after you met them at a bar. Don’t. Do. It.

3. Double opt-in. Two yeses are better than one; and your list will be cleaner, more engaged, and more valuable for it.

4. Follow GDPR, CAN-SPAM, and CCPA. The rules have expanded since 2019. California’s CCPA joined the mix, and more states have followed. Know which laws apply to your audience, not just your location.

5. Remind people how they signed up. Every opt-out email should include a clear, human reminder: “You’re receiving this because you signed up at [X] on [date].” It reduces spam complaints and respects the relationship.

UNDERSTAND THE PLATFORM
Because Reading on a Tiny Screen is the Default Now

6. Respect your readers’ time. Every word should earn its place. If you wouldn’t read it yourself at 7am on a Tuesday over your first cup of coffee, don’t send it.

7. Mobile first. Desktop second. In 2019 this was “design for desktop, keep mobile in mind.” In 2026 it’s simpler: design for mobile, test on desktop as an afterthought. Over 60% of email opens happen on a phone.

8. Single column for skimmers. Still true. Your newsletter isn’t a printed newspaper. Multi-column layouts break on mobile, confuse the eye, and signal a cold “hey everyone” rather than a warm “I wrote this for you, Gentle Reader.”

9. Offer a plain text option. Originally framed around smartwatch users, now extend this to wearables, car displays, and anyone who reads email in an accessibility context. A clean plain text version is a gift to a wider audience than you think.

USE YOUR WORDS
Content Decisions Make or Break the Relationship

10. Skip image-heavy newsletters. Images slow load times, get blocked by default in many email clients, and can make your newsletter completely unreadable for someone on a slow connection. If the newsletter only makes sense with the images, it doesn’t make sense.

11. Always write alt text. If an image fails to load, the alt text is what your reader sees. Make it descriptive and useful, not just “fun-image1.jpg.”

KNOW THY READERS
Say Their Name, Not a Pet Name

12. Say their name by personalizing the To: field. “Hey [FirstName]” still works. “Hey Buddy” does not - unless a subscriber’s name is Buddy, but I digress. Including their actual name instead of a generic one shows you care. If your email platform can’t personalize the greeting, it’s time to find a new platform.

13. Say your name by branding your From: name. “newsletter@” is not a name. Neither is a string of numbers. Send from a recognizable name - ideally your name plus the brand - so recipients know immediately who it’s from before they open it.

FIRST IMPRESSIONS MATTER
Subject Lines Are Invites

14. Understated sophistication wins. The era of “OPEN NOW!! 🔥🔥🔥” subject lines is over and is the equivalent of “hey u up?”- spam filters and reader fatigue killed it. Specific, curious, and human beats loud every time.

15. Words, sentiment, and emojis all carry weight. One well-placed emoji can add warmth. Three in a row signals desperation (see #14). Test what resonates with your specific audience. Don’t assume.

16. Test across demographics and devices. A subject line that feels fresh to one reader feels out of touch to another. Dark mode, different email clients, different screen sizes. Test broadly.

17. Smart preview text is your second subject line. The preview text - the snippet that appears after the subject line in most inboxes - is one of the most underused pieces of email real estate. Write it intentionally, every time.

EYES UP HERE
Above the Fold Details Gain Interest

18. Include a “View in Browser” link. Still standard. Still often forgotten. Still appreciated by the reader whose email client is doing something weird.

19. Brand your header. The header is *you” in branding form. It should look like you, every single time, so readers know immediately who they’re about to grab a table with.

20. Say their name again. You said it in the To: field. Say it again in the greeting. It signals the email was written for a person, not corporate list broadcast.

21. Lead with something worth seeing. An image, a gif, a bold statement - something that earns the scroll. Dark mode note: test your hero image - and your entire email - in both light and dark mode before sending. What looks stunning in one can look broken in the other.

FOCUS ON THEM
What You Think You’re Saying Vs. What They Actually Read

22. A nickel for every word drafted in. A dime for every word edited out. It’s still the best editing rule I know aside from Hemingway’s “Write drunk. Edit sober.” The tighter the writing, the more respect it shows for the reader’s time. This one will never expire.

23. Lead with value before the sell (or sale). Does an initial discount code help bring folks in? Sure - but don’t make it the only reason folks wait to come back. This tactic was - and remains - a super common mistake by constantly promoting sales, discount codes, and similar tactics that dilute the brand’s value - and creates “discount loyalty,” which means folks only patronage when there’s a discount. The fix? Create a relationship by giving something genuinely useful - insights, tips, and updates - and lets the subscriber know you appreciate their time with you; before you make the ask, like to buy, reserve, or donate.

24. A clear CTA button. One primary CTA per email, maximum. A newsletter with five equally weighted buttons has no call to action at all - it just has buttons.

25. Write for the reader, not for yourself. What does your audience actually want from this email today, in the context of their lives? Not what you want to tell them. What they want to receive. No one likes a taker, so be a considerate giver.

26. Connect content to your site. Every newsletter should have at least one path back to your website - a deeper read, a resource, a page. The newsletter starts the conversation; your site continues it.

KEEP ONE FOOT ON THE FLOOR AT ALL TIMES
Footers are the Part Brands Often Skip Crafting While Subscribers Search For It As If It Were An Escape Hatch

27. Build a footer template and use it every time. Consistency here is legally and relationally important. Your footer is the contract; it should always include the same core elements.

28. Make the unsubscribe link obvious. Hiding it in 8pt gray text on a gray background is not a retention strategy. It’s a spam complaint waiting to happen.

29. Offer a “share with a friend” option. Word-of-mouth is still the most powerful growth channel for newsletters. Make it one click.

30. Link to your social platforms and website. The footer is where people go when they want more of you. Give them somewhere to go.

PLAN FOR HUMAN INTERACTION, NOT MACHINES
Use Your Email Platform Smartly

31. Use funnels with clear intent. A welcome sequence, a re-engagement sequence, a post-purchase sequence - each should have a purpose and an end point. Automated doesn’t mean thoughtless or set-and-forget.

32. Segmentation matters more than ever. “One size fits all” was already questionable in 2019. In 2026, with AI-powered personalization accessible to brands of every size, sending the same email to every subscriber regardless of location, behavior, or interest is leaving real engagement on the table.

33. Celebrate your readers. Anniversaries, milestones, birthdays if you have them - small moments of recognition build loyalty that no campaign can manufacture. This one is chronically underused.

34. Schedule with awareness. Calendar awareness - holidays, news cycles, cultural moments - still matters. What’s new: send-time optimization is now standard in most platforms - tools that send each email at the moment each individual subscriber is most likely to open it. Use it.

CREATE FOR A HUMAN, NOT AN ALGORITHM
The Newsletter-To-Platform Pipeline Matters

35. Adapt newsletter content for each platform. Not “edit.” Adapt. What works as a newsletter section becomes a LinkedIn post, a carousel, a short video teaser. The content is the same; the format and framing are completely different.

36. Build a dedicated sign-up landing page. Still essential but now this page needs to work for link-in-bio tools (Linktree, Later, Sprout, etc.), LinkedIn newsletters, Substack, and anywhere else someone might be clicking through to subscribe.

37. Use your best content as a teaser. A snippet from your most recent newsletter, adapted for the platform, is still one of the most effective sign-up drivers. In 2026, short-form video teaser content drives even more sign-ups than static posts - worth experimenting with if the format fits your brand.

38. Use platform-native sign-up tools. Meta Lead Ads and LinkedIn Lead Gen Forms have gotten significantly more powerful since 2019. They reduce friction dramatically - no landing page required. Worth testing as a complement to your existing sign-up flow.

SAYING GOODBYE
Wrap It Up With Intention

39. Skip the safe sign-off. “Best,” “Regards,” and “Thanks!” are the email equivalent of a formal handshake at the end of a first date that went really well. You can do better. I believe in you. The sign-off is a personality moment - use it. Make it yours. Make it memorable.

40. Tell them how to reach you. Or find you. Or follow you. The newsletter relationship shouldn’t exist only in the inbox; give readers a way to extend it. (Hello website link… social links… video links…)

41. Entice with what’s coming next. If able, offer one sentence about what the next newsletter will cover. It’s the easiest retention hook in the playbook, and almost nobody uses it.

A great newsletter isn’t a broadcast. It’s a relationship built one send at a time, with the same care you’d put into any relationship worth keeping.

The platforms have changed since 2019. Substack now exists - and with its own rules. AI writes subject lines now - use it as a starting point, not a finish line. Dark mode broke half the email templates we spent years perfecting.

But the fundamentals? The consent, the care, the respect for the person on the other end of the send button? Those haven’t moved an inch.

Treat every newsletter like you’re still trying to earn the next date. Because you are.

Before I sign off: there’s an important distinction between a newsletter and Substack. In a newsletter platform, you own the subscriber list - whatever happens to other platforms down the road, that list is yours. On Substack, you get something valuable too: a brand introduction tool and a way to maintain an audience. But you don’t own the list.

More on that difference and others - as well as which one might be right for you - next week.

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