If you’ve ever typed “May newsletter ideas” into Google and ended up with a listicle of 89 unofficial holidays (hello, National Lumpy Rug Day), you know the struggle.
There’s a difference between ideas and good ideas. And not all “marketing holidays” will work for your eCommerce brand. Before you commit email copywriting and email design resources to a campaign, you need to sift “that’ll work” from “that’ll do”.
In this article, we outline a lean, result-driven approach to the month of May, including some strategic tips and engaging May newsletter ideas you can use to generated some pre-summer hype.
May: Your Pre-Summer Power Play
May sits in that strange in-between zone: Q1 is over, summer hasn’t started, and there’s no “tentpole” retail event dominating inboxes.
That’s what makes it a good time to experiment and clean house. Smart brands are using May to:
- Re-engage subscribers who didn’t bite in Q1.
- Test new content formats and A/B angles without the pressure of big sales goals.
- Warm up audiences for upcoming summer drops or promos.
Basically, now is the time to do everything you can to soften the blow of that summer sales slump. Many brands experience a drop of between 20-40%, so every effort you make right now will count in the long run. And relevant, engaging May newsletter ideas can soften the blow by increasing revenue in the run-up to the summer slowdown.
May the 4th Be With You: Lean Into the Cringe
Even if you don’t sell light sabres or have a single Star Wars reference in your brand guide, May 4th is too fun to ignore. It’s a pop culture moment with built-in share-ability. And you don’t need to force a tie-in. You just need to embrace the playfulness.
Think interactive: let your audience “choose their side” in a product quiz, or spotlight items that are “rebellious” vs. “classic”. You could even build a one-day campaign around “galactic” bundles or drop a time-limited discount that vanishes at lightspeed.
- “Choose your side” product quiz: Let subscribers pick between products or collections framed as Jedi vs. Sith. Bonus points for follow-up flows based on their choices.
- Lightspeed flash sale: A one-day-only deal with a cheeky Star Wars reference. Add a countdown timer for urgency.
- Customer costume contest or themed UGC: Ask for photos of customers using your product in full space-nerd glory. Feature them in your next send.
If your brand does have a Star Wars flavor, then this is a chance to engage loyalists with fan-favorite products, nostalgia, or UGC. Of course, if your audience overlaps with cult fandoms, they’re probably expecting this email. So it’s a good idea to go slightly off script, and to include a good offer in the email.
Small Business Week (May 5- 11): This One Can Actually Be All About You
Consumers love supporting small brands. They just need a reminder of why it matters.
Use this week to share a behind-the-scenes look at your operations, or celebrate some major milestones in the story of your business. You can also lean into the “why” behind your business, whether it started as a one-person passion project or a 20-person team. These stories may stick out as self-promotion at other times of year, but here they make perfect sense, which is why they should be central to your May newsletter ideas.
But remember: overproduced storytelling isn’t the goal. Instead, focus on genuine human. moments:
- Those late-night packaging marathons
- The first customer review that made you cry (for better or worse)
- The way your team makes big things happen on small budgets
If you’re not a small business yourself, partner with one. Curate a special collection or limited-time offer that celebrates makers, creators, and underdogs. This really deepens brand credibility with audiences who care about values.
Mother’s Day (May 12): Emotional Revelance, Not Generic Gifting
Mother’s Day doesn’t just belong to florists and jewelry eCommerce brands. Any brand can show up with care, as long as the message is thoughtful and authentic. That might mean featuring a founder story about lessons you learned from your mother, or spotlighting real customers and role caregivers play in their lives.
But proceed with caution: Mother’s Day can be a difficult time for some. Including a thoughtful opt-out in your emails before Mother’s Day is a great way to show that you really do care:
If you’re selling physical goods, don’t just push a gift guide. Try positioning it as a curated solution for last-minute shoppers or a way to honor someone non-traditional:
- Stepmoms
- Aunties
- The friend who always remembers your birthday
Even digital brands can use this moment. A campaign around mental load awareness, or self-care for caregivers. This all shows genuine awareness of your audience’s day-to-day challenges.
Memorial Day (May 27): Respectful Storytelling
Memorial Day is a big retail moment. But it also holds emotional and cultural weight. So leading with “50% OFF” headline can feel tone-deaf. The brands that win here are the ones that balance commemoration with value.
Start by acknowledging the value of the day with a short note, a moment of silence, or by highlighting a cause that your brand supports. Then transition to the promotional angle with thoughtful positioning:
- Helping your customers prep for a long weekend
- Getting summer-ready with appropriate deals
- Simply enjoying a small moment of ease with the people who really matter
If you’re running a sale, consider building in a charitable tie-in. Donating a portion of proceeds to a veteran organization, or spotlighting veterans in your customer base adds depth to the message.
