Instead of sending less email to combat poor engagement, marketers should focus on making their content better. Jay Schwedelson argues that audiences get annoyed by boring, irrelevant emails, not frequent ones. A valuable, exciting email can be sent daily and will still be welcomed by subscribers.

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The concept of a single best day and time to send an email is misleading. Instead, marketers should vary send times throughout the week to reach different segments of their audience. The key metric is the aggregate number of unique individuals engaged weekly, not the performance of a single blast.

Generalist World's newsletter achieves a 45% open rate by focusing on consistent utility. Every Tuesday subscribers get curated jobs, and every Friday a podcast. This reliability ensures subscribers see value in every email, rather than relying on unpredictable content.

Businesses limit content output fearing audience fatigue, but the real issue is often low-quality content or production bottlenecks. An audience's appetite for high-value content is nearly insatiable; focus on improving quality and output, not reducing frequency.

Email providers prioritize senders with high engagement. Sending at least five emails per month generates more opens and clicks, signaling credibility. This counterintuitively leads to higher average open rates and better inbox placement, contrary to the common fear of over-sending.

Focusing on email open rates can lead to clickbait subject lines and weak copy. Instead, orient your entire outreach strategy around getting a reply. This forces you to write more personalized, engaging content that addresses the recipient's specific pain points, leading to actual conversations, not just vanity metrics.

Contrary to the fear of over-sending, emailing at least five times per month improves deliverability. Email providers view consistent recipient engagement (opens, clicks) as a sign of a credible sender, leading to better inbox placement and significantly higher open rates.

Jay Schwedelson argues Send Time Optimization (STO) is 'garbage' because it creates confirmation bias. By sending your email when a user typically opens messages (e.g., 8 a.m. Monday), the feature ensures your email arrives alongside many others, increasing competition in the inbox and hurting your performance.

Sending all your automated emails at a predictable time, like 9 AM, trains your audience to ignore them, turning them into "wallpaper." To break this pattern and make automations feel less robotic, vary the send times significantly, even using unconventional hours like 8 PM.

Incorporate simple, conversational questions into emails to encourage replies. This engagement signals to email service providers that your content is valuable, improving deliverability. It also helps build a stronger relationship with your audience by starting a two-way conversation.

Gary Vaynerchuk's Wine Library saw immediate sales spikes by increasing email sends from weekly to daily. However, this strategy ultimately destroyed high open rates and engagement. The lesson is to prioritize long-term customer value and empathy over short-term revenue goals.