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HELP MY NEWSLETTER

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Your welcome sequence is a retention disaster. Here is how to fix it in the next 15 days.

Let me guess: You send 3 welcome emails. Maybe 5 if you are ambitious. Week 1, week 2, done. You think you are doing a good job because you "set expectations."

You are leaving 40-60% of your subscriber lifetime value on the table.

A newsletter operator I worked with last month was losing 52% of new subscribers by Month 4. Fifty-two percent. She had no idea WHEN people were dropping off, WHY they were leaving, or WHAT to do about it. Her welcome sequence? Three generic emails in the first week. Then crickets.

We built a 12-month welcome track with 9 strategic checkpoints. Four months later, her Month 4 retention jumped from 48% to 71%. Same content. Same audience. Just a smarter system for keeping people engaged.

January is when people try new newsletters. You have 2 days to get this system in place before Q1 starts and you miss the biggest subscriber acquisition window of the year. This edition breaks down exactly how to do it.

Part 1

Why your 3-email welcome sequence is costing you thousands

The conventional wisdom says: "Send a warm welcome, set expectations, deliver your lead magnet, done." That advice worked in 2018. It does not work now.

The data that nobody talks about

Publishers using extended welcome sequences (8+ touchpoints over 12 months) retain subscribers at 40% higher rates than those using standard 3-email sequences. That is 40% more revenue per subscriber. But 90% of newsletter operators are still running 2018 playbooks.

Here is what is actually happening

Your new subscriber is excited for exactly 72 hours. Then reality hits. They get busy. Your emails start competing with 147 other newsletters in their inbox. You fade into background noise.

The drop-off pattern nobody measures:
Month 1 to Month 2: 15-20% churn
Month 2 to Month 3: Another 10-15%
Month 3 to Month 4: Another 8-12%
Month 4 to Month 5: The cliff. 20-30% gone.

By Month 6, you have lost half your new subscribers. And you have no idea why because you stopped measuring after the welcome sequence ended in Week 2.

Part 2

The 12-Month Welcome Track: How smart operators keep subscribers engaged all year

Stop thinking "welcome sequence." Start thinking "first-year engagement track." This is not 52 emails. This is 9 strategic checkpoints that turn retention from a mystery into a calendar.

The 3 phases that matter

Phase 1: Activation (Days 0-21)
Mission: Get the first click, first reply, first saved send. Train engagement behavior immediately.

Phase 2: Habit (Weeks 4-12)
Mission: Turn "reads sometimes" into "reads automatically." Build the rhythm.

Phase 3: Identity (Months 4-12)
Mission: Catch the drop-off before it happens. Turn readers into advocates.

The minimum viable framework

Week 1: Welcome + one tiny action (single button click for personalization)

Week 2: Quick win + soft reply prompt

Week 3: Segmentation poll (tag them into a track)

Month 2: "How's it going?" checkpoint (one-click rating)

Month 3: Case study + "want more like this?" poll

Month 4: THE CRITICAL ONE. Recommitment email. "Still building or paused?" Two-button choice. This is where you save the 30% who are about to ghost.

Month 6: "What would make this a must-read?" Short survey.

Month 9: "What have you built?" Win collection + permission to share.

Month 12: Anniversary email + referral ask for loyalists.

That operator I mentioned? She was losing 52% by Month 4. After adding just the Month 4 recommitment email, she saved 18% of people who were about to churn. One email. $3,200 in saved annual revenue. That is the power of strategic checkpoints.

Quick Start

You do not need to build all 9 emails this week. Start with ONE.

Everyone reading this wants to do everything. You will get overwhelmed and do nothing. So here is your assignment for this week:

THIS WEEK: Build your Month 4 checkpoint email

Subject: "Quick question: Are you still building this year?"

Body: "You subscribed 4 months ago. A lot changes in 4 months. Quick check-in: Are you still actively working on [topic], or have priorities shifted?"

Two buttons:
Button 1: "Still building" (tags them as active, keeps in main sequence)
Button 2: "Taking a break" (moves to quarterly digest)

Schedule it: Set it to trigger 120 days after subscription. That is it. One automation. Five minutes to set up in beehiiv. This single email will save you 15-20% of people who were about to silently churn.

Build the others later. But get this one live before January ends. January signups will hit that Month 4 checkpoint in May—right when engagement nosedives for most newsletters.

Next 30 days: Add Week 1-3

Once Month 4 is live, spend February building your first 3 weeks. One email asking for a single click. One asking for a reply. One with a simple poll. That is your activation phase handled.

By March 1, you will have 4 checkpoints live. By June, you will have data showing exactly where people drop off. That is when you optimize.

Part 4

Three ways operators mess this up (and how to avoid them)

Mistake #1: Building all 9 emails before testing any of them
Ship the Month 4 checkpoint first. See if it works. Then build the rest. Do not spend 3 weeks building a perfect system that never goes live.

Mistake #2: Making every email an "ask"
One ask per email. Week 1 gets a click. Week 2 gets a reply. Week 3 gets a poll response. Do not stack 4 CTAs in one email like a desperate carnival barker.

Mistake #3: Tracking vanity metrics instead of retention
Who cares if your welcome email has a 62% open rate if 50% of those people are gone by Month 5? Track Month 1-2-3-4-5-6 retention. That is the only number that matters.

The fix

This is a measurement system first, a retention system second, and a revenue system third. Get the checkpoints in place. Let them run for 90 days. THEN optimize based on what you learn.

📰 This Week's Big Email News

5 stories every newsletter operator needs to read

Newsletter monetization shifts toward sponsorships as paid models plateau

If you are still betting everything on paid subscriptions, this is your wake-up call. Sponsorships are where the money is moving. Read the full story →

Gmail to let users change their addresses while keeping data

Major platform news from Google. This affects deliverability, list hygiene, and how you track subscriber behavior going forward. See what it means →

Email's enduring advantage in an AI-disrupted marketing world

While everyone chases AI tools, email keeps winning. Here is why your inbox strategy matters more than ever. Read why →

The speed trap: Why real-time marketing wins quarters but loses decades

Stop optimizing for this week. Start building systems that compound over years. This ties directly into why your 12-month welcome track matters. Read the full piece →

The inbox has seasons most marketers ignore them

January is prime time for new subscriber acquisition. Most operators miss it completely. Do not be one of them. Learn the seasonal strategy →

🎁 Our gift to you

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You will leave with actionable information and a strategy that will get results on your VERY NEXT send.

We normally charge $2.50/minute on Clarity ($50 value), but subscribers get access pro bono using this special link for our VIPs.

Claim Your Free Consultation

Your move

January signups will hit Month 4 in May. Get this built now.

Every subscriber you get in January, February, and March will hit that critical Month 4 checkpoint between May and July. That is when 30% of them will silently disappear—unless you have a system to catch them.

You have 2 days before Q1 starts. Build the Month 4 email this week. Add the first 3 weeks in February. By March 1, you will have a retention system that 90% of newsletter operators do not have.

The operators who build this system in January will know exactly where their subscribers drop off by summer. The ones who "get around to it later" will still be guessing why their retention sucks in December. Which one are you going to be?

Hit reply and tell me: Are you building this in January, or are you putting it off? I read every response and I will hold you accountable.

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