(We all suck at this. Yes, even the "successful" ones.)
I've been doing this for over 20 years. I've worked with newsletter operators at every level—from 50 subscribers to 500,000 subscribers. From complete beginners to people making multiple six figures from their lists.
And you know what? Almost every single one of them is terrified they're doing it wrong.
The person with 10,000 subscribers thinks they should have 50,000 by now. The person making $5K/month from their newsletter is convinced they're leaving $20K on the table. The "expert" everyone follows on LinkedIn? They're drowning in imposter syndrome and technical issues they're too embarrassed to admit.
Nobody actually knows what they're doing. We're all just figuring it out as we go, comparing ourselves to people who are ALSO figuring it out as they go, and feeling like failures because we can't see their behind-the-scenes chaos.
You know what stops most newsletter operators from succeeding? It's not lack of subscribers. It's not bad content. It's not even technical issues.
It's the constant, nagging fear that they're not "ready" yet.
Not ready to monetize. Not ready to pitch sponsors. Not ready to raise prices. Not ready to position themselves as an expert. Not ready to ask for the sale.
They're waiting for some magical moment when they'll suddenly "deserve" success. Spoiler alert: that moment never comes. You just start doing the thing anyway and figure it out as you go.
Even after 20+ years, I sometimes hover over that send button and think "is this good enough?" The answer is: it doesn't matter. Done is better than perfect. Your subscribers would rather get decent content consistently than perfect content sporadically.
"I can't charge for this—people might not think it's worth it." Here's the truth: if you're providing value, people WANT to pay you. Giving everything away for free doesn't make you generous. It makes you broke and resentful.
Someone else's newsletter is crushing it and yours isn't growing as fast. So what? Their subscriber count doesn't affect yours. Their success doesn't prevent yours. Stop scrolling, start shipping.
SPF, DKIM, DMARC, DNS records, deliverability scores—it's a lot. Most people are one Microsoft rejection away from a complete meltdown. And you know what? That's NORMAL. This stuff is genuinely complicated. It's okay to ask for help.
You think you need more credentials, more experience, more case studies before you can position yourself as an authority. Meanwhile, someone with half your knowledge is out there charging 3x what you charge because they had the audacity to call themselves an expert and deliver value.
You're so focused on getting NEW subscribers that you're ignoring the gold mine you already have. Quality beats quantity every single time. 500 engaged readers who trust you will make you more money than 50,000 zombies who ignore your emails.
Everyone is winging it. The difference between people who succeed and people who don't isn't talent or luck or some secret strategy. It's willingness to be messy, to suck at first, to send the email even when it's not perfect, to ask for money even when it feels uncomfortable, and to keep showing up even when the metrics aren't exploding.
Because I'm tired of the guru bullshit. I'm tired of newsletter "experts" pretending they have it all figured out while behind the scenes they're dealing with the same deliverability nightmares, engagement drops, and revenue anxiety as everyone else.
I'd rather be honest: Newsletter operation is hard. Technical stuff breaks. Engagement fluctuates. Revenue is unpredictable. And that's okay.
The newsletter operators who win aren't the ones who never struggle. They're the ones who struggle, figure it out (or ask for help), and keep going anyway.
I will never pretend I have all the answers. But I will always give you the realest, most practical advice I have. No fluff. No hype. Just what actually works based on 20+ years of seeing what breaks, what fixes it, and what makes the difference between newsletters that die and newsletters that thrive.
If you're tired of feeling like you're the only one struggling... you're not. If you're ready to stop pretending you have it figured out and actually get some real help... let's talk.
No sales pitch. No judgment. Just 15 minutes where you tell me what's really going on and I tell you what I'd do about it.
Book Your Free Reality Check CallReal talk, no BS,
— Jenn Gibbs
Founder, Help My Newsletter | 20+ Years Making Email Work