What Happened When I Stopped Writing Emails Like Everyone Else

The accidental discovery

I was supposed to send a polished newsletter about my services. Instead, I sent an email at 11 PM saying, “I messed up a client project today and here’s exactly what went wrong.” I wasn’t selling anything. I was just venting.

Within an hour, I got seven replies. People weren’t asking me to buy anything. They were telling me about times they messed up the same way. They were thanking me for not pretending to be perfect.

That email brought me more business than six months of “professional” content.

Why everyone’s email advice feels wrong

I started paying attention to my inbox. The emails I actually read weren’t formatted perfectly. They didn’t follow some magic structure. They just felt like someone talking directly to me about something they cared about.

The emails I deleted? They all felt the same. Polished. Generic. It could work for anyone.

So I started asking people why they opened my emails. The answers surprised me. Nobody said “great subject line.” Nobody said “clever hook.” They said things like “I wanted to know what you’d say about that,” or “you always have a weird take on stuff,” or “I was curious if you dealt with this too.”

They weren’t following email marketing rules. They were following me because I seemed real.

The problem with my old approach

I used to think about my email list like my audience. The right structure. The right tone. The right offer at the bottom.

But that’s not what builds people’s trust. People trust you when you’re consistent with who you are, not when you execute a strategy perfectly.

My best emails came from me being a little frustrated. Sharing something that didn’t work. Asking for help because I genuinely didn’t know the answer. Admitting when someone else’s idea was better than mine.

That’s not in any email playbook because playbooks can’t capture realness.

What I actually talk about now

I email about the specific problems I see people struggling with. Not the problems I think they should have. The actual ones I notice.

Last month, someone asked me how I got better at managing client expectations. I sent an email explaining that I don’t think I’m good at it. I told them exactly what I do, why it works about 60% of the time, and what blows up the other 40%. I asked what’s worked best for them.

That email got more responses than anything I’d written in months.

I also share emails about how I’m evolving my work, no fake enthusiasm, just real reasons behind the changes I’ve made.

I occasionally write emails showcasing others who do it better, linking to them and admitting they’ve solved things I’m still working on. That builds trust differently. It shows I’m not pretending to know everything.

The email nobody tells you to write

I send an email when I realize I’ve been wrong about something.

A few months ago, I sent an email saying I’d been giving bad advice for two years. Not in a dramatic way. Just: “I used to advise X, but I’ve learned it falls short.” Then I offer what I believe now

Three people replied and said they’d done what I suggested, and it hurt them. I responded to each one.

That email cost me something. It made me look less like an expert. But it made me look like someone who actually thinks about their work.

How I actually choose what to send

I look at my week. What I figured out after the fact What did I see someone else struggle with that I could explain?

What did I get wrong? What did someone teach me? What surprised me?

That’s what I write about. Not what would generate the most opens. Not what’s trendy. What actually happened?

I write it; however, it feels natural. If I’m frustrated, it sounds frustrated. If I’m excited, it sounds excited. If I’m confused, I say that.

Why don’t I worry about my list size?

I’ve got about 800 people on my list. Some of them haven’t opened an email in six months. I don’t care. They get an email every other week, whether they open it or not.

The 200 people who consistently open my emails? They’re the ones who matter. They reply. They share. They remember me.

I’ve turned down offers to buy email lists or use growth hacks to get bigger numbers. A huge list with no engagement is just noise.

The people who are on my list because they want to hear what I think. That’s real.

What happens when you actually show up like this

It took about four months before people started asking if I offered services. They didn’t ask because of my sales pitch. They asked because they already knew I was good at what I do.

When I did tell them about what I offer, it landed differently. They weren’t skeptical. They already trusted me.

I’ve gotten consulting clients, speaking gigs, and partnerships from this list. But not because I was good at selling. Because I was consistent about sharing how I think.

The weird part nobody talks about

Sometimes people unsubscribe because my emails aren’t what they expected. That’s fine. I’d rather have people who actually want to hear from me than people who are just seeing if I’ll eventually pitch them something.

Sometimes I send an email that nobody cares about. I’ll get one open and two clicks. I don’t panic. Next week I will send another one.

Sometimes I send something I think is boring, and it gets tons of replies. I never know what’s going to land.

But the pattern that works? Consistency and realness. Every other week, I show up, and I share something true.

Starting this week

If you want to try this, here’s the only real rule: send something you actually care about explaining.

Not something that will grow your list. Not something that will get opens. Something you genuinely think other people should know.

Write it the way you’d explain it to a coworker. Use words you actually use. Share the part that surprised you.

Send it. Don’t agonize over it for a week.

Do that every two weeks or every month. Go with a plan you’ll actually stick to.

Watch who replies. Those are your people.

That’s the actual strategy. Show up regularly with real thoughts. The trust and opportunities are built from there.