Afraid of bothering people: is emailing your audience often too pushy?

Sunday evening. The newsletter has been ready for three weeks. You've reread it, fixed two commas, changed the subject line four times. The cursor is hovering over "send". And it stays there.

The usual thought crosses your mind. "Oh well, I'll send it next week, I don't want to clog up anyone's inbox." You close the laptop, and the draft sits there for another month.

Let me tell you how I see it, as someone who has stared at that draft more than once. That thought looks like good manners. In reality it's making you disappear.

Do too many emails annoy your subscribers?

Start from a fact. The people on your list didn't end up there by accident. One day they read something of yours, thought "this is interesting", and left you their address. They literally asked to hear from you.

When you don't write, that request goes unanswered. After two months of silence your name in their inbox belongs to a stranger, and the first email you send really does feel like an intrusion. You turned it into an intrusion yourself, by disappearing.

That's the paradox. People who write rarely because they're afraid of bothering anyone end up bothering people more, because every time they reappear they have to introduce themselves all over again.

And what if someone unsubscribes? That's fine. Someone who unsubscribes is telling you the topic isn't useful to them anymore, and saving you from talking to an empty room. A shorter list of people who read you is worth more than a long list of people who've forgotten you.

How often should you send a newsletter without being annoying?

The right frequency is the one you can keep up with messages that are worth opening. Once a week, every two weeks, once a month. The number matters less than the regularity, because regularity creates an appointment. When people know your email lands on Tuesdays, they start looking out for it.

There's only one test to run before you hit "send". If a colleague I respect sent me this email, would I open it? If the answer is yes, send it. If it's no, forget about frequency and rewrite the content.

A useful message usually has two ingredients. Something the reader can use straight away, whether that's a calculation to run or a mistake to avoid. And at most one request, clearly stated, at the end. Put three different requests in and none of them gets through.

"Yes, but I don't know what to write." I know, that's always the next line. You already have the material, and it's sitting in your inbox. Open your clients' latest emails and look at the questions they ask you. The ones that keep coming back, the ones you always answer with the same paragraph, the ones that make you think "really, again?". Each of those is a newsletter. The answer you give one person, written well once, also helps the other two hundred who had the same question and never dared to ask.

Is following up on a quote too pushy?

This is where the fear of bothering people costs you real money.

You sent the quote ten days ago. No reply. In your head the silence already means something. They're not interested, the price was too high, they went with someone else. So you don't write, because you don't want to be the one who keeps chasing.

Try looking at it from the other side of the table. Your potential client got your quote in the middle of a hundred other things. They opened it, thought "I'll look at this properly later", and later never came. Their silence far more often means they forgot than that they're saying no.

A short, friendly, concrete message does them a favour. "Just checking whether you've had a chance to look at the proposal. If anything needs clearing up, we can talk it through in ten minutes." You remind them of something they were interested in and make it easier for them to answer. And if it's a no, at least you know, and you can stop waiting.

If what really stops you is the moment of asking for the work, I go into it here: Afraid to sell: why is it so hard to pitch to people you know?.

What actually annoys your readers?

The message written for the writer's sake. The email that exists only because you "have to stay visible", with nothing inside. The post about how busy you are. The follow-up that adds nothing and just asks "so?".

Broken promises annoy people too, like the newsletter announced as weekly that then turns up every four months. And so does the tone of someone who apologises in every line for writing at all.

What almost never annoys anyone is the person who gets in touch regularly and leaves something useful every time. In fact, that person becomes a reference point. They're the name that comes to mind when you have that problem, because they reminded you of it recently.

In the end the real enemy is your own inertia dressed up as good manners. Your reader's inbox has very little to do with it. When someone who's good at their job doesn't make themselves heard, they let somebody else take that place in people's minds.

So reopen the draft. Read it once, just once. Take out the apologies. Hit "send".

Then watch what happens over the next two days. Someone will reply with one line: "thanks, I needed this". Someone else will forward the email to a colleague. Hardly anyone will write in to complain. It's the same thing I found out as a teenager at the café counter: the fear in your head is much bigger than what actually happens.

If you've got more than one draft sitting in the drawer, and the Sunday evening scene keeps repeating itself, let's grab a coffee. In thirty minutes we'll work out what's holding you back and what to actually write to the people who are waiting to hear from you.

Frequently asked questions

How often should I send a newsletter to my subscribers?

There's no single right number. Regularity matters more: weekly, every two weeks or monthly, as long as it's consistent and every email contains something useful. Regularity creates an appointment and keeps you on your readers' minds. Pick the frequency you can keep up without filling your emails with empty content.

Will people unsubscribe if I email too often?

Some will, and that's normal. People who unsubscribe often no longer find the topic useful, and a list of interested readers is worth more than a long, distracted one. Unsubscribes tend to rise when messages are empty or purely promotional, far more than because of frequency alone. Look at what you write before cutting how often you write.

When should you follow up after sending a quote?

After a week or ten days without a reply, it's reasonable to get in touch. A client's silence most of the time means they forgot, not that they said no. A short message asking whether they've had a chance to look at the proposal, and offering to clear up any questions, is a service, not pressure.

How do I email clients without coming across as pushy?

Only write when you have something the reader can use: a calculation to run, a useful question, a mistake to avoid. Put at most one clear request at the end. Don't apologise for writing. A simple test: if the same message reached you from a colleague you respect, would you open it?