When you email someone at an agency or on the client side, they already know why you're reaching out.

You want to work with them.

You'd love to shoot something for their company.

You think your work would be a great fit.

They know all of this before they even open your email.

So stop telling them that.

Here's what I see all the time:

Someone sends a long email introducing themselves, explaining their entire background, listing their credentials, talking about how passionate they are, how much they'd love to work together, and oh by the way here's my reel.

It's exhausting to read.

Or worse, it's generic. A blanket email clearly sent to 1000 people with no personalization. No acknowledgment of who I am or what I do. Just a pitch.

And then there's the email that assumes there's just a pile of work sitting around waiting to be assigned. As if all they need to do is introduce themselves and the job is theirs.

None of these work.

Not because the person sending them isn't talented.

But because they're trying to close the deal in email number one.

Your first email isn't about getting the job.

It's about getting the conversation.

Think about a movie trailer. It doesn't tell you the whole story. It gives you just enough to make you curious. Just enough to make you want to see more.

That's what your first email should do.

Make them want to talk to you. Make them curious about you. Make them want to click your link.

Not because you convinced them. But because you made it easy and interesting.

When I was freelance, my approach was simple:

Lead with curiosity about them.

Not fake curiosity. Real curiosity.

I'd reference something specific about their work. A campaign they just launched. A project I saw on their LinkedIn. A career move they made that caught my attention.

Then I'd ask a genuine question.

"That last campaign must have been tough. How did you pull it off?"

"I saw your job history with X, Y, and Z companies. How did you get into that line of work?"

"I loved the work you're doing with [specific project]. Would love 15 minutes of your time to chat about that."

Then, almost as an afterthought: "Also, here's a link to my reel."

That's it.

Short. Specific. Curious.

I wasn't pitching. I was starting a conversation.

And I knew something critical: time to them is precious.

So I didn't ask for an hour. I didn't send a five-paragraph essay. I made it easy to say yes.

Here's what most people don't understand:

One email is not enough.

These people are busy. Really busy.

The distractions they have in the office. The amount of emails they get. It's insane.

So if you send one email and never follow up, you're not even on their radar.

But here's the thing: staying top of mind isn't annoying. It's welcomed.

Don't be a stalker. But don't be a stranger either.

And whatever you do, don't get in your feelings when someone doesn't reply right away.

That's the loop people get stuck in: "They didn't respond. They must not like my work."

No. They're just busy. Or they didn't see it. Or they saw it but got pulled into a meeting and forgot to respond.

Your job is to make it easy for them to remember you exist.

Not by spamming them. But by showing up consistently with something useful, something curious, something that makes them think, "Oh yeah, I should respond to this person."

Stop trying to get the job in the first email.

Stop trying to convince them you're qualified.

Stop writing essays about why you'd be a great fit.

They already know you want to work with them. That's why you're emailing.

Your job is to make them want to talk to you.

Lead with curiosity about them.

Keep it short.

Include your work, but don't make it the centerpiece.

Get the call. Your first email gets the conversation.

The conversation gets the relationship.

The relationship gets the work.

This week, pick three people you want to work with.

Find something specific about their work. A project. A career move. Something that shows you actually paid attention.

Write a short email. Two or three sentences. Lead with curiosity about them. Ask a genuine question. Include your reel at the end.

Send it.

Then follow up a week later if you don't hear back. Not with "just checking in." With something else that's useful or interesting.

See what happens.

Your first email isn't about pitching.

It's about making them curious.

Make it short. Make it specific. Make it about them.

Then let your work speak for itself.

Because the people who book the most work aren't necessarily the most talented.

They're the ones who make it easy to say yes.

If this hit, share it with someone who needs to hear it.

See you next week.

— Chris Whitten