✍️ Don’t Send That Follow-Up. Just Follow Through.

Why chasing old pitches is the freelance equivalent of texting your ex.

A question keeps popping up in our community:

“I applied to a few jobs last week. How long should I wait before following up?” - New Subscriber

And I get it. It feels like the responsible thing to do, like you’re being professional, thorough, persistent.

But here’s the thing Amy and I have learned after years of freelance work:

We have never — not once — had a follow-up with a client (*we didn’t already have a contract with) turn into actual work or, at the absolute bare minimum, become a worthwhile project.

Not once.

Let me say that again for the people maintaining giant Notion databases full of “follow up in 5 days” reminders:

The jobs you want? They start immediately. The clients worth having? They respond when they’re ready.

The Dating Analogy (Stay With Me)

You send a pitch to someone who seems perfect. The job listing matches everything you want. You imagine the project, the rate, the creative freedom. You mentally furnish the whole relationship.

And then… silence.

So you start drafting the follow-up. Maybe something casual. “Just bumping this to the top of your inbox!” Maybe something eager. “Wanted to make sure you received my application!”

Here’s the problem: while you’re crafting the perfect second message to someone who hasn’t responded, you’re not writing the first message to someone who might.

Fantasizing about what you want something to be takes you away from the immediate stuff you can actually control.

Luck Is the Residue of Design. But You Can’t See It Looking Backward

There’s this idea that luck is just preparation meeting opportunity. True. But the thing nobody tells you is: you don’t get to reverse-engineer it.

You can’t track your way into fortune. You can’t spreadsheet your way into momentum.

The design that creates luck? It’s built by volume. By throwing more thoughtful pitches into the world. By finding the jobs that actually make your heart sing and going after them with intention — not by circling back to the ones that already said nothing.

Looking backwards makes you miss what’s in front of you.

What Actually Works

The writers in our community who are landing work? They’re not optimizing their follow-up cadence. They’re doing this:

Applying to more jobs. Not spray-and-pray—but consistent, thoughtful, thorough applications to roles they genuinely want.

Moving forward. If a pitch didn’t land, they let it go and pitch something else.

Trusting the signal. Silence isn’t a puzzle to solve. It’s information. And the information is: they’re not ready, or you’re not the fit. Either way, you’re better off elsewhere.

Because here’s the truth that applies to clients, collaborators, and basically every relationship in your life:

You never have to convince or remind anyone of something they actually want to do.

The clients who are half-in, half-out, wishy-washy, needing a nudge? That energy doesn’t get better once you’re working together. It gets worse.

Delete the Tracker. Keep the Momentum.

If you’ve been spending even a fraction of your time maintaining a follow-up database, here’s your permission slip to stop:

Unless you have a signed contract, you don’t need a system for that client.

The only system you need is forward motion.

Keep iterating. Keep finding the roles that excite you. Keep becoming undeniable.

The magic isn’t in the follow-up.

It’s in the follow-through.

your fan,

kyle