How to Send Follow-Ups as a Freelancer Without Feeling Pushy

Too scared to send that follow-up email or LinkedIn message? You’re not alone. Almost every freelancer hesitates — worrying about being annoying, pushy, or even embarrassing themselves.

But here’s the truth: 88% of my freelance clients came from follow-ups.

In fact, in the past two years, only two clients hired me without a follow-up—and they were the ones who found me first (inbound leads).

If you’ve been holding yourself back from sending follow-ups, this is your sign to stop waiting. Let me show you why follow-ups are essential, what’s actually going on when clients don’t respond, and how I’ve landed thousands of dollars in freelance contracts simply by pressing “send.”

Why You Can’t Afford to Skip Follow-Ups

Here’s the hard truth: you cannot succeed as a freelancer if you’re too afraid to follow up.

Think about it: if you don’t reach back out, you’re leaving potential money — and long-term clients — on the table. You might be telling yourself things like:

• “I don’t want to annoy them.”
• “They probably don’t even like me.”
• “I have no business contacting this person.”

But actually? You have no business if you don’t contact that person.

Why Clients Don’t Respond (It’s Not About You)

So, you sent a pitch or Letter of Introduction (LOI) and never heard back. Before you spiral, here’s why that might be:

• They’re too busy to respond right now
• They don’t currently have the budget for freelancers
• They need to run it by their boss and haven’t gotten approval
• It’s not the right time in their content cycle
• They didn’t even see your email (hello, crowded inbox!)
• They don’t check LinkedIn daily

None of this means they don’t want to work with you. It just means the timing isn’t right. Which is exactly why following up matters.

What Your Follow-Up Could Lead To

Follow-ups are often where the magic happens. Almost every time I’ve gotten a client on LinkedIn, it was because I followed up—or messaged right when they were looking for help.

Here are a few real results from my own follow-ups:

• $36,000 contract: I followed up twice before landing this client. It turned into a 12-month retainer.
• $10,000+ contract: I followed up four times (once per quarter for a year). On the fourth try, they said, “Your timing is perfect!” I’ve been writing their blog posts ever since.
• $6,500 contract: A second-time follow-up turned into a six-month project.

The point? Don’t assume a “no response” means “no.” It might just mean “not right now.”

Pro Tip: Track Your Leads

Want to follow up without forgetting who you pitched last month (or last year)? You need a lead tracker.

Here’s how I set mine up:

1. Create a column called “To Connect With.” Add any company or person you’d love to work with.
2. Each time you send a pitch or LOI, move them into “LOIs Sent.” Add the contact person, their email/LinkedIn, and (optional) paste your pitch into the task comments.
3. Set a due date to follow up—14+ days later for email, 30 days later for LinkedIn.
4. Keep notes on responses so you can track progress over time.

Set something like this up in Asana, Trello, Notion, or whatever tool you like to use. It’s cheaper than a CRM and more customized to what you’ll actually need.

You can swipe my client lead tracker template for Notion for free here: Get the Lead Tracker Template

Try This: Follow-Up Without Fear

When in doubt, keep your follow-up short and simple. Here’s a template to get you started if you’re networking on LinkedIn:

“Hey [name], I’m going to be taking on new clients starting [date you’re available]. Do you need any help with [your service] at [their company]?”

Follow-ups are where freelancers win. They show persistence, professionalism, and timing—three things clients actually value.

No, seriously, I’ve sent this exact message to some of my now clients 6 times before they became my clients.

So the next time you hesitate before sending that message, remember: every “yes” I’ve gotten came from pressing send one more time.

FAQs About Follow Up Emails

How many times should I follow up with a potential freelance client?

Once the initial relationship is established (I’ve introduced myself, asked if they work with freelancers, and offered my availability – each message spaced out two weeks apart), I usually follow up 7 times – once every 3 months. Many of my long-term contracts came after the fourth or fifth follow-up.

Won’t I annoy potential clients if I follow up?

Not if you’re professional and respectful. Most people are busy—they appreciate a reminder. The key is to keep it short and direct.

What if they never respond, even after multiple follow-ups?

Move on and keep pitching other clients. Your energy is better spent building relationships with people who are ready to hire or interested in your services.