Embracing the Fear of Cold Pitching as a Freelance Instructional Designer

Let's be honest—cold pitching makes my stomach drop a little. The thought of sliding into a stranger's inbox to say, "Hi, I think you could use my help," feels bold in a way I'm still working up to. However, in the freelance world, time waits for no one. So here I am, not cold pitching yet, but planning. Preparing and building the courage to start.

What Even Is Cold Pitching in the Freelance World

Cold pitching for freelancers means reaching out to potential clients who haven't posted a job. It's proactive, strategic, and (from what I hear) powerful. As a freelance instructional designer, that might mean:

"What’s Your Pitch?" — a question every freelance instructional designer faces when preparing to cold pitch for new clients.

• Reaching out to a nonprofit whose onboarding course might need a refresh.

• Messaging an HR manager about fixing the employee training flow.

• Sending a friendly note to a school or university about modernizing a course.

These actions may feel daunting, but they open up a world of possibilities, especially for those of us trying to find work beyond Upwork or job boards.

So, Why Haven't I Done It Yet?

• Fear of rejection. Or worse — total silence.

• What if it's annoying? I don't want to come across as spam.

• What if they actually say yes? That presents a whole new level of anxiety.

  
  

But all of that? It's fear, not fact. And I've already tackled scarier things in life — like training a population of 200 chimpanzees or trying to chase a loose feral cat through a vet clinic. (Though some days, I'd still choose the cat.)

The fear of rejection is real — cold pitching can feel intimidating, even for seasoned freelance instructional designers. But discomfort often signals growth.

What I'm Doing Instead (For Now)

I'm taking small steps to prepare for cold outreach as a freelance learning designer. 

Here's what that looks like:

1. Collecting Examples of Good Pitch Messages

I'm researching cold email formats that feel genuine and aligned with my voice. The best ones include a personal touch, showcase value, and respect the reader's time.

2. Listing 10 Organizations I'd Love to Work With

These could be nonprofits, schools, or startups focused on education and learning. I'm drawn to groups where instructional design can make a real impact, especially in tech, equity, or community initiatives.

3. Creating a Cold Pitch Template that Sounds Like Me

A good cold-pitch email doesn't have to be stiff. I'm writing one that feels conversational but professional — something that makes me proud to hit "send."

4. Reminding Myself that Being Ignored Doesn't Mean I'm Not Good

Over 70% of cold outreach emails go unanswered. That's not a measure of your talent — just your timing.

My Plan Moving Forward

Next month, I'm setting a goal to send my first four pitches. There is no pressure to land a contract — just the goal of starting. Of getting visible. Of creating opportunities outside of freelance job boards.

I'll break this into manageable chunks — maybe one per week. That gives space to reflect, adjust, and build confidence.

If You're Hesitating Too…

You're not alone. Many freelancers — especially those in creative or learning design roles — feel uncomfortable with cold pitching. But maybe we don't have to feel "ready." Maybe we just need to be willing.

Cold pitching isn't just about booking work. It's about reaching the people who didn't know they needed you — until you showed up. So, let's focus less on rejection… and more on what might go right.

A peaceful pathway inviting exploration and new beginnings.

Final Thoughts

If you're a freelance instructional designer or creative pro trying to grow without burning out on job boards, this might be your sign to try cold pitching, too. Start small. Be human. Don't wait for permission.

And hey — if you're reading this and you are someone who might need help with online training, eLearning, or course design… I know a girl. 😉