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I’ve been helping creative professionals get gigs for more than 15 years. First as an agent for freelance art directors, copywriters and fashion illustrators, and now as a business coach, teaching freelancers and entrepreneurs how to land their own dream clients. We all know that if you want to build a thriving creative business, simply hanging a shingle and waiting for the clients to beat a path to your door won’t cut it. You’ve got to hustle! And whether your goal is to stay top of mind with an ideal client, or grab the attention of an agent or headhunter, being persistent is key.

But persistence (like hustling) has a bit of a bad rap. We want to be liked—not thought of as a pest—so we shy away from reaching out. As an agent, I got approached all the time and some approaches were far more effective in compelling me to take action, whether that meant checking out a website or making a referral to a client.

The following approaches struck a chord with me – some for good reasons and some not so good. They were made in the context of the freelancer-agent relationship, but readily apply to the talent-client relationship.

1) The L.A. based fashion illustrator seeking New York representation

An up-and-coming illustrator emailed me to introduce herself and share her work. Her email was friendly, well-written and concisely communicated the following:

• A description of her style (influences, inspiration, etc.)
• Her experience
• Her goals
• Why she felt she’d be a valuable addition to my roster
• An invitation to take a look at her work and share my feedback

Here’s why her approach worked: Even though I wasn’t planning to take on new illustrators at the time, her professional email and request to look at her work and share my feedback prompted me to do just that. She followed up by sending a beautiful watercolor painting as a thank you. Do you think I’ll remember her? You bet!

2) The children’s book illustrator with a passion for fashion
The second example came from a successful children’s book illustrator who was looking to break into fashion illustration. She introduced herself in a well-written email that prompted me to check out her website. Here’s what she included:

• Highlights of her career
• Her social media following
• Her love of fashion illustration
• Why she felt she’d be a good addition to my roster
• Why she wanted an agent (even with her ninja organizational skills and work ethic ”of a bull,” she could no longer handle everything on her own)

Here’s why this approach worked: in addition to her talent (which was clear), she positioned herself as engaged, professional, and having a laser-like focus on her goals. She also demonstrated an understanding of what I needed from the talent I represented.

3) The Swedish based 3D and motion graphics designer looking for a US rep
The first email communicated that he was writing upon the suggestion of a mutual client (if you have a name, always use it!) I responded, but since I didn’t have an immediate need—and wasn’t entirely clear on what he offered— didn’t take it much further. He continued to stay in touch by phone and one day caught me when I had time to talk in more detail. In that call he was able to define what he did more clearly. He sounded so great I wrote a blog post just about him. That would not have happened had he not been so persistent.

Now, let me share an example of an email approach that did not work:

4) An illustrator thinking about getting an agent
I received an email that read: “I'm entertaining the idea of an agent and I'm going to be in NYC on Friday. I would love to get the chance to meet with you. Please let me know if that is possible.”

Here’s why this approach didn’t get any traction:

• By starting with “I’m entertaining the idea of an agent…” she positioned herself as someone who didn’t have much focus or commitment. Having an agent seemed like a passing fancy.
• She didn’t tell me anything about herself – no website, no language, no images. Nada.
• She went straight to asking for a meeting without giving me a good reason.
• She wasn’t respectful of my time.

Here are the takeaways:

• Figure out how you want to position yourself before reaching out.
• Do your research so that you can speak to a specific need you will fulfill or to the benefit the client will gain from meeting with you. Make the meeting worth their while.
• Be respectful of people’s time and energy. Be succinct and thank them for their time in advance.
• Include an image in the email, if you can. People are more likely to read something with an accompanying image.
• Follow up. People are busy and don’t always respond right away. Here’s how I do it:

- Initial outreach—an email or call

- If I call and get voicemail, I follow up with an email (that references the message I left)

- Follow up 4-5 days later

- Follow up 1 week to 10 days later

After that, I ask if I can add them to my mailing list as a non-intrusive way to stay in touch. Don’t forget to communicate what they will get out of that newsletter when you ask. Most people will say ”Yes.”

You have one chance– and about 5 seconds –to grab someone’s attention in an email, so be bold, strategic, and respectful. Give it all the charm you possess. Persistence does pay off!

Justine Clay has been helping freelance creative talent build thriving careers for more than 15 years. As the founder of Plum Creative, she built a track record of making the perfect match between high-level, independent creative professionals and clients that included Vogue, Bloomingdale’s, Henri Bendel and West Elm.

Justine’s desire to share her knowledge with more than the handful of people she represented led her to found Pitch Perfect in 2010. As a business coach for creative professionals, Justine helps her clients define what makes them unique, create a clear marketing message and get more, high-quality, better-paying clients. Justine’s services include one-on-one coaching, workshops and talks. She is also a regular contributor to the Freelancer’s Union blog and Umano.