How to be Persistent Without Being a Pest

By Justine Clay

Freelancers and entrepreneurs need a well-developed “hustle muscle.” Simply hanging your shingle and expecting clients to beat down your door won’t cut it, so what’s a humble creative to do?  Whether you want 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 get approached all the time; some approaches are far more effective in compelling me to take action, whether that’s checking out a website or making a referral to a client.  

The following approaches struck a chord with me, so I thought I’d share them with you. While they were made in the context of the freelancer-agent relationship, they just as readily apply to the talent-client relationship.  

1) An illustrator reached out to introduce herself and share her work.  In her email, she 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 

At that time I wasn’t planning to take on new illustrators, but I reviewed her work, sent her a few thoughts, and invited her to stay in touch. She followed up by sending this beautiful painting of me as a thank you.  Do you think I’ll remember her?  You bet!



2) The second example comes from a successful children’s book illustrator with a passion for fashion. 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 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 understood what I need from the talent I represent. 

3) The last example comes courtesy of Nick Ericson, a designer who specializes in photo-real 3D-design and motion graphics for the fashion and beauty industries. Based on the recommendation of a mutual client, Nick approached me first by email.  I responded, but because I didn’t have an immediate need—and wasn’t entirely clear on what Nick offered—I didn’t take it much further.  Nick continued to stay in touch by phone and one day caught me with 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 and why:

“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.”

  • By starting out 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 any good reason to have one.

Here are the takeaways:

  1. Figure out how you want to position yourself before reaching out
  2. 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.
  3. Be respectful of people’s time and energy. Be succinct and thank them for their time in advance.
  4. Include an image in the email, if you can. People are more likely to read something with an accompanying image.
  5. Follow up. Here’s what I do:
  • 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!

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