Kyle Webster, IllustratorBeing a creative person and doing what you love doesn’t mean you’ll spend the rest of your life struggling day-in and day-out. According to Kyle Webster, an award winning illustrator living in Winston-Salem, NC, you can achieve success as a creative, if you follow the formula. Starting small, honing your craft, building relationships, and exercising patience is the key.

Securing high profile clients such as The New Yorker, The New York Times, Wall Street Journal, BusinessWeek, Entertainment Weekly, Scholastic, Nike and several others didn’t happen overnight for Kyle.

“I had to be realistic about what I could and could not achieve based on what stage I was at in my career. So, I didn’t immediately reach out to the New York Times. Instead, I created drawings and sent them to various small free weekly newspapers in the country, then to regional and state magazines before approaching national publications,” said Kyle.

Starting small provided an opportunity for Kyle to work in his field, hone his craft, build his portfolio, and build relationships with others in the industry who were also starting out.

“When I was ready to approach the national publications, I could say with confidence I’ve been working for several years and here is my work and these are my strengths. You have to know what you are good at and promise “only” what you are good at,” said Kyle.

In addition to having a strong work portfolio, trusted relationships are key. “I used the phone just as much as I used email so I could have more of a personal relationship with my contacts. Having personal relationships benefited me in ways that I would have never predicted. Many contacts I did work for at the start of his career moved on to art director positions for notable publications including USA Today and many others. Many had fond memories of working with me at the start of their careers so they often called on me to do work for them later,” said Kyle.

What other advice do you have for creatives desiring to succeed in his/her craft?

“As a creative, I think we want so badly to get out immediately and start working. It doesn’t matter how good your idea is if you can’t communicate it effectively. You need to know where you are in your career in relation to where others are in your field. Study people you admire in your field and ask yourself, what makes their work good? Then look at your own work through that same lens. Is it as good as what is out there in the landscape? If not, then put in the many hours needed to improve your work. You have to do things with the intention of getting better – don’t do something just to pass the time. Be conscious and work with the intention to improve. Then, and only when you are ready, should you approach the right people at the right stage in your career,” shared Webster.


  • Start small
  • Hone your craft
  • Study who is successful in your industry
  • Build relationships and maintain relationships through email, phone, and face-to-face conversations

Marketing a creative business on a budget can be a challenge. Will Kyle’s formula for success work for your creative business? Why or why not? Join the conversation and post your comments on our blog or Facebook page.

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