Interview with Holly DeWolf


Today we have a special treat Diners, an interview with illustrator, writer, mentor, and teacher, the always inspiring Holly DeWolf. So grab a seat at the counter, get ready to talk the creative talk over a cup of coffee, or three.

Welcome to the Doodle Diner Holly, how do you take your coffee?
I love my coffee strong, hot and with a little cream please. I’ll need a big mug! 🙂

How did you come up with the idea to write a book about breaking into the illustration business?
This book came out of few places. First, I saw a need and decided to take on the challenge. Like many illustrators I was frustrated after I left school. I had more business and self-employment questions than answers. As time went on I soon realized I was not the only one. I decided to research the industry and discovered a love for it. From that came a willingness to chat about it. I guess that is how the mentoring thing came about. Secondly, I needed to shake up my own career. I had hit a point in my creativity where I needed a ‘creative sabbatical’ so to speak-I needed to reinvent myself or kick my career into another direction. Instead of waiting for the opportunity to come to me, I decided to make the opportunity myself. Lastly, finger injuries have a funny way of forcing your hand in strange ways. A bad day and a bad run in with a dog left my right hand in such bad shape that I could barely hold a pencil. My career was up in the air and I needed to think quick. After the dog incident I surprisingly became very fearless and what better way to use that energy than sending out a book idea! It all made sense!! Ha!

You are an illustrator, writer, mentor, and teacher, do you enjoy one role more than the others?
Naturally illustration is my first love and creative passion. I could never give up painting. I really enjoy chatting about illustration and creativity either casually or professionally. To me I love seeing and helping talent on the verge of greatness.

But naturally, we creatives are great at many things so when creative opportunities arise we can try them with ease. Often times when we realize there are few rules to creating or rules to this career for that matter, it frees us up to be open and relaxed with the concept of new things. So to me I am big on trying anything for my work either professional, personal or promotional. I guess this is why I try to throw in a creative hour daily to shake things up. This is a no rules, no plans kind of event. Often trying new ways of working adds to my illustration process through discovery and often through making mistakes as well.

You interviewed so many illustrators for your book, did that inspire any changes to your own creative process?
Yes it did. I have always wanted to combine my painting with digital so I am inspired to try that. Also, I am inspired to try some new markets for my work and perhaps think about an art agent come the future. I love being on the verge of a new creative experience. With that said, when the book came out came a need to teach and put on a gallery show. Reinvention is a large part of creativity so to me its all part of the package of this very interesting career I am so lucky to be a part of.

Do you have a different creative process for writing than when you are illustrating?
I think because I am narrative based the transition was a comfortable one. The notes that I make to come up with concepts were very similar to how I created the book. One big difference was time of course. I know how long certain concepts take as well how long painting takes. Writing a whole book was time consuming and this involved much shuffling of my schedule so much so that at one point it was all I could realistically focus on. Sometimes you just have to do what is important right now and then tell yourself that it’s good enough.

The nice thing about writing a book is that is in sections-chapters that is. So having a theme for each step along the way helped. I like choosing themes and often do this in my work especially when doing personal/promotional work. What the book did teach me is the concept of just rolling with it and letting go. This change was good for me. We often try to control our creative process. Rolling with ideas allowed me to just be free and open to all possibilities. The book changed me in many ways. It was exactly what I needed to do at this point in my life.

How long did it take to write your book?
It took me approximately 14 months to write the manuscript including adding contributing illustrators and illustrations plus editing, alterations and proofing. It was a labour of love though. I enjoyed every minute of it. And I want to do it again very soon.

Can you share any advice for illustrators that may be considering writing their own book?
A good approach is to break down your book submission into sections. First, I would have a definite concrete idea. Then, define your purpose, your theme, your audience, a possible title, and your inspiration. Give your dream publisher something to work with such as an introduction or a table of contents. Some publishers want to get a grasp on how you write and also the ‘voice’ of your book so provide a chapter or more. Send a Bio along with enough information that is relevant about you and your career, experience and whatever else will be useful towards the book.

Another word of advice is this: look for opportunities. Look for a need, a gap, something unique and fill that void. Sometimes opportunities are missed because many are not paying attention to what is missing and more attention is placed on what has already been done. Set yourself apart by looking at what this industry needs-a unique creative edge. There are endless books displaying illustrations but if you can create a book that educates, inspires and helps, then you have created something really special.

One of the things that I love about your book is that you’ve drawn insight, and inspiration from so many different sources. Is that something you have always done, or something you learned along the way?
That is definitely something I have always done. To me creativity is contagious-one idea leads to a thought, a visual, a sketch etc. I write everything down. I collect snippets of thoughts, ideas, bits of images, words, quotes, music lyrics, you name it. If it rocks me creatively I make sure I keep it by storing it either in a notebook, bookmarking it on my computer, my cork board, or in an file for future inspiration. Also ideas can be recycled for future projects as well. I believe in keeping an image file. I keep snippets of images for reference. You never know when you may need to illustrate something completely different. I am very narrative based so words are pretty important. I could not live without an online thesaurus. Word play is fun and can help jump start images quickly. These are some of the creative habits that I keep.

It takes a lot of work, and time to break into the illustration business, when did you know that you had finally made it?
I knew I had finally made it when I stopped worrying about making it…make sense? Basically I stopped worrying about accolades, awards, applause, money, my lack of experience, and what other illustrators were doing. I stopped comparing myself to other illustrators. I stopped seeing it as a job and more as a career, a personal creative drive and a process. I went back to basics and re-learned things I was taught in art & design school about loving the process and staying out of the box.

One big challenge we face as illustrators is getting ourselves out of the dreaded creative bubble. Getting myself involved into a creative community also helped me feel connected to my career on a new level. I do believe being ‘on-line’ is one of the greatest assets to illustrators. We now have a voice and a community which is helping this industry come together. The more we write about it, chat about it, mentor, blog about it and showcase it helps make it better for all of us.

You have injected a lot of your wonderful sense of humour throughout your book, can you share a story about a time where having a sense of humour saved the day?
That pretty much describes most days while juggling kids, mess, noise and a very very flexible schedule. One time I was doing a podcast online and I needed my 7 year old to be quiet for me. So I knew she was about to come home and I thought it would be fun to make signs and maps to guide her around the living room to keep her busy and quiet while I was chatting away on this podcast. The first sign was on the stair railing with ‘Shhhh…Working’ on it and another was ‘Mum is a Blabbersationalist….can you spell that out?’ and it went it on from there. In the end I got the podcast done and some really cool art from my daughter. Luckily my 3 year old was asleep at the time. It could have been one of those hair pulling moments but with kids you can problem solve creatively in a pinch when needed. Distractions are wonderful things.

One last note: Sometimes it feels there comes a point in a creative persons life when we should rock the boat…more!! With that said, it does not mean when adopting this new philosophy that it comes smoothly without any bumps and trip ups. Having a sense of humor has really saved me especially on those days when I am pretty sure a mushroom cloud will suddenly appear above my house or when my computer just says No! I truly believe if you can successfully work at home and stay creative without blowing it up…. you can do anything!! Thanks for the interview! Cheers!

I would like to thank our special guest Holly DeWolf, for visiting the Doodle Diner. While I put on a fresh pot of coffee please enjoy the links below, featuring Holly’s brand new book: Breaking Into Freelance Illustration: A Guide for Artists, Designers and Illustrators now available on &

Holly DeWolf online:

Illustration provided by Holly DeWolf. © Holly DeWolf


5 Responses to “Interview with Holly DeWolf”

  1. princesstomato Says:

    Thanks for joining us at the Diner, Holly.
    Very inspiring interview!

  2. valgalart Says:

    Firstly this was a great interview, pickle, you have a career in interviewing and second Holly everything you say is good and real! The internet is definetly changing the landscape for all the venues ie music, movies, art, lits, etc into a new arena that we are on the cusp of and it is very exciting! Like being a pioneer in the new age. Really great and valuable info for all artists young and old alike Holly! Wonderful words and I love your humour too. Thank you Holly and Pickledog!

  3. sketched out Says:

    Great, inspiring interview!!! Big thanks to Holly. Reading this really revved me up and I’ll be heading to Amazon to pick up a copy in a few minutes. Among the many great tips and advice I especially liked the discussion about looking for gaps in the industry to fill and also, how she knew she’d made it when she stopped worrying about making it! Thanks again Holly! Brilliant!

    … aaaand…David, I agree with Val, you really did a smashing job with the interview. Great questions. You rock!

  4. roberta baird Says:

    Terrific interview… Holly you truly inspire!
    David… you rock!!!

  5. Applied Arts Wire » Breaking Into Freelance Illustration Says:

    […] also been profiled/interviewed as she’s promoted the book on various sites, namely Doodle Diner, Escape from Illustration Island and My Life List […]

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