1. When did you realise you wanted to be a designer?

I started working in design primarily because it was the only marketable skill that I had. When I was in college (The State University at Albany, in Albany New York) I majored in English Literature and minored in Russian Literature. (I often say I have a degree in reading.) I also wrote for the student newspaper and became the Arts and Feature editor in my senior year. As part of the role of editor, you were required to lay out and design the paper. I found that to be something truly magical.

I loved doing it; in fact, I loved it as much if not more than the actual editing and writing of the newspaper! When I graduated, there wasn’t much I could do with an English degree; I didn’t want to be an account executive in an ad agency. But I had the skill of being able to do what is now considered old school drafting skills. My very first job was working as a freelance designer paste-up artist at a magazine and I’ve been climbing the design ladder ever since.


2. How did you get started and what was the biggest hurdle you overcame?

My first decade out of college was full of what I call experiments in rejection and despair. I knew that I wanted to do something special, but, frankly, I didn’t have the courage to pursue my dreams. When I graduated, I didn’t feel confident enough, optimistic enough, or hopeful enough to believe that I could get what I really wanted. I dreamed of being an Artist and a Writer, but inasmuch as I knew what I wanted, I felt compelled to consider what was “reasonable” in order to safeguard my economic future.

I thought it was prudent to compromise and I told myself it was more sensible to aspire for success that was realistically feasible, perhaps even failure-proof. It never once occurred to me that I could succeed at whatever I wanted. My biggest obstacle to overcome was MYSELF! I was consumed by self-censorship and was certain what was impossible for my life before considering if it was even possible.

3. What’s been your most successful way of getting clients?

For me, it’s been one of two ways: networking at conferences and other industry gathering and events, and cold-calling! I built nearly an entire branding business from cold-calling. It’s really difficult and you experience a ton of nastiness and rejection, but I’ve found that it is the single most successful marketing tool I’ve ever utilized. Especially now, when most people rarely use the phone to talk on!



4. How do you get clients to stay with you and use you for more work?

Seven tips for getting and keeping clients (but you need to do them all):

  1. Over-deliver mind-blowingly good work
  2. Develop a deep, trusting relationship
  3. Do what they ask you to do even if you don’t agree, but do what you think is right AS WELL
  4. Don’t fall on the sword for the work, fall on the sword for the relationship
  5. Understand that common vocabulary does not equate with common behavior and learn how interpret your client’s unique way of communicating
  6. Know what you are talking about and NEVER lie
  7. Avoid compulsively making things WORSE


5. Do you ever have issues with clients paying late? How do you manage that?

Make sure you ALWAYS ALWAYS ALWAYS have a contract. If you do work without a contract you will always encounter a situation wherein you will not get paid. Make sure you have payment terms clearly indicated in the contract and avoid at all costs allowing payment terms beyond 30 days. You are not a bank!

If you are still having clients pay late, then sadly, you will have no recourse but to stop doing the work until you are fully made whole. It will be difficult, you will likely feel guilty and sad, but remember: the client is putting you in this situation by not paying you, and you must not accept being treated in this way.

6. What does your typical work day look like?

I’m work on a lot of different things, and I’ve always been that way. Several days a week I am at the School of Visual Arts, where I run a graduate program in branding and also teach an undergraduate class in design. If I am in a season of Design Matters, I spend a considerable amount of time doing research and preparation for my upcoming interview.

I am working on curating TWO art exhibits; I am beginning work on a new book, I am always working on Print magazine, where I am the editorial and creative director, and I always have work to do on the three boards I am a part of: The Joyful Heart Foundation, Performance Space 122 and The Type Directors Club. I’m busy but I love what I am doing and feel so incredibly grateful for these amazing opportunities.

7. Any piece of advice/wisdom that you’d like to give the readers at This Design Life?

Ten bits of advice:

  1. Be fearless when asking people for business.
  2. Find lots of clients. Because it’s impossible to know which of them will be good.
  3. Work harder than anybody else that you know.
  4. Never give up if it is something that you really want.
  5. Don’t lie about what you know and what you’ve done.
  6. Do not be afraid to want a lot.
  7. Things take a long time; practice patience.
  8. Avoid compulsively making things worse.
  9. Finish what you start.
  10. Often people start out by thinking about all the things that they can’t do. Once you take that path, it’s very hard to get off of it. Shoot high and shoot often.

Debbie Millman is an educator, artist, brand consultant and host of the radio show Design Matters.

Debbie is also the author of six books, including two collections of interviews that have extended the ethos and editorial vision of Design Matters to the printed page: How to Think Like a Great Graphic Designer and Brand Thinking and Other Noble Pursuits. Both books have been published in over 10 languages.

Chris Green

Chris Green at This Design Life
Chris Green is a designer and marketer. He runs an agency called Calloway Green and is also the founder of This Design Life.