Interview by Madeleine Dore
Photography by  Maggie Shannon

Debbie Millman:
Designer, artist, author, educator

Though Debbie Millman is an established author, artist, educator, brand strategist, host of Design Matters podcast, editorial director of Print magazine, and for 20 years was the President of the design division at Sterling Brands – she feels like she’s just getting started.

“I left Sterling last year and that completely liberated my days,” she says. “It sounds so goofy and kind of cheesy but I feel like I'm just getting started.”

Debbie’s schedule now has more flexibility and freedom, working at New York City’s School of Visual Arts on the branding graduate program she co-founded in 2009.

“I'm a lot happier now with this type of routine – previously I had a full-time day job and a full-time night job. It was hard, but I did it and I got through it because at the time it didn't feel unmanageable. Now, I think I'd go crazy if I had to ramp up to that workload because I’d have no time to just think and create.”

Freedom brings more options in her creative work to consider and play with, but perhaps most importantly, is combined with a newfound deliberateness.

“I’m fifty-five and I do feel a sense of urgency because I don't want to run out of time. There is that if-not-now-when feeling,” says Debbie.

In our 20s, 30s, 40s – and even our lifetime – we can so easily ignore that our days are not infinite; that we may run out of time, that we may not be able to do everything we want to do. Acknowledging that life is in fact finite can be one of the biggest motivators for creative work.

“Life is going by fast and now that I'm midway through, it's even faster. There's even more urgency to be much more deliberate about what I want and what I don't want.”

Having a strong resolve about what you truly desire be the key to not being limited by a false sense of capacity.

“I just try to do what I want to do even  if it means having to work a little bit harder,” says Debbie. “I've always taken on more than I could do, and I've always spent more time working than doing anything else, but I love it.”

For Debbie, work is not laborious, but a privilege. “I've worked for a really long time to get to a place where I'm being offered commissions to do projects that are amazing. I try to make that my priority,” she said.

How can aspiring designers, artists, writers and creative entrepreneurs reach similar heights? The first step may be to dream without fear. For years, Debbie Millman has shared an essay exercise with undergraduate and graduate students she calls Your Ten-Year Plan for a Remarkable Life after having she experienced the profound effect it had on her life and career when she did hers more than a decade ago.

“I think it was twelve things that I was hoping for and I think eleven of them have come true. They were big, audacious things. It’s spooky.”

The second step? “Just keep experimenting,” says Debbie. “If you want to do something, do it.”

And finally, “Savour every day. Savour every day.”

“Just keep experimenting. If you want to do something, do it. Savour every day.”
Photography by Brian Emerick

A day in the life

Photography by Chris Dibble


I’ve never ever been a morning person. Actually, this is the first time in my life that I've been getting up without significant help from an alarm clock. I try to get eight hours of sleep, so I usually get up between 8 and 9am.

I love sleeping and I treat it sacredly. There can be stigma around sleep in our culture that I find really sad, given how important it is and how much better a person feels, how much more productive they are in the hours they are awake if they do get enough sleep. It is when we regenerate our cells and organise our memories, experiences, and subconscious. I feel that I work better, I have more energy, and I'm happier, healthier when I have enough sleep.

If I don't get enough, you don't want to be near me because I'm cranky and I get overly hungry and I'm just not fun to be around.

“I’ve never ever been a morning person. Actually, this is the first time in my life that I’ve been getting up without significant help from an alarm clock.”

Mid morning

I like to spend an hour or more reading, seeing what's happening on the planet and trying to avoid looking at Donald Trump's Twitter feed. I read The Wall Street Journal, The New York Times, CNN, Politico, Slate, Brain Pickings, Brand New, of course Design Observer, Lit Hub and a couple of other gay lady sites.

That’s of course when I have the luxury of being at home. I don't always have that luxury – sometimes I have board meetings or have to be at the School of Visual Arts early.

When I’m home, after reading I'll start doing some work: emails, writing, illustration work, phone calls, or conference calls.


Usually somewhere between twelve and one, I head into the School of Visual Arts (SVA). But I'm out and about a lot, so I don't just sit in my office all day – I'm often going to other places for meetings.

I walk everywhere, and I'm really fortunate that I get to walk back and forth to SVA everyday. It gives me a lot of time to come up with ideas, decompress on my way home, things like that.

For lunch, I’ll sometimes have a salad, sometimes pizza, sometimes a bag of pretzels, sometimes left over dinner.


If I keep track of all my deadlines, and I know exactly when I need to do certain things, and I've carved out time, then I don't get anxious. But if things start to pile up and I haven't been able to organise them or write them down, then I get really anxious because I feel like I'm missing something and something’s going to fall through the cracks.

I've been working through a two-year calendar that keeps track of all my deadlines until the end this year. I'm sort of mortified by the notion of having to start fresh. 

I write everything down – I keep a running to-do-list that I check off when things are done, and I have a Google calendar so that the people I am connected with can keep track of what I'm doing or where I am.

“I like to spend an hour or more reading, seeing what’s happening on the planet and trying to avoid looking at Donald Trump’s Twitter feed.”
Photography by Lisa Congdon


I teach till 9.00pm two nights a week, and then I'm usually in the office for another hour so doing paperwork and following up with things. If I'm not teaching, I might still be at the office, depending on what I'm working on, or I might be working at my studio at home. The messy work will be at my home studio – I keep the paint, felt, materials and thousands and thousands of coloured pencils there.

Photography by Lisa Congdon


I'm also really obsessed with the news, so when I come home from work, I have three shows that I tape every night, the Rachel Maddow Show, Hardball with Chris Matthews show and The 11th Hour with Brian Williams show. I tend to watch them no matter what time I come home because I have to keep up with the nightmare we're living through.

I usually go to bed at midnight or 1am. I could stay up even longer, but I have to force myself to go to sleep. I'm somebody that doesn't do transitions that well. I love being up late. I love the quiet. I love the dark. So I have to really force myself to go to sleep. As difficult as it is for me now to go to sleep at night used to be how difficult it was for me to wake up in the morning.

If I can't get comfortable, I sort of just try to lay flat on my back, my hands at my sides, no pretzel shapes, and just try to relax.

“I’m somebody that doesn’t do transitions that well. I love being up late. I love the quiet. I love the dark. So I have to really force myself to go to sleep. As difficult as it is for me now to go to sleep at night, used to be how difficult it was for me to wake up in the morning.”

Weekend routine

I’ll spend the weekends pouring over the weekend edition of The New York Times. I also spend time playing with my dogs Duff and Scruffy. If it’s nice out I might do some gardening, though I have a black thumb.

If I have a Design Matters episode to record on Monday or Tuesday, I will spend all of Sunday working. 

At least once a month, I spend the weekend with my brother, his wife and my niece and nephew on Long Island. 

One of my favorite things to do is to lay on my bed and look out the window. I’m very lucky that I can see some sky and I can watch the clouds go by or see the stars at night. There is nothing like that type of quiet contemplation. I don’t consider it meditation, but it’s something really spiritual. I’m not focused on anything, I’m just letting my thoughts go by and I treasure that time.

Photography by Lisa Congdon

Life lessons from Debbie Millman  

1. On letting go of the career trapeze…

It was tremendously scary leaving Sterling. So much of my identity was wrapped up in my day job and in being {resident, but I weaned myself away. A very dear friend of mine, who I had a business with when we were in our 20s, sold his business long before I sold mine and he gave me some advice. He said, “Don’t go cold turkey, transition out.” I listened to him and I did that.

I went down to three days a week and then I went down to one day a week. By the time I was a year into doing one day a week, I was ready to go. Back then, I felt like I was desperate to make changes but I was terrified. I had mentioned this to a woman who I had met who was the former general manager of Puma. She had quit her job and started a retail specialty food store in Massachusetts.

I said, “How did you do it? How did you get the courage?” She said that one day had to let go of the trapeze. I had this vision of my arms and legs all tangled up on my trapeze – I was locked into so many things that I couldn't even fall if I wanted to. It was just a matter of trying to organise my trapeze, my time and my fear.

2. On making difficult decisions…

In some ways, you have to take a leap of faith. You have to decide what is more important: doing it or not doing it. If you can't decide, it might not be as critical as you think. But if it is, it will get to a point where the critical mass will push you to take that step and that it won’t seem so hard anymore. I look back and I’m like, “What was I so worried about?” I’ve always been that way.

3. On the myth of the last opportunity…

I’ve always had this fear that this was the last opportunity for employment, the last opportunity for love, the last opportunity for creativity and it’s just not true. It’s just this perpetual lie that I’m hoping I’m not telling myself as much anymore.

Part of that was realising that I could rely on myself. When you realise you can rely on yourself – that no matter what– you can rely on yourself, you’re not as worried about ending up homeless living in garbage piles.

4. On why we can and should take things personally…

If you’re a person, everything is personal – that's just the way I feel. I’ve come to recognise that my own sensitivity is not just emotion, but it’s empathy. It’s how you position it, how you frame it. You could say I’m too emotional, or you could also say I’m deeply aware of what’s happening in the world, deeply connected to the world, and I wouldn’t want it any other way. What other way is there to live?

“If you’re a person, everything is personal.”

5. On how everyone thinks they’re an imposter…

Everyone is scared and insecure and worried. There are very few people that I’ve interviewed, if any, who just walk around thinking they are great all the time. Maybe we think that we’d like to be happy all the time or feel great all the time, but I think that would take away from the power that those feelings have.

We know people put on a lot of facades, especially now with social media, where you can position yourself as happy and beautiful all the time. It’s just not possible to really be that way.

6. On what she wished she knew…

I wish I knew I was talented. I wish I knew I was pretty. I so regret not knowing that now.

Seth Gordon says this really well. He said, "If I changed anything, I wouldn’t be here necessarily." I’m really happy being here. If any of those things meant that I wasn’t going to be here, I don’t know that I would change anything. Mostly, I wouldn’t be so hard on myself, wouldn’t beat myself up so much. I wouldn’t take everything so seriously in terms of my worth and my value.

7. On busy being a decision…

I say busy is a decision. If you want to do something, you find the time. You make the time to do them. If I'm being offered an opportunity to do a project that might cut into something else, I'll try my best to make it work.

Sometimes I get myself into trouble because I'll say I want to do something and then I'll have the idea about what it is I want to do which is far more grandiose than it necessarily needs to be and then I'm pulling my hair out because I have to get it done. 

Sometimes I make more trouble for myself than I really need to, but ultimately, I don't remember the anxiety and the stress as much as being proud of what I did.

8. On recognising emotions will pass…

The older you get I think, the less stressed you get. I still get stressed. I'll get snappy and impatient, and I’m probably harder on myself than I need to be, but it passes. When you get older, you realise that most emotions pass and you don't get so worried or caught up in them – you don't have to respond right now if you're upset. You can wait a couple of hours or a day or two, and that tends to be really beneficial to everybody involved.

Photography by Chris Dibble

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