Ep 100 – Debbie Millman – Lessons in Leadership, Design, and Abundance
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Featuring: Debbie Millman
In the 100th episode of Agency Bytes, I couldn’t think of a more fitting guest to mark this milestone than the legendary Debbie Millman. As a designer, writer, educator, and the pioneering host of Design Matters, Debbie has shaped the creative industry in ways that continue to inspire me and so many others. In this conversation, we dive into her remarkable journey—from leading Sterling Brands to an Omnicom acquisition, to her impact on branding and design education, and even the evolution of her own 20-year podcasting career. She shares invaluable insights on leadership, overcoming rejection, embracing an abundance mindset, and finding inspiration in unexpected places. Plus, we discuss her upcoming book Love Letter to a Garden and the deeply personal connection between creativity and growth. It’s an episode filled with wisdom, warmth, and a celebration of resilience in the creative industry.
In this episode, we dig into:
• Debbie’s leadership at Sterling Brands and the journey to an Omnicom acquisition
• The evolution of Design Matters and what 20 years of podcasting has taught her
• How an abundance vs. scarcity mindset changed her creative path
• The impact of Milton Glaser’s mentorship and his powerful five-year vision exercise
• Advocating for women in design and her role in Omnicom’s Omniwomen network
• Dealing with rejection, imposter syndrome, and the realities of a creative career
• Her new book Love Letter to a Garden and the inspiration behind itSo, whether you’ve been here since episode one or you’re tuning in for the first time, thank you for being part of this journey with me. I sincerely hope you enjoy this special 100th episode of Agency Bytes with the one and only Debbie Millman!
Key Bytes
• Debbie became a shareholder at Sterling Brands in 1998.
• Leadership requires balancing financial acumen with creative passion.
• Debbie's management style was demanding yet fair.
• The acquisition by Omnicom was a pivotal moment for Sterling Brands.
• Debbie actively mentors and advocates for women in the industry.
• Her podcast, Design Matters, has evolved significantly over 20 years.
• Debbie's closing statement reflects her commitment to making a difference.
• The podcast has maintained a loyal audience despite industry changes.
• Debbie's early writing for Armin Vitt's blog sparked her design journey.
• Milton Glaser's teachings on scarcity and abundance were transformative for Debbie.
• Writing a five-year plan helped Debbie visualize her future.
• Debbie emphasizes the importance of teaching and sharing knowledge.
• Rejections are a common experience, and feelings are temporary.
• Travel serves as a major source of inspiration for Debbie's work.
• Debbie's upcoming book combines her love for gardening and visual storytelling.
• Debbie encourages embracing both successes and failures in one's career.
• Believing in oneself is crucial for achieving goals.Chapters
00:00 Celebrating Milestones: The 100th Episode
12:37 Navigating Challenges in a Changing Market
18:06 Empowering Women in Creative Industries
24:42 The Evolution of Design Conversations
33:35 Navigating Rejections and Setbacks
42:05 Upcoming Projects and Personal Growth
Named “one of the most creative people in business” by Fast Company, “one of the most influential designers working today” by GDUSA, and a “Woman of Influence” by Success magazine, Debbie Millman is also an author, educator, designer, and podcast pioneer. Debbie is the host of the Webby and Signal award-winning podcast Design Matters, one of the first and longest-running podcasts in the world; Chair of the first-ever Masters in Branding Program at the School of Visual Arts, Co-owner and Editorial Director of PrintMag.com, and the author of seven books on design and branding. Debbie is the recipient of a Cooper Hewitt National Design Award and a Lifetime Achievement award from AIGA, the Professional Association for Design. She is currently a Harvard Business School Executive Fellow and was recently invited to the Design Advisory Board of Canva.
Contact Debbie on their website or through the SVA Branding program.
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Steve / Agency Outsight (00:05.14)
All right. Welcome to Agency Bytes, a podcast dedicated to helping creative entrepreneurs thrive. I'm Steve Guberman from Agency Outsite, where I coach agency owners to build the business of their dreams. Today, I am beyond thrilled to welcome the incredible Debbie Muleman to the Agency Bytes for our 100th episode. A little bit about Debbie for those who may or may not know, but Debbie's been named one of the most creative people in business by Fast Company, one of the most influential designers working today by Graphic Design USA.
and a woman of influence by Success Magazine. As the host of Design Matters, a Webby and Signal Award winning podcast, and one of the first and longest running podcasts in the world, Debbie is a true pioneer in the creative space. She's also the chair of the first ever Master's in Branding program at the School of Visual Arts, co-owner and editorial director of printmag.com, and the author of seven books on design and branding. Debbie spent more than two decades at Sterling Brands.
where she was the driving force behind its incredible growth from a team of 15 to over 150, leading the agency to become a branding powerhouse that was ultimately acquired by Omnicom. For accolades or countless, she's a Cooper Hewitt National Design Award recipient, an AIGA Lifetime Achievement Awardee, and currently a Harvard Business School Executive Fellow. And just recently, she joined Canva's Design Advisory Board.
As I was approaching my hundredth episode, I knew I wanted to invite a guest who has made a profound impact in our industry and on me personally. And there was really only one person I could think of for this milestone. So I put out into the universe that I wanted Debbie to be on my centennial as my centennial guest. And lo and behold, coincidentally, I met Steve Picanza, who was gracious enough to connect us. And here we are, Debbie. Welcome to the show. is an absolute honor to have you here.
Debbie (01:54.68)
Thank you, Steve. Thank you for that really wonderful introduction and I'm really impressed by your research.
Steve / Agency Outsight (02:02.33)
I re-listened to a dozen of your podcast episodes. I've been listening for 20 years. I'm like a huge fan. I have a couple of your books on the shelf behind me. I watched your most recent interview with Seth Godin. I watched probably another maybe two or three of those. And so I just have been long time inspired by the work you've done both as a creative professional, but in just the administrative part of the creative.
that we have and so I'm just I was like mom or Debbie Millman for 100th guest and so here we are.
Debbie (02:39.822)
Thank you. I'm honored.
Steve / Agency Outsight (02:43.7)
Um, I, so I have a handful of questions and I typically don't pre question things, but we'll see where this goes. And so I want to start because most of our listeners are agency owners, creative professionals. And I want to start asking about your time at Sterling and early in my career. I knew of you and Sterling, and I thought you were the owner. And it wasn't until recently that I discovered you weren't the owner, but you took it from 15 to 150. And ultimately.
to an acquisition and when a lot of owners come to me, say, Steve, I wanna sell my business, coach me to get there. And they're not ready to sell at all, but we do the work to get them in the position to sell. And so I'm curious for you, leadership role as a creative professional, what were some of the essential characteristics that you had to like bring forth in order to grow and be more hands off over time and.
advise your team and guide them into this growth that you were experiencing.
Debbie (03:46.51)
Well, I was an owner. I became a shareholder in the company in 1998. So I got there in 1995. And my original offer letter from the senior partner, Simon Williams, indicated that if I had essentially performed well enough that I would be eligible at the time for Phantom stock.
Steve / Agency Outsight (03:56.52)
Okay.
Debbie (04:16.854)
And in 98, so I had, I got there and just really hit the floor running. had already built a network of potential clients to pitch when I was at Interbrand right before. And left in 95 to go work at Sterling and had a non-compete. I had to manage through that, but I.
Steve / Agency Outsight (04:24.116)
Okay.
Debbie (04:44.344)
had a lot of people that I had been talking to that I hadn't gotten business from yet. So when I got to Sterling, I really was almost successful from day one. And I remember in that first year, I brought in business from Pillsbury, from General Mills, from McNeil Health, which owned Tylenol at that time. And...
Steve / Agency Outsight (04:50.708)
Mm-hmm.
Debbie (05:12.63)
Unfortunately, we were getting fired from all of those jobs. Now at the time, the design staff was primarily British because Sterling's original place of business, their birth of business was the UK. And so when they came here, a lot of the designers from the UK came along. And so there was a very British.
visual language to the work that we were doing, which eventually became coveted, but at the time was really hard to sell. And so we ended up getting fired. And at the time I was really worried about my reputation. And Simon Williams, at that point, I had come in as Senior Vice President of Biz Dev, and then he promoted me to President of the Design Division.
Steve / Agency Outsight (05:50.876)
Sure.
Debbie (06:10.998)
And then I was able to really influence the culture of our group. within, so that was within two years. So the very next year when we were gangbusters, I approached Simon and wanted to sort of check in with him about my potential for ownership. And he was at the time a little bit skittish about it. And, you know, I loved my job.
Steve / Agency Outsight (06:40.212)
Hmm.
Debbie (06:40.902)
I was working 24 seven. This was really my first big, big time, continuous success. I had some at, at Interbrand, but it was a very different situation here at Sterling. was making an impact. felt like I was really reaching a place in my career that I had only dreamed about. And so in those initial years, that was all I wanted to do. You know, I'd given up and I talk about this and that ultimately
Steve / Agency Outsight (07:07.508)
You
Debbie (07:09.874)
led to a little bit of a shift in how I was thinking about my creativity in the next decade. But initially I was just like, I'm giving up everything else and I am doing this full time, 24 seven, no more painting, no more writing, no more guitar playing, no more anything, no more marriage. I'm just doing this. And I loved it.
So when Simon at the time was really skittish initially, and you know, who wouldn't be giving up shares of an organization that suddenly turned a corner and is doing really well. So I did something that I don't even know how I got the balls to do. I said that if I didn't get shares, I would leave. Now, Steve, I went home that night and cried because I'm like, what?
Steve / Agency Outsight (07:54.148)
Wow
Debbie (08:00.748)
What the F did I just do? I love this job. I don't want to leave. And so it had just like popped out of me. And fortunately, he offered me some stock right at that point. And then over the decades that I was there, two decades, I kept getting an increase that was correlated with my performance.
Steve / Agency Outsight (08:00.948)
Mm-hmm.
Debbie (08:26.452)
And so by the time we sold, was the second largest shareholder at Sterling. And so, you know, that was wonderful and life-changing and still something that I'm just incredibly grateful having the opportunity to do because while I was really good at selling, somewhat good at managing, somewhat terrible at sort of details, so had a lot of good people working with me.
Steve / Agency Outsight (08:28.724)
Wow.
Debbie (08:57.186)
I don't know that I ever would have had the...
to even consider selling. But that was Simon's goal from the beginning, which is why it was inserted into my offer letter. And so in regards to your first question, there were really two things. One was margin, because that was really, you know, there were two things, margin and reputation. That's it, the quality of our work, the quality of our finances.
Steve / Agency Outsight (09:21.548)
Mm-hmm.
Steve / Agency Outsight (09:30.1)
Yeah.
Debbie (09:30.246)
And Omnicom was really, really strict about both. We hired a COO, an incredible man named Craig McCaffrey, who was based in Sydney, Australia, but came to New York to help us sort of get our margin in order. And he was both ruthless, but also kind. And initially I was really put off.
in working with him because suddenly everything was also a financial decision. And while I obviously wanted to make money, I was much more motivated by the design impact. So suddenly I had these two pockets that I had to consider. And while I always wanted the company to do well and be able to give bonuses and so forth,
Steve / Agency Outsight (10:01.8)
.
Debbie (10:20.832)
I wasn't hammering down on the margin to a degree that he was forcing us to do. But we got our books in order and ultimately OmniCom wanted us for both our design capabilities and our financial acumen.
Steve / Agency Outsight (10:38.876)
Yeah, that's a tough line to juggle or tough line to balance knowing you're passionate about the work and you want to do great work but also the numbers guy is like yeah but you need to charge more for this and do you remember like what the target margins were back then that you were chasing?
Debbie (10:54.818)
The minimum that at that time this was.
17 years ago. No, can't be.
I'm going to do the math. I'm going to my calculator. Math isn't my heart.
Steve / Agency Outsight (11:07.092)
27 years ago.
Ha
Steve / Agency Outsight (11:14.056)
We went to art school, not math school. We were told there would be no math.
Debbie (11:16.878)
I hate you.
Debbie (11:20.942)
17 years ago, it was 17 years ago. We sold in 2008. yeah, 17 years ago, 2008, the minimum margin was 26%. And now I think they, and even then as we had a five year earn out, they were really looking by the end more like 32.
Steve / Agency Outsight (11:23.388)
Wow, okay.
Steve / Agency Outsight (11:33.575)
Okay.
Steve / Agency Outsight (11:42.514)
Good. Yeah, super healthy. you know, a lot of people say, the bigger the agency or the more the are the margins smaller. And the reality is 30 percent is 30 percent, no matter if you're a million dollar agency or a hundred million dollar agency. So.
Debbie (11:52.526)
I mean, you don't want to go cutting into the bone in order to those returns. And sometimes you really do have to invest in order to be able to ultimately get those returns. But at that time, they expected as the company they were acquiring for us to have all of that in order.
Steve / Agency Outsight (11:56.798)
Yeah.
Steve / Agency Outsight (12:11.452)
Yeah, interesting. Yeah, what a ride that must have been for you, for the team that you brought along with you and people I'm sure that you groomed along the way into their own leadership roles. You said something about your management style a few minutes ago, like, you know, not great at details, okay at leadership. What do you, how would you define your leadership style in that environment?
Debbie (12:19.162)
yeah.
Debbie (12:37.374)
example, lead with example, I worked really hard. I think that, you know, I was told by a lot of people that I was always demanding, but always fair.
Steve / Agency Outsight (12:38.612)
Okay. Yeah.
Debbie (12:52.27)
I learned a lot about leadership, obviously, working at Sterling. to his credit, Simon Williams was very much into the best possible training for the staff. Certainly in the first decade I was there, we were always working with coaches and...
organizational psychologists to really teach us. mean, leadership is really messy and everybody has a leadership style. If they work at developing one. I don't really believe that leaders are born. I do believe it's a skill. I mean, I certain people are charismatic and that can certainly help, but it doesn't always quite a lot, quite, quite a few of the best leaders were introverts. And, you know, there's always a different way that people.
Steve / Agency Outsight (13:14.739)
Mm-hmm.
Steve / Agency Outsight (13:33.236)
Right. Yeah.
Debbie (13:43.214)
communicate their power. so we were really encouraged to find our own and use it for the betterment of the business. You know, not to say that it was always easy. You we sold the company in 2008. We sold the company in June of 2008. So if you remember back at that time, by October of 2008, the world was crashing.
Steve / Agency Outsight (14:02.58)
Yeah.
Debbie (14:07.406)
So, you know, we would not have been able to sell the company if we had spent another three months negotiating. No one knew that was coming. Although there were signals, because I do remember at the time, a lot of commodities, the prices were starting to rise, like butter and milk and eggs and so forth. And everybody was like, what's going on? What's going on? And then, you know, obviously the crash.
so we were, we had a five year earn out, which was very lucky because if we had a three year earn out, that first year would have seriously impacted us because after that, in that first year, I wasn't even sure we'd get another payment because of how bad. And, know, so that meant really.
Steve / Agency Outsight (14:31.572)
Sure. Yep.
Debbie (14:50.796)
looking at how we were positioning ourselves, staffing, especially that first year you're owned by OmniComm and then the world falls apart. The first thing they're going to do is, what can we cut? And we didn't want to be operating in that mindset. So that was really, really challenging. The year leading up to the acquisition.
was incredibly exciting, know, meeting with all the big wigs and making presentations to, you know, John Wren, who was the chairman at the time and all of the finance people. And we weren't just being courted by Omnicom. We were also being courted by a couple of other major holding companies because our COO and our CEO, Simon Williams, really, you know, we were essentially offering ourselves and then hearing what those offers would be.
Steve / Agency Outsight (15:37.924)
Sure.
Debbie (15:39.622)
And so we got three offers and we chose Omnicom. And that was really heady meeting with all these like super senior executives that had this giant responsibility of these large holding companies. chose Omnicom, which was interesting because I had left Interbrand, which was part of Omnicom. And so to go back was...
Steve / Agency Outsight (15:58.42)
Sure.
Debbie (16:02.668)
sort of had a nice symmetry to it. And I loved being part of OmniComm at the time as the president of the design division. I was the most senior woman in the organization at Sterling. And so I became part of the Omni Women Network and was on the governing board and met women who I'm still friends with to this day. there was so much collaboration. I mean, I met Carl Heiselman,
dude at Wolfholens. And then we started collaborating. We did a fantastic project with Wolfholens. We started working with the agencies that working with Kraft. so it was phenomenal. And then Omnicom also had an education program called Omnicom University that was a collaboration between Harvard Business School and Babson. And I did that. I had three sessions in that. And that...
Steve / Agency Outsight (16:32.032)
Okay.
Debbie (17:00.682)
expanded my brain power enormously. And that's where I met Francis Fry. And that's who invited me all these decades later to be part of the Harvard Business School Fellowship Program.
Steve / Agency Outsight (17:14.608)
Wow. Full circle there. You, and you mentioned, yeah, well, so you mentioned, I don't remember exactly what you just called it, but the Omnicom Women's Group.
Debbie (17:17.25)
Yeah, you live long enough and everything sort of connects.
Steve / Agency Outsight (17:27.028)
Omni women, I see you from a distance as such an inspiring female creative professional. And I, and I try so hard to mentor, elevate, you know, female students, professionals, entrepreneurs, et cetera. And, and so I, how do you define that as part of what you do intentionally? Or is that just kind of because, you know, I just said you're the senior most
Debbie (17:27.402)
I'm using it. Yep.
Steve / Agency Outsight (17:57.17)
female creative, you just kind of fell into that. That's something that you intentionally hold on to, to try and elevate other female creatives.
Debbie (18:06.2)
Well, I was an advocate for quite a few people within the organization. I always responded to people that were willing to work hard, willing to grow, willing to challenge themselves, that were ambitious. I spent a lot of time early on doing a lot of training, doing a lot of in-house.
Steve / Agency Outsight (18:18.484)
Mm-hmm.
Debbie (18:32.398)
positioning work to really understand the kinds of clients we wanted to go after, what kind of work we wanted to do. My particular fascination has always been with fast moving consumer goods.
And so that was, and that had already been the concentration at Sterling. And so, you know, I was interested in working with the biggest brands in the world. And so we had to adjust our pitch for that. And that was pre Omnicom. Once we were part of Omnicom, that was a real advantage because we were able to network within the various other agencies. But that was always my interest. so I was...
Steve / Agency Outsight (19:02.228)
Mm-hmm.
Debbie (19:14.464)
really at the time committed to us all having the same values about the work we were doing. So that was very, very intentional. Did I have a partiality to...
Steve / Agency Outsight (19:14.9)
Yeah.
Debbie (19:30.67)
Certain kinds of people? Yeah, I did. And the one thing that I can say is that I know that people were like, oh, Debbie has her favorites. And I did. My favorites were the people that worked hard, that were really committed, that were extremely loyal to the organization, that were really profoundly committed to the betterment of the business, the betterment of the work. So yeah, I did have favorites. Now as...
An educator, I still have the same tendencies. I tend to also pay particular attention to women of color, probably because I'm married to one, and the LGBTQ community, which I'm okay with. I'm okay with
Steve / Agency Outsight (20:08.008)
Mm-hmm. Mm-hmm.
Steve / Agency Outsight (20:15.371)
Absolutely. I'm okay with it too. In you care. I absolutely think that's perfectly fine. Good for you. Yeah, absolutely. So shifting gears to your podcast, Design Matters. 20 years. Mind blowing.
Debbie (20:28.662)
I know. the time this is out, when is this going to come out?
Steve / Agency Outsight (20:32.756)
January or February of 2025.
Debbie (20:36.588)
Yeah. So February 4th, 2025 is my 20 year anniversary. And I started it. I started it from my office in the Empire State Building. And I love that I could actually say broadcasting live from the Empire State Building because most people that say that most radio stations that say that just have an antenna on the Empire State Building, they don't have their radio offices. So I could legit say that.
Steve / Agency Outsight (20:41.712)
Mazel Tov, congratulations. That's amazing. Mind blowing.
Steve / Agency Outsight (21:00.596)
Hahaha
Debbie (21:04.558)
Um, so I used to, I used to pull down the shade in my office, close the door. And I remember, you know, people being starstruck when like Malcolm Gladwell came through the door. Um, so it was, it was a really, um, brand new, exciting, fun thing for me to do. There's not even a scintilla of knowledge at the time that I'd be doing this 20 years, 20 years later.
Steve / Agency Outsight (21:04.679)
Yeah.
Steve / Agency Outsight (21:31.423)
I get it. I get it. mean, I started this and I was like, I'll do a few episodes and see how it goes. I'm a fraction of the way through where what you've accomplished, not even, you know, dropping the bucket, but I can understand how 20 years goes by and the amount of people you've touched with that podcast, the amount of just inspiring.
humorous, educational, string tugging content is just mind blowing. I'm curious. I haven't spent the time to compare early Debbie Millman interview style to recent interview style. I'm curious. Have you seen an evolution in how you've interacted with guests over the years?
Debbie (21:56.568)
Thank you Steve.
Debbie (22:10.584)
my God, don't go back and listen to the early episodes. They're unlistening. They're unlistening. First of all, when I started the podcast, I was doing the episodes, as I said, in my office. And so I was sitting facing my guests, probably three feet apart. So I was sitting in my desk chair. They were sitting on the other side and we each were holding a telephone handset.
Steve / Agency Outsight (22:14.366)
Hahaha
Steve / Agency Outsight (22:35.924)
Hahaha!
Debbie (22:37.71)
So the echo that you were hearing at the beginning when we were setting up the tech today, well, magnify that by 10 when, you know, two handheld phones and your, echo is bouncing back and forth. was being then squished through a modem to my producers who were in Arizona. And so I often say that those early episodes sounded like episodes of Wayne's World. They were that bad. And, you know, I don't even know why, like people, early, early people, early guests on the episodes.
Steve / Agency Outsight (22:59.93)
Wow.
Steve / Agency Outsight (23:03.924)
Right Yeah
Debbie (23:07.382)
are still friends with me. It was so bad. And I had no idea what I was doing, but I didn't grow up thinking, you know what? One day I want to be a podcaster. That was not part of my purview. That was not even in my language. It wasn't even in the language when I started. And so I've grown along with the podcast and that's been probably what's kept me so interested in doing it that
It's a very different show than it was 10 years ago. It's a different show than it was five years ago. And if it wasn't, I'd probably be bored because I don't like to repeat myself so much. And the guests, the quality of the guests that I've had is just a gift. It's just a gift that people are willing to talk with me for an hour or two.
Steve / Agency Outsight (23:43.112)
Mm.
Debbie (24:01.158)
And so I've learned so much and I'm so grateful and my audience has stuck with me. And even when, Apple changed the iOS and no more, podcasts were being downloaded just organically once they were subscribed, I still, I still kept my good audience and, and the show is still growing and I'm still growing. So can't ask for more than that.
Steve / Agency Outsight (24:18.608)
Mm-hmm.
Steve / Agency Outsight (24:26.825)
Yeah. So one constant, and you talked about this recently, one constant has been your closing. It says we can talk about making a difference, we can make a difference, or we can do both. Where did that come from?
Debbie (24:42.178)
Well, back in 2004, I was writing for Armin Witt's blog, Speak Up, which was the very first design blog. Armin Witt created that, I believe, in 2003.
Steve / Agency Outsight (24:56.228)
He was just on episode 92 last week, so there you go.
Debbie (24:59.598)
Yeah, my dear, dear, dear friend Armin, I am the godmother to both of his children. Yep. Yep. Absolutely. We had a very auspicious beginning because initially Speak Up was quite critical of me. But then I ended up becoming part of the fray and started writing for the blog. And there was a conversation back then it was very spirited.
Steve / Agency Outsight (25:06.833)
my god! So beautiful!
Debbie (25:28.628)
hundreds of comments, hundreds of participants. And there was a conversation about, I think it was poster design and do posters really make a difference? You the same conversations we still have about design. And so people were talking about, you know, do they make a difference? And I said something like, well, we can talk about making a difference or we can make a difference. I wrote that. I had no memory of that. Armin had a poster contest.
Steve / Agency Outsight (25:39.026)
Okay.
Debbie (25:57.154)
where people had to find a line from the podcast, from the blog, from any of the conversations, they could pick anything they wanted to make a poster out of it. So Dawn Hancock, the great designer, Dawn Hancock, the founder of FireBelly in Chicago, picked that phrase, we can talk about making a difference or we can make a difference. And she made a poster out of it.
Steve / Agency Outsight (26:13.462)
Yep. Sure.
Debbie (26:20.812)
And I was like, really chuffed, like, my God, this is amazing. And it was really, it was exactly at the time of my launching the podcast. And so I thought, this is such a great sentence, but what if we can do both? What if we can talk about making a difference and make a difference? And so talking about making a difference was talking about making a difference on the show. And then making a difference was with our behavior after. And so that's what I decided to use. And I...
have used it ever since. It's the one, aside from my being the host, it's the one constant.
Steve / Agency Outsight (26:51.867)
And it's perfectly apropos because you talk about making a difference on your show and in all the things you do in your career and in your life and your marriage and everything. And then you also actively.
do that in all those areas of your life as well. yeah, it couldn't be more perfect. Your recent interview with Seth Godin, the live one for Creative Mornings, talked about a flashback again 20 years ago. You had a class with Milton Glaser and he introduced you to the mindset of scarcity and abundance. And you briefly talked about that, I'm curious, how did that education or
Debbie (27:05.518)
Thank you.
Steve / Agency Outsight (27:30.802)
like what he opened your mind to shift your path in life based on decisions you made based on scarcity and abundance.
Debbie (27:39.95)
That was a really defining experience for me. I can say, you know, in the same way that I can say, Speak Up was, my experience with Speak Up was a defining moment. In many ways, the, even Speak Up led me to the class with Milton because...
through my relationship with Speak Up, I then started writing for print magazine. When you were a writer for print magazine, you'd get an early copy of the magazine directly from the publisher or the printer. And in that issue of, think my first article, there was an ad for Milton Glazer's summer intensive at the School of Visual Arts. This was long before I started teaching there. And
Steve / Agency Outsight (28:23.508)
Well
Debbie (28:26.892)
Because I had an early issue, I was the first person that signed up and it was a first come first served kind of situation. It wasn't something you had to apply to. You just paid and you got in. So it was like the first 30 people and lo and behold, I was in that class and it changed everything for me. It changed everything for me. First of all, being taught by Milton Glaser was such a privilege and
Steve / Agency Outsight (28:54.152)
Mm-hmm.
Debbie (28:56.878)
Unlike Seth, who didn't really enjoy the experience that much, I lapped it up. I was in heaven. And I hadn't really ever thought about the world between the continuums of scarcity and abundance. And when he said that, I realized that I had spent pretty much my whole life thinking that this was the only chance for anything I was offered or fighting for and held onto it so tight. And...
That was not the only major shift. The other big, big, big shift was my participating in the exercise that he had all of his students do, which was writing your five-year plan for your future self. he asked us to write, it was the culminating exercise in this intensive, and he asked us to write an essay as if it were five years into the future.
Steve / Agency Outsight (29:39.156)
.
All right.
Debbie (29:54.486)
envisioning a life where we could do whatever we wanted with it. And it wasn't a process exercise. It was a visioning exercise. So don't think about how you're going to make it happen. Just assume it's happened already. And so I wrote this essay. I put my whole heart and soul into it. He said it was a magical exercise and that people were always contacting him and telling him how powerful it was. And, and I just believed it hook, line and sinker and was so desperate for a
different kind of life that I'm like, if this is magic, sign me up. And it was, and it wasn't, you know, it was magic in that I had the, I had everything, everything. It took more than five years. It actually took 13 years for everything on my list to happen.
Steve / Agency Outsight (30:25.66)
Yeah.
Debbie (30:42.892)
But the fact that it happened at all is still incredulous to me. And they were big, big, big goals. They weren't like, I want a better relationship with X, and Z, or, I want to get a new car. You they were really big.
Steve / Agency Outsight (30:49.434)
Right.
Debbie (31:05.886)
Now looking back, it's incredible to me that I was able to achieve, receive those things. And I really truly believe that I have Milton to thank for that because he gave me the courage to consider other possibilities. And now those possibilities are the fabric of my life.
Steve / Agency Outsight (31:31.136)
Wow
Debbie (31:33.782)
So I, he stopped teaching a couple of years before he passed. And I asked if I could, cause I, at that point, one of the things on my list was teaching at SVA. And that happened within like a year of my taking this class, which had no correlation. wasn't because I took the class that I was able to get a position at SVA. But I asked him if I could start teaching that exercise. So I got his permission.
And I extended the year. rather than five years, because most of the people in his class were working professionals. Most of my students were like seniors in college. So it was a very different scenario. And I, because it took me so long and I was, I was still in the process at that point. I didn't even know if those other things were going to happen, but it was, you know, on its way to the five year point. I.
Steve / Agency Outsight (32:03.636)
Okay. Interesting.
Debbie (32:29.482)
if I could change it to 10 years. And so that's what I did. that's, that's still is. So I teach, I teach both my grad students and my undergrad students at SVA this exercise.
Steve / Agency Outsight (32:40.184)
I think it's a beautiful exercise. It's something that I've done for a lot of years. And the ability to visualize and manifest the things that you want in your life and the impact you want to have on other people. Yeah, I just think it's so beautiful. And then when you're able to step back and say, these are the things that I want to have happen or.
where I want to go with life and then you can kind of reverse engineer them and nerd out about the activities that'll get you there and I to me like I see Milton as Just a super impactful designer some of the the marks that he's put into the world and things like that I Honestly never would have thought that he would have been like deep on that level to introduce an exercise like that And so that's really really beautiful
Debbie (33:08.078)
All
Debbie (33:26.914)
He was a really great teacher. And he often said that teaching was actually the most important thing that he was doing with his life.
Steve / Agency Outsight (33:28.724)
Yeah.
Steve / Agency Outsight (33:33.62)
I believe that, yeah. So on that topic, a few years ago, somebody came out with a new I Love New York logo.
do an updated version with an emoji heart. Did you have any input, like any response to that?
Debbie (33:44.52)
yeah, the deep.
Debbie (33:52.142)
think it was a redesign. It was as, yeah, it was like sort of an extension of sorts. Like they were really, really clear, I think, that it wasn't a redesign, that it was a way of using the heart in this new campaign. I don't know. was, I don't like to say bad things about people's work.
Steve / Agency Outsight (33:54.032)
It was a floated concept.
Steve / Agency Outsight (34:17.943)
You
Debbie (34:19.682)
Unless they're mean to me. It was okay. You know, it doesn't, it doesn't have the staying power of I Heart York. I mean, I travel all over the world now and there's no place I go that there isn't an I Heart Lisbon or an I Heart, you know, Saudi Arabia. There's an I Heart for everything now. And I think it's going to be We Heart Dubai anytime soon.
Steve / Agency Outsight (34:27.336)
Yeah.
Steve / Agency Outsight (34:40.115)
That's true.
Yeah.
God, I hope not. Yeah. So thinking about all that you've accomplished and all the impact that you've had, tons of accolades, walls of awards, I'm sure. And I don't necessarily love this word, but I think it's just a good way to define it. Can you talk about a failure or a setback that was impactful for you?
Debbie (35:07.086)
You know, I have so many, I don't know if I would say failure or setback. I would say I have so many, I have a lot of rejections and I still have a lot of rejections. You know, the only, I cry. You know, I wallow. I, you know, we metabolize all of our feelings. So one thing I have learned with age is that feelings don't last forever.
Steve / Agency Outsight (35:16.115)
How do you deal with them?
Debbie (35:30.146)
they change all the time. And we metabolize so many of our feelings. And I think that, you know, if you feel heartbroken, the best thing to do is allow yourself to feel heartbroken so that you can begin to work through the heartbreak. So, you know, I used to get...
Steve / Agency Outsight (35:44.308)
Mm-hmm.
Debbie (35:47.532)
I used to get a lot more angry when things didn't go my way, but really underneath anchor is just grief and sadness. so finally, thankfully, I just, I just feel sad when, when things like that happen and I get really down on myself and catastrophize a bit and, know, feel like nothing's going to ever work again and back into that scarcity mindset. But I tend to pull myself out because I have had enough of them to know that it's
Steve / Agency Outsight (36:04.852)
Mm-hmm.
Debbie (36:17.408)
It's not forever. And there is going to be somebody somewhere that does appreciate what I do. you you can't win, mostly you can't win awards unless you apply to win, you know, so the Signal Award or the Webbies and so forth. So, you know, I don't win every year and...
I was nominated 10 times before I actually won a Webby. And so every year I was like, I'm never going to win, never going to win, never going to win. is it bridesmaid, never a bride? And even now, you know, that I have won, I'm like, should I apply again? Because if I don't win, I'm going to be really bummed that I haven't won, but then I've already won, so shouldn't somebody else win? you know, it's all of this inner crap. you know, I write things that don't get approved or, you know,
Steve / Agency Outsight (36:40.648)
Wow. Yeah.
Debbie (37:05.23)
they don't get printed. And, you know, there are times when I get really down on my ability and I'm envious of other people's then I just have to remember that that's stupid to do. Social media sometimes makes it hard not to compare. So I just feel what I feel and get over it. I don't, I generally don't.
Steve / Agency Outsight (37:24.297)
Yep. Yeah, grief, teach it.
Debbie (37:34.838)
try to contain it like in my own personal private life. Like Roxanne gets a of my tears.
Steve / Agency Outsight (37:41.94)
Yeah. Yeah, the people closest to us, they get the brunt of it and they help us, you know, comfort us through it. and I agree that I think grief is such a great life lesson on how to deal with rejection and, you know, the things that we get angry about is, you know, inability to accept what reality is and what's happening. And so it's really good to hear that you also experience the same kind of imposter syndrome and all the feelings that we all feel and all these feelings are so temporary. So
We just have to remind ourselves. yeah. Curious about your, where you get inspired from and you inspire so many women, young creatives, entrepreneurs, people in our industry. Where do you draw from? And you talked about earlier, like you poured everything into your career and you put aside the fine art and the music. And I know these are back in your life now, but like, where do you draw your inspiration from?
Debbie (38:34.542)
I really, I have to say just through the world because I'm not looking for inspiration. I'm not seeking, oh, that museum show is giving me inspiration. I try to experience as much as I can and then try to be open to what that might inspire in me. But I guess if I had to pick one thing, I would say travel.
I decided in my mid fifties that I was going to try to see as much of the world as possible in the rest of my life. And I have been trying to do that. I've gone on a couple of National Geographic expeditions, an expedition to Antarctica. And so those experiences inspire the little visual stories I do on Instagram.
Steve / Agency Outsight (39:15.796)
Wow
Debbie (39:29.462)
I recently went on a trip on an excursion and rather than write stories about the places that I was going to, I just did visual essays. I did one on birds, I did one on butterflies. So I find a lot of inspiration traveling and experiencing different cultures. That being said, I also get a lot of inspiration from reading. I read a lot. I love to look at art.
I love live theater of any kind. I love live theater. So, you know, I get inspired by people I work with. get inspired, you know, I do a lot of work with Mariska Hargitay. I get really inspired by her. And then of course my wife, who's like the most inspiring person on the planet.
Steve / Agency Outsight (40:00.828)
Hmm.
Steve / Agency Outsight (40:05.798)
Mm-hmm.
I loved the way you walked through the story of your romance with her. I think it was on a Brene Brown episode or maybe you were on her podcast, one or the other.
Debbie (40:30.638)
She actually invited Roxanne and I together and we talked about it.
Steve / Agency Outsight (40:34.536)
That's what it was. Yeah. And it was at a time, I believe when I was starting to fall in love with my now fiance and just an absolutely inspiring story and just your transparency and like all of it. I, and I'm in love with Renee Brown and everything that she talks about as well. And so the whole thing just carried me and lit me up. And so I was so grateful for all of those, stories that you shared and every bit of the romance. Yeah.
Debbie (40:45.314)
Thank
Debbie (41:02.104)
Thank you, Steve. Thank you. It's best thing that's ever happened to me.
Steve / Agency Outsight (41:05.822)
You deserve it. That's amazing. You absolutely deserve it. You both do.
Debbie (41:09.326)
Thank you. And it was in my second 10 year plan. I did one in 2017. It was 12 years later. at that, remember I told you at year 13. So at that point I was starting to feel like, maybe I should write another one. And I put it off and put it off and put it off. so because I gave myself a deadline of the end of the year in 2017, I literally stayed home New Year's Eve and did it New Year's Eve 2017.
Steve / Agency Outsight (41:12.134)
Okay, so you did it again and that came about in the second one.
Debbie (41:35.438)
Um, so into the first day of 2018 and, um, Roxanne and I had our first date, October 9th, 2018. And in my, in my plan, I was like, I really, really want to find my true love.
Steve / Agency Outsight (41:40.532)
Wow.
Steve / Agency Outsight (41:48.66)
But imagine that a creative professional hitting the deadline at the last minute. That's just how we operate. Nothing wrong with that. What's next other than 20 year episode on February 5th? What's next big stuff for you?
Debbie (41:54.286)
Right. Yep.
Debbie (42:05.802)
have such a big thing coming, Steve. I'm so excited about it and nervous too. I've written another book. It'll be out April 15th.
Steve / Agency Outsight (42:15.956)
You can pre-order it now online folks. I got mine and you should get yours.
Debbie (42:20.714)
and it's called Love Letter to a Garden. And it is a visual story about my quest throughout my life to be able to grow things, live things like plants. And it's part memoir, part visual story and...
It's been the most fun I've had as far back as I can remember making this book. It's all drawings and paintings and photographs. And it has a bit of my travel in there and plants and flowers and all kinds of flora that I've experienced seeing over the last 10 years. and that'll be out and I'm, I'm just, I hope the world likes it as much as I enjoyed making it.
Steve / Agency Outsight (43:13.673)
I'm sure they will. I'm a nerd gardener and
You know tons of flowers and plants in the house and so when I saw you announced the pre-order I'm like if this is anything like anything you put out before I need to have this in my possession and I remember I think was your design matters book or all the photos that you had you had taken like how proud
Debbie (43:33.408)
No, didn't take them. I photo edited them. didn't.
Steve / Agency Outsight (43:36.18)
Photo edit, okay, yeah, yeah, yeah. And so I remember you talking about that and I was like, this photo, this new book is right up my alley. So yeah, I'm excited for it. Are you guys gardeners or is it more the attempt to be? Okay.
Debbie (43:44.43)
Thank you. Yeah. I am. I'm a gardener. So basically I have had outdoor space in Manhattan since the early nineties. That was always one of the things that became sort of a prerequisite for wherever I wanted to live. And I gave up neighborhood for outdoor. So
Steve / Agency Outsight (44:01.78)
Mm-hmm.
Debbie (44:05.996)
For many, many years, I lived in what was considered kind of a crack neighborhood, but then it changed and evolved over the years to a highline neighborhood. But prior to that, it was a pretty intense drug block, but it was the only apartment that I could afford that also had outdoor space. And so I had tried over three apartments to have a garden, and it was always super challenging and I didn't know what I was doing.
over the decades just kept trying and mostly failing. And then COVID happened. I decided, Roxanne and I decided because her house when we met was in LA, mine was in New York, that we'd be in LA for this time together. We'd have cars and the ability to see more sky and so forth. And so I started a garden in her house, which is now our house, because we live together, obviously. And that was...
sort of the expansion of my heart in even sort of bigger and more meaningful ways because suddenly I was growing things we were eating, successfully. And even now, one little lime plant that I had, I then ended up planting in the ground. And this is the first year, it's been five years. This is the first year we have like a major.
Steve / Agency Outsight (45:15.512)
Yeah.
Debbie (45:30.19)
we'll have a major harvest of limes. I'm looking at the tree right now through my window and it's like mind blowing that this has happened.
Steve / Agency Outsight (45:37.834)
I love that. I got into gardening through the grief process after losing my daughter and it was literally the grounding place I needed and the work that I did in the garden and nurturing something to life and killing things also and now fast forward five years we get so much gratitude out of the bountiful harvests and the food we make and
filling our freezer with soups things. And so I fully relate that like it is our heart that like we put into this thing. You the joke is, you you spend all this time and money and you save $3 at the grocery store by growing all these tomatoes, but it is, it's rejuvenating. And yeah, I'm excited for your book.
Debbie (46:15.758)
Absolutely. And I'm really sorry about your daughter. didn't know that and I'm truly, truly sorry.
Steve / Agency Outsight (46:20.648)
Thank you, thank you. I'm not gonna hold you hostage too much longer. I typically will wrap these up with some random rapid fires, but I'm not gonna give you the same ones that I give other people because this is number 100 and you are a different type of guest for me. So first is super simple. What's your favorite typeface these days?
Debbie (46:41.86)
my God, such a good question. I have a soft spot for a really dumb old typeface, which has been my go-to answer because it's still my favorite. It's the typeface used in the Mary Tyler Moore opening title, and it's called Peño. And it was one of three typefaces I had in my college newspaper. So it was always the headline type or mostly always we had Gaudi, Souvenir and Peño. I still have a spot in my heart for all three.
Steve / Agency Outsight (47:06.674)
Well, I believe it. Okay, cool. What's one of the most gratifying campaigns that you've ever worked on?
Debbie (47:15.31)
you know, the Joyful Heart Foundation to try to eradicate the rape kit backlog and sexual violence. Also the No More work I did, which preceded my work on the Joyful Heart campaign or the Joyful Heart work. I'm now on the board of the Joyful Heart and for many years was the chairperson of the board. But the work that I did for No More and then the Joyful Heart Foundation is probably the most important work I've done.
Steve / Agency Outsight (47:17.972)
Hmm.
Steve / Agency Outsight (47:41.172)
Love that. And then finally, and I hate saying finally because I just feel like we just hit record, but if you could go back in time and give the younger version of Debbie some advice, what would that be?
Debbie (47:58.178)
Believe in yourself. Don't compromise. You can do anything you put your mind to.
Try not to think that every opportunity is the last one, because it won't be. See the world from abundance and not, from a point of view of abundance and not scarcity.
Steve / Agency Outsight (48:21.313)
I love that. Debbie, thank you so, so much for joining me, for joining whoever's listening out there in podcast world and for all the work that you've done. As long as I've, you've been on my radar 25ish years. You've been an absolute inspiration to my career and my creative profession and some of the hard work that I've done as well. And so I'm just so grateful for you and for your time today. So thank you very much.
Debbie (48:46.328)
Thank you so much for such a heartfelt, beautiful conversation, Steve. I'm really, really grateful to have had this time with you. Thank you.
Steve / Agency Outsight (48:54.91)
Me too. Thank you.