Ep. 209: Holly Howard on Business Growth for Creative Entrepreneurs

Polymath Holly Howard has lived many lives. A former professional ballet dancer, bassoonist, medical researcher and board-certified music therapist, she’s pulled from science, art, and design to create a one-of-a-kind path for herself. Now, she runs the successful culture-first business consultancy, Ask Holly How, to help creative entrepreneurs grow personally and professionally, and better understand that business and creativity are more powerful when wielded together. 

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TRANSCRIPT

Amy Devers: Hi everyone, I’m Amy Devers and this is Clever. Today I’m talking to business consultant Holly Howard. Holly is one of these exceptional folks who appears to be in full command of both her right and left brain. She brings her many creative talents to her work helping creative entrepreneurs “grow their businesses without sacrificing their souls.” Named Ask Holly How, she describes her business consultancy as “culture-first” and founded on the principle that successful entrepreneurship resides at the intersection of self-evolution, business growth, and the creative pursuit. If that sounds like music to your ears (it does ot mine) it’s no accident, Prior to founding Ask Holly How, Holly was a board certified music therapist, she also plays the bassoon, has been a medical researcher, a professional ballet dancer, and a VP of operations and finance. All of this adds up to a suite of skills, experience and knowledge that she deploys in the name of helping creatives thrive. Since founding Ask Holly How in 2012 she’s worked with over 1000 businesses, has taught at Pratt and RISD and hosts a podcast called Cultures within Capitalism. As you’ll hear, Holly has a perspective on business growth that is as refreshing and creative, as it is immediately revelatory and actionable -  no wonder, she’s been on every side of the equation and knows the best place to look for the answers is on the inside… Here’s Holly…

Holly Howard: My name is Holly Howard, I’m the Founder of Ask Holly How and I am located in Brooklyn, New York. I think creativity, beauty and design, is truly a form of hope and I love being able to facilitate that. 

Amy: That just gave me hope hearing you say that. I think it’s so true because art inherently has to cast a vision that doesn’t exist, and so it has to come from a place of hope because even if the art is provocative or traumatic or repulsive, it’s hope that through, by going through that you can recover or you can offer some sort of healing gravitas that sometimes can’t just be worked out through language, it needs to bypass language in order to touch you, pull the strings of your souls in a really magical way. 

Holly: Yeah, absolutely. 

Amy: I am also not surprised to hear you say that considering. So running a culture first business consultancy means that you are actively engaged on the day-to-day with creative entrepreneurs, helping them solve problems, but orient themselves and clarify their mission and grow their business so that they can actually participate in the creative process in a healthy way, and a sustainable way, right? 

Holly: Yeah, absolutely and I love that you said that because that’s what I try to emphasize. Oftentimes there seems to be a divide between creativity and business and people will even express that I’m the creative side, I’m not the business side. And I try to help people understand that the business side is actually there to facilitate your creativity. Structure is there to facilitate creativity and so if you can really embrace that, then you can really indulge in the creative process. But when we resist that, it’s actually when we have a hard time indulging in the creative process. 

Amy: Yes, or if we just try to power through and do the creativity thing but without the business structure, then what I think happens, and I’m kind of speaking for myself, is you end up treading water. I’ve heard you talk, I’ve listened to some of your podcasts and you have a lot of really, really wonderful resources on your website, so I think that’s very generous, right there. And I’ve heard a little bit about your background, I know that you grew up in the Midwest and then became a ballerina and then went into music therapy and I want to talk to you all about that because I can tell how that informs the way you think about business. It’s one of the reasons I really resonate with the way you think about business. But going back to the very heart of the matter is why do we have this cultural narrative that creatives shouldn’t make money? Or the ‘starving artist’ narrative that sort of confounds creatives to the point that they can’t even really see a future for themselves that is thriving? 

Holly: Yeah, I don’t know where the narrative comes from and I think it’s so sad. And I was giving somebody an example of it this week, when I started, so I’m about 12 years in now, I’d gone to a meeting, it was at this organization called The Freelancers Union. And in the meeting somebody said, “Freelancers, it’s always feast or famine.” And I remember in that moment thinking, is it? I don’t think it’s going to be. And I’ve never had a famine. And it’s just interesting to me that we adopt these mindsets without questioning them and I think that big one of like the starving artist, to be an artist you can’t make money. You can’t be business savvy. I hear a lot of people say they’re creative, so they’re not numbers focused. Like a lot of divided mindsets. And I don’t know where it comes from. I don’t know the origin, but I think it’s so unfortunate that we’re so quick to adopt it without questioning it.

Amy: I don’t know where it comes from either, but I can sort of patch together a collage of my own experience, that kind of I think is pretty relatable, other people have the same thing. But I’m middle-aged now and my parents were silent generation and so I was sort of raised in a family where hard work and academics were really emphasized and the way to measure success was grades and the epitome of success was getting a good job, working hard for the man and getting a promotion and then retiring. So that was the formula and there wasn’t really any understanding of well, what if what I want to do is on my own or starts from scratch? And that was considered risky. Right? Or insecure. So then there were all these micro moments of dissuasion, well meaning parents, I’m sure mine aren’t the only ones, who really kind of just want to gently shove you into something where they’re going to feel more relaxed about, like please go be a dental hygienist or something that’s a little more fixed or secure or stable in their minds. And so there was no… I had no vision for how to value the work that I was going to put into the world, unless it came to me through getting a promotion or a raise. But if I’m my own boss (laughs) I don’t know how to price my work, how to value my work or even how to give myself a raise. 

Holly: Yeah, I totally agree. As you mentioned, I’m Midwestern, I grew up in a family where, I remember when I got my first job as a music therapist and it was in a hospital and my dad said to me, basically like that’s it. This is your job, you know, you’re gonna be here forever. And I was like oh my god, I’ll die, I’ll die if (laughs) this is it, oh no. And I think that my parents, my dad was extremely traditional, he was actually a CFO himself, but my mom was a teacher and she has an interesting background where she grew up on a farm in really rural Illinois. And she wanted to be like a stewardess on airplanes and her parents said no, they were like, you can’t do that, you have to go to college. And it sort of started this trajectory for her where she was denied what she wanted to do. And so I think that because of that she was then able to support me in a way that she felt like she never got supported. So when I was in high school, as I was sort of coming towards graduation, I really wanted to be a professional ballet dancer, which I think in some ways, you know, it’s like okay, you know. (Laughs) That sounds not stable at all. 

Amy: But it also sounds like… (laughter) I can hear the argument my mom would have, would be like, of course we support you, you’re really good, we want you to do everything that you can do, but that’s a really tough business and… (Laughs)

Holly: 100%, and it wasn’t until my dance teacher sort of had to have a conversation with my mom. My dad wasn’t like that involved and just being like, you have to let her do this because also just to go back, my dad had lost his job when we were younger, he was an alcoholic and that was a very traumatic experience for my family because he was the primary breadwinner at the time. And so it also put into this like, this mindset that work is scary, it could go away, you need security, you should just take a job and stay with that job. And money can go away at any time. And my mom did, she was very much wanting to support me to go out and dance, she would give mixed messages almost immediately about like, how are you going to make money? Can you do this forever? What if you don’t get an education? So it’s like you grow up with all of these mixed messaging. And I do think it’s well meaning, we want you to be okay, but they don’t realize, it’s not a supportive way. And then it actually creates these extremely divided mindsets that we try to overcome as adults. 

Amy: Yes, overcoming the divided mindsets. The other classic one is the punk rock ethos of making money means selling out to the man, and my art is compromised.  And that’s not doing anyone any favors either. (Laughs)

Holly: Yeah, I’m also middle aged, like tail end of Gen X and do you know Janeane Garofalo, the comedian and she was in Reality Bites. And there was an article, feature of her in The Times, maybe like a year or two ago, because she was talking about selling out and how she’d never sold out. And I remember that message so strong, like in the 90s, you don’t sell out. But what I try to explain to people, but you also don’t hide. I think people hide behind this idea of like, I’m not going to sell out and hiding helps nobody. It helps no one in the world. 

Amy: Right, right, hiding I think also kind of is a cousin characteristic to the false humility of not wanting to be, like promote yourself, even if yourself is your business. It’s so self-defeating (laughs), it’s so ingrained, it’s deeply uncomfortable to engage in. 

Holly: Yeah and I think it’s an interesting question and thought because it’s like, how do we think about where our talent comes from or where our creativity comes from? When I think about that question a lot I’m like, I don’t know, I think sometimes it comes from something bigger than me. So when I think of self-promotion I don’t think about me per se, I think about this thing that I feel like should be shared with the world. 

Amy: I want to talk about that more because there’s a couple of thoughts around marketing that you have that I think could be really revolutionary, really paradigm shifting for all of the creatives I know. And one of them is this idea that actually your creativity is a gift. So marketing is basically you sharing your gift. And the gift comes from somewhere else, so you don’t even necessarily need to take credit for it. (Laughs)

Holly: Totally, yes!

Amy: And then the other idea, and we can get into this now or later, but marketing without social media. 

Holly: Oh yeah, my favorite. 

Amy: That sounds like relief! Can you even do that? Is that a thing? Please tell me it’s possible? (Laughs)

Holly: It’s 100% a thing, it’s the most amazing thing. Whenever people ask me about it, I can talk about it for hours, just how transformative it was. I’ve been off of social media since September of 2020, so three and a half years now and it was something I had thought about, especially after the pandemic had started. I just started to realize, I’m not sure if this is a really great space for actually communicating with people. And so I just made the decision to leave. And I quit social media like I quit smoking, I used to be a smoker in high school and after, when I was a dancer. And like a pack a day smoker. And then one day I just quit, I was like, I’m done, and I quit cold turkey and for the most part I don’t smoke, although I occasionally do, but not like that. (Laughter) But the same thing with social media, I left and there was never like, oh, I’m really wondering what’s going on in that space. It just never came back to me and I found a more creatively fulfilling existence without being in that space and it just, yeah, it was a revelation actually. 

Amy: I think we kind of all understand what it does to us, personally and also we read how mental health has gone down since social media has risen and our teens are not doing well with it. But I’m still trapped in this idea that I can’t run a business without marketing through social media. Tell me how to get out of that trap? 

Holly: Yeah, I think it goes back to what we were talking about, about mindsets, right? When we’re told you can’t be creative and business savvy at the same time, that was a myth about social media that I felt really inspired to challenge. When everybody would say, oh no, you can’t grow a business without social media, you can’t thrive. And a lot of what we hear nowadays, more so related to kids, oh you’ll be left out if you’re not on social media, so you have to let them be on social media. But again, it’s not… it’s just not true. And what’s leaving social media dead for me was it helped me expand my mind of all the ways I could be marketing myself and thinking about what marketing is. And this is… I teach a whole class about running a business without social media and this is what I teach people. It’s like once you take something away, it’s sort of like a challenge. It challenges you to think about, well what are other ways I can share my story? What are other ways I can be connecting to people? It also starts to make you think about the difference between quality and quantity. When I’m teaching this class, we talk about the experience that your audience or your customer or your client is having when they come in contact with your work. I’m like so what state of mind do you want them to be when they discover you, when they’re engaging with your work? Are we doom scrolling and then all of a sudden I come across a $30,000 sofa that you’re trying to sell me? Probably a very jarring experience for people. And so when you really start to think about, oh yeah, what experience do I want people to have? It’s actually not the best experience for people and there are so many other things we can be doing to connect. 

Amy: Just knowing that there’s a whole class that you’ve built around this idea means that there’s support and that there’s enough actual nutrition to sustain a class that means it’s not just a flimsy idea. It’s not somebody’s fun notion that we can do without social media. It’s like no, actually here’s the framework, here’s the armature, and here’s the exercises and here’s the homework. And it’s deeply, deeply doable and ‘figureoutable!’ (Laughs)

Holly: I don’t want to say this to make it sound negative, but it is more meaning like you do have to be a little bit more intentional. Because I think it’s so easier for us to think that we’re doing something when we post and scroll, instead of like huh, stepping back, reflecting, really thinking deeply about people and connection and what we’re putting out into the world. And I think that that is sometimes a hard mindset shift for people because especially in the 21st century in the last decade as social media and digital marketing sort of rose to prominence, I think we were sold this idea of like everything should be easy and minimal effort. Just put up your website. 

Amy: Right, this frictionless idea of build the funnel and just catch rain. (Laughs)

Holly: Yeah. 

Amy: But I think when you are more intentional about the efforts that you’re putting in and maybe they’re more concentrated and the impact is a little bit more measurable, you might be able to actually trace that time, like if you were to gauge the quality of the time you’re spending, you might actually enjoy it more than the sort of cheap, fast, task-oriented nature of getting your social media stuff done. 

Holly: Yeah, I like to say it’s the difference between margarine and butter. I like to compare social media to margarine, sort of this manufactured engagement where butter is like this natural, rich thing. And so it is true. It’s far more rewarding, you learn so much about yourself, about other people and it’s a lot more sustainable. 

Amy: Let’s learn some more about you. You mentioned that your dad was an alcoholic and lost his job and he’s a CFO and that’s from, our generation that’s what we tend to think of is stability and yet alcoholism and losing the breadwinner in the middle of your life is the definition of instability. How has that affected you? 

Holly: Yeah. (Laughs) It’s funny because sometimes people would be like, oh yeah, so-and-so has a drinking problem and the way I like to describe my dad, who has since passed, is Don Draper. If you’ve ever watched Mad Men, my father was literally fired because he had vodka in his desk drawers, and this was the 80s that he got fired. He was that severe of an alcoholic where he’d drink just so much vodka every day. And so the word ‘destabilize’ is a great word to apply to growing up like that because it is so unstable. But I think it informed everything about how I am. He died five years ago now and when I wash it back up and say, he eventually got sober. So he got sober in the 90s at some point and then never drank for the rest of his life until he died in 2018. He got sober, but he never dealt with anything. 

Amy: Yes. 

Holly: So it’s like that’s gone and he could hold a job and talk about unstable, like my parents divorce, but then they ended up getting back together, but my dad moved into the basement while we all lived upstairs. (Laughs)

Amy: Okay. 

Holly: It was a wild arrangement. But when he died, and I spoke at his funeral, I said, you know, in a lot of ways he made me a really rich person because I learnt so much about the lesson of compassion and the fact that we are all just deeply flawed. And nobody is perfect and what do you do with that information? How do you incorporate that information? 

Amy: Yeah. Just to bring this back to your present day life then, does that mean that your consultancy is led by compassion and what does that look like in terms of talking to the people that you’re working with? 

Holly: Yeah, I say my business consultancy is really about the intersection of business growth and personal growth, with this realization that everything that we do in business, whether we’re trying to make more money or we’re trying to build a team or we’re trying to market ourselves or we’re trying to create this long term vision, it’s really rooted in who we are as a person. So all of these mindsets, all of our history is the foundation of how we start to think about all of those things. So often when we can’t make money, it’s oftentimes I see a lot, especially in the design community, I think it’s interesting. We had judgements about people who make a lot of money and we’re trying to sell to them and that’s really hard, that tension then. It actually keeps us from being able to sell to them. So it goes back to, what have we experienced as humans that’s actually coming out into all of these business practices. And I say the compassion part is because it gets deep. I tell people when we start working together, we’re going to get really uncomfortable. There’s going to be discomfort, things are going to come up. I oftentimes end up referring people to therapy or couples therapy to digest all of these things that we end up surfacing through the business planning. But I’m able to sustain it and keep going with them because I can have a lot of compassion for what they’re going through. 

Amy: So this I where your background, I find so fascinating. Let’s just start from the ballerina years because that’s creative in and of itself, but then there’s more science and creativity that comes together in this beautiful explosion of really interesting background. So take me there. 

Holly: Yeah, when I graduated high school, I left three weeks afterwards to go into a Joffrey Ballet training program in the summer, I went away, I did it and I came back and I was like, I can’t go to college, I have to be a dancer.. So I did, I dropped out of school. I ended up getting a contract with the Ruth Page ballet, which was in Chicago during the dancers union, the AMGA union and was sort of off to the races in the fall of ’96. And I got a role in The Nutcracker, which was like the Ruth Page ballet's big production that fall. And then I started auditioning and this is interesting because talk about divided mindsets. After Nutcracker wrapped in the spring, you go on audition tours and you deal with a lot of rejection. I had pretty low self-esteem at the time, I was always the tallest and it made me feel really insecure. So I went on audition tour and I was like, yeah, this is not stable, I need to go back to college. So in the next fall I ended up… while I was still training fulltime as a ballerina, going to Loyola University in Chicago. So I would go to the dance studio from 10:00 to 6:00 and then I would get to Loyola from 6:30 until 9:00 at night and do that five days a week and then I would go to Starbucks on Friday evening and work at Starbucks Friday evening, Saturdays and Sundays. 

Amy: Oh man! 

Holly: Yeah, it was rough. 

Amy: I can see where this is heading. (Laughs)

Holly: And I ended up getting mono. So by the end of that year I was super sick, I actually had to finish my studies remotely. I ended up pausing dance and…

Amy: But the universe had to intervene, they were like, you can’t continue doing this, we’re going to have to shut you down. 

Holly: 100%, yeah. So I did. I stopped and at that time I sort of reflected and I was like, all right, I’m going to go back and I’m going to give dance one more try. But when I went back I was really focused on getting into one company only at that point, I was really obsessed with Twyla Tharp and she had set a lot of work on this company called Hubbard Street in Chicago, so I was like, I’m going to do this audition and if I get it, I’m going to stay and if not, I’m going to go to college. And I didn’t get the audition and I was like, that’s it, and I walked out of the dance studio and I never went back, which was extremely dramatic and unfortunate, but I didn’t have a lot of emotional intelligence at that time. So I ended up just leaving and at the time I had played the bassoon in high school and I was pretty good at it. There’s a competition called All State Honors Band and I made the All State Honors Band and so I was like, all right, I’m pretty good at this, I’m going to pick my bassoon back up and audition to go to Berklee School of Music in Boston. And so I did, I auditioned and I got in and that’s when I left and went to Berklee, which is where I studied music therapy. 

Amy: Looking back now that we have the benefit of hindsight, dramatic as it was, was leaving dance at that moment… did you have any regrets or did you have to process, you know? 

Holly: Oh yeah. I had tons of regrets and such an identity crisis because even though I’d only danced professional two and a half years at that point, I was in it really intensively all throughout high school. And it was extremely hard to acclimate to the ordinary world. Like the dance world is so specific and it’s so insular in a lot of ways, and it’s so routine. You have a regimen; you have a routine and then when all of that was gone I really did not know how to relate. Because as a dancer, I didn’t go out, I wasn’t social, because you’re so consumed with it and you’re social with your dance friends and the theater and all of that. But it was extremely hard to process that identity crisis, which is why I didn’t go back for a long time because I just couldn’t, it was so painful. And it just took time. The irony is that I ended up going to school at Berklee in Boston and while I was dancing professionally I’d also gotten into a Boston ballet training program and I turned it down because I was too scared to leave Chicago, which was where I was living. And I ended up, once I’d moved to Boston to go to Berklee I ended up going to the Boston Ballet to train on the weekends and so it was like a nice way to sort of like digest that and reintegrate it into my life and like move forward with it all. 

Amy: I’m happy to hear that because you can’t have a bad breakup with ballet and then just have to hide from it the rest of your life. You need to like, no, we can be friends, and I loved you so much… there’s still a lot of good things about you. (Laughs)

Holly: Yeah, totally and now my husband and I go to the ballet here in New York City all the time, when it’s in season and I love going to it and I love that I have the knowledge and experience to really understand it and to take it all in. 

Amy: Yes, you can deeply appreciate the art form when you understand all of the energy and effort that goes into it, which is one of the reasons why I… well I’m grateful that you’re supporting creatives through what you do, but it’s also one of the reasons why I think your podcast and hopefully this podcast is helpful, is when you understand just the energy, motivation, dedication, effort and grit that goes into bringing an idea from nothingness into reality, you start to have a lot more appreciation for all of the choices that were made, all of the artistic choices, but also a lot of the difficult and personal sacrifices that went into it. 

Holly: Yeah, absolutely. 

Amy: So from ballet to Berklee School of Music, and was this… bassoon performing kind of what you were thinking? Or what was the program? 

Holly: Yeah. So when I went there I ended up becoming a music therapy major. And music therapy is essentially a combination of a music degree and a psychology degree, a therapy degree, and so that’s what I studied and bassoon was just my principal instrument, as they call it at school. 

Amy: At the time this would have been mid-90s, late 90s?

Holly: Late 90s and early 2000s, yeah. 

Amy: How accepted is music therapy as a therapeutic modality at the time? Is it still on the forefront? 

Holly: Yeah, at that time it was definitely established, so you had to become board certified and the biggest advocate for music therapy at that time was a doctor named Dr Oliver Sacks and if you’ve ever seen the movie Awakenings with Robin Williams, that’s the story of his time up at this hospital called Beth Abraham up in the Bronx. And so he did a lot as a neurologist to really advocate. He was a lover of music himself and when he started working with Dr Tomaino, who was the head music therapist up there, he really saw it. And so he really took it upon himself to advocate. And I really believe did a lot for the field because there’s certainly a lot of skepticism about what music therapy is and the impact that it can have. And so because of everything that Dr Sacks was really engaged in, music and the brain became a big thing in the 90s and that’s sort of the path that I took. So when I was a music therapist I really specialized in Parkinson’s, dementia, traumatic brain injury, aphasia, anything essentially that has to do with the brain. And music is amazing for your brain. We respond to rhythm without even realizing it because it’s innate within us. We learn to talk through singing, so there are different parts of the brain, so if we have a stroke and we can sing, we can teach ourself to talk again. We use rhythm to help, when we have strokes or any issues with gait, so it’s pretty phenomenal. And also working with dementia patients, the whole thing about dementia is that you can remember things that happened a long time ago, even when you can’t remember what happened yesterday. And music is embedded in our memory. So people get so engaged with music when they have dementia because they can’t think about it, it’s just part of ourselves essentially and so they just react and their bodies react and they’re completely engaged and they can sing songs from their childhood, all the way through without thinking. And it’s really transformative. 

Amy: Wow, that must have been really transcendent to see too, and to see the power of it and the effect it was having on people. 

Holly: Yeah, for sure, and I think it really was one of the times where our brains are amazing. When you really think it out, your brain, and you really study it, it’s this incredible thing that we have been gifted and don’t even fully understand how it works all the time. And it can do remarkable things, which is why sort of to connect back to stories that we tell ourselves, like there’s so much possibility. I got really into this field of neuroplasticity, which is changing your brain, because that’s a lot of what music therapy does, it helps with neuroplasticity. And we don’t even lean on that. It’s like there’s so much to lean on in that sense and we’re not even aware of it, or we don’t embrace it. 

Amy: Now I’ve got to ask; how does music and neuroplasticity play into your consulting business? 

Holly: I would say in a few ways. One, I always tell people that growth is all about change. Clients are coming to me because they want to grow a business and anything that we look at, when we think about growth, is about change. There’s a sort of cheesy saying that is, ‘what got you here, won’t get you there.’ Meaning you have to make a change. So it’s about new… we have to tell ourselves new stories, we have to create new mindsets, we have to create new habits, we have to take different actions. Helping people understand, especially when people come to me and they say, “I’m not a numbers person,” or, “I’m not business.” I’m like, you can change your brain, your brain can change. It’s not fixed, we’re not fixed as humans. So really helping people understand that. And I do bring in a lot of personal growth to the work that I do in the business consulting with people. 

Amy: How do you draw the line between, if you can change, you can change your brain, you can become a numbers person, if you don’t think you are, maybe it’s just telling yourself something different. How do you work with your inherent nature and change yourself at the same time? 

Holly: In business there are these tests, they’re like strengths and weaknesses. I think it’s even called ‘strengths finders,’ is the test, and I’m sure there’s a lot of other ones like that. There’s a lot of personality tests that come up in business and I tell people the issue with that is that if we look at our strengths and weaknesses and we see them as fixed, we’re going to have a really hard time achieving our vision. I think we all inherently know what it is that want out of life. I do think even that takes time for people to reflect, like they haven’t spent a lot of time, but once we do, we don’t want to see ourselves as fixed in terms of like… if we say something is a weakness, we do have to work with it, like you were saying, it is about thinking differently, but it’s about different habits. For example, I’m working with a client right now, not in the design world, but we had to have a real come to Jesus moment about financial planning. And she didn’t want to do it, she didn’t want to look at her numbers, and we’ve been working together for years. And then she sent me this email and she was like, I did it, I had a conversation with myself last week, there were tears, I yelled at myself, I just had to come to terms with the fact that I can do this and I’ve actually been avoiding it. And I think that that’s… we have to have hard conversations with ourselves sometimes. To your point about how do we work with those things, I think we have to become aware of them, but not see them as limitations. And that we have to realize that we are responsible for changing them. 

Amy: That makes it much more of an opportunity for growth than something that could be a potential roadblock. And when you have to work around a roadblock, a construct of a roadblock that is your own resistance getting in the way, you spend more energy going around it than you do just going through it, right? (Laughs)

Holly: Yeah, for sure. 

Amy: But it does sound like overcoming your own resistance is a big part of business growth. 

Holly: It’s a huge part of it and I tell people a lot, the technical things that people want to learn, maybe like how do you write a business plan or how do you create a financial plan, you can actually find so many free resources online. And there’s tons of books available. But it’s really about why. Why am I not taking that action? Or why am I not holding myself accountable, or why don’t I see myself in that way? Or why does this terrify me? That’s what’s at the root of all of those things. 

Amy: How do you help people with that? It’s one thing to help them see it, but then how do you help them learn the new habit or keep going to that place that’s really uncomfortable, but is necessary? 

Holly: I think I’m good at holding non-judgmental space for people. And I have a lot of patience… like I have a client who is in the design space who I’ve been working with since 2016, and he had written me a funny email a few weeks ago because we just did a lot of technical things within the company and it was like, it took us years to get there, even though we had been talking about this needs to be done, this needs to be done, this needs to be done. And he finally did it, he finally took that step and I think this goes back to compassion. There’s a lot of times where I could be judgmental and just cut the cord and walk away, but I realize change is really extremely hard for people. And as long as they’re willing to take the tiniest step forward, you probably know the movie, What About Bob? In What About Bob, Bill Murray gets the book, Baby Steps, is the therapy book. And that’s what I tell people, it’s just baby steps. It’s not like… tomorrow I’m going to get up and do this thing perfectly, or tomorrow I’m going to get up and I’m going to be a totally different person. It’s about, I took a tiny step forward today and I’m going to take another tiny step forward and in 365 days I’ll have taken 365 steps forward, instead of one giant leap. 

Amy: It sounds so logical, but I can also see how having somebody, being accountable to somebody like you, who is also non-judgmental is helpful in the process. Because I can wake up tomorrow and say I’m going to take one tiny step, but you’re not going to track my progress. (Laughs) So if I don’t, it’s just me. (Laughs) Anyway, I want to go back to music therapy because you didn’t stay there for long. Tell me what happened after that? 

Holly: So after that I graduated, that’s what brought me to New York. I actually came to New York to do an internship at Beth Abraham, which is where Oliver Sacks was. He wasn’t there at the time, although we did crossover on a case study when I was there as a music therapist. 

Amy: That’s kinda cool. 

Holly: Yeah, it was very cool. And so I came, I did music therapy for, I think a year and a half, or two years, and then I decided I was going to be a doctor, because of that, because there was a lot of resistance internally, it was still not very validated that music therapy was actually impactful and I was like well, if I become a doctor, I can really help build this bridge because I can speak both languages and I loved the brain. I was either going to be a neurologist or a neurosurgeon because neurosurgery is also like really fascinating. 

Amy: I bet!

Holly: Yeah. I ended up taking a year off. I went through a very intense breakup and I was like, I’m just going to take a year off. I waited tables in Brooklyn, had a lot of fun and then I went back to Columbia to get my pre-med because I didn’t have any science background. So I went back to Columbia…

Amy: Don’t gloss over the ‘had a lot of fun’ chapter though. I ask this because I also had a lot of fun and I frequently look back to those years and I harvest wisdom from those years. The adults in your life might look at you and say, why are you wasting your life and it’s like no, I’m having the best conversations I’ve ever had, even if they’re at 4:00 and we’ve had something to drink. 

Holly: Yeah. 

Amy: And I’m meeting so many people because I’m less inhibited and I’m out and I’m doing things. It was a very fertile time, but you can’t keep it up forever. But as a chapter, it’s something.

Holly: Yeah, it definitely was. It was an amazing time, that was 2004 and I was in Brooklyn and I was in Williamsburg and that time in and of itself… there’s a documentary called Meet Me in the Bathroom, about the music scene at that time. But it was like every night you were going out and it was like the strokes and the rapture and LCD sound system and TV On the Radio and the Yeah Yeah Yeahs and Chk Chk Chk, you’re just like… and you thought it would las forever in some ways. 

Amy: Yeah. 

Holly: And the thing about waiting tables is like, you don’t have any responsibility, right? So you’re totally free. And we would be on our bikes every night going out, Max Fish was still open, the Lowry Side was this amazing creative hub and it was incredible. And it was also pre-social media too, so there was none of that, like there was a lot of debauchery, none of it was caught on camera. (Laughter)

Amy: Yes! Yes!

Holly: You were totally free. And also just to go back to leaving social media, I feel that again, I feel that freedom that I never felt when I was on it. And I think that freedom is so liberating. But yeah, that time, to your point, it was so artistically inspiring, I ended up connecting with a music producer who also had gone to Berklee, but like 20 years before me and he would bring me in to record on people’s albums on my bassoon. And so that was also very fun. 

Amy: Yeah!

Holly: And just like something that I sort of have now in my pocket. But yeah, I totally agree, I think that that time… and I tell people that all the time, I’ve actually told people, you should just step away and go and wait tables for a year. Because he’s like, I still need to make money. I was like, the freedom that you have when you’re in a job like that is so valuable. 

Amy: And I think that job, not just that job, but that time was also pivotal for you because you did go back to school to become a doctor. But then you’d already built this kind of community in the restaurant world that ended up being… even as unanticipated as it may have been, it ended up being a channel toward what you’re doing now. 

Holly: Yeah.

Amy: This is another thing I always want to remind people; you may have a path, you may think you have a plan, but it’s okay if it doesn’t go linearly. You don’t realize all that you’re learning, even on your detours. 

Holly: Oh yeah, for sure, and I think the detours, I’ll fast forward a little bit, but I think it’s a good point. After I finished my premed and I was a medical research at Lenox Hill Hospital then too, I had decided I wanted to go to Harvard and study with this certain person to do a MD PhD and this professor, her name was Dr Ellan Langer and she just had a book that came out and a student of mine, Chelsea from Green had texted me this podcast and she was like, this woman is amazing. And it was Dr Langer and I was like, oh my god, well one day in 2008 I had written her a letter and I wanted to go study in her lab and she invited me up to Harvard. I met her. We talked. I read some of her work and then it ultimately didn’t work out and it was devastating for me, but I would never have been a business consultant had I gone to Harvard that year and I was just saying, you don’t realize these things, it just feels so crushing and I was so lost after that. But then because of where I was, I ended up becoming a business consultant, which created all of these amazing opportunities that I could have never envisioned, and I didn’t envision at that time.  

Amy: I listened to your… and I recommend all of your listeners go back and listen to your personal story, which is episode one of your podcast, Cultures Within Capitalism. 

Holly: Yeah. 

Amy: Because I learned so much about you and this isn’t a full repeat, I think we’re having a different conversation. But the piece of it that was really fascinating to me is you learned your business savvy on the job. You learned by doing. You learned because you were waitressing and the owner of the restaurant wanted to take leave to have a baby and you assumed a management position. And that was where (laughs) you did a lot of your ground level learning. Describe that experience to me and what were the things that you had to learn and did you feel like you had to learn with a gun to your head or what was the experience like? 

Holly: Yeah, I had no idea what management was, I had no idea how to run a business. But I was pretty depressed at that point in my life. Like really struggling in terms of finding purpose and finding meaning. And I didn’t know the path forward. 

Amy: How old were you? 

Holly: It would have been right after I turned 30. 

Amy: Thirty, and so at this point you’ve also tried being a professional dancer, tried being a music therapist, tried going to medical school and so you probably were feeling like… I got to find something and I’ve tried all the good stuff, what’s left for me. 

Holly: Totally and I think what was interesting about that is that when I was a medical researcher, I was at Lenox Hill Hospital and I worked for this doctor, Dr Ranawat and he is legend. He actually created the implants; if you get a hip and knee replacement he has like the patents to those things? And he was an incredible figure. But when you’re up at like an Ivy League school and you’re premed and you’re working for this world renowned surgeon, a lot of doors open for you. He’s a member of these private clubs, you get invited to things, it’s like you go wait tables and people, especially in Williamsburg at that time, treat you like shit. (Laughs) And it was so ego crushing, and the fact that I had over $100,000 in student loan debt, where I was like, what am I doing? Not only is my ego being crushed, but I have to pay back, it was like $120,000 or something and it was really hard on so many levels. And so like trying to find purpose, what does this all mean. Why am I here? What am I supposed to be doing? Just were questions that took me years to resolve. So when I was offered this opportunity to manage the restaurant, it at least gave me daily purpose and also intellectual stimulation where I was like okay, let me figure out what’s going on with the finances. Let me figure out what is a company culture, why are we wasting so much food? Why is nobody doing their job they’re supposed to do, oh, because they don’t have clear job descriptions. It was really the opportunity for me to figure out all aspects of how you actually run a healthy business. And I got really into it, I read tons of books and just taught myself on the job. So it really helped me realize, these things matter, these practices really matter. They help you understand why you are or aren’t making money. 

Amy: So you were able to turn that business into a profitable one, yes? 

Holly: Yeah, so we were able to turn it around and within a year we were able to offer everyone…health insurance, paid time off, we were above… New York didn’t have a minimum wage, that like 15 minimum wage, we were above that at that time. And so we were able to put all these benefits and good practices into place and I was able to go to congress and talk at a congressional briefing about the fact that sick days are important, health insurance is important, like all these really good business practices. And it was also sort of like at a time that was inspiring New York to put the sick days mandate in place and paid family leave. 

Amy: Wow, so your work was not just helping that one restaurant, you took it national. (Laughs)

Holly: I think it goes back to this idea that we were talking about earlier. Just facing possibilities, thinking about possibilities, instead of accepting, which I think was sort of the rhetoric of like, oh restaurants, you can’t do that, saying like how can we make this possible, and using that as the compass to make decisions and take action. 

Amy: So catch me up to now. Why do you say you’re a culture first focused consultancy?

Holly: So when I started learning about business, I got really into learning about company culture and company culture is this idea of… our culture is essentially how we show up in the business. It’s our behavior, it’s our beliefs, it’s our actions. A lot of times when we’re talking about culture, we’ll hear things like company values are our purpose and in all my research and my practice as a consultant, it was true that you can have a beautiful business plan, you can have the most detailed financial plan, you can have the most awesome marketing plan, but if the company culture isn’t good, meaning if like the behavior isn’t good, if the mindsets, if we’re not accountable to those things, it doesn’t matter. And so when I work with my clients, I’m always talking about like okay, we have to understand what the company culture is and then we can build a plan for growth, or then we can build your team, or then we can put your financial plan in place. Because the culture is really like the soil. If we think about a business, we can think of the culture as the soil, we can think of our infrastructure as the trunk of the tree. We can think about our plan as like the branches. But if you’re putting all those things into soil that has no nutrients or is really hard and can’t get water and everything it needs to survive, it’s not going to work. 

Amy: That makes perfect sense. Do you find that you run into resistance, I think for some of the things that are appealing about a business plan and a financial plan is that they’re measurable, you sort of commit to a kind of formula and culture is so not (laughs) formulaic. 

Holly: Yeah, it’s not formulaic, is right and everybody’s culture is different. There might be some overlaps, but if you’re doing it right, it should be so deeply personal to you that it is different from everybody else and that’s actually what helps you thrive. But you’re right,I think we do have this tendency to be like, if I can’t measure it, it doesn’t matter sort of thing. Which is unfortunate and going back to music therapy too, I think the reason that I’m able to think different about business is because music therapy thinks different about medicine and what healing actually means and accepting that there are some things that we don’t understand and that we can’t put our finger on, but we can see them and they’re working.

Amy: I know that one of the ways that you help people get clear on just how to grow their business and what they want their business to grow into is by asking them how they want to spend their days. Why do you want to spend your days doing this? What is the purpose for you here? 

Holly: I think in some ways I have the most interesting job in the world. I probably meet with 30 different companies a month and that’ll fluctuate and rotate, like who those 30 different companies are. But I have such an insight, I think, into an economy in a way that nobody else does. And into like the inner workings and sort of behind the curtain of that economy and a real understanding. And I really, just to go back to this idea of art is the highest form of hope, I think that if we can create good jobs and healthy companies and people’s creativity can thrive, then we’re going to live in a better world, the world is going to be better for it. And so I feel really lucky to be able to participate in that process. And I see so much. I mean I’ve been through marriages, divorces, childbirth, so many things that happen with people personally and to be able to witness all of that transformation is really rewarding. 

Amy: It sounds to me like you found your calling. You’re in the right spot. 

Holly: I think I’m in the right spot, but I’m not done yet…

Amy: No, because your brain can change and because you’re looking for possibilities everywhere. That means you’ll never be done. But isn’t that the excitement of every day? 

Holly: Yeah, for sure, it definitely is, and I think also liberating, being in middle age, because I think part of why I was so existentially depressed in my 30s is this idea, I thought it was like you found this thing and then that was like your path. And now I’m like, oh no, you can keep changing until the day you die. 

Amy: Yeah, I was looking around at all the services and resources that you offer on your website and in addition to consulting you’re offering a lot of information, but also some programs that anyone can sign up for, correct? 

Holly: This is the class that’s sort of like a mini MBA, it’s a six month program. It’s really a one year program because you’re in the group for a year, but the classes actually run six months and we look at every aspect of your business from your company culture to your leadership, to your long term vision and goals, to your financial plan, marketing and sales, operating systems, all of the things. And it really helps people who have already established a business who are ready to set that long term vision and say, this is what I want to do, I’m all in and I need to do it all. And it’s really actually where I met the design community. I was teaching at Industry City, which is here in Brooklyn and a lot of manufacturers in that area ended up coming to the class and that’s really where I got involved with the design community and a lot of designers went through that program. 

Amy: And so it’s six months, but you’re in the group for a year, is it in person, is it only for locals or is it online? 

Holly: Yeah, it’s online now. It was in person in New York, but once the pandemic hit it’s been online, which has been really amazing now because it’s worldwide. So we have people across the country and then sometimes from other countries as well, so it’s an amazing way to meet community too. 

Amy: Yeah, why do you choose creatives, it kind of makes sense to me, but I want to hear from you, why creatives are your chosen niche in terms of this kind of work? 

Holly: I find them really inspiring, I find the work that people do, that I work with really inspiring. I want it to exist in the world. I want them to be able to engage with it every day. I think it’s a total myth that you can’t be creative and make a lot of money and I think I really like to prove people wrong, or if people are like, that can’t be done, I’m like let me show you. I realize I like that. I think helping creative people see that you can flourish and that this is valid, I think is something that inspires me. 

Amy: One of the things that I think would probably be working very synergistically in this relationship with you coaching creatives is that you’re a creative yourself and so often creatives go into these situations where they’re invalidated almost because there are so many unknowns they’re dealing with in terms of the creative process every day, it’s almost like they’re not taken seriously or they’re given… the feedback they’re given is tinged with exasperation or frustration, that they’re not conforming to this measurable rigid scientific protocol almost. If they did, that would kill what it is that they’re doing on some level and yet they still can put in the structure and the foundation, but it’s really hard to do that with somebody who is judging you or invalidating you in the process. 

Holly: Yeah. I totally agree and I think that goes back to maybe the culture of education and I think people can be well meaning and still do really damaging things. I think that we can be well meaning and give people complexes about not being numbers worthy or we just drive home that narrative that like, oh, that’s the creative thing, now we’re going to do this real work or something like that. 

Amy: I love that you’re there supporting and helping, not just business growth, but business growth by way of personal growth. What’s coming up that you’re excited about? 

Holly: I think there’s a few things that are coming up. So I’ve just put together a group of guest teachers, we’re going to do a two day leadership seminar, it’s the first time I’ve ever done this, because I also think a lot of times when creatives go into business, they don’t see themselves as leaders and leadership is definitely something that creatives struggle with because we’re never told we’re a leader, we’re never developed as leaders. And I’m really excited about that because I also think leadership can save the world and I think we’re in a time where we need leadership so bad. 

Amy: Yes. (Laughs)

Holly: And we don’t have great examples and so I’m really excited to put that together and to do that as well. 

Amy: That’s amazing, I hope to take one of your classes or at least check in with you after them and I’m so happy to hear that you think of creatives as leaders because I do too and I think we need more possibilities and more hope in leadership. 

Holly: For sure. 

Amy: Thank you so much for sharing all of your wisdom and your story and your personal challenges, this has been really, really nutrient dense and beautiful. 

Holly: Thank you Amy and thank you for everything that you do in the podcast, I think it’s such an amazing resource and I also appreciate your approach to just the personal, like incorporating those life histories and I love your phrase, ‘nutrient dense,’ I think that’s what makes that experience rich at the end of the day. 

Amy: Hey, thanks so much for listening for a transcript of this episode, and more about Holly, including links, and images of her work - head to our website - cleverpodcast.com. While you’re there, check out our Resources page for books, info, and special offers from our guests, partners, and sponsors. And sign-up for our monthly substack. If you like Clever, there are a number of ways you can support us: - share Clever with your friends, leave us a 5 star rating, or a kind review, support our sponsors, and hit the follow or subscribe button in your podcast app so that our new episodes will turn up in your feed. We love to hear from you on LinkedIn, Instagram and Twitter X - you can find us @cleverpodcast and you can find me @amydevers. Clever is hosted & produced by me, Amy Devers, with editing by Mark Zurawinski, production assistance from Ilana Nevins and Anouchka Stephan and music by El Ten Eleven.  Clever is a proud member of the Surround podcast network. Visit surroundpodcasts.com to discover more of the Architecture and Design industry’s premier shows.

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Holly Howard, photo by Ryan Page

Holly and her college roommate and bestie, Jesse, recording up in the Catskills.

Ballet photo of Holly in 1997, her professional portrait when she hit the audition circuit

Roe Ethridge portrait from 2004 — Holly at Marlow and Sons

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Clever is produced and hosted by Amy Devers with editing by Mark Zurawinski, production assistance from Ilana Nevins and Anouchka Stephan, and music by El Ten Eleven.

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