Holly Howard of Ask Holly How

Portrait of Holly Howard of Ask Holly How


Words by:

Holly Howard + Present Studio

For Holly Howard, a two-hour walk is a benchmark for a good day. We recently caught up with Holly to talk time and the uniquely personal ways in which she spends it.

Holly Howard is the founder of Ask Holly How, a business consultancy in which she thoughtfully guides creative entrepreneurs by way of private consulting and catered program offerings. Michelle and I first met Holly while taking her Beyond the Feed: Post-Algorithmic Marketing for Growth course last fall, an invaluable experience which completely transformed our approach towards marketing from wholly avoidant to inspired. One conversation with Holly makes abundantly clear how absurd it is to adhere to any societal standards of a life well-lived. For Holly, a two-hour daily walk is both a pleasure and a necessity. For another, it may be agony. And that’s all okay.

I recently listened to a podcast episode which concluded an interview with baker Cheryl Day with the following reflection:

“We always talk about time well-spent as if time can be spent foolishly. But what if indeed you can’t spend time. Time is simply a way for humans to try to understand existence. In that case, every moment is, perhaps, infinite. And by living in the moment, you never really run out of time.”

Holly has undoubtedly spent time in such a way–an eager, infinite endeavor to understand her own self. Read below for our full interview with Holly. We hope you feel equally as inspired by our conversation as we did.

A side profile of a woman with a mullet.

Holly and her mullet, The Excelsior. :)

PS: We first met while taking your marketing course, an incredible class we constantly cite and recommend to our peers. We realized that we don’t actually know much about your background aside from the bits we’ve gleaned from your class and newsletter. Can you share your story and how you built Ask Holly How?

Yeah, so I’ll just sort of go all the way back. I didn’t go to business school, so becoming a business consultant was something that sort of naturally evolved because my background is really varied. Out of high school, I was actually a professional ballet dancer. I did that for three years and then decided to go to college (a bit later than my peers). I sort of picked my bassoon back up again and wound up at Berklee School of Music studying music therapy.

After college, I came to New York for an internship and practiced as a music therapist thereafter for a couple years. I sort of decided I had gone as far as I could with that and decided to become a doctor. I went back to school to get my premed degree and also worked as a medical researcher at Lennox Hill Hospital. When I got ready to apply for medical school, I really had an existential crisis. I was just around 28 and re-evaluating everything. I had come out of a bad breakup and was like, what am I doing with my life?

So I went back to working in restaurants. I waited tables and eventually the restaurant I was at needed someone to manage it because the founder was taking paternity leave. I didn’t know anything about business at the time, but I thought sure, I need something do. It really gave me the space to learn on my own. And that’s where I started reading a lot of books and learning about company culture, systems, and marketing. This was right around the time of the ‘08 recession, back when a lot of businesses started popping up in Brooklyn. A lot of what we commonly see now–farm to table, small food producers–were so new back then. I started consulting in 2010, left my restaurant job in 2012, and really just evolved from there.

PS: The curious, meandering mode of living that you’ve demonstrated is so inspiring. Personally, there are times when I’m frustrated that my interests feel like competing or that I’m not following some linear path to where I should be. How have your thoughts regarding this evolved?

When I quit dancing and went back to college, I was three years behind my peers and I felt so old. And that just sort of continued because I changed so much. I would feel so far behind my peers–not meeting what we might think of as “cultural milestones” in terms of getting married, having kids, or buying a house. I wasn’t doing those things because I was always regenerating. I think what I realized about myself in reflecting on my past is that I prioritized my own creative and intellectual growth over what might have been more traditional markers of progress in somebody's life.

I prioritized my own creative and intellectual growth over what might have been more traditional markers of progress in somebody's life.

Oftentimes I would feel uncomfortable, thinking “Am I just not figuring out my life?” or “Am I not able to commit to a path?” But I knew I was never coming from a non-committal space. It was more a feeling of “I can’t imagine not doing all of these things.” Having to tune out a lot of the cultural programming in terms of how your adult life should look has become really important for me.

PS: It sounds like you’ve always been able to follow your intuition and ignore these prescribed social milestones.

Yeah, for sure. The older I get, the harder it becomes not to follow my intuition. I think, well, I made it this far in following what I believe in. It’s something that gets easier, I think, the more that you flex that muscle.

PS: We know that you’re currently pursuing a Masters in religion. With the investment that higher education requires, there’s seemingly a utility or monetary payoff necessary from a degree. Was that financial leap a scary one for you?

I’ve always grown up with debt and I’ve never been debt averse. I totally understand when people are like, “Is this going to get me somewhere?” or “Is this useful?” but debt has done a lot of good things for me. There were also a few things that happened in my life personally that just changed the way I thought about all this.

Both of my brother's wives died in their early 40s–one had a heart attack and one had a pulmonary embolism. I was the same age as them both times. And when that happens, you’re just like, “What if I die tomorrow? Did I live the life I wanted?” That divide between practical and following your curiosity sort of melts away. I always tell people the most important question you can ask yourself is “How do you want to be spending your days?” Because your days add up to your life. And that’s just how I organize, how I spend my time, how I prioritize.

I always tell people the most important question you can ask yourself is “How do you want to be spending your days?” Because your days add up to your life.
PS: I’d love to throw that question back to you. How do you want to spend your days and, thus, life?

I love to learn. It just invigorates me so much–as much as a good workout does. My days start at 4:00AM. I have coffee. I meditate. I journal. I spend a lot of time by myself and then I have a pretty full client load, either seeing private clients or teaching classes.

I have a few daily non-negotiables. First is journaling and reflecting. Second is walking for two hours. And finally, reading. As long as I get to walk two hours, meditate, and read what I like, I feel like everything else is open for whatever comes up that day.

PS: Are you reading anything good right now?

Yeah, I’m reading a fiction book called Demon Copperhead by Barbara Kingsolver.

PS: Me too! Are you liking it?

I love it. Yeah. I really love it. My mom's relatives are from southern Illinois, which most people don't realize is like the same line as Tennessee. It's actually very south so there's a lot of similarities between the small town where she’s from and the story’s setting, even though it's in Appalachia. I think it's so good, but also just so depressing.

PS: Yes, I love the language. You really get into the world of the novel. I’ll have to follow up on the ending with you.

I’ll tell you this quirk about me. I actually have already read the last 100 pages.

PS: Oh my gosh. No spoilers.

It drives my husband crazy. I actually read like a researcher most times, scanning and pulling information. So when I read fiction, it sort of helps me to slow down and be like, you know how this is going to end so just take your time.

PS: So you mentioned that you have 30 active clients at a time. Do you work with people for years? What’s the normal kind of engagement?

Yeah, I'll work with people for years. I have clients from 2012 that l still talk to, but it becomes very different through the years. Usually the way that it works is that it's really intensive up front– whatever the business needs to achieve or put in place or change. And then people like to be able to check in once a month or whenever some big life event happens. It’s a really interesting part of my job as people realize they want to make changes to their business as they’re having children, going through a divorce, getting married, moving across the world, etc. All the personal things that happen and how that impacts a business and how you have to evolve with that.

PS: Are there seasonal ebbs and flows to your business?

Yeah, there definitely are. I tend to get really busy at the end of December and into January-February because people are like, “New Year! I want to do things differently. I want to have a plan.” And then I would say same with September. As people head into the fall, I think there’s a sort of a back-to-school vibe or it’s just generally a time when we rethink where we're at in life. So those tend to be really busy times.

PS: And you’ve crafted your courses around these times?

Yes, the big program [Business Growth For Creative Entrepreneurs] runs January through June. So it is like a real start to your new year to build your plan. And then the marketing program [Beyond the Feed: Post-Algorithmic Marketing for Growth] which starts in September is more of the back-to-school idea, learn and take this plan into the new Year.

PS: You work with a lot of creative entrepreneurs. Can you share any themes that arise of particular areas where businesses are seeking help?

I think people commonly feel like, “How did I get here?” All of a sudden they've built a business based on what thought they were supposed or what they saw their peers doing. Another theme that comes up a lot is when people start to realize that they want their time back. Be it they've created really bad boundaries with their business or bad boundaries with their employees. They’re trying to get their time back. I also work with a lot of entrepreneurs in their early to mid-40’s who are having some big existential moments. Finally, another common theme is money and people feeling like they’re not paying themselves what they would like to earn.

PS: And how do you address these? These are such big questions.

Yeah, these are really big questions because they're so existential. To sort of go in backwards order, when people aren’t making the type of money they want to be making, the practical part is that they don’t have a financial plan. But there’s also the emotional and psychological aspect around pricing as well–people feeling like they can’t charge X amount or not feeling empowered to speak their worth. You have to address the practical and psychological together.

PS: That’s kind of a form of therapy in a way, if you’re surfacing all of that for people.

Yeah, so when I went to school to become a music therapist, I actually had to train as a regular therapist in systems of psychotherapy. I come with all that background and understanding. So I’ll work with people on a lot, but I also tell people to seek an outside therapist when there are deeper issues that aren’t appropriate for us to dig into. I send a lot of people to couples therapy, too.

PS: There’s an incredible throughline in everything you’ve done in helping people. It’s really beautiful.

Because I did come out of school with so much debt, I used to joke that I don't even use any of my degrees. But the reality is, I really do. Everything I learned when I was premed in terms of data and science, for example, ties over to marketing and how much you have to understand your own analytics and financial planning. I realize it's all connected and really feeds each other.

PS: How do you approach your own values vs. your business’ values? Can those be the same? Or different?

So the way that I like to think about it is that your business values should be personal to you, but they're only a slice of the pie of who you are as an entire human being. My business values are very personal, but there’s also a whole subset of values in my personal life that actually don't fit into my business. In this era where we're trying to find meaning in our work, your work should have meaning, but it shouldn't be the only meaning in your life. Have an awareness of what other values guide your life that actually don't fit into your business and make sure you're nurturing those just as much too.

Your work should have meaning, but it shouldn't be the only meaning in your life.

Do you know the author David Sedaris? He walks like 20 miles a day. I remember reading that in an article and feeling so jealous! I wish I could do that and realized I really just like to be out walking. So when I ask myself how do I measure whether I’ve had a good day, if I’ve walked two hours–no matter what fluctuates with my client work or business–I feel like I’ve had a great day. So that’s the way I try to explain it to people. You do have to have personal values in your business because you want to be inspired by them and move that forward. But you also want to remember that you’re a whole human being and give that equal attention as well by knowing what values you hold for your personal life.

PS: What are your own personal definitions of success that stray from society’s?

I mean, walking is one. As long as I’m walking two hours a day, I think, “I’ve made it!” I also have to finish my medical school degree. I don’t know if I’m going to practice as a doctor afterwards, but it’s something that’s really important to me. My husband and I have made a ritual of lighting candles every night for dinner. It’s the tiniest things that are the most impactful and make the biggest difference over time.

PS: It sounds like there’s a consistency here. You’ve made them rituals.

Yeah, totally. I think it’s so important to find the rituals that are really meaningful to you and stay focused on them. I’ve had the privilege of working with over 1000 companies over the last eleven years and, while that’s a small sample size in a lot of ways, you do start to see pattens. The most successful people are the ones that really know who they are and are able to be consistent in that. They know the vision for their life and are able to tune out the noise.

PS: Has the noise ever been an issue for you?

Big picture, I would say no. But it took me a minute to realize that. It’s one of the reasons I left social media. I genuinely didn’t find there to be anything there for me. I’m realizing how much I love mystery. Now that I’ve left social media, there’s so much more mystery. Wondering what people are up to and then coming together. These moments feel valuable and prioritizing that sense of mystery has enriched my life so much.

PS: I think the best I’ve ever felt is when I’ve made my own rituals non-negotiables. Sometimes I feel a sense of guilt or selfishness that moves me away from prioritizing these things, so it’s incredible to hear that you’re doing them.

I don’t feel any guilt or selfishness at all. But I will say, I think if my sisters-in-law hadn’t died, I might never have had this awareness. I just feel like I live with an awareness that it could all end tomorrow. Not to make light of the situation, but when you go through these tragedies, you think okay, how can I transform this into something meaningful?

PS: Any present inspirations?

I'm really appreciating old bands that are coming back with new records. There's a band called Everything but the Girl who’s just put out a new record after two decades. That was so inspiring to see people who are sort of in my age range still generating really incredible art. I have a client that I won't name, but I'll just say that they're in their eighties and they are regenerating themselves. It’s so inspiring to me that even in your eighties your can still be at your creative peak.

PS: We need more exposure to that. What with “30 under 30” lists and the like, it becomes debilitating to feel that change is possible.

Yeah, I always called myself a late bloomer. Not to discredit people that achieved a lot in their twenties and thirties, but I never related to that. You can do anything at any time. The inspiration is out there.

Thank you to Holly for taking the time to chat with us! Check out Holly's website to learn more about her course offerings and services.

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