Business consultant Holly Howard
Photo: Ryan Page

To Be a Successful Entrepreneur, Follow Holly Howard’s Content Plan

The business coach seeks out stories across disciplines that convey different points of view and encourage self-reflection.
By Tiffany Jow
October 4, 2021
9 minute read

According to business coach Holly Howard, those looking to run a flourishing enterprise should begin by taking a deeper look at themselves. “I always say there’s no business growth without personal growth first,” says Howard, who served as a professional ballet dancer, music therapist, medical researcher, and professor at Pratt Institute, among other roles, before starting her Brooklyn-based consultancy Ask Holly How, in 2012. Since then, she’s worked with more than 500 businesses and founders, guided by the belief that effective entrepreneurship requires self-evolution, company growth, and the pursuit of creativity—and that all three must be present for success. “I work with people who want to be self-reflective,” she says, noting that that desire is important because it questions intent. “When we think about what our motivations are—‘How will my vision impact the world?’—we start to break down the connections between our everyday actions, and the bigger picture we see.”

In addition to her client work, Howard teaches an annual business course from January to May (registration for the 2022 session opens Nov. 1) and hosts a Zoom book club. She also writes a weekly newsletter, a treasure trove of wisdom, links, and resources she’s encountered, that encourages the personal development she challenges her clients to seek—and shows, perhaps inadvertently, that she challenges herself to do the same. Notably, references to strictly business-related stories are all but absent. (A recent issue, focused on the value of paying attention to the physical world, cited a performance by the New York City Ballet, a conversation between A.I. researcher Lex Fridman and futurist and computer scientist Jaron Lanier, and an excerpt from Neil Postman’s classic book Amusing Ourselves to Death, which outlines the destructive effects of television on politics and public discourse.) It’s not that she isn’t interested in what they have to say. “The big role that media plays in my life is to [allow me to] consume a lot of different points of view,” she says. “It’s also super important for me to read across disciplines, which is why I incorporate science, religion, and philosophy into my intake. I find that gives me a deeper understanding of what is possible with human evolution, and therefore, the evolution of future leaders.”

Curious as to what this approach looks like in her day-to-day life, we recently asked Howard to share her robust content intake, which spans Natalie Wynn’s YouTube channel to Tristan Harris and Aza Raskin’s Your Undivided Attention podcast, and serves as a tasting menu for anyone looking to better understand others, and themselves.

How do you start your mornings?

I get up at 4 a.m., work out, have coffee, and digest a lot of newsletters. A few of my favorites are Maybe Baby by former Man Repeller editor Haley Nahman, Letters from an American by Heather Cox Richardson, Dense Discovery, and The Crucial Years by Bill McKibben, whose Substack just launched. I also read Glenn Greenwald’s newsletter. I appreciate people who are willing to be critical of liberals—and I should preface here that I am one—or someone who looks thoughtfully at their own party. Patti Smith’s newsletter, The Reader Is My Notebook, is really beautiful. She writes three or four times a week, and shares stories, songs, and recordings.

What books are you reading?

For our next book club meeting, which takes place November 9, we’re reading The Conversation by Robert Livingston. It’s about racism and organizations, and how to think about it from the principles of psychology and sociology. I’m also reading Beyond Belief: The Secret Gospel of Thomas, by Princeton University professor Elaine Pagels. I am not religious, but the [Gospel] talks about how you have to bring out what’s inside of you—because if you don’t, it will destroy you. And I just started A Hunter-Gatherer’s Guide to the 21st Century, co-authored by Heather Heying and Bret Weinstein, which is about evolution and modern life. I also recently bought Anthro-Vision: A New Way to See in Business and Life by Gillian Tett [the guest on Ep. 24 of our At a Distance podcast], and Uncivil Agreement: How Politics Became Our Identity by Lilliana Mason.

I have a lot of books in the mail that haven’t arrived yet, too. These include The Right to Sex: Feminism in the 21st Century by Amia Srinivasan, Clarity & Connection by Yung Pueblo, and A Carnival of Snackery, which is David Sedaris’s diaries from 2003 through 2020. I think he’s so funny, but I also appreciate that he’s talked about how, during the pandemic, he’d walk around for eight hours a day and pick up trash. There’s a mundane-ness about him that I really love.

What podcasts do you listen to?

M.I.T. researcher Lex Fridman’s podcast is super interesting to me. He’s in computer science, but his questions are very deep. I’m always pleasantly surprised by his vulnerability and willingness to ask tough questions. On Being with Krista Tippett is a regular one for me, as is Breaking Points, hosted by Krystal Ball and Saagar Enjeti. She’s liberal, he’s conservative, and they do this show to bring together different points of view. There’s also Your Undivided Attention, by the creators of The Social Dilemma documentary. Its conversations are very influential in my business-growth philosophy and connect back to the idea of self-reflection, particularly in asking why we use the media we do.

I’m also listening to the Dateline podcast…. I’ll listen to any true-crime podcast. I just finished one about the Murdaugh murders, and another one called Spooked. I have a friend who’s super into these, so she sends me recommendations.

Last, this isn’t a podcast, but ContraPoints, a YouTube channel by Natalie Wynn, is really great. She’s a trans woman with a Ph.D. in philosophy, and goes into heavy present-day topics, but in an amazing, theatrical way that makes it easy to digest the information.

Favorite TV shows?

I left social media a year ago, and after doing that, I ended all of my streaming subscriptions, too. There was always something I could never keep up with. I now only have HBO Plus, and just watched The White Lotus. The other thing I watch is PBS, via its video app. I love British crime dramas, like Endeavour. It’s hands down my favorite. It’s set in Oxford, in the forties or something. Watching it, you feel entertained but also like your brain is being challenged at the same time. Nothing seems like your attention is being taken advantage of.

What newspapers and magazines do you read?

In the last year, I started reading the Christian Science Monitor. It was on a recommended reading list by Noam Chomsky, who said it was one of his favorite publications. For every article, there’s a little blurb about why they wrote it, so you have an understanding of their motivations, which is fascinating. I also read The New York Times, The New Yorker, and Harper’s. I used to subscribe to the National Review as a counterpoint to The New Yorker, but then, when I started reading Substacks with different points of view, I unsubscribed. But it helped me to actually read about what right-wing people think, as opposed to just hearing about it from left-wing publications.

We’re living in a world where we’re asked to pit ourselves against each other instead of finding common threads, and having discussion and dialogue. Since leaving social media and cleaning my media diet, I feel much more hopeful and inspired by the world than when all I saw was my own point of view reflected back at me by an algorithm. I’ve realized that the world is such a rich, diverse place.