You didn't think I was going to celebrate my 10th anniversary without some reference to a 90's anthem and especially one that likely holds the key to what is missing from the pursuit of entrepreneurship in the 21st century—brining together both the analytical & intuitive forces that will move capitalism from extraction to enrichment.

I have written about my thoughts on the girlboss era previously so I won't rehash those. But in light of The New York Times declaring the sunsetting of the girlboss, I thought it a perfect time to continue to offer more perspective about what this next era of entrepreneurship might look like if we are to rightfully honor the feminine in business and move away from divisive rhetoric that confuses gender as an indicator of capacity for change.

And without restating the equal forces of the masculine and feminine aspects of entrepreneurship today I want to focus on one major feminine force that is often overlooked or discredited when it comes to growth; and the healthy masculine structures that allow this force to flow. And that force is mystery.

There are plenty of highly regarded business books that will talk about the power of luck in business. Heart, Smarts, Guts and Luck and Competing Against Luck are a few that come to mind. What's interesting about most of these publications is that they're often trying to describe, analyze, and articulate a mystery. I was reminded of this compulsion when I was listening to a recent unedited episode of onbeing with Rachel Naomi Remen. Dr. Remen speaks to her own early struggles of being both analytical and allowing for some things in healing to be left unexplained. As a trained scientist, I can relate. Who are we as humans if we can't utilize our intellect to provide certainty? And how do we cultivate the humility to embrace the fact that we can't always know why some things work and others don't. 

What we've seen in the last decade with algorithms and ad spends is the tantalizing idea that we can have exact certainty about the impact of our efforts. When we make financial projections with only one model instead of 3 (cautious, likely, and optimistic) we're betting it all on our impulse for certainty. And when we believe that our product is filling a "need" we're unconsciously overriding our own capacity for humility, again centering the idea of certainty of demand. 

But mystery isn't about not taking action and waiting for things to magically happen. It's about setting ourselves up so it can happen. And that's where the healthy masculine comes in. I have written my thoughts on the wounded masculine in entrepreneurship here. And what I'll further say about this topic builds off of what Steven Pressfield speaks about in his books Turning Pro and The War of Art. Pressfield gives a lot of advice on setting yourself up to allow the muse to flow. We accept that in creativity, there's some mysterious force beyond us that makes art great. But if we don't have the discipline of routine or structure we often won't experience that force.

The same stands in business. If we don't build the structures and do the right work of the entrepreneur, we can't expect the feminine force of mystery to connect us to those clients we've been wanting to work with but never returned our emails, or connect us to that source of funding we weren't initially pursuing, or create that opportunity for expansion that wasn't even on our radar, or bring that team member into our life when we weren't even looking. And if we deny that mystery has any credit for our success, we cut ourselves off from our capacity to think creatively about possibilities. We create incomplete ecosystems of engagement with our consumer community and we forgo our ability to express creatively and we become more calculating. 

When we over-prioritize and become overly dependent on those efforts that we believe guarantee us certainty as we've been doing in the last decade, we continue to muffle the feminine force of mystery. Are we finally ready to heal our own inner masculine so that we can actually experience the feminine and open up to what it might actually look like to let those forces co-exist? Your daily actions will tell. I, for one, can't imagine my business success without it. 


I’m so excited to share with you the official podcast of Ask Holly How, Cultures within Capitalism. This podcast serves to highlight the Clients & Students of the Ask Holly How community with a focus on company culture. You can listen to the trailer to learn more about it (and the origin of our theme song😸) and this interview I did with Matt Little to learn more about my history and the wild journey that lead to the beginning of Ask Holly How

And for our first official interview, I’m super excited and honored to share this episode with Alex Daly, founder of Daly. When it comes to communication, nobody does it better than Alex and Daly. Daly is a communications agency that digs deep to tell untold stories for people and companies who truly believe and invest in what they're doing. Alex is inspiring and thoughtful and her words of wisdom are generous. We talk about all things company culture, building a company, pivoting a company, vulnerability, and leadership. I always learn something from listening to Alex. Join us! 


As we look towards the next 10 years, we’d love your feedback so we can continue to meet and exceed your expectations and guide you through these rapidly changing times. This survey takes about 10-15min to complete. We are grateful for your time looking forward to hearing from you.


As we build towards opening a school, there are lots of changes on the horizon at Ask Holly How. I’ve recently updated my website where you can learn more about my company values, an update of services, and browse the recently updated Resource Center. This new page is broken into 4 categories: Listen, WatchRead, and Do. You can find the newsletter archive, some creatively questionable videos that reinforce my philosophy of business (like this 2012 gem😹), worksheets to guide you on your journey starting with this audit of your company values, and most exciting, the new podcast! 

Stay tuned for more one-off classes, more week-long seminars, more practical resources, more media, and more opportunities to connect within the community.

Thank you to everyone who has opened their doors and dreams to me. In the wise words of Soul II Soul: 

Keep on moving

Don't stop, like the hands of time

Click-clock, find your own way to stay

The time will come one day


This summer, we'll do one book club in late July. We'll read Jonah Sach's most recent book, Unsafe Thinking. This is a free event and will be hosted on Tuesday, July 19th at 7PMEST via Zoom. Please email me to register. 


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Ask Holly How · 8801 Shore Road · Brooklyn, NY - New York 11209 · USA

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