In June of 2022, I will reach a major milestone marking 10 years of Ask Holly How.  As I move towards this, I wanted to spend time reflecting on what I've observed in hopes that together, we might continue to build a community of businesses that prioritize culture-building and experience capitalism in a way that contributes to human flourishing instead of extracting from it.  And I also wanted to share a quick update about where AHH is headed. 

Over a year ago, I announced my plans to return to medical school and I'm still on that path. I have taken a slight (lol) detour to get a Master's Certificate in Religion and so my timeline has been pushed a few years but it is still an active pursuit. Why, you ask, might someone who runs a successful consultancy want to return to med school in their mid-40s? The answer I constantly come back to has a lot to do with the topic of this newsletter, what it means to find purpose in life and in business. My interest in entrepreneurship has always been at the intersection of business growth and personal growth.  And I look forward to sharing more about my progress on that front as it unfolds. 

I also announced my vision to open a school for entrepreneurship which I continue to work towards as well. And part of the preparation for opening my version of a school is to provide you with more insight into the Ask Holly How community. That means this year I'll be launching a podcast, doing more instructional videos, putting out a zine, and offering more classes. Stay tuned for more announcements with those initiatives.

Both of these pursuits will build upon what I've learned in the last decade, not be a departure from it. AHH continues to grow and this year I'm excited to welcome Matt Little as a collaborator both in the Business Growth Progam and Consulting. Working together allows this community to expand and to be able to bring you more resources. #TogetherEveryoneAcheivesMore

In this newsletter, we'll continue to go deep inside the experience of entrepreneurship looking as much at the philosophical as the practical. We'll prioritize staying grounded in the human experience of entrepreneurship. In doing so, I hope to engage you in what Octavia Butler calls an act of hope: The very act of trying to look ahead to discern possibilities and offer warnings. 


Over the holiday break, I read the new book, Out of Office, by journalists Charlie Warzel and Anne Helen Peterson. I would consider OOO a must-read for all founders, not because I agree with everything in it, but because I think the conversation is important. Over the course of reading the book, which is focused on how to improve remote work, and the state of work in general, I found myself becoming increasingly uncomfortable and combative (in my mind) with the authors even when I did agree with them. I couldn't figure out why I felt so irritated until I got to the final chapter which is called, "Letters to Workers". In this chapter they write,

"We love to talk about kids' personalities, how unique and weird and joyful they are. We don't grow out of those characteristics so much as subsume them with duties. But they remain the building blocks of our humanness, the enduring difference between us and robots. We must preserve those inclinations toward delight and whimsy, toward the ineffable and the unimpressive, the feeling you can't re-create with a machine or optimize for peak productivity. They are worth rediscovering not because they will allow us to rest, and, as such much us better workers but because they anchor us to who, at heart, we've always been."

This, in my opinion, is where the book should have started, not ended. Or, this is the book, I would have liked to have read on this topic. When we think about work, its role of it in our lives, and how we might improve it for everyone, it is tempting to isolate our era of existence and the experiences we have currently and solve for them accordingly. But the problem we're trying to solve goes much further back than the manifestation of the physical office and our departure from it. It goes back to the 18th Century when Adam Smith and David Hume were friends. 


Most people know Adam Smith as the father of Capitalism (thanks mostly to his mother for cooking his meals and doing his laundry!) but less discussed was his relationship with David Hume, the Scottish Philosopher, and the influence of theology on the creation of Capitalism. In his book, Religion and the Rise of Capitalism, Benjamin M. Friedman explains, "The creators of modern economics lived at a time when religion was both more pervasive and more central than anything we know in today's Western world. And, crucially, intellectual life was more integrated then. Part of what Smith taught, as a professor of moral philosophy at the University of Glasgow, was natural theology. He and his colleagues and friends were continually exposed to what were then fresh debates about new lines of theological thinking. I argue that what they heard and read and discussed influenced the economics they produced."

Understanding the context of the rise of capitalism could help us understand why almost 250 years later we're still navigating the dynamics of its origin. Our modern purpose of work has never existed without the influence of that state of theology. We point the finger at capitalism and our modern work experience when we should be pointing the finger beyond, to our unending drive to seek meaning


I was reminded of this again when in his most recent substack, L.M. Sacasas wrote about an essay in the Cut discussing the rise of the Notion and other knowledge-management systems. The essay in the Cut speaks to the Notion influencer (amazing!) and the radical level of self-documentation that some users develop. What Sacasas goes on to discuss is our approach to these types of platforms. He says, "It’s not technology per se, it’s a spirit that is brought to bear on all facets of our experience."

Much of his essay questions the experience of optimization. But what exactly are we optimizing for?

"For some people at least, the idea seems to be that when we are freed from these mundane and tedious activities, we will be free to finally tap the real potential of our humanity. It’s as if there were some abstract plane of human existence that no one had yet achieved because we were fettered by our need to be directly engaged with the material world. I suppose that makes this a kind of gnostic fantasy. When we no longer have to tend to the world, we can focus on … what exactly?"

This brought me back to Out of Office and Peterson & Warzel's comments on subsuming, the very characteristics that make us human, with duties. Sacasas warns, Do not mistake planning for purpose, or activity for action. But so much of work nowadays is often consumed with planning & activity. In their book, they speak of the busyness we experience with modern work. And I believe the reason why is because we often fail to understand the purpose of our business and the purpose of our life outside of our business. Sacasas ends with:  

The freedom to say Yes or No in terms of our own purposes—it would seem that the first step in the direction is to clarify for ourselves what exactly our own purpose are or should be. To do this, it seems to me that we need to play the role of Socrates to ourselves, questioning our motives and desires, asking ourselves why we do what we do, seeking to radically, that is to the roots, weed out the various ways we’ve accepted uncritically the default settings of our techno-economic order.


As research shows, we as a people are becoming more "spiritual but not religious". Whether people fall into either of those categories or solidly atheist (much like Hume would have been labeled) I have often pondered if we have taken our need for organized meaning-making and unconsciously thrown it onto our work in a desperate attempt to fulfill a craving for rituals, purpose, doctrine, and community. Without clearly defining the purpose of our business and the purpose of our life, we fail to find the delineation between what our business should and shouldn't provide for us in terms of meaning. 

Because entrepreneurship has taken on such religious fervor, we often forget that our business exists to support our life, our life does not exist to support our business. That's a challenging distinction to make when we don't pause to understand the purpose of the business in the first place. And the thing about the purpose is that it can only come from you. It can't be crafted for you. I was reminded of this on New Year's when I went to see the Sophie Tauber-Arp exhibit at MoMA:   

Only when we go into ourselves and attempt to be entirely true to ourselves will we succeed in making things of value, living things, and in this way help to develop a new style that is fitting for us. 

In this new year, I hope you find that delineation between the purpose for your business and the purpose for your life. And in doing so, I hope you contribute to a new style of entrepreneurship that is fitting for the 21st Century. 


THIS IS THE FINAL WEEK OF REGISTRATION FOR THE 2022 BUSINESS GROWTH PROGRAM. Thank you to everyone who has helped spread the word! We are now 21 companies, and 26 students nationwide. There are 4 more spots open for the Monday cohort group. For more details about the course including a bit of history, the philosophy of the program, feedback on who should attend, Syllabus, Calendar, FAQs, and much more, check out the full Program Manual here. If you still have questions, don't hesitate to reach out!

When you're ready to register, email Holly ( by responding to this email. Please indicate:

  • The Monday Cohort Group
  • If you have additional team members that would like to attend
  • Payment option:  Full Fee OR Payment Plan

We'll save your spot and we look forward to working with you in 2022!


This January we'll be reading Anthro-Vision by Gillian Tett. We will meet on Tuesday, January 25th at 7pmEST via Zoom. This is a free event, please email me to register.


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