Welcome to Pyramid! (I want you to hear this clearly)

The Evolution of Ask Holly How

Where I’ve Been, Isn’t Where I’m Going

Hello! If you’re receiving this email, it’s because you’ve either subscribed to Pyramid Schemes directly or you’re a former Ask Holly How Newsletter Subscriber. For those of you in the latter category, as I mentioned in December, all of my writing will shift to this Substack. And here we are.

This is just a welcome email. A moment to step into the joy and sorrow that is already 2026. This newsletter will be different from my previous work. I’ll still be sharing philosophical takes on culture and work, but I’ll also be providing more practical advice on building sustainable work here. Not in a LinkedIn Lunatics sort of way (unless that is your vibe and I salute you and support you living your truth!).

People should not feel it’s wrong to feel joy in the center of grief.

Patti Smith on Anderson Cooper

When I was home over the break, my husband picked up a copy of David Foster Wallace’s This is Water. I remember when he gave this speech, but it was good to reread it and especially while on break. My aim with Pyramid is to create a space for the creation of work where you choose: you choose how to construct meaning from the experience you are having. Entrepreneurship is a privilege. How we orient ourselves within it is our choice. We can be a lunatic (s/o if that is your vibe) or we can be awake to the water we are living in.

The purpose of this evolution is to bring this work to a wider audience and to give us more opportunities to connect both online and in person. There’s also something much, much bigger brewing that I’ll start to tell you about next week! You can expect free monthly workshops, quarterly book clubs, and Substack lives with some really great guests. For now, this is to say hello. And if you have any book recommendations or workshop topics that interest you, please drop them in the comments! I’m glad you’re here and ready to scheme with me.

---