As I close out this arc of my business, I’m taking a hard look at what has served me—and what no longer does.
What worked when I was just starting out that doesn’t fit anymore?
What didn’t exist back then that now forms the foundation of my work?
And what needs to evolve so the work can go deeper and serve you better?
Which brings us to the end of another chapter.
This Wednesday’s Deeper Business Dialogue will be the final public Dialogue of the series.
I’m sharing why, because it might help you reflect on what’s ready to shift in your own business too.
3.5 Years. 45 Classes. All Free.
In March 2022, I taught my first free class—Radical Strategy: Design Sustainable Cycles In Your Business. (Even back then I was talking about cycles!)
Eight people registered, four showed up live, and I was hooked.
I loved sharing what I was exploring in real time and workshopping ideas with people who were equally curious.
Also, 2022 was the peak "high-ticket mastermind" era. Even I was in a five-figure program that wasn’t a fit for me. I became committed to building my business without gating my foundational thinking behind a paywall.
So I taught.
Every month for almost four years, I hosted some kind of free class or Q&A. Most were brand-new teachings and frameworks, and all were offered for free with a replay.
Over 600 people registered for at least one class, with rave reviews like:
“Jessica puts her heart and soul into these workshops. While there’s no lack of free content online—i.e. webinars disguised as helpful but really just a long sales pitch—this is the exact opposite. Thoughtful, honest and useful info in a nurturing environment. You can thank me later! ;)”
These Dialogues helped me grow my business, refine my methodology, and stay connected to so many of you.
And yet… it’s time for them to evolve.
Why end something that was working?
It’s no longer the best no/low-cost entry point into my world.
When I started the Dialogues, it was me and 117 email subscribers.
I had no public body of work: No guest podcasts. No Aggressively Human. No YouTube. No organized blog content.
Definitely no book.
And no cohort. No Membership.
The only way to work with me was 1:1, which is not ideal as a first step for many.
When I started, those free classes were the only way to get a feel for my work.
But by 2025?
There’s an entire ecosystem of free and low-cost ways to learn from me—available 24/7, with no waiting for replays:
- A YouTube channel full of value
- An organized blog
- A 300-page book for less than the price of a restaurant meal
- A Membership with a complete learning roadmap and weekly rhythms
The Dialogues no longer need to be the entry point to my world—and aren’t even the best option for that anymore.
The awareness level of attendees has widened too far.
When people stay in your world for years, the range of awareness grows.
Some people are encountering me for the first time. Others have been immersed in my frameworks and language for years.
It’s really hard to speak to both at once.
If I speak primarily to newcomers, long-time followers stop seeing the value.
If I speak to the people who know my frameworks inside and out, I risk confusing first-time attendees.
The only way to create depth and momentum is to have a shared baseline.
So moving forward, the monthly Dialogues will be focused on Members—people who already have access to the foundational content and shared vocabulary, so we can actually go deeper.
I want to invest more intentionally in the people who want to invest with me.
The Membership has quietly become one of my favorite parts of the business.
Now it’s where the actual rhythm of the work happens:
- Weekly Sacred Sales Hour
- Planning together
- Tracking metrics together
- Monthly Q&As and trainings
- A light, low-noise community
It has been such a joy to watch Members’ businesses blossom over time—not just in a one-off workshop, but month after month.
And I want to pour more into that in a way that’s consistent, focused, and structured.
By keeping the Dialogues inside the Membership, I can shape the monthly classes around what Members are currently navigating, because I know their businesses and they know the foundational material. I'm excited to spotlight more members and guests next year as experts in the Membership.
Join Me for the Final Public Dialogue
Fittingly, the finale is called “What Is Enough?”
Bring your book if you have one — we'll be covering Chapter 5.
Come celebrate the close of this chapter.
And if you’ve valued the Dialogues or this newsletter… consider joining the Deeper Foundations Membership.
This is the best deal I offer—no Black Friday discounts coming.
The Membership is designed to give you the resources, rhythms, and relationships that make a right-sized business sustainable.
You get live support:
- Weekly Sacred Sales Outreach Hour
- Monthly Live Q&A + new teachings
- Monthly Tending & Metrics calls
- Seasonal Planning Rituals
You get a curriculum:
- Core Foundations library with essential trainings
- 25+ past Dialogues
- A clear learning roadmap
You get a light, human community:
- Monthly Classifieds thread
- Curated intros
- A small, not-overwhelming forum
Plus:
- A 30-minute intro call with me
- 10% off every program and class
All for $30/month or $300/year.
One member put it best:
The Deeper Foundations Membership has changed the way I do business and encouraged me a great deal personally. The weekly meeting rhythms have provided consistency in an aspect of the work that I've always struggled with. The whole philosophy of business and how to grow one is refreshingly human-centered rather than focused simply on the economics. Deeper Foundations is a vital and needed antidote to the "hustle" and "win at all cost" cultures that dominate the world of start-ups.
This is yet another ending to a chapter of my work.
But it’s also the next step in an exciting new arc.
If you want to go deeper with others who are also leaving the Casino of hype-filled advice, the Membership is where that happens.