Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

Sep 14 • 4 min read

Should I open it, or should I keep it sealed?


I’m on my couch, refreshing the UPS tracking page every hour on the hour. Somewhere in Charlotte, a cardboard box is inching toward my front door. Inside is the first printed copy of my book and workbook for me to approve.

My book is called Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works, a field guide for expert entrepreneurs (and you can read the first chapter today).

Until I open the box—and until I make the “pre-order” live on my site—two realities exist at once, like Schrödinger’s Cat for entrepreneurs. This book is either a breakout or a non-event, and both possibilities are true in this moment. The moment I start to sell it, I’ll start to know.

My dream is that it becomes a seminal text for service-based entrepreneurs. That it’s passed along by word of mouth, like I pass along the books that have shaped my life.

But the fears are real. Maybe no one notices and a handful of people from this list buy it and that’s it. Or people do notice and it sparks backlash.

I have some control over what happens next.

I can choose to make the book really visible or keep it quiet. I can choose to execute on an audacious marketing plan for the next 3-5 years, or just quietly distribute books to existing members and clients.

But I don’t have full control. I don’t control timing, sentiment, or algorithms. The book might resonate with the particular consumer mood in 2025. Or the content might simply not land. I can’t know, and as a lover of plans and order, that gap is unnerving.

It is safer here, in the liminal space. As long as I don’t turn on pre-orders, every future is still available. The dream can remain perfect and untested. But safety can also keep us stuck.

Once I announce it for sale, I can’t “un-launch.” I will be an author in public. My words will live in the world: quoted, critiqued, even scraped by AI. I can’t materially change much once it’s printed.

This isn’t just about a book. It’s the same precipice before any launch—a new brand, a new product, a new price, a new name. As long as we stay here, before the launch, every version of success and safety is still available.

But to be an entrepreneur is to leap into the unknown.

At some point you have to trade infinite possibility for real feedback. You choose to be observed. You accept that you’ll be different on the other side, no matter the result. Because it’s the leap that changes you.

So when the box arrives on Monday, I’m choosing to open it and hold my book. I’m turning on pre-orders. Not because I know what will happen, but because the only way to know is to launch.

What precipice are you standing on right now—a launch, a pivot, a leap? Hit reply and tell me.

P.S. Assuming the proof looks good, pre-orders will open sometime next week. You’ll be the first to know!

Join the Findable Everywhere Challenge, starting September 15.

Delivered by Meg Casebolt, the best co-host in the world, Findable Everywhere is a 5-day training to help you show up where your dream clients are searching on Google, on ChatGPT, and beyond.

Here’s what you’ll learn:

  • What’s already working on your site (so you can double down)
  • What your audience is actually searching for
  • How to spot invisible competitors (and stand apart)
  • How to polish your first search result without tech overwhelm
  • How to stop panicking about AI and start using it to your advantage

Daily bite-sized trainings. Live Q&A. Actionable prompts. And your $97 ticket can even be applied toward Meg’s membership if you want to go deeper afterward.

NEW EPISODES

Remixing Work with Erika Tebbens (Part 1)

What does it take to walk away from something that’s “working”—even if it’s not working for you anymore?

In this episode, Erika Tebbens joins us to talk about her career pivot out of entrepreneurship and into employment. After years of running a successful, values-driven consulting business, Erika realized that being her own boss no longer served her well. So she made a bold move: she got a job, at a dream company, in a field she deeply cares about. And how Erika’s move back into food systems so perfectly aligns with the Aggressively Human ethos.

UPCOMING EVENTS

Each month we'll discuss a chapter in my upcoming book, Leaving the Casino: Stop betting on tactics and start building a business that works.

Each dialogue is 12-1pm ET.

September 17: What's the Impact You Want to Have?

October 22: The Responsibility You Carry

November 19: What is Enough?

Community and Reads

Reflections On Writing a Daily Newsletter for 30 Days | Corey Wilks

I loved reading Corey's 30 days of daily newsletters (and actually, he wrote a few based on some questions I had!).

But what does it take to write a daily newsletter? What results did he see in his business? What changes did he see in himself?

The answers may surprise you.


The death of the corporate job. | Alex

This went semi-viral two weeks ago on Substack, but I still wanted to share it. More so than I ever have, I encourage people building their business to have some sort of stable job: part-time, fractional, even a full-time job that's just not cognitively demanding.

What's emerging isn't the collapse of corporate work—it's something more interesting. People are building parallel systems of actual value while maintaining their corporate personas.
I know developers who do their "official" job in the morning and build their own products in the afternoon. Marketers who run their agencies from their corporate desks. Consultants who've automated their actual deliverables and spend most of their time on side projects.
They're not quitting. They're using the corporate infrastructure—the steady salary, the laptop, the stability—as a platform for building something real. The corporate role hasn't died; it's become a funding mechanism for actual work.

Jessica Lackey

START INVESTING IN YOUR BUSINESS FOUNDATIONS

  • Deeper Business Membership: Access the rhythms, relationships, and resources that make real businesses work. Perfect for learning the foundations or maintaining your momentum.
  • Define Your Foundations Cohort: The foundational curriculum, coaching, and community if you're ready to stop throwing tactics at the wall and start building real, sustainable foundations. The next cohort opens again in March.
  • Refine Your Foundations 1:1 Consulting: When you're looking for individual support to grow or scale your business. One spot open for October,

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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