Deeper Business

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

Nov 09 • 6 min read

Completing not just the launch, but the whole arc


You can now buy an international physical copy or the Kindle edition of Leaving the Casino!

My book is now live on Amazon, where you can buy a physical copy of the book outside of the US. The Kindle/ePUB version is also available and included in any direct purchase you make on my site.

And if you've got a copy, make sure to leave a review! Will you be my 10th review?!

"Her writing is honest, grounded, and incredibly refreshing. No gimmicks, magic formulas just real frameworks, thoughtful questions, and strategies that make you slow down and genuinely reflect on what you’re building and why."

Ever since my book released six weeks ago, I’ve been feeling a deep tension.

My head keeps saying, “What’s next? Come on, we need to keep building your vision.”

My body and soul are saying, “Stop. No more right now. No new things.”

And I'm listening to my body.

Because it’s not just the end of a book launch.

It’s not just the end of the year.

It’s the end of the entire first five-year arc of my business.

When we see our work as a series of nested cycles—each with its own horizon—we start to understand how to harness energy at the peaks and honor the natural pauses at the ends.

The Micro: Seasons and Sprints

This is the smallest cycle: the season or sprint, usually two to three months long.

This is where launches, projects, and deliverables live. It’s the rhythm of doing.

Every year, I have at least two major sprints when I launch Define Your Foundations, each lasting about eight weeks.

This year, there were four extended sprints layered on top of those:

  • Q1: Finishing the book
  • Q2: Rebrand + Website
  • Q2: Ending my last COO engagement and launching my first course
  • Q3/Q4: Launching the book

Sprints focus effort and create momentum. But stacking too many of them leaves no room for recovery, and some take far more out of you than others. (No wonder I was tired this year!! Do not recommend trying to do this all in a single year.)

This is the Mars energy—the planet of action and motion.

Reflect: What sprints have you taken on this year?

The Mezzo: Chapters and Years

This is the rhythm of focus and meaning: the orbit that asks, "What am I exploring or strengthening in this year?"

Two to three months is rarely enough to complete a transformation, but a year can hold a distinct evolution—a visible growth ring on the tree.

Each chapter of my business has carried its own theme:

  • Years 1–2: Getting started and building my book of business beyond subcontracting through fractional COO work.
  • Years 3–4: Creating my body of work—the essays, illustrations, videos, and curriculum—and strengthening my network.
  • Year 5: Culmination—rebrand, book, and course launch.

I couldn’t have imagined in Year 1 that this is where I’d end up in Year 5. But I didn’t need to. I only needed to decide how I wanted to grow this year and then choose projects and sprints that supported that growth. And importantly, not take on "Year 5" projects in Year 1.

Reflect: What was the primary focus of your chapter this year?

The Macro: Arcs

When we start a business, we expect rapid results. That’s what the Entrepreneurial Casino sells us.

But in reality, it takes at least three to five years to go from seed to stable ecosystem.

Taken from my colleague Corey’s blog:

Kevin Kelly, renowned entrepreneur and writer, once talked about a friend who arranged his life in blocks of 5 years:

“Five years is what he says any project worth doing will take.

From the moment of inception to the last good-riddance, a book, a campaign, a new job, a start-up will take 5 years to play through.

So, he asks himself, how many 5 years do I have left?

He can count them on one hand even if he is lucky. So this clarifies his choices. If he has less than 5 big things he can do, what will they be?”

If the sprint is what you do, and the chapter is how you build, the arc is who you’re becoming.

It’s the layer of discipline, foresight, and identity—the Saturn energy that sets direction for the long term.

As I reflect on the book, the rebrand, and the change in my client profile, it’s clear this year was prolific because it marked the harvest period of a five-year arc.

Launching the Leaving the Casino book and the Deeper Foundations brand closed the first major arc of my business life.

This cycle is complete.

And while ideas for the next one are already forming, the end of an arc isn’t a moment to push forward.

It’s the moment to release what’s not coming with me, to rest after the harvest, and to quietly begin cultivating curiosity again. It’s the time to plant the seeds of the next arc.

Reflect: Where are you in your current arc of business and life?

The Pause between Cycles

Sure, I could keep pushing—jump from one sprint to the next, ignoring the true end of an arc. But that would ignore where I am in the rhythm of my own business.

Right now, the work isn’t about acceleration; it’s about completion—finishing what’s already in motion, closing open loops, and taking the rest I’ve been promising myself for five years.

Because when you build in arcs, you don’t just work harder perpetually. You build assets that compound over time, systems that sustain you during quieter seasons, and space to dream before deciding what’s next.

That’s the true rhythm of sustainable work: not endless momentum, but movement with meaning.

The sprints teach us to act.

The chapters teach us to focus.

The arcs teach us to trust the long game—to recognize where we truly are in the cycle and to let time do some of the work for us.

NEW EPISODES

Ensh*ttification is by design (and what to do about it)

The platforms we built our businesses on are breaking down—and not by accident. In this episode, Jessica and Meg take on ensh*ttification, the term coined by Cory Doctorow to describe how digital platforms inevitably decay over time. From Facebook and LinkedIn to Substack and AI, they discuss the predictable four-phase cycle that turns once-useful tools into algorithmic wastelands.

It’s part diagnosis, part “what now”: a conversation about recognizing when the rules have changed, when to adjust your strategy, and how to build resilient foundations that outlast the next platform crash.

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.

November 19: What is Enough?

Community and Reads

2026 Readiness Assessment | Marissa Garza

Don’t let your 2026 turn into a season of chaos.

You’ve got big plans for your business—new hires, launching products, and increasing your marketing. But before you greenlight those plans, you need to know whether they're actually ready for production.

Get your 2026 Production Readiness Report and know exactly which of your businesses's strategic initiatives are truly ready for prime-time execution—and which ones will waste your time, money, and team capacity if you move too soon.

If you want Succession-level execution—not Tiger King chaos—this is your pre-production meeting.


The Pratfall Effect | Caroline Fay

I often find founders spending half an hour perfecting a single email to a prospect.
Sure, you should take the time to ensure you look competent. But competent doesn't mean perfect.
When you’re emailing to schedule an intro call, don’t be afraid to look human – whatever that means to you.
If you’re emailing with a prospect who’s in a buying cycle with you, before you pen that five-paragraph missive answering their product questions… go back to the prior concept, and ask to jump on a quick call instead.

Jessica Lackey

START INVESTING IN YOUR BUSINESS FOUNDATIONS

  • Leaving the Casino: The book for expertise-based business owners with the grounded strategies and practical frameworks to build a business rooted in values, sustainability, and intentional growth.
  • 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 will enroll in March - but you can always join the Membership and get support in the meantime!
  • Refine Your Foundations 1:1 Consulting: When you're looking for individual support to grow or scale your business. Apply now for 2026 openings.

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


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