Deeper Business

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

Jun 21 • 5 min read

When my brain feels like it's been stuffed with cotton balls


Just a week ago, I was flying high: had just gone to an incredible offline event with Jay Clouse’s The Lab, saw some business besties in Boston, and had so many ideas for my summer series on the Expertise Paths…

… then immediately got hit with The Crud(TM), an upper respiratory virus that knocked me on my butt. On Tuesday night, I had to sleep upright to avoid the searing throat pain from post-nasal drip. By Friday, I felt like I had my head jammed full of cotton balls as I napped in and out of a Netflix binge.

(Running Point Season 2? A fun diversion. Voicemails to Isabelle? A charming movie to nap to. Re-bingeing Younger? Yes please.)

So I was largely away from my business for a week, and somewhat sidelined for my business for another week, but business keeps happening. Just a year ago, I would have struggled to step away for a week, and certainly not two. What changed, and why can my business keep running?

Have I achieved the holy grail of “passive income”? Not at all.

I’ve simply spent the last five and a half years ferociously building layers of resilience into my business model.

Resilience vs. The “Passive Income Promise”

As an expert-led business, your business does come with “key person” risk. At some point, you will need to take time away from your business or have schedule flexibility, for illness or caregiving, family needs or personal investments, for planned yearly vacations to rest and recover. You need to be able to do these things without risking what you’ve built while being able to keep funding your life.

The allure of the “passive income” promise is that by changing your business (largely to a scaled education or agency model), you can step away from day to day operations or delivery. However, adapting your business this way requires you to often shift your client base, change your delivery style or offers, and switch your marketing to a significantly more traffic- and volume-based approach than serves your intimate services business. You end up dumping time, money, and attention into audience building, complicated technology, and course creation that often detracts from the time you would spend building profit into your delivery-based business.

Instead of playing the passive income game, build real resilience to your business. Look at ways to build in buffers of time, energy, and attention, so you can incorporate flexibility and “give” into your business for when it matters.

Real resilience has four levers:

  • Reducing the “key person” risk by codifying key portions of your business
  • Evaluating alternative delivery structures that accommodate flexibility without building a different business entirely
  • Incorporating resilient marketing strategies that leverage your existing efforts and assets
  • Building the ultimate resilience: cash

How I’ve built resilience into my business with these levers

Resilient Delivery

I spent the last year overhauling my cohort materials and membership. This means that for all of my clients, even my 1:1 clients, they have proven resources, tools and templates that they can work on in their own time without relying on my energy.

And the Membership’s beloved weekly Sacred Sales Hour and Weekly Planning/Tending co-working calls? They are largely led by members (who are paid for leading those calls). Even when I’m not working, participants in my world can keep getting results.

Resilient Revenue Streams

The bulk of my revenue is still 1:1 consulting. But I shifted away from high-intensity Fractional COO work (which kind of was a full-time job that was hard to take time away from) to delivery styles that have more buffer room. I can stagger out when clients onboard (I’m not taking new 1:1 clients in July because of travel), and can still support my clients with asynchronous support while I’m out at a conference or when I’ve lost my voice!

Resilient Marketing

No longer do I have to rely on the content hamster wheel to speak to new people who find me. They can dive into the rabbit hole of my work with over 70 podcast episodes, a robust blog, a YouTube channel, and a book! New newsletter subscribers get at least a week of hearing from me and getting my best resources through a welcome sequence. I might take time off, but referral partners keep referring me, thank you and birthday and “Welcome to the Membership” cards keep arriving, and the flywheel continues to move.

Resilient Cash

I knew I would be taking some time off this summer, so I planned for it. I frontloaded all of my course launches and curriculum overhauls to be done by May. I also planned for substantially fewer expenses, since I’m not rebranding or publishing my book. YTD I’ve made about the same amount of revenue but my expenses are down 30%. This gives me a much more robust cash buffer for a slightly slower summer, while still knowing how I’ll pay myself.

None of this happened by accident. It happened because I spent years making intentional decisions about how to structure my work and building the layers of assets, systems, and processes that you see today.

I cover this in much more depth in my book Leaving the Casino. Get the full chapter and more details on these four levers of resilience (plus the other frameworks for building a business that works) and grab your copy today! Available direct from me, on Amazon, or many major retailers.

If you *do* want to build a membership as a source of resilience in your business, there's no one I'd rather you learn from than Jay Clouse.

Jay is hosting a free 3-day summit on memberships this week, June 23–25. Jay built The Lab — about 340 members, nearly $500K/year in recurring revenue — on a single membership. I'm a third-year member and raving fan. Over three days, he’ll cover why memberships work in 2026, what actually makes people renew, and you walk away with a 30/60/90-day roadmap. Free to attend.

NEW EPISODES

"Would Recommend": How to build customer experience with Nikki McKnight

In this episode, we talk with Nikki McKnight—Meg’s romance-podcast co-host, operations expert, and newly minted Certified Customer Experience Professional—about why she niched her business down into customer experience and launched a new business podcast called Would Recommend.

We dig into the difference between customer experience and customer journey, why emotions are what actually drive referrals, and how matching your brand promise to your real experience builds (or breaks) trust. There are frameworks—Nikki cannot help herself, and neither can we—but mostly it’s a conversation about the gap between what we say we deliver and what it actually feels like to be on the receiving end of it.

Community and Reads

AI's Brokenomics | Ed Zitron

Sometime early in Q1 2026, Anthropic and OpenAI moved all of their enterprise customers to token-based billing, meaning that instead of using subsidized subscriptions with varying (and ridiculous, as I’ll get into) rate limits, big businesses suddenly had to pay for their AI usage based on the actual tokens they used.
Many hailed this as a masterful gambit, assuming that organizations would have near-infinite budgets for AI services that had yet to prove themselves useful.
It only took a few months for OpenAI and Anthropic’s customers to start sweating.
In the middle of April, The Information’s Laura Bratton likely burst the AI bubble with a piece about how Uber had burned through its entire annual token budget in a single quarter.
In a single podcast, Andrew Macdonald gave the entire tech industry permission to say the truth: that nobody was actually able to show any ROI despite its massive costs.

Read this deep dive plus the OpenAI financials leak as you consider how you're using and deploying AI tools.

Exclusive: OpenAI Losses Increased Nearly 8X in 2025, With Spending Hitting $34 Billion

Jessica Lackey

START INVESTING IN YOUR BUSINESS FOUNDATIONS

  • Leaving the Casino: The guide for expert-led business owners who want to build a real business rooted in values, sustainability, and intentional growth.
  • Deeper Foundations 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 start in September.
  • Refine Your Foundations 1:1 Consulting: When you're looking for individual support to grow or scale your business.

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


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