Jessica Lackey Consulting

Helping experts design, build, and run sustainable and right-sized business.

- Group Programs for emerging business owners to build foundations in business planning, strategic planning, and operations/finance/systems.

- 1:1 Consulting / Coaching for business owners who want to grow or scale sustainable businesses.

- Fractional COO Services for visionary CEOs looking for your integrator partner.

Founder and CEO

The Upside

Consulting Member

Boon Health

Leading strategic planning and operational excellence as we build a more resilient world.
- Account Management
- Reporting for Customer, Client, and Coach Metrics
- Leading Operations Team and setting processes and standards

Director of Operations/Strategy Advisor

SheEO™ 

SheEO is a global community of radically generous women + non-binary folks
working on the World’s To-Do List. Activators activate their buying power, networks
and expertise to create an equitable and sustainable world. Since launching in 2015,
7,000+ Activators around the world have collectively loaned out $7M to support
100+ SheEO Ventures. Learn more and Activate: https://sheeo.world/

Activator

Zefyr LLC

Over three years, served as Senior Consultant and Chief of Staff for Zefyr Consulting, a group of Footwear, Apparel & Accessories industry experts dedicated to helping companies in the footwear and apparel industry drive long term value through improved performance and optimized partnerships in their supply chain operations.  Let us help you achieve sustainable results faster.

- S&OP, IBP and Supply and Demand Planning Strategy and Implementation
- Facilitated semi-annual strategy sessions
- Facilitated weekly Leadership Team meeting
- Implemented digital marketing presence, including monthly blogs, LinkedIn presence, and YouTube

Chief of Staff

Electrolux

Lead forecasting, inventory planning and management, and the executive S&OP review process for the North American Sector.

Senior Director, Sales and Operations Planning

Nike

Drive global process and technology development to improve cross-functional business planning processes.

Director, Global Sales and Operations Planning

Lead Inventory Operations for North America, providing accurate forecasts and managing inventory health throughout the distribution network.

Director, North America Inventory Operations

Lead Demand Planning and Operations for North America Women's and Soccer Categories to serve consumers with the right product, at the right place, and at the right time.

Director, North America Demand Planning

Drive definition and deployment of strategic plans that extend Nike’s position as among the leading value chains in the world.

Director, Global Operations Strategy

Apple Inc.

Worldwide Supply Demand Management Intern

McKinsey & Company

Associate

Business Analyst

I’m Jessica Lackey, ex-corporate warrior turned deep business and operations strategist.

I spent my career in the trenches of business - like Harvard Business School, McKinsey Consulting, and Nike. Which means I know business - and I also know exactly what it’s like to be forced into toxic productivity, hustle culture, and pigeon-holed into judging success by the bottom line. I bring that expertise in business strategy, combined with a human-centered perspective, to help grow and scale sustainable expertise businesses.

--------------------------

So your business has hit a plateau - maybe even an existential crisis.
- You’re dropping balls you can’t afford to drop
- You’ve hit the upper limit of your capacity - so doing more and hustling harder isn’t going to be the answer
- Your revenue outlook looks questionable at best - loss of a key client or referral partner or industry shifts
- You might not even be making enough profit to make it worth it
- Or maybe everything is working smoothly… but you want to keep evolving without sacrificing the balance you’ve built

You’re facing a threshold point where you have to make some decisions about your business -- and simply “working harder” to get to the other side isn’t possible.

You’ve tried all the short-term fixes. You’ve read the books, listened to the podcasts, joined the group masterminds, and taken all the programs. You’ve hired an accountant yet you still might not know where the money’s going. Maybe you’ve even hired some contractors, an assistant, or a team to help you grow. 

And yet you’re still stuck.

Now’s time to go deeper into your business and really diagnose what’s not working and build a stronger business from the roots up. You need to understand and shape your business in a way that truly works for you… not using a formula that worked for someone else. No longer be distracted by shiny objects- it’s time to anchor into the stuff that matters and TRULY begin to run your business like a phenomenal leader.

Stop implementing the strategies that worked for someone else’s business, and begin to run the business designed for you.

 https://www.jessicalackey.com/ or DM.

Integrator | Coach | Chief of Staff | Strategy | Operations | Business Strategist

Jessica Lackey

Leaving the Casino is now an award-winning book as the recipient of a Platinum MarCom Award!

In the Thought Leadership category, Leaving the Casino was awarded the HIGHEST honor! Thank you to Fabi Preslar and SPARK Publications for a stunning layout, Hollie Arnett for the interior illustrations, and my editor, my beta readers, and everyone who's purchased a book.

MarCom Awards honor excellence in marketing and communication while recognizing the creativity, hard work, and generosity of industry professionals. Since its inception in 2004, MarCom has evolved into one of the largest and most-respected creative competitions in the world, with about 7,000 print and digital entries submitted each year from dozens of countries.

(Haven't gotten your copy yet? You can snag one here: https://lnkd.in/eBGxF-KF)

Author, Leaving the Casino | Helping experts grow predictably profitable businesses through business foundations | Ex-McKinsey, HBS, Nike

My head wants to keep pushing. My body is saying absolutely not.

With my recent book launch, I hit three nested endings at once: a launch, a year, and a creative arc.

This year included 4 major sprints:

• Finishing the book manuscript
• A full rebrand
• Wrapping up a COO role and launching a course
• The actual book launch

No wonder I was tired. (P.S. Do not recommend doing this all at once). 

But I'm learning something: There's a difference between end-of-sprint tired and end-of-arc completion.

Sprint tired means you need a short time period off.

Arc completion means something deeper. You transformed from where you started to where you are now. 

The work now isn't to sprint harder or pivot faster.
The work is to complete and rest.
The work is to let your curiosity return so you can plant the next seeds.

When you build in arcs, you create space to dream before deciding what's next.

I used to think momentum meant never stopping. Keep shipping. Keep building. Keep posting.

But true rhythm is momentum with meaning, not endless movement.

So I'm sitting in this ending. Not rushing to the next thing. Not filling the space with busy work.

Just letting the completion settle.

The pause between cycles isn't wasted time. It's strategic positioning for the next arc.

What are you completing right now? Are you giving yourself space to actually finish it?

The best way to leave the Entrepreneurial Casino is to do it with friends. And the  joint communities of Deeper Foundations and Lex Roman's Legends?!? You couldn't ask for better humans to do better business with.

Come join us to talk about the book in December!

Build your internet business with me at revenuerulebreaker.com

Need a business reset? I'm hosting Jessica Lackey to discuss her new book "Leaving the Casino." Close out your year with a fresh foundation! 

This book is perfect for you if you're:
- Rethinking your business model
- Feeling like your business isn't sustainable
- Worried about what 2026 holds for you
- Just getting started in business
- Coming back to your business after time off

Get your copy of "Leaving the Casino" and join us Friday, December 12 to talk about how to apply it in your business.

In this book, Jessica steers us away from the entrepreneurial casino of quick fixes and funnels and invites us into a world where we can build something that's truly our own. If you've ever bought a course or a program thinking it would change your life, you're gonna love her thoughtful approach.

Come hang with us on Friday, December 12 at 9am Pacific/12pm Eastern 📗

The event is FREE but I highly recommend buying the book (discount code when you register!) https://luma.com/ntdwehsq

Are you asking the right questions in your business?

A wonderful conversation with Diann Wingert and the ADHD-ish podcast today, all about how we leave the Entrepreneurial Casino.

And it couldn't have come at a better time, before we're bombarded with Black Friday sales — before making that purchase, ask: do you need a course to get better at a marketing strategy or business model that isn't aligned with your brain and business model?

Check out our podcast today: https://lnkd.in/emK8SUKd

You're sprinting hard—but sprinting toward what? And is that sprint even right for where you are in the larger journey?

You need three different timescales running at once: the Micro, Mezzo, and Macro cycles.

And most people only track one (and often the wrong one).

The three cycles work like this:

→ Micro = Sprints (2-3 months)

This is what you do.

The project, the launch, the thing you ship. The rhythm of doing.

Every year I run at least two Define Your Foundations cohorts. This year I also stacked: finishing the book, rebrand + website, ending my COO work + launching my first course, and the book launch itself.

Sprints create momentum. But they need to ladder up to something larger.

→ Mezzo = Chapters (12-18 months)

This is how you build.

The theme of your year. The capability you're strengthening. The visible growth ring on the tree.

Each chapter of my business has carried its own focus:

• Years 1-2: Building my book of business
• Years 3-4: Creating my body of work—essays, curriculum, network
• Year 5: Culmination—rebrand, book, course

A chapter gives your sprints direction. Without it, you're just busy.

→ Macro = Arcs (3-5 years)

This is who you're becoming.

The identity shift. The transformation from seed to stable ecosystem.

My first five-year arc? Going from "getting started" to "established body of work + book in the world." That arc is complete. The next one is forming, but it's too early to name it yet.

Arcs move slow and structural, with permanent impact.

Here's the trap I see everywhere:

People stack sprints back-to-back without asking: Does this sprint serve my chapter? Is this even the right sprint for where I am in my arc?

They're running Year 5 sprints in Year 1. Or launching when they should be learning. Or creating new offers when they should be strengthening what already exists.

The problem isn't lack of execution. It's sprinting without a map.

You need all three cycles because:

→ Sprints without chapters leave you busy with nothing lasting to show
→ Chapters without arcs create skill without direction
→ Arcs without sprints stay in the dream phase forever

Ask yourself these three questions:

• What sprints did you run this year? Did they ladder up to a bigger chapter, or were they random?

• What was your chapter's focus this year? If you can't name it in one sentence, you probably didn't have one.

• Where are you in your current arc? Beginning (seeding), middle (building), or end (harvesting)?

Once you can see all three cycles, everything gets clearer.

You stop sprinting harder and start sprinting smarter.

Which cycle are you missing right now?

The real spooky season? Black Friday and New Year's sales. We convince ourselves THIS time will be different, that January will magically give us more time.

Before you buy that course, tool, or coaching program:

Ask yourself if you can pay ALL THREE COSTS.

Because most people only think about Cost 1.

And that's why their credit card statements are full of things they never used.

The framework breaks down to three costs:

Cost 1: Financial investment

This is the obvious one. The $997 course. The $199/month software. The $15K mastermind.

But nobody asks the real question: Does the value match your specific situation and goals?

I've seen people drop $15K on coaches when a $50 book and 3 focused conversations would've done the trick. Perhaps my book?

(And look - if you need advice on something, just email me. I'm not charging you $15K for a conversation.)

Cost 2: Learning investment

This is where most purchases stall out.

You bought the thing. Now you need 2-3 hours per week to actually learn it and implement it.

That social media course? You need time to watch the videos, take notes, and test the strategies.

That productivity app? You need time to set it up, learn the features, and migrate your workflow.

Most people can't pay this cost. They're already trying to do more than they have capacity for.

So the purchase sits there. Unopened. Unused.

Cost 3: Ongoing maintenance

Even after you learn it, you need ongoing effort to maintain it and see results.

That CRM? You need to update it weekly or it becomes useless.

That workout program? You need to show up 3-4x per week or you won't make the promised "gainz"

That newsletter you started? You need to write somewhat routinely or your audience might mark you as spam.

This is the cost that kills momentum 3 months in.

The reality:

If you can't pay all three costs, you're wasting money.

No matter how good the Black Friday deal is.

No matter how much you convince yourself "this time will be different."

So before you buy:

Do the math on your calendar. Where are those 2-3 hours per week coming from? What are you pruning to make space?

If you can't answer that, save your money.

Which cost do you struggle with most - the upfront learning investment or the ongoing weekly maintenance?

3.5 years. 45 classes. Over 600 registrations. And one final public Deeper Business Dialogue this Wednesday.

In March 2022, I taught my first free class.

Eight people registered. Four showed up live.

And the next month I taught another one, and the month after that.

I had no idea those free classes would become a nearly-four-year rhythm that would shape my business and connect me with so many of you.

What these Dialogues gave me:

A space to workshop ideas in real time. 
Permission to teach what I was still exploring. 
Connection with brilliant, curious humans building businesses differently.

They were proof that you can build without gatekeeping your foundational thinking behind a high-priced paywall (or a paywall at all).

One of you once told me: "This wasn't a sales pitch disguised as helpful content. It was simply helpful."

That mattered more than you know.

To everyone who showed up live, watched a replay, asked brave questions in the chat, shared your struggles and wins, told a friend—thank you.

You made this chapter so special.

Here's what's next:

The Dialogues will continue for Members, where we can go deeper every month on new trainings and topics, drawing from our shared foundation. 

And there are more ways than ever to enter my world if you're curious about building a right-sized, sustainable business—YouTube, the Leaving the Casino book, the Membership.

But I want to close this chapter the right way.

Join me Wednesday for "What Is Enough?": the final public Dialogue.

Bring your Leaving the Casino book if you have one. Let's close this chapter together.

Here's to everything we've learned together. And to what comes next.

Register here:

Open article: Book Club: What is Enough? · Zoom · Luma by luma.com

Book Club: What is Enough? · Zoom · Luma

Every activity in your business has a job to do. The question is: Does it still have that job?

When I started free monthly trainings (my Deeper Business Dialogues) in 2022, the job was clear.

Be the primary entry point to my work. Give people a feel for my methodology. Build audience from 117 email subscribers.

It worked.

Fast forward to 2025, and that activity isn't doing the job well anymore. 

So what do I do? Should I keep them, evolve them, or prune them?

Here's the framework you can use to evaluate activities in your business:

1. First, name the job this activity currently does.

Not what you want it to do. What it actually does right now.

For the Dialogues? Towards the end, the job they were doing was mixed and muddled.

2. Next, ask if it still needs to do that job, or if something else does it better now.

My book, blog, and YouTube channels are much more effective at welcoming people into my work and worldview now.

3. Can the activity do a new or different job? 

The same activity can do a new job. My Dialogues are now an opportunity to go deeper with Members, showcase *their* expertise, bring in guest speakers, or teach new frameworks. 

4. Decide to evolve it or prune it.

Sometimes activities end (like when I quiet quit Instagram a few years ago). I enjoy having my attention back for longer-form marketing.

Or you can evolve it, which is why my monthly Dialogues are now members-only. 

As you move into 2026...

What activity in your business served you beautifully in one season but needs to evolve (or end) in this one?

You can still get my "98.5% off" Black Friday sale, even though the rush is over.

We obviously start with the obligatory value stack:
In this bundle, you get 6 of my never-been-released courses:
- Business Models & Offer Architecture Course — $500 value
- Pricing Foundations Course — $300 value
- Sustainable Marketing Course — $300 value
- Right-Sized Hiring Course — $300 value
- Time Management & System Design Course — $300 value

Total value? At least $1,700.

But you can get these "courses" for 98.5% off.

You'll get 300+ pages of written content (no videos to watch!) plus an accompanying workbook (to help you implement), with 15+ unique frameworks (not just stories of what's worked for me)...

For just $25.

This might be the only  deal that actually saves you money in the long run.

Because once you understand what kind of business you're running, what's right for your stage of business, and frameworks for making decisions, you stop:

Wasting money on courses you don’t need

Chasing tactics that don’t make sense for your business

Paying for strategies designed for someone with a team, an audience, and capital you don’t have

So what is this wildly-underpriced, "never seen before", Black Friday bundle that's now suspiciously still on sale?

My book: Leaving the Casino!

A full-color, practical field guide for experts who want a right-sized, sustainable business without the hustle and hype.

The equivalent of a $1,700 course library—priced like a paperback.

Now, full disclosure: this “Black Friday exclusive” is available every single day at the same price. But when else am I going to remind you that a guide to building comprehensive business foundations can cost less than dinner out?

Diann Wingert Coaching

Business strategy and coaching for ADHD-ish solopreneurs ready to create a profitable, sought-after business by eliminating complexity, confusion, and overwhelm.

Business Strategist & Coach

Diann Wingert, LCSW, BCD

Private psychotherapy practice, focusing on adults with personal, career and family challenges impacting their wellbeing.

Psychotherapist In Private Practice

San Gabriel Children's Center, Inc. - providing competent and collaborative mental health services

Provided clinical direction for multiple programs with responsibility for a staff of 100 serving severely
emotionally disturbed children, adolescents and young adults, ages 6-21 with a variety of psychiatric
diagnoses, developmental disorders, learning disabilities, substance abuse problems and history of
physical, sexual and emotional abuse, neglect and exposure to trauma and family violence.
Responsibilities included staffing, training, clinical supervision, managing budget, program coordination
and development and compliance with all government mental health contracts.

Director Of Clinical Services

Keck Medicine of USC

Provided administrative and clinical supervision for a staff of 20 masters level clinical social workers in adult acute care medical and surgical hospital including cardiothoracic, liver and kidney transplant, cystic fibrosis, bariatric surgery, and locked inpatient behavioral health units. Responsibilities included staffing, training, clinical supervision and compliance with JCAHO requirements

Social Services Manager 

Children's Hospital Los Angeles (CHLA)

Developed and supervised clinical training program for graduate students combining medical and
psychiatric social work by providing mental health treatment to populations of chronically ill children and
their families. Supervised post-graduate fellow in pain management program. Responsibilities included
staffing, training, coordination with USC School of Social Work and clinical supervision of graduate
student interns

Coordinator, Behavioral Health Training 

USC Suzanne Dworak-Peck School of Social Work

Adunct Assistant Professor 

Aviva Family and Children's Services

Provided clinical supervision and management of intensive community outpatient programs serving
severely emotionally disturbed children and adolescents and their families in System of Care (SOC)
and Wraparound programs. Responsibilities included staffing, training, clinical supervision and
compliance with the LA County Department of Mental Health contracts.

Assistant Director, Community Mental Health 

Provided clinical supervision to a team of medical social workers serving chronically ill children and
families in divisions of rheumatology, gastroenterology, nephrology, cystic fibrosis, cardiothoracic
transplant, and rehabilitation. Responsibilities included clinical training and supervision of unlicensed
Masters level social workers gaining hours toward licensure, direct clinical responsibility for rheumatology patients

Team Leader

Five Acres--The Boys'​ and Girls'​ Aid Society of Los Angeles

Provided individual, group and family therapy to a caseload of abused and neglected emotionally
disturbed girls, coordinated interdisciplinary team meetings, advocacy at LA Children’s
dependency court & Individual Education Plan meetings with schools

Unit Social Worker

I help small business owners, creatives, and independent professionals who have made the leap to self-employment but are not standing out and being paid as the experts they are.  

I am a former psychotherapist, a certified coach, and a serial business owner.  I finally got sick of watching less talented and hard-working people pass me by because they had the one thing I didn’t have - the ability to package their genius and stand out in a crowded marketplace. 

Focus and consistency don’t come naturally to me, but I learned to build the skillset and the mindset that they require, and you can too.   It really is possible to resist shiny object syndrome, rabbit holes, time blindness, and missed opportunities.  

If you’re willing to do the work, I can show you the way.

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Jessica Lackey

Diann Wingert

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The Battle

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Diann Wingert

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jessica Lackey's LinkedIn Performance

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