Meet the Author: Jessica Lackey

We’re kicking off this year’s Meet the Author interview series with a phenomenal conversation. Jessica Lackey is a business strategist extraordinaire—and she has a book-writing process that any subject matter expert could learn from.

We talked about everything from the thinking-sharing-teaching-writing feedback loop Jessica developed to her strategies for marketing the book and getting reviews. No matter what stage of the writing or publishing process you’re in, there’s something interesting here for you!

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Jessica Lackey is a business strategist and founder of Deeper Foundations. With experience at McKinsey & Company, Nike, and an MBA from Harvard Business School, Jessica blends operational rigor with values-driven strategy. Her work helps expert-based entrepreneurs build sustainable, right-sized businesses—without falling into hustle traps or one-size-fits-all formulas. She’s known for her holistic, systems-minded approach rooted in integrity, sustainability, and human-centered growth.

You can learn more at her website, Deeper Foundations and check out her book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business that Works.

Tell me about your journey to writing Leaving the Casino. I love the title!

There was a part of me who always kind of wanted to write a book, but I didn't set out to write a book. I wrote a newsletter every week, and in December of 2022, I saw someone who talked about his writing coach in Substack. I was like, “You know what? I want to get to know myself better through writing.”

So I hired this person. We started writing some pieces, and we started with some “getting angry” pieces. I don't remember when it happened, but it became very clear that this was a shell of a book. I was like, “This is what I want to write about.” April of 2023 is when I opened the Google Doc for the Leaving the Casino book.

What has the writing process looked like?

It was kind of a back and forth. The Leaving the Casino book is structured in two parts. It's the big decisions that you need to make about your business and the big, big questions that you need to answer before making the big decisions.

A lot of this was writing and then testing it in my newsletter and in classes. I would write, “Okay, what do I think is the problem with pricing, and what do I think are the approaches of pricing? What do you have to decide in advance to make those decisions?”

I was writing in my newsletter, and then I was teaching the content, and that was most of the back half of the book. I really finished the front half, which was about the big decisions, in a two-week sprint last Christmas.

So you have this great feedback loop where you're thinking, sharing it in your newsletter, and teaching. What kind of feedback were you incorporating?

A lot of examples. You know, business books are filled with the same Steve Jobs and IKEA stories and things like that. I was like, “This doesn't apply to this person. Why not? And how does that need to incorporate into my business?”

In the chapter on resilient business models, I'm like, they're doing something that's resilient and they're doing something that's resilient. I had a pile of sticky notes and examples and things like that.

I had what I would call the big containers of my ideas, and then I would just start collecting examples as I went. Fun fact, I got every part of my book illustrated. So every framework I put in the book, I had an illustrator along the way, but I was not for the book. It was for YouTube.

But then it's like, oh, this has to be in the book, right? All my business frameworks got a YouTube video. They got a class of some sort. I taught it live so that I could understand where my language and explanations were falling flat, or where there were edge cases that didn't fit in that I needed to adapt.

You have this whole content library of test cases that can help promote this book. What a brilliant strategy. Was that something that you were doing intentionally the whole time, or did that develop organically?

It started organically, and then it became intentional. The first anchor piece I ever wrote was all about business models, because I got really annoyed. One of the things I got really angry about was when I was in this mastermind program.

This teacher was an ethical person, but she was teaching everyone, “Okay, premise, development, check messaging, check marketing.” She started teaching people how to set up a launch calendar, and I'm like… I'm a fractional COO. I don't launch.

These are coaches, and they don't have audiences where you can launch a class. They aren't selling courses. So this advice doesn't fit our business models, but there's no clarity around that.

That was the first piece that we worked on. That piece became an article, and I actually pitched it and got it into Every before they changed their focus via AI.

Then I'm like, “Well, how does choosing your business model impact these other decisions, and how do these decisions impact each other?”

That was when I started thinking about how I make this all multi-purpose, because people raved about my business model article. I taught it as a business model course, and therefore it then needed to be the illustration, which needed to be a YouTube video.

It started out organically, an article at a time, but then it became a multi-purpose asset, because if I'm writing this, I should teach on it, and if I'm teaching on it, then it should go as many places as possible.

Were there other ways of getting into the writing that you found helpful?

Because this is a business book for business people, a lot of the questions were about what common things my clients were running into.

Sometimes it was anger. Sometimes it was, what are the concepts I'm repeating over and over again and again, and not as much anger, but curiosity. Why does the conventional wisdom not work? Why don't I agree with the conventional wisdom?

I would say, 50% of the book, people will be like, “Check. We've seen this before.” 50% of the book will be like, “No, this is actually brand new from Jessica.”

There's this belief about hiring. I wasn't angry at the advice, which is like, “Hire before you're ready, and hire out the $10 tasks” and things like that. “Stay in your zone of genius.”

But I observed what happened when people came to me. They'd outsourced their lead gen, they'd added an assistant, they'd hired somebody as an agency, and then they ran out of cash. Or they hired a lead gen firm that basically cost them money but did nothing. You can't really outsource sales particularly early.

So it wasn't anger, but it was more like exploring why these conventional approaches that actually work for bigger businesses just weren't right for the audiences that I serve.

How were you sitting down and getting writing done? You also have a business. How did the writing fit in?

Just in your day-to-day, mornings and weekends and retreats. A lot of the parts of the book that are written for the businessy things would be newsletters. I would cobble together the newsletters and then be like, “All right, this is an 80,000-word newsletter compilation that needs to be 10,000 words. How do I distill it?”

Some of the more business parts were compilations of newsletters until I edited them down, or transcripts of classes.

When it came to do chapters that were net new, for example, there was a chapter on responsibility that I hadn't really written about.

I was like, “I thought I was done with the manuscript.” I thought I was done. “Oh, I just have to finish some parts up.” I looked at it and looked at it and the responsibility chapter was just angry bullets. That was it.

I had to actually sit at the coffee shop. For the Christmas holiday, I basically took five hours a day, and I wrote at the coffee shop. I was like, “Okay, we have to finish the first draft before I go back to work.”

A lot of mornings were spent writing, particularly for the easy stuff. The harder pieces were weekend retreats, and then they were two weeks off of client work, and that's when I finished all the hard parts.

Some of the chapters were easy to write, and some of the chapters were very hard to write. Like the hiring chapter, I couldn't get my framework dialed in. That was the last chapter I finished, even though it was not the last chapter of the book.

The other last chapters I finished were the responsibility and impact chapters, because I hadn't written a lot on those, and so they were less fleshed out. I will say I did use ChatGPT occasionally to be like, “Okay, here's some starting points. What are angles?” I didn't let it do any writing, but what are angles or perspectives that I didn't consider to help me flesh it out.

My responsibility chapter, it's like, what's that? What responsibility do you want to carry in your business? The first time I wrote it, it was very much like, “This is all the unethical shit that they're doing to you.”

But I reframed the chapter to say, “Let's assume that you are an ethical business owner or someone with values aligned.” There's no punitive payment plans. You're not failing to deliver services. You're not micromanaging. You're not asking someone to work an 80-hour work week at $7 an hour.

Assume you're not doing those things. What are the trade-offs that have to be made for different levels of responsibility in your business? The responsibility of your clients, your team, yourself, your community? Let's assume again, even if you're not unethical, there still are trade-offs to be made.

That was actually a hard chapter. I hadn't thought about it until I was like, “I was just angry,” and then I was like, “Oh no, I actually need to give examples of trade-offs versus just, ‘Don't do bad shit.’”

You mentioned working with a coach at the beginning of this process. Is that someone you worked with through the whole process? What other tools did you use?

She was the dev editor through the whole project. She was the writing coach for a while, and then it became dev editing. I worked with my publisher for line edits and proofreading.

Having a deadline was helpful. The teaching was actually really helpful for this nonfiction book. I was always writing my book. I just wasn't always writing the book. I was writing the book in my head, but blocking my calendar was helpful.

I did a writing retreat with some colleagues where I nailed down a chapter on resiliency. That's the antidote to the passive income promise. I'd already collected all of the things in my head, and I'd been organizing.

So when I sat down to the page, I wasn't like, “Let's just create a chapter.” I had a pretty detailed outline, and I had collected a bunch of examples. Thankfully, my brain works where I can keep it up here versus having to totally always put it on my notion database.

When I went to do the chapter, I'm like, “I just taught a class on this because I wanted to.” I went to my class slides. That's much easier for me, to frame a concept versus putting it in prose.

What has the publishing process been like?

I did a beta read. I used this thing called Help This Book. It’s kind of like a Google Doc where people can review and leave comments and things like that on a digital copy, which was really cool.

Two people fully read it. One person read most of it. That was really helpful. They're like, “I want to see more of this.” Or they're like,”This would be a good example here.” I used that tool and I did a round of edits with them.

Then I officially handed over my final manuscript to the publisher at the end of April. We did the first round of layout, and then we did a round of editing with that. Then it went to the proofreader.

I got the final manuscript back literally right before we sat down. I briefly looked through it, and there's very little left to be edited. Two chapters have already gone out wide, as it were, because I'm doing a book club for people to help promote the book in advance.

People who have registered have gotten two chapters and one picked up an eagle eye typo that I did not notice.

What comes next once the book is launched? How are you planning to market?

The standard launch team, trying to get on podcasts, and things like that.

This sounds super egotistical. I read a lot of business books, and I know what makes a bad business book that you just don't look at again, and what makes a good business book. And I've written a good business book.

I've written something that doesn't have fluff. It's very practical. For those who don't know me, I'm a practical kind of gal, so I really think this is going to be something that spreads.

I'm going to make a YouTube series about, “Can we get me to 100 reviews?” I'm going to do that until it takes me to 100 reviews. Can I get 200 reviews in a year? I have a list of 1,500 people, and so I probably can get 50 reviews out of that. I've got a bunch of clients, things like that.

I want to get it on podcasts. I'm going to do a book tour next year, so Amelia [Hruby] and I, we're going to try to do a joint event, at least one. I’m going to travel. My husband and I were already planning it, like, this is our 2026 travel strategy.

I'm going to go to every city where I have a reason to go and do a book event. Yes, on my own dime, but you can do it for pretty cheap, and hopefully this will be a rallying point for a lot of the people I work with. “Someone wrote a book for us.”

This is such a rude question when you're getting ready to launch, but what comes next creatively?

I’m going to be restructuring and refilling all my cohort classes for the fall because I didn't have enough to do. I'm going to be transforming it from a six-month cohort to a 12-month program with more information.

Each one of those, I'm doing it in a kind of semester or quarter type seasonal focus. Each one of those might be a book. I have a couple of other book ideas percolating in the mind space.

I really do believe that there's very little robust business education. Not marketing education, business education for soloists and small teams. I don't see anyone racing to put down systems and structures around that, because it's not sexy and it's a little hard to sell.

In the book, there's the chapter on pricing, and some people are just like, “Double your prices!” And I'm like, “Here's five approaches to thinking about price, and here's how to evaluate across the approaches, and here's what you should do if it turns out the pricing for this approach is different than that approach, and how to bridge the gap.” I haven't seen any of that in print.

You already have such a good ecosystem for building content, testing it, iterating on it, and then developing it into a book.

I will say that finishing the book has been the hardest thing, because with a blog post, you just finish, right? It's done. I've read my book now, cover to cover. I didn't even spot one of the typos.

But finishing the book, it’s like, “Oh, it needs summaries. It needs citations.” I spent four hours one day pulling every book that I cited a page from and having to go find them. There are things that I read a decade ago—I don’t know where I got the phrase from, but I remembered it, and I had to go find it.

I don't know if everyone else would have gone through the trouble of trying to find the book citation, but I'm like, I got this somewhere.

Finalizing the summaries and going through every chapter and making sure it was symmetrical across the chapters was really important to me, but I couldn't do that until the book was done. I found on my round two proofreadings that in every other chapter, the reflection questions were numbered and in this chapter, it's bullets. It was consistent on the page, but not across the chapters.

Like, I have to do the index. They gave me the index, and I had to go through and I had to edit the index. So, when I put the word profit in there, I meant it to go to one part of the book. Of course, I use the word profit like 100 places in the book. So I had to be like, “All right, remove these words from the index, and make the rest go to this section.”

I had to edit the index on Saturday at like eight o'clock at night because my husband's out of town. This seems like a good time to edit my book index when I have nothing else to do, right?

Finishing a book is much harder than just writing 80,000 words.

If you were to give a piece of advice to someone who wants to write a book, especially a business book, what would you tell them?

My biggest piece of advice is there's two types of books: the quest and the capstone. Some books you write along the way, and some books you write in a 90-day sprint.

If you choose to write a quest book, recognize that your voice is going to change dramatically as you write the book. You are changed by the writing. The chapter you wrote when you started is probably going to need to be re-edited by the time you finish, even if the content is the same, because you are a different human looking at it in different ways before.

That's what happened to me. The responsibility chapter was one the second chapter I wrote, and I was like, “I don't even recognize this person.” I got back to it two years after I'd written it.

What is the best book you've read recently?

The book that had the most impact on this book, in a way I didn't expect, was Robin wall Kimmerer’s Braiding Sweetgrass (affiliate link*). I referenced that book. I call your pricing portfolio the three sisters planting method.

A lot of the ideas and the chapter about what is enough are referenced from her description of sweetgrass harvesting. If you didn't harvest, it would get clogged up and it would not grow. So you can’t over-harvest, but you can't under-harvest. That feels like sales, right? You can't over-ask, but if you don't ask, nothing happens. Business books that reference non-business book metaphors—I'm going to be very excited when I don't have to read business books for a while.

I can now go read other things to refill my cup, as it were, creatively, because there's only so much you can only read about some marketing percentage before you're like, “It's all the same.” What I really want to do is something on business model personalities. And you know what? I need to go read some astrology.

Meet the Author interviews are lightly edited for clarity.

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I absolutely loved Jessica's approach to writing, publishing, and marketing her book—particularly the feedback loop of having an idea, teaching it, and then writing about it. Don't forget to grab your copy of Leaving the Casino!