The Five Big Questions Entrepreneurs Must Answer

In this episode, I’m sitting down with my good friend, business strategist, consultant and author, Jessica Lackey, for a candid conversation about what it really takes to build a sustainable business—especially when you have an ADHD-ish brain. 

Jessica shares her journey from Harvard, McKinsey, and Nike to the wild world of entrepreneurship, revealing how even with such impressive credentials, she found herself trapped in the endless loop of online business tactics, quick fixes, and shiny promises.

Drawing on her upcoming book, Leaving the Casino: Stop Betting on Tactics, and Start Building a Business That Works, Jessica explains why so many of us end up gambling away our sanity (and savings) on the latest tactics, instead of building actual strategies that work for our lives and brains. 

Get ready for frameworks, real talk about defining your own version of success, and practical advice on bringing more intentionality and enoughness into your business (and life). It’s time to leave the casino behind—and reclaim your agency.

Top Takeaways from this Episode:

Start with Strategy, Not Tactics: 

The endless cycle of purchasing the latest digital course or marketing hack often leads to overwhelm, wasted resources, and lost confidence. Sustainable businesses are built on strategy and thoughtful decision-making, not reactive, one-size-fits-all tactics.

Ask Yourself the Big Questions: 

Before chasing the next big thing, get clarity on key fundamentals:

• What type of business do you really want to run?
• What stage are you in?
• What is the right pace and amount for your life and brain?
• What level of responsibility and commitment matches your reality?
• What does “enough” look like for you? These questions ground your business in reality instead of fantasy.

Don’t Compare Your Solo Journey to the Big Players: 

The polished marketers often have large teams and structures flattening out the chaos. If you’re a team of one (especially with an ADHD-ish brain), your output and path will—and should—look different.

There’s power in slowing down, cutting through the noise, and building a business that fits you—not a casino of empty promises.

About Jessica Lackey 

Jessica Lackey is the founder of Deeper Foundations, a consulting and training firm that helps expertise-based business owners grow and scale sustainable companies rooted in stronger business foundations. She brings a unique blend of corporate expertise and soulful business building, drawing on an MBA from Harvard Business School, a coaching certification from iPEC, and experience at McKinsey & Company and Nike, Inc. Jessica has supported over 200 entrepreneurs through her programs, blending systems thinking, operational rigor, and deep values alignment. She lives in Charlotte, North Carolina, with her husband.

Jessica can be reached at https://deeperfoundations.com/

Buy the book, or get a free chapter: Leaving the Casino by Jessica Lackey

Mentioned during this episode:

• Digital Course Academy - Amy Porterfield
• Gary V - Gary Vaynerchuk
• Codie Sanchez
• Robin Wall Kimmerer’s book, Braiding Sweetgrass
• Elizabeth Gilbert’s book Big Magic 

Want to share this episode with a friend who's still in the entrepreneurial casino? https://bit.ly/episode-blog-290 



© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved.