The Big Questions Every Business Owner Needs to Ask, with Jessica Lackey

Many entrepreneurs struggle with online tactics and shiny promises that lead to overwhelm rather than sustainable results. In this episode of ADHD-ish, host Diann Wingert and business strategist Jessica Lackey explore how an ADHD small business owner can re-evaluate core strategy and align business operations with authentic goals.
Discover how an ADHD-informed business strategy helps you create a solid foundation instead of gambling on short-term trends. If you are a business owner with ADHD looking for grounded ADHD business coaching to align your offer, energy, and values, this conversation delivers essential insights for sustainable growth.
EPISODE HIGHLIGHTS & TIMESTAMPS:
- Leaving The Entrepreneurial Casino
- Strategy Over Tactics For Sustainable Business
- The Five Big Business Questions
- ADHD And Entrepreneurial Overstimulation
- Defining Enoughness And Business Success
- Embracing Your Business Stage And Pace
- Intentional Constraints And Creative Autonomy
- Decision-Making Frameworks For Neurodivergent Entrepreneurs

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 atdeeperfoundations.com
Buy the book, or get a free chapter: Leaving the Casino by Jessica Lackey (deeperfoundations.com/casino)

Mentioned during this episode:
• Digital Course Academy - Amy Porterfield (amyporterfield.com/dca-waitlist-2025)
• Gary V - Gary Vaynerchuk (youtube.com/garyvee)
• Codie Sanchez (codiesanchez.com)
• Robin Wall Kimmerer’s book, Braiding Sweetgrass (milkweed.org/book/braiding-sweetgrass)
• Elizabeth Gilbert’s book Big Magic (elizabethgilbert.com/books/big-magic)

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

The Big Questions Every Business Owner Needs to Ask, with Jessica Lackey

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