Small Business Ownership: 5 Must-Ask Questions
Asking the right questions can shift you out of “casino thinking” and into intentional, sustainable strategy.
Most of us never answer the big questions—because no one is asking, and the casino profits when we keep pulling levers instead of claiming our own agency.
The Casino Metaphor: Why Entrepreneurship Feels Like a Gamble
For so many in small business ownership—especially those who are neurodivergent—the journey starts with patching together random tactics, purchased programs, and the latest social media advice in hopes of hitting the elusive "jackpot." The problem? We end up spending money (and sanity) pulling the lever, but the only ones consistently winning are the people selling us more solutions.
Jessica Lackey, with a background at McKinsey, Nike, and Harvard Business School, knows from hard experience that sustainable small business ownership isn't built on tactics alone. Her best-selling book, "Leaving the Casino: Stop Betting on Tactics and start Building a Business That Works," explores how to replace this game of chance with real strategy—and how improving mindset and performance for neurodivergent entrepreneurs in particular can benefit from reclaiming their agency.
Why Tactics Aren't Enough (Especially for ADHD-ish Brains)
From Instagram courses to LinkedIn "blueprints," entrepreneurs are constantly bombarded with advice and conflicting messages. Jessica describes the all-too-familiar spiral: buying digital course after course with promises of passive income or viral growth, only to find none of them fit your unique business or the way your brain works. For neurodivergent business owners, this casino-like barrage isn't just distracting—it can be actively damaging, stifling decision-making and confidence, undermining both mindset and performance for neurodivergent entrepreneurs.
As I’ve pointed out, we literally forget that we have critical thinking abilities, because no one's asking us the right questions. Nobody says, 'What kind of business do you want? What's your capacity? How much money do you really need to make?' We become convinced that buying the next tactic is a required rite of passage, especially when influencers and marketers parade six- and seven-figure goals as the only real markers of small business ownership success.
Strategy Starts with the Right Questions
Jessica proposes an antidote: before you choose your marketing plan, pricing, or explore different business models, first answer the "Big Questions." These five foundational questions, which shape her consulting and new book, are essential for small business ownership clarity:
What business are you actually running? (A coaching practice, a course platform, a service agency?)
What stage of business are you at? (Are you planting seeds, nurturing sprouts, or scaling up?)
What impact do you want to have? (Is your goal intimate, one-on-one transformation, or mass-market influence?)
What level of responsibility do you want? (Do you want to manage a team, steward a community, or remain a solopreneur?)
What is "enough" for you? (How much money, time, flexibility, and creative freedom do you truly need?)
Every tactic sold to entrepreneurs assumes you've already answered these questions and selected from various business models. But most of us never do—because no one is asking, and the casino profits when we keep pulling levers instead of claiming our own agency.
Reclaiming Confidence: Intentional Choices & Healthy Constraints
Building confidence, especially for ADHD-ish business owners, isn't just about "thinking positively." Jessica advocates for getting out of the advice-overload cycle, cutting down on noise (and unsubscribing from toxic content), and bringing in decision-making frameworks—critical components of mindset and performance for neurodivergent entrepreneurs. For example, pricing shouldn't rely only on what feels good or what others charge, but on assessing your real hourly rate, market demands, and the kind of impact you're after.
Jessica also highlights the importance of intentional constraint for sustainable small business ownership: "If you need creative novelty, how do you build that into your business and life in a way that still honors your goals?" She points out that successful, visible entrepreneurs have teams, flattened-out processes, and a level of structure that a solo entrepreneur can't and shouldn't try to imitate. Understanding which business models actually fit your capacity is essential.
The Final Word: Agency, Accommodation, and Redefining Success
The big takeaway? You get to define what your small business ownership looks like. Structure isn't the enemy—used intentionally, it supports your creativity and protects your mental health, enhancing mindset and performance for neurodivergent entrepreneurs. Not everything you love needs to be monetized, and it's not "failure" to have a down year or keep your business as a fulfilling side hustle.
Jessica's advice for ADHD-ish entrepreneurs: reclaim your decision-making power, embrace intentional trade-offs, and build structure that serves your purpose, not the casino's endless cycle. Choose business models that fit your brain, not someone else's blueprint. Sustainable, rewarding small business ownership isn't luck—it's clarity, agency, and strategy, on your own terms.
If you'd like to hear the full episode on the ADHD-ish Podcast, you can do that here.
