When you’re an entrepreneur in recovery, you’re operating with two simultaneous transformations. Your personal life is rebuilding around sobriety, clarity, and accountability. Your business life should be doing the same. Yet most entrepreneurs in recovery lack a framework to assess the actual health of their business—beyond surface-level metrics like “revenue is increasing” or “I’m getting clients.”
Business health isn’t just about money. It’s about sustainability, growth potential, team dynamics, operational efficiency, and alignment with your values. For the sober entrepreneur, it’s also about ensuring your business supports your recovery, not compromises it.
This three-part business health assessment is designed to give you a comprehensive snapshot of where your business actually stands. It takes 2-3 hours to complete properly, and the insights will guide your next 90 days of decisions.
Part One: The Foundation Assessment
Your business foundation consists of five critical elements: clarity, positioning, market fit, pricing, and systems.
Clarity asks: Do you have a written definition of what your business does, who it serves, and what specific problem it solves? Not a mission statement. Not a tagline. A crystal-clear, one-paragraph description that a completely unfamiliar person could read and immediately understand what you offer and why someone should care. Many entrepreneurs in recovery have clarity about their personal transformation but haven’t translated that into clear business positioning. Grade yourself: 1-10, where 10 is “I could recite this in my sleep and it would convert anyone.”
Positioning requires: Can you articulate why someone should choose you over alternatives? Not because you’re nice. Not because you’re authentic (which is assumed). What’s the specific competitive advantage you’ve built? For sober entrepreneurs, this might be your lived experience, your specific methodology, your community, or your unique angle on transformation. Grade yourself: 1-10 on how clearly you can explain this differentiation in one sentence.
Market Fit examines: Are you selling to people who actually want and need what you’re offering? This is where many passionate entrepreneurs miss the mark. You might have an amazing offer, but if it’s not what your market is desperate to buy, you’re working against the current. Survey your past five paying customers: Did they seek you out because they were already hunting for your solution? Or did you convince them they needed it? If it’s the latter, your market fit is weak. Grade yourself: 1-10.
Pricing scrutinizes: Is your pricing aligned with the value you deliver and the market rate for similar solutions? Research what others charge. Compare your pricing to their offerings. Be honest about whether you’re underpriced, fairly priced, or premium-priced. Remember: pricing isn’t fair if you’re undercharging for genuine value. That’s a leak. Grade yourself: 1-10 on whether your pricing feels aligned and justified.
Systems evaluates: Can your business operate without you for a week? Not because you want it to, but because the basic operations have enough structure that things don’t fall apart? This includes client onboarding, delivery, communication, billing, and follow-up. Grade yourself: 1-10.
Your foundation score is the average of these five grades. Anything below 6 means your foundation needs immediate work. Between 6-8 means solid foundation with room to strengthen. Above 8 means you’ve built something resilient.
Part Two: The Revenue Health Assessment
Revenue health isn’t just about how much you’re making. It’s about where it comes from, how predictable it is, and whether you’re over-dependent on any single source.
Revenue Diversification: How many revenue streams do you have? If 80% of your revenue comes from one client, one product, or one channel, you’re operating with high risk. A single client leaving, a platform change, or a market shift creates catastrophic impact. For sober entrepreneurs, this is especially dangerous because financial stress can be a relapse trigger. Grade yourself: 1-10 on diversification. (Ideal: 2-3 revenue streams, no single stream above 60% of total revenue.)
Revenue Predictability: Do you know, with reasonable certainty, what your revenue will be next month? If you have recurring revenue from coaching packages, memberships, or retainers, this is predictable revenue. If 100% of your revenue depends on one-off sales, it’s unpredictable. Unpredictable revenue creates chronic stress and leads to poor decision-making. Grade yourself: 1-10 on predictability. (Ideal: 50%+ of revenue is recurring/predictable.)
Revenue Growth Trajectory: Over the past 90 days, is your revenue trending up, stagnant, or down? This isn’t about panic if it’s down. It’s about awareness. Where is the trend heading? Are your current marketing and sales activities generating more leads, the same, or fewer? Grade yourself: 1-10 on positive trajectory.
Unit Economics: Do you understand your cost to acquire a customer vs. the lifetime value of that customer? If your customer acquisition cost (CAC) is $200 and the average customer lifetime value (LTV) is $300, you’re barely profitable. If CAC is $200 and LTV is $2,000, you’re healthy. Grade yourself: 1-10 on understanding your unit economics. (If you score below 5, spend time calculating this immediately—it’s foundational.)
Customer Retention: What percentage of customers return for additional services, upgrades, or referrals? High retention (60%+) means you’re delivering genuine value and building a sustainable business. Low retention (below 30%) means you’re constantly chasing new customers and burning out. Grade yourself: 1-10.
Your revenue health score is the average of these five grades. Below 6 means your revenue model is fragile. 6-8 means it’s workable but needs strengthening. Above 8 means you’ve built sustainable revenue architecture.
Part Three: The Leadership and Capacity Assessment
This final assessment is personal. It’s about you as the leader and your capacity to scale.
Energy and Burnout: On a scale of 1-10, how sustainable is your current workload? Are you heading toward burnout, or do you feel energized? For sober entrepreneurs, burnout is a critical risk factor. Exhaustion clouds judgment and can trigger old coping mechanisms. Grade yourself honestly.
Decision-Making Quality: How confident are you in your business decisions? Do you second-guess yourself constantly, or do you make decisions with conviction? Do you consult your values and long-term vision before deciding, or do you react to short-term pressures? Grade yourself: 1-10.
Delegation and Team: Are you trying to do everything yourself, or have you built a team that handles significant portions of your business? For solo entrepreneurs, this might mean outsourcing. For team leaders, this means actual delegation with trust. Grade yourself: 1-10.
Alignment with Values: Does your business align with your personal recovery values? Does it support your sobriety, or does it undermine it? Does it allow for the lifestyle you want, or does it demand constant sacrifice? Grade yourself: 1-10.
Learning and Growth: Are you continuously learning and improving, or are you stagnant? This includes reading, taking courses, finding mentors, and experimenting with new strategies. Grade yourself: 1-10.
Your leadership and capacity score is the average of these five grades. Below 6 means you’re at risk of burnout or misalignment. 6-8 means you’re functional but need to prioritize your own development. Above 8 means you’ve built a sustainable leadership practice.
Interpreting Your Assessment
Add up all three scores. A total score of 6+ across all areas means your business is fundamentally healthy, and you should focus on optimization. A score of 5-6 means you have some serious vulnerabilities that need attention. Below 5 means your business is in crisis mode and needs fundamental restructuring.
The assessment also shows you where to focus. Your lowest-scoring area is your priority for the next 30 days. Attack that weakness, then move to the next one.
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