Free checklist
Before you leave an alcohol-centered career, take stock.
The Exit Readiness Checklist is a short, free set of prompts for people who suspect—or already know—that their work in wine, beer, spirits, or hospitality no longer fits the life they want.
Who it’s for
For the moment between knowing and doing.
Maybe your job keeps you around alcohol every day and that no longer works for your sobriety. Maybe it’s the culture, the hours, or simply the life you want to build. Either way, the hard part is rarely the decision itself—it’s figuring out how to leave without losing your income or your footing.
This checklist doesn’t tell you what to do. It helps you see your situation clearly enough to make your own plan.
What’s inside
Seven things to figure out.
Know your financial minimum
The income you actually need, your runway, and the benefits a transition has to replace.
Identify your workplace exposure
How close your work keeps you to alcohol, and which situations are hardest.
Separate career from identity
Who you are without the title, and what you want to keep as you leave.
Inventory your transferable skills
The hard and people skills that carry into other fields.
Consider a bridge job
Interim work that buys stability while you build what comes next.
Decide what you will not recreate
The hours, habits, and cultures you refuse to repeat.
Plan the first 90 days
Small, concrete moves for this week, this month, and day 90.
The checklist is a planning prompt, not medical, mental health, legal, or financial advice. If you are physically dependent on alcohol, stopping suddenly can be dangerous—please talk to a medical professional.
Why it exists
The Winemaker’s Dilemma was started for people facing the same question its founder did: what do you do when the career you built is centered on something you can no longer be around? The checklist is the simplest useful starting point—a way to turn a heavy, abstract decision into questions you can actually answer.
See the fuller Exit Plan guideFree download
Get the checklist.
Enter your name and email and download it right away. We’ll email you a copy too.