In this episode of Headspace for the Workplace, I sat down with psychologist, author, and organizational consultant Dr. Abby Medcalf who spent years working with executives in mergers and acquisitions to address substance use at the leadership level. The conversation centers on one of the most common and least-discussed dynamics in high-performance workplaces: leaders who are quietly reconsidering their relationship with alcohol and don't know why their efforts to change keep failing.
Dr. Abby's own story adds weight to the conversation. She came into this work through recovery from heroin addiction in her early years, which led her from a planned legal career into counseling psychology, and ultimately into a PhD in organizational psychology. That combination of lived experience with addiction plus deep expertise in how organizations and leaders function, gives her a uniquely practical and compassionate lens on the culture of high-performance drinking and why it so often goes unaddressed.
The centerpiece of the episode is the Motivational Wheel - a research-backed framework developed by Prochaska and DiClemente that maps how humans actually move through habit change. Dr. Abby walks through each phase (pre-contemplation, contemplation, determination, action, maintenance, and relapse) and identifies the single most common mistake leaders make when they slip back: jumping straight back to the action phase instead of returning to their why. The episode closes with a reframe that is both simple and profound: take action from inspiration, not from negative motivation.
Why This Matters in the Workplace
The High-Performer Blind Spot
In most organizations, high-performing leaders receive a quiet, unspoken pass on their relationship with substances. The logic is straightforward: if they're hitting targets and driving results, nobody wants to disrupt the machine. The quarterback drinking a case every weekend gets overlooked because the focus is entirely on performance output. The result is a system that inadvertently rewards dysfunction, protects it from scrutiny, and leaves the leader without the support they need until a crisis forces the issue.
The Numbers
• Approximately 10% of executives have a substance use disorder which is roughly equivalent to the general population rate, meaning seniority offers no protection
• Alcohol is initially effective at reducing anxiety (which is precisely why high-stress leaders reach for it) but carries a rebound effect that worsens anxiety over time
• Research shows that most people cycle through the Motivational Wheel an average of four times before successfully changing a habit. This means relapse is the norm, not the exception
• Organizational cultures that normalize or actively encourage drinking (kegs in hallways, alcohol-centered client entertainment, post-deal celebrations) structurally increase risk for leaders who may already be vulnerable
• Leaders who rely on alcohol as their only anxiety management tool are operating with a narrowed coping toolkit that will eventually fail them
The Cultural Complicity Problem
Dr. Abby identifies specific workplace cultures - finance, sales, tech - that have historically centered alcohol in their identity and their relationship-building. When drinking is woven into how deals get done and how belonging is signaled, the individual leader's relationship with alcohol becomes a cultural issue, not just a personal one. Any serious approach to substance use at the leadership level must grapple with the environment that shapes and sustains the behavior, not just the individual who is exhibiting it.
Why This Matters Beyond Alcohol
While the episode focuses primarily on alcohol, Dr. Abby is explicit: the Motivational Wheel and the why-before-what principle apply to any habit a leader is trying to change - sugar, smoking, overworking, screens, or any other behavior that is being controlled rather than released. The framework is universal. What makes it relevant to leadership specifically is that leaders are trained to attack problems with strategy and action and that instinct, however effective in business contexts, actively undermines the change process when it's applied to deeply embedded personal habits.
In this episode, we’ll answer:
Why do leaders struggle to change their relationship with alcohol?
What is the Motivational Wheel and how does it relate to habit change?
How does alcohol affect high-performing executives differently?
How can workplaces address substance use among senior leaders?
What resources does Dr. Abby Medcalf offer for executives and leaders?
Two Tactical Takeaways from This Episode
Tactical Takeaway #1: When You Relapse, Go Back to Your Why — Not Your To-Do List
The most common mistake leaders make after a relapse is jumping straight back to the action phase of change: returning to meetings, reinstating rules, rebuilding the structure that worked before. Dr. Abby argues this is the wrong move. The action phase is only effective when the contemplation phase has done its work - when you have genuinely excavated your why and made it concrete, written, and visceral. Without that foundation, all the action in the world is a house built on sand.
The practical instruction is simple: make a list. Write down every negative consequence your drinking (or whatever the habit is) has produced. Every embarrassment. Every missed moment. Every body signal you've minimized or dismissed. That list is your why. And that why is the only reliable fuel for the action that follows. If the list is short, or if you find yourself explaining away each item, you're not ready for action yet — and that is important and honest information.
WHY IT WORKS
Humans are naturally gifted at minimizing, forgetting, and rationalizing especially around behaviors that provide short-term relief from real stress. The written list counteracts the goldfish memory that lets us convince ourselves "it wasn't that bad." It also activates the contemplation phase deliberately rather than waiting for the next crisis to do it. Leaders who do this work before returning to action are building on a foundation of genuine motivation rather than shame or external pressure, which research consistently shows produces more durable change.
Tactical Takeaway #2: Take Action From Inspiration, Not Negative Motivation
Dr. Abby's closing insight reframes the entire architecture of change. Most people try to stop a behavior because they are running away from something - the shame of a comment, the fear of a health result, the pressure of a relationship. That is negative motivation, and while it can produce short bursts of behavior change, it is inherently unstable. The moment the acute pressure eases, the motivation evaporates.
Inspiration-driven change is different. It is powered by a clear, compelling vision of who you want to become and how you want to feel not by what you are trying to escape. In practical terms, this means leaders must spend time not just cataloguing the costs of the current behavior, but also articulating what they are genuinely running toward: the quality of presence they want with their family, the level of performance they want at work, the version of themselves they want to meet on the other side.
WHY IT WORKS
Negative motivation creates urgency without direction. Inspiration creates direction without urgency which is far more sustainable. When a leader can articulate, specifically and emotionally, what they are building toward, they have something to return to every time the old pull resurfaces. I reinforce this with the simple reframe: running toward something is fundamentally different from running away from something - in energy, in sustainability, and in outcome.
ABOUT ABBY MEDCALF
Abby Medcalf is a straight-talking psychologist, best-selling author, speaker and podcast host who helps people become confident, direct communicators in every relationship, whether it’s with a partner, coworker, or their own inner critic.
With over 35 years of experience, a masters in counseling psychology and a PhD in organizational psychology, Abby blends science-backed strategies with humor, candor, and just the right amount of bossy. She’s helped thousands of people stop people-pleasing, set boundaries that stick, and finally feel calm and connected, especially to themselves. Her unique background in both mental health and business gives her a rare ability to bridge the personal and professional without the fluff or jargon.
Whether she’s handing out scripts to say “no” without guilt or debunking myths about emotional regulation, Abby delivers love-drenched truth you can actually use (and probably laugh at). She’s been a featured expert on CBS and ABC, and her advice has appeared in the New York Times, Women’s Health, Fast Company, Success Magazine, Psychology Today, and the Wall Street Journal.
She’s the author of the #1 Amazon best-seller Be Happily Married, Even if Your Partner Won’t Do a Thing, along with Boundaries Made Easy and The Boundaries Made Easier Workbook. Her top-rated podcasts, Relationships Made Easy and Workplace Therapy with Dr. Abby Medcalf and are heard in over 190 countries and brings practical wisdom to thousands of listeners every week.
SHOW NOTES
abbymedcalf.com
https://substack.com/@abbymedcalfphd