From Snow Removal to the C-Suite: Stephen Sokoler’s Journey to Leadership

Stephen Sokoler, founder and CEO of Journey, shares how proactive mental health practices and daily habit formation can lead to healthier, less stressful lives. From running snow removal businesses to leading Journey Meditation, Stephen dives into the challenges of mental health in the workplace, entrepreneurship, and the value of meditation for personal growth and well-being. In this episode, we look at proactive mental health, workplace wellness, behavior change, executive leadership, HR, entrepreneurship, and the importance of mindfulness. These themes shape how we understand and approach mental health in today’s rapidly evolving corporate and personal spaces. Key Takeaways: Proactive mental health focuses on daily habits for stress reduction and overall well-being. Societal shifts are changing the narrative from mental illness to mental wellness. Bridging HR and executive leadership is essential for advancing workplace mental health support. Stephen Sokoler’s entrepreneurial journey illustrates the diverse paths to success, from snow removal to wellness tech. Meditation is a powerful tool for fostering personal growth, clarity, and alignment with one’s values. Kindness and presence are key to living a meaningful life, both personally and professionally. Chapters 00:00 Who is Stephen Sokoler? 03:23 Proactive Mental Health 06:22 Shifting Societal Understanding of Mental Health 11:41 Bridging the Gap: HR and Executive Leaders 14:31 Journey's Proactive EAP 18:09 Entrepreneurial Journey: From Snow Removal to Journey 25:21 Starting a Bar and the Challenges of the Hospitality Industry 32:00 Discovering Meditation and the Journey to Mental Health 38:36 Becoming a Kinder Leader and Manager 45:34 Advice to Younger Self: Be Kinder Connect with Stephen here: https://www.linkedin.com/in/stephensokoler/ and visit Jouney to learn more about Proactive Mental Health here: https://journey.live/ Connect with WRKdefined on your favorite social network The Site | Substack | LinkedIn | Instagram | X | Facebook | TikTok Share your brand across the WRKdefined Podcast Network Learn more about your ad choices. Visit megaphone.fm/adchoices