As the seasons of our careers change, so does our perspective on the work we do and the lives we lead. This heartfelt discussion with Greg Storey, a dear friend and former owner of Happy Cog, not only traces his professional voyage from bagging groceries in Alaska to the boutique agency world and through the corporate colossus of IBM Design, but it also unravels the beauty of midlife career introspection. Embracing change, Greg has moved from leading companies to imparting wisdom through coaching, a journey that mirrors my own pivot towards fitness and mental health coaching, where the reward lies in guiding others to their zenith.

Join us for a reflective and thought-provoking episode where we celebrate the rich tapestry of our past experiences, while keeping an eager eye on the horizon. We revel in discussions about the legends who’ve shaped our industry, touching on the privilege of choosing our own adventures and the vitality of continuous engagement with our creative endeavors.

This episode is also a candid exploration of the complexities of the workplace, from the integration of AI to the dynamics of leadership. We debate the current resistance to remote work models, advocate for leadership that empowers and supports, and tackle the tough emotional realities of decision-making, like firing employees. Whether you’re a seasoned vet or just starting out, there’s wisdom here for anyone navigating the undulating paths of their professional landscape. Join us and take away invaluable insights that will enrich your approach to work and life.

Greg Storey



Greg is an active leader in the digital community by providing leadership for Dribbble, Creative Mornings, and Amazing People Design List communities. In 2011, he co-founded the Bureau of Digital, a supportive community for studio owners, operators, design and project management leaders. He is the co-host of the podcast Sprints and Milestones and is a co-author of the book Remote Work for Design Teams.


Let me tell you about the time Happy Cog* almost tore itself apart about a year after I merged my studio, Airbag Industries, into the company, and how that event sparked the foundation of Same Team Partners.

“Leaders are often stuck and they seek help, but it’s not working as they would like.”


(0:00:01) – Reflecting on Careers and Taking Stock
Greg’s journey from Happy Cog to IBM Design, midlife introspection, coaching and mentoring, and purposeful work and life stages.

(0:16:51) – The Future of Design and Aging
Nature’s experiences, choosing one’s path, staying open to opportunities, staying current in design, and remaining hands-on in creative work.

(0:22:34) – Continuous Learning and Fundamental Practices
Technology evolution, traditional design practices, and fundamental principles drive personal and professional growth.

(0:28:02) – Training and Tool Skills for Success
Taking initiative and hands-on experience are crucial in today’s technology-driven workplaces, with generational differences in understanding digital tools.

(0:34:46) – Virtual Teams and Office Dynamics
Airbag Industries merges with Happy Cog, facing challenges and cultural differences while transitioning to a single company.

(0:43:57) – Remote Work and Leadership Accountability Debate
Leadership models must embrace remote work’s potential for innovation, empower teams, and address fear of change.

(0:51:16) – Leadership and AI in the Workplace
Tech leaders’ handling of internal conflict and public backlash, using Basecamp’s no-politics mandate as an example.

(1:01:38) – The Challenges of Firing Employees
Terminating employees is emotionally challenging, but facing it head-on and having open discussions is important.

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