Alright – so today we’ve got the honor of introducing you to Dr. Isaiah Pickensharo. We think you’ll enjoy our conversation, we’ve shared it below.
Dr. Isaiah, thank you so much for making time for us. We’ve always admired your ability to take risks and so maybe we can kick things off with a discussion around how you developed your ability to take and bear risk?
Taking risks has been a journey of intentional growth and an unshakable trust in my purpose. I’ve learned to see challenges not as obstacles but as doorways to greater impact. This perspective became deeply personal—and life-changing—in October 2020.
At the time, I held a position I had worked hard to achieve: Assistant Director for the UCLA-Duke National Center for Child Traumatic Stress. It was a role where I excelled, helping individuals and systems heal and thrive in the face of trauma. By all accounts, it was a dream job—comfortable, impactful, and respected. But comfort, I realized, is not the same as fulfillment. Deep down, I knew I wasn’t fully unlocking my potential. I had a vision for something greater, something that could transform systems and lives beyond the pain of trauma and toward a reimagination of success grounded in well-being. To honor that vision, I made the bold decision to leave the security of that role and dedicate myself fully to building my company, iOpening Enterprises.
At the same time, I made an equally profound decision to marry the love of my life. She’s everything I could ever hope for in a partner—brilliant, compassionate, and supportive. But our union came with its own complexities. She is of a different faith than my family, and our love challenged long-held traditions and expectations. Saying “yes” to her meant stepping into uncharted territory, risking misunderstanding or even disapproval from those closest to me. But I knew with every fiber of my being that loving her and building a life together was worth every risk.
These decisions weren’t easy, but they were necessary. Early in my career, I realized that psychology isn’t just about understanding people—it’s about empowering them to live their best lives. That realization gave me the courage to embrace uncertainty, trusting that on the other side of fear was a life of deeper purpose, connection, and fulfillment.
Every step I’ve taken—whether pursuing advanced education, leaving a secure job, launching my company, or committing to the love of my life—has required me to lean into uncertainty with purpose. Risks worth taking are rooted in preparation and an unflinching commitment to our core values. They push us to grow, to align more authentically with who we are, and to create a life that truly reflects our deepest aspirations.
I’ve learned that growth and comfort rarely coexist. But I’ve also discovered that the rewards of stepping into discomfort—empowered people, meaningful change, and a life filled with love and purpose—are always worth it.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
My journey has always been about transformation—helping people, organizations, and systems unlock their full potential. As a clinical psychologist, I’ve dedicated my career to understanding what drives people and how we can create environments that allow them to thrive. I founded iOpening Enterprises (iOE) with a clear mission: to reimagine success. For us, success isn’t just about hitting numbers or achieving goals; it’s about centering well-being at the heart of productivity. We believe it’s possible to achieve extraordinary results without sacrificing the wellness of the individuals who make those results happen.
We’re a professional development company that trains organizations and schools worldwide to build thriving workplace cultures where employees want to stay. What sets us apart is our approach. At iOE, we believe that every individual has the capacity to thrive, and every organization has the potential to create an environment where thriving becomes the norm. Our work is rooted in emotional intelligence, trauma-informed practices, and cultural responsiveness, which means we’re not just teaching skills—we’re empowering leaders and teams to understand themselves and others on a deeper level. This unlocks innovation, collaboration, and a sense of purpose that drives lasting success. We do this by going way beyond training to help organizations build internal teams of champions who can continue the work after we finish. We specifically help grow emotional-intelligence skills that help people at work manage conflict effectively and develop organization-wide processes that support productivity without sacrificing well-being.
What excites me most about our work is seeing real transformation happen. I’ve seen leaders shift from feeling stuck in old patterns to embracing bold, people-centered strategies. I’ve witnessed teams that were struggling with burnout rediscover their passion and align around a shared vision. Organizations that were simply surviving evolve into places where people genuinely love to work because leaders found new ways to align their goals with the well-being of their teams and create environments that don’t just demand excellence but nurture it. Watching people and organizations embrace this reimagined version of success and find breakthroughs inspires me every day.
We’re also expanding our impact in exciting ways. One of our newest initiatives is the Elevate Work Culture Transformation Program, a comprehensive blueprint for organizations to build thriving workplace cultures, reduce turnover, and promote meaningful growth. Additionally, we’re launching a program to help schools support educators dealing with burnout and promote their well-being–so they feel fueled to continue teaching our children. Whether it’s designing programs, coaching leaders, or delivering keynotes, everything we do is about creating environments where people can be their best selves.
Our mission is to show that productivity and wellness aren’t mutually exclusive—they’re partners in achieving true success. We help organizations embrace this balance, unlocking potential in ways that inspire lasting change. It’s a mission I’m deeply passionate about because I want to live in a world where success is synonymous with fulfillment and well-being.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Looking back on my journey, three qualities stand out as truly transformative: reflection, resilience, and faith. Each of these has been pivotal in shaping who I am and what I do, and they’re qualities I encourage anyone to cultivate as they begin their own path.
The first is giving myself time to reflect and learn about what truly drives me. Early in my career, I realized that I couldn’t make meaningful decisions without understanding what I valued most. Taking time to reflect—through journaling, meditation, or simply pausing in the busyness of life—has been the foundation for every major decision I’ve made. It’s what allowed me to step away from a comfortable job to pursue my full potential and build my company. My advice? Make space for reflection. Ask yourself, “What really matters to me?” and “What kind of life do I want to create?” When you’re clear on your values, every decision becomes an opportunity to align with what’s truly important.
The second is seeing every day as a new opportunity to reach success, no matter what happened before. Life is full of setbacks, but I’ve learned that yesterday doesn’t define what’s possible today. Every day is a chance for rebirth. Adopting this mindset has kept me moving forward, even in the face of challenges or doubts. For those early in their journey, I encourage you to embrace the idea of progress over perfection. Some days will feel like leaps forward, others like small steps, but every day offers a chance to grow. Success isn’t a straight line—it’s a commitment to show up, learn, and try again.
Finally, faith has been a cornerstone of my journey—faith that something greater than me is driving me toward a higher purpose. There have been moments of uncertainty and fear, but my belief in a bigger plan has given me the courage to take risks and trust the process. For anyone starting out, I encourage you to find what fuels your sense of purpose, whether it’s faith, a vision, or a deep connection to your values. When you believe that your work has meaning beyond yourself, it gives you the strength to persevere.
These qualities—reflection, resilience, and faith—aren’t just skills to develop; they’re mindsets to embrace. They’ve allowed me to navigate uncertainty, pursue my purpose, and build a life I’m proud of. Wherever you are on your journey, I encourage you to invest in these practices. They’ll help you not only achieve success but do so in a way that aligns with who you truly are.
How would you describe your ideal client?
Our ideal clients are organizations that understand the profound connection between a thriving workplace culture and sustained excellence. We partner with companies that are committed to creating environments where employees want to stay—not because they have to, but because they’re inspired, supported, and valued. These organizations recognize that success isn’t just about getting the work done; it’s about achieving excellence in a way that prioritizes both professional performance and personal well-being.
Organizations come to us for a variety of reasons. Some are navigating leadership transitions and want to ensure stability while fostering growth. Others are grappling with burnout, employee retention challenges, or strained relationships between managers and their teams. Many are forward-thinking companies in hyper-growth mode, eager to proactively embed well-being into their culture through systems like performance reviews, engagement surveys, and peer coaching for emotionally intelligent collaboration. And others seek to create belonging-centered work environments that drive innovation and bring out the best in their people.
We also work closely with organizations that specialize in supporting other businesses, like accounting firms, human resource service providers, and insurance companies. These partners often have deep insight into when a company is ready to invest in its culture, and together, we help clients improve their internal functions in ways that benefit both their people and their bottom line.
Ultimately, our ideal clients share a common vision: they want to build work cultures where success and well-being go hand in hand. They know that by investing in their people, they’re not just solving immediate challenges—they’re setting the foundation for long-term growth, innovation, and fulfillment. If that sounds like your organization or one you work with, we’d love to partner with you to make that vision a reality.
Contact Info:
- Website: https://www.iopeningenterprises.com
- Instagram: @drisaiahpickens
- Facebook: https://www.facebook.com/IsaiahPickens
- Linkedin: https://www.linkedin.com/in/isaiah-pickens-phd-he-him-66092825/
- Youtube: https://www.youtube.com/@iopeningenterprises
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