Growing up on Chicago's South Side, I was immersed in the roller coaster ride of entrepreneurship, working alongside my parents, who owned and operated eight different businesses by the time I was 20.
As the oldest of five, working across three generations of family businesses, I lived, ate, slept, and breathed the up and down cycles from concept and idea to success and failure.
This immersive, hands-on approach of learning by doing, built my confidence as a leader while providing invaluable lessons in adaptability, tenacity, and resilience. It was these early entrepreneurial apprenticeship-like experiences, that laid the foundation for facing change and uncertainty throughout my career, whether navigating the corporate landscape of a Fortune 500 company or forging my own path as a serial entrepreneur.
Fast forward to today, as an executive coach, data scientist, and four-time award-winning CEO of Organized SHIFT and the AI-powered technology startup, iSHIFTx, my mission is clear: to revolutionize learning and development for the modern leader.
Shaped by entrepreneurial roots and grounded in skills cultivated through consistently managing change, risk, and improvement, Organized SHIFT equips leaders with personalized coaching solutions and burnout-free strategies for sustainable growth. With over 5,800 leaders empowered to SHIFT amidst the relentless pace, complexity, and disruption of today's modern workplace, our commitment is to upskill 1,000,000 leaders by 2028.
Reflecting on my own journey, I can truthfully say that educating modern leaders for entrepreneurship goes far beyond teaching them how to draft a business plan. It's about nurturing a mindset that embraces innovation, sharpens critical thinking for problem-solving, and cultivates the readiness to lead diverse and multigenerational teams. Today’s entrepreneurship education is about instilling a sense of purpose and the practical skills needed to confront unprecedented change, challenge, and disruption head-on.
It is from this holistic perspective that I present the top five essential skills that entrepreneurs must master to SHIFT. These versatile and invaluable qualities are not only crucial for entrepreneurial ventures. They lay the foundation of personal development for professional growth, success, and advancement across any industry or job title.
Grit:
Leadership is one of the most complex and difficult roles in business. This is especially true for the Black (41%) and Women (25%) business owners who often lack the bandwidth, skills and resources to transform crisis and disruption into opportunities for growth.
"To be resilient is to survive the shock or disruption, and remain the same. –Landi Spearman"
Entrepreneurship is like a rollercoaster—full of ups and downs. But those tough times teach us grit and resilience—the skills you can't put a price on.
Grit isn't just a word for me. It's in my DNA. Shaped by growing up in the hustle and bustle of running eight different family businesses alongside my parents in some of Chicago’s toughest neighborhoods, resilience wasn't just a choice—it was a necessity. Knee-deep in entrepreneurship from day one, every decision we made held the weight of our family's livelihood. As the oldest of five, I was treated less like one of the kids and more like a manager in training, always gaining a first-hand look at tackling tough decisions. My mother and father’s ability to weather storms, pivot when necessary, and keep moving forward as a team, despite the odds taught me invaluable leadership lessons.
Seeing firsthand what it means to remain steadfast in the face of adversity, I know that “failure isn’t the end– it’s just another opportunity and lesson.” Through grit, I‘ve learned that each setback prepares me to emerge stronger, more resilient, and better equipped to face the challenges ahead.
As I lead my ventures and coach entrepreneurs and leaders, I bring that same gritty spirit. No matter what hurdles I face, I know I've got what it takes to push through. Grit isn't just about surviving; it's about thriving to emerge stronger on the other side. These traits aren't just for starting a business; they are what make great leaders in any field.
Continuous Improvement:
In the dynamic and ever-changing world of entrepreneurship, continuous improvement is a cornerstone skill for anyone seeking success.
Staying curious, actively seeking new knowledge, and fueling ongoing learning and development to stay ahead of the curve results in reinvention, refinement, and the ability to respond to change. Learning by doing, taking decisive action, and pivoting to navigate the ever-evolving nature of entrepreneurship are transformative traits for the success of any career.
One aspect of continuous improvement is assessing your own “current state.” Today, as some companies relax education-related requirements, entrepreneurs can chart their own path to continuous improvement through certifications, online education, accelerators and incubators, cross-functional projects, and expanding lived experiences. I learned a lot as an entrepreneur from being unafraid to fail. I believe that “failing creates lessons to be learned, but it is how you SHIFT your response that matters the most."
In the fast-paced world of entrepreneurship, continuous improvement isn't just a skill; it's a game-changer. By staying curious, learning from experience, and never being afraid to try new things, we not only adapt to change but thrive in it. Whether it's pivoting our strategies or honing our skills, the journey of continuous improvement keeps us sharp, innovative, and ready to tackle whatever comes our way.
Innovative Thinking:
Entrepreneurs constantly innovate to solve problems, find solutions to challenges, identify gaps, and meet market needs. Innovative thinking values diversity of thought and perspective, takes risks, evaluates constraints, and explores what is outside the box. An innovator’s mindset generates creative ideas, thinks critically about problems, and inspires others to scale, remain competitive, and grow.
In 2021, in response to the disruptions caused by the Coronavirus pandemic, I leveraged innovative thinking to pivot Organized SHIFT, my change leadership firm. Partnering with healthcare tech provider DuetHealth, we pioneered a mobile technology application to collect daily wellbeing information safely, effectively, and measurably. Providing instant feedback and tailored recommendations for employees returning to work, we expanded options for leaders to adapt to the challenges of disruption.
Today, the proprietary SHIFT approach is grounded in thinking differently about the experience of change. By harnessing the power of innovative thinking to address critical gaps and barriers caused by stress, SHIFT has equipped over 5800 leaders through innovative and immersive learning experiences. Recognized as an industry trailblazer, I am honored to have earned designations as a Woman Who Means Business, Entrepreneur of the Year and the Mentor of the Year in the Tech and Innovation ecosystem.
Influence:
Building a tech startup or running a business involves interactions with a wide range of stakeholders and strategic partnerships. As an entrepreneur, I’ve learned never to underestimate the impact of one's presence. Regardless of background, entrepreneurs often navigate complex networks and forge connections with individuals from diverse races and genders. These relationships serve as bridges to new opportunities, accessing different networks, and opening new doors.
Influence, however, isn't just about networking. It’s about building meaningful relationships based on trust and mutual respect. To cultivate influential connections, entrepreneurs must proactively engage with their allies and sponsors, keeping them informed about successes, achievements, and milestones to make it easier for them to advocate on their behalf.
Last year, being named a Houston Top 15 Coach marked a pivotal moment in my journey. Inspired by my father, who mentored entrepreneurs and taught me to see leadership as a lens for identifying gaps, opportunities, and solutions to positively influence the most vulnerable, it was at that moment that I committed.
I believe that the ability to influence stands alone in its ability to have a compounding impact and effect on others. And being accepted into the 2024 technology accelerator cohort, CodeLaunch, further ignited my passion. As I watched startup Founders pitch solutions to scale their impact, I sought a way to combine my 20+ years of expertise in Change Leadership, Learning, and Development with coaching and technology to amplify my influence.
Within 90 days, I emerged as one of forty founders to survive four intense elimination rounds. Leveraging my influence, I swiftly recruited a talented team, partnered with Spanish-speaking coders and developers, and delivered a cutting-edge mobile coaching platform, powered by the latest in generative AI.
And before an audience of 1,000 in the fourth largest city in America, my innovative leadership solution, designed to provide on-demand answers to tough questions in real-time, captured the prestigious 2024 Judges' Top Choice award. This moment marked the beginning of a new chapter for me as a startup founder, in the technology and innovation industry, ready to create a greater influence for women and minorities.
Self-Awareness:
Entrepreneurs develop self-awareness through strategic planning, risk-taking, and decision-making under pressure, gaining valuable experiences across various domains. Self-aware leaders understand their strengths, weaknesses, and stress behaviors, cultivating emotional intelligence.
Self-awareness isn't just a skill I've honed; it has been the cornerstone of my journey as an entrepreneur and leader. Throughout my career, I've been thrust into challenging situations and tested to the limits as a young Black female executive in male-dominated corporate and manufacturing industries. In each instance, emotional and cultural intelligence proved paramount, highlighting the importance of self-awareness.
Recognizing biases and emotions during critical negotiations and conflicts fosters open and honest team communication. Collaborating more effectively and navigating conversations towards successful outcomes start with self-awareness. Entrepreneurs who continuously become more self-aware enhance their leadership capabilities and foster cultures of empathy, introspection, and personal growth for their organizations and teams. Accurately assessing oneself and effectively communicating areas of improvement is critical for aligning team members, mentors, and coaches toward shared goals. This skill is highly transferable and significantly contributes to leadership roles in any field.
Ultimately, the entrepreneurial journey provides a wealth of experience and invaluable skills. Entrepreneurs are empowered to overcome their own challenges and inspire, lead, and foster meaningful connections while driving results across a diverse range of stakeholders. This journey equips them with the skills, experiences, and mindset needed to thrive in any field or career. And, entrepreneurship plays a vital role in driving innovation, economic growth, upward mobility and societal change. Coupled with a relentless drive and commitment to making a difference, entrepreneurship is the foundation for success and meaningful, enduring change.
