Leadership
Empowering Lives: A Journey of Financial Freedom and Personal Growth w/ Evangelist Bertha Winston
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www.retiredanddebtfree.com
www.thewinstonexperience.com
www.destined2millions.com
Evangelist Bertha Winston is a renowned financial expert, writer, and international speaker whose influence extends far beyond her immediate community. She has graced the covers of prominent magazines like Forbes One, Black Woman magazine, Soigne’ + Swank magazine, Nspire magazine, and GLEBB magazine. Her feature on the cover of Women Empowered to Win Global magazine for Mother’s Day and her recognition on a billboard as one of the «2024 Top Women in Business and Ministry» underscores her widespread impact.
Bertha Winston’s literary journey is as impressive as her public presence. She has authored several bestsellers, including «Empowered To Win 4th Edition,» «UNSHAKABLE FAITH,» «Redirect, Redefine & Renew You,» «Love Like You’ve Never Been Hurt,» and «Love, Lead and Let Go.» Her recent releases, «Women Empowered to Win,» «The Glory of His Presence,» and «9 Voices 1 Message,» introduced in Toronto, Canada, demonstrate her dedication to financial empowerment and personal growth.
Having retired from her position as an office manager at a prestigious law firm in the District of Columbia, Bertha has redirected her energies toward guiding people on how to create passive income streams and achieve a debt-free retirement. Her life embodies resilience and faith, serving as a beacon of hope and inspiration to those striving for financial independence.
At the heart of Bertha Winston’s mission is her company, The Winston Experience and Destined2Millions. Through this platform, she guides clients towards achieving financial freedom and creating wealth. What sets The Winston Experience apart is its commitment to treating clients like family. «We don’t judge them, and they feel like we are family and are comfortable working with us because they know that we are going to fight for them to reach their financial goals,» Bertha explains. The company has developed systems that clients can plug into, providing peace of mind and the assurance that they are in good hands.
Bertha’s approach to financial education is unique and impactful. Her methods are designed to help clients grow their money faster and gain the resources needed to help their communities. The emphasis on personal connection and unwavering support is what makes The Winston Experience a standout in the financial services industry.
Beyond her professional achievements, Bertha Winston’s life is a testament to the power of faith and resilience. As a dynamic educator and influencer, she continues to inspire others on their journey to financial independence. Her ability to blend financial expertise with personal empowerment has made her a sought-after speaker and a beloved mentor to many.
Tell us about the latest books that you have published.
I’ve recently published three books that I’m very proud of. The first is «Women Empowered to Win,» which is a collection of inspiring stories from women who have overcome significant challenges and achieved great success in their lives. It’s a testament to the strength, resilience, and determination of women from all walks of life.
The second book is «The Glory of His Presence,» which delves into the profound experiences and testimonies of individuals who have encountered divine presence in their lives. It’s a spiritually uplifting read that showcases the transformative power of faith.
Finally, «9 Voices, 1 Message» is a collaboration featuring nine different authors, each sharing their unique perspectives and insights on a common theme. It’s a rich and diverse collection that brings together a variety of voices to deliver a powerful, unified message,which was introduced in Toronto, Canada.
Can you share a personal story that exemplifies how you embraced change and discovered your true potential?
When I was 62 years old, I found myself at a crossroads. I wanted to retire, but I discovered I had not planned properly and was not financially in a position to retire; therefore, I had to work 10 more years before I could retire. I had always been passionate about helping people, and I enjoyed the moments when I could provide financial advice to friends and family, seeing how it made a real difference in their lives. However, the idea of retiring to pursue something uncertain was daunting.
One evening, I attended a seminar on financial planning, and the speaker’s passion was infectious. It reignited something in me. I realized that it wasn’t too late to make a change, and I decided to take a leap of faith. I enrolled in a financial coaching certification program, dedicating my evenings and weekends to studying. It wasn’t easy balancing work, studies, and family, but my determination grew stronger with each passing day.
Upon completing the program, I faced another significant challenge: building a client base from scratch. I leveraged my network, offering free workshops and seminars to showcase my expertise. Slowly but surely, word of mouth began to spread. Each client success story fueled my passion, reaffirming my decision to embrace this new path.
One particular client, a young couple burdened with debt and financial anxiety, stands out in my memory. Through consistent coaching and personalized financial planning, they managed to turn their situation around, eventually buying their first home. Seeing their joy and knowing I played a part in their journey was incredibly fulfilling.
Looking back, the decision to embrace change at 62 was one of the best decisions I have ever made. It not only allowed me to discover my true potential but also brought a sense of purpose and fulfillment that I had been missing. Now, as a financial coach at 73, I continue to inspire others, showing them that it’s never too late to pursue your passion and make a meaningful impact.
How are you helping people in the finance and credit world?
As a financial coach, I help individuals and businesses navigate the complexities of finance and credit through personalized guidance and education. My approach includes:
- Financial Literacy Education: I provide workshops, seminars, and one-on-one coaching sessions to educate clients on fundamental financial concepts, such as budgeting, saving, investing, and credit management. By enhancing their financial literacy, clients are better equipped to make informed decisions.
- Customized Financial Planning: I work closely with clients to develop tailored financial plans that align with their unique goals and circumstances. This includes creating budgets, setting savings targets, planning for retirement, and managing debt.
- Credit Improvement Strategies: I assist clients in understanding their credit reports and scores, identifying areas for improvement, and implementing strategies to enhance their creditworthiness. This can involve disputing inaccuracies, reducing debt, and establishing positive credit behaviors.
- Debt Management and Reduction: I help clients develop strategies to manage and reduce their debt, whether it’s through consolidating loans, negotiating with creditors, or creating repayment plans. The goal is to alleviate financial stress and move towards financial stability.
- Investment Guidance: I provide insights into various investment options and help clients build diversified portfolios that match their risk tolerance and financial goals. This includes education on stocks, bonds, mutual funds, and other investment vehicles.
- Ongoing Support and Accountability: I offer continuous support and accountability to ensure clients stay on track with their financial goals. Regular check-ins and progress reviews help clients remain motivated and make necessary adjustments to their plans.
Through these efforts, I empower clients to achieve financial independence, build wealth, and secure their financial future.
How has your experience as the eldest of eleven children influenced your approach to leadership and motivation?
While I am the eldest of eleven children, my upbringing was distinct as I was adopted and did not live with my biological siblings. This unique situation has still influenced my approach to leadership and motivation in several ways.
Knowing that I have biological siblings with different life experiences has heightened my awareness of diverse perspectives. This understanding helps me appreciate the varied backgrounds and viewpoints within my team, fostering an inclusive and empathetic leadership style.
Growing up in an adoptive family taught me resilience and adaptability. These qualities are essential in leadership, enabling me to navigate change and uncertainty with confidence. I encourage my team to be flexible and open to new ideas, helping them thrive in dynamic environments.
Although I did not grow up with my biological siblings, the knowledge of their existence instilled in me the importance of connection and relationships. I prioritize building strong, supportive relationships within my team, emphasizing collaboration and mutual respect.
My unique family background has reinforced the significance of individual growth and self-discovery. As a leader, I strive to understand the personal and professional aspirations of each team member, providing opportunities for development and growth tailored to their needs.
Understanding the complexities of family dynamics, both biological and adoptive, has deepened my empathy and compassion. I lead with a focus on understanding and addressing the emotional and practical needs of my team, creating a supportive and nurturing environment.
Recognizing that everyone’s journey is different, I motivate my team by understanding their individual motivations and aligning them with our collective goals. This personalized approach helps each member feel valued and driven to contribute their best.
While my experience as the eldest of eleven children is unconventional, it has profoundly shaped my leadership and motivational approach. I lead with empathy, adaptability, and a focus on building meaningful connections, ensuring that each team member feels supported and empowered to achieve their full potential.
What advice would you give to someone who is facing a difficult period and needs to find their inner strength?
Facing a difficult period can be incredibly challenging, but finding your inner strength is essential to overcoming adversity.
1. Acknowledge Your Feelings: Accepting your emotions is the first step. It’s okay to feel overwhelmed, anxious, or upset. Acknowledging these feelings without judgment can provide clarity.
2. Set Small, Achievable Goals: Breaking down larger challenges into smaller, manageable tasks can help create a sense of accomplishment and progress. Celebrate each small victory.
3. Seek Support: Don’t hesitate to reach out to friends, family, or a support group. Talking about your struggles can provide relief and new perspectives.
4. Practice Self-Care: Prioritize activities that nurture your physical, emotional, and mental well-being. This could include exercise, meditation, hobbies, or simply taking time to rest.
5. Stay Positive: Focus on positive aspects of your life and things you’re grateful for. This can shift your mindset and provide motivation to keep going.
6. Learn and Adapt: View challenges as opportunities for growth. Reflect on what the situation can teach you and how you can use this knowledge in the future.
7. Financial Management: Since financial stress can exacerbate difficult times, create a budget and identify areas where you can cut costs. Seek professional financial advice if necessary.
8. Stay Connected: Maintaining social connections can provide emotional support and practical help. Engaging with a community can reduce feelings of isolation.
Remember, everyone has inner strength, and often it’s through facing and overcoming challenges that we discover just how resilient we are.
Featured
The New Leadership Advantage: Why Human Judgment Matters More in the Age of AI
Artificial intelligence is changing more than the way companies work. It is changing what companies expect from their leaders.
For years, leadership was often associated with expertise. The person who knew the most, had the most experience, or could solve the hardest problem naturally moved into a position of authority.
In 2026, that model is being challenged.
AI can now analyze information, generate reports, summarize meetings, assist with strategy, write code, automate administrative work, and support increasingly complex business decisions. According to the World Economic Forum, roughly a third of workplace tasks are already automated, while organizations are placing greater value on distinctly human capabilities such as judgment, communication, empathy, and problem identification.
The strongest leaders of the next decade may therefore not be the people with all the answers.
They may be the people who know how to ask the right questions.
Leadership Is Moving From Expertise to Orchestration
AI does not eliminate the need for leaders. It changes their role.
A modern leader increasingly manages a combination of people, technology, automated systems, outside partners, and AI tools. Instead of personally controlling every decision, leaders must determine which decisions can be delegated, which require human judgment, and where technology needs stronger oversight.
This creates a new kind of leadership challenge.
Efficiency is relatively easy to measure. Trust is not.
An AI system may help a company finish a process faster, but employees still need someone who can explain why that process is changing, what the change means for their careers, and how they fit into the organization’s future.
That responsibility belongs to leadership.
Research highlighted by the World Economic Forum shows that 97% of HR leaders surveyed believe human-centered skills are more important in the AI era, while 64% say identifying new problems is becoming more valuable than simply solving existing ones.
That is an important distinction.
When technology becomes better at solving known problems, human advantage increasingly comes from recognizing opportunities and risks that technology has not yet been asked to examine.
Employees Need Direction, Not Just Technology
Companies around the world are investing heavily in AI, but buying technology is not the same as transforming an organization.
Employees are being asked to learn new systems while simultaneously wondering how automation could change their responsibilities.
This makes clarity one of the most valuable leadership skills in 2026.
People need to understand where the organization is going, why changes are happening, and what skills will help them remain valuable.
Recent workforce research points to skills gaps as one of the defining challenges facing organizations as AI adoption accelerates. Companies are increasingly focusing on reskilling, redesigning roles, improving internal mobility, and building more adaptable workforce structures.
Leaders who simply announce new technology may create uncertainty.
Leaders who connect technology with opportunity can create momentum.
The Best Leaders Will Build Future Leaders
There is another challenge developing quietly inside the AI economy.
Many entry-level tasks traditionally helped younger employees build judgment and experience. Preparing reports, performing basic analysis, handling administrative work, and solving smaller operational problems created opportunities to learn how businesses function.
AI is beginning to automate some of those tasks.
That creates efficiency today but could create a leadership-development problem tomorrow.
The World Economic Forum has warned that organizations need to rethink how younger workers gain the practical experience that traditionally prepared them for management.
Companies cannot assume leadership talent will develop automatically.
Managers will need to deliberately give employees opportunities to make decisions, evaluate AI-generated work, communicate with customers, manage uncertainty, and take responsibility for outcomes.
In other words, organizations must automate tasks without accidentally automating away the experiences that develop good leaders.
Trust Will Become a Competitive Advantage
Technology moves quickly. Human confidence usually moves more slowly.
That gap matters.
Organizations with strong leadership cultures will be able to introduce new technologies without creating unnecessary fear or confusion. Employees are more likely to experiment, learn, and adapt when leaders communicate openly about both opportunities and risks.
This does not mean leaders need to have complete certainty.
In fact, modern leadership increasingly requires being comfortable saying, “We don’t know yet, but here is how we are going to find out.”
That type of transparency can be more powerful than pretending to have perfect answers in an environment that changes every month.
The Leader of the Future Is an Enabler
The AI era is not reducing the importance of leadership.
It is exposing the difference between authority and leadership.
Authority can tell people what to do.
Leadership helps people understand where they are going.
As technology becomes more capable, the qualities that make human leaders valuable become clearer: judgment, curiosity, courage, empathy, communication, accountability, and the ability to create direction when certainty is unavailable.
The organizations that succeed will not simply have the most advanced AI.
They will have leaders who know how to combine advanced technology with capable, confident people.
That may become the defining leadership advantage of the AI age.
Leadership
The New Leadership Skill of 2026: Knowing What to Automate—and What Must Stay Human
Artificial intelligence is no longer simply changing how companies work. It is changing what companies need from their leaders.
In 2026, the question is no longer whether businesses should use AI. The bigger question is whether leaders know how to lead in an AI-powered workplace without losing the human qualities that make organizations successful.
Recent developments across the business world make this shift clear.
Google recently reorganized leadership within its DeepMind AI division as competition among major artificial intelligence companies continues to accelerate. The changes included a new leadership structure, shifting teams and a stronger push toward commercializing its Gemini technology.
At the same time, companies around the world are searching for more workers with AI-related skills. In the United Kingdom, AI or related tools appeared in 9.4% of job postings by the end of June 2026—a record high—even as overall job postings declined.
These developments point to something bigger than a technology trend.
AI has become a leadership issue.
Leaders Can No Longer Delegate AI to the Technology Department
For years, major technology decisions could be handed to the IT department.
That approach will not work with AI.
Artificial intelligence can now influence marketing, customer service, hiring, research, operations, sales, content creation and strategic planning.
That means the CEO, founder or department leader must understand enough about AI to make decisions about how it should be used.
Leaders do not necessarily need to become programmers. They do, however, need to understand what the technology can do, what it cannot do and where using it creates the most value.
The companies that succeed may not be the companies with the most AI tools.
They may simply be the companies whose leaders know how to use those tools more intentionally.
Speed Is Becoming a Competitive Advantage
One lesson coming from today’s AI race is that large organizations can have enormous resources and still struggle when decision-making becomes too slow.
Reuters reported that structural challenges, disagreements over resources and bureaucracy were among the issues cited by sources familiar with Google’s AI efforts.
That lesson applies far beyond technology companies.
Organizations must be able to test ideas, review results and make changes faster than they have in the past.
A leader who takes six months to make a decision about something competitors are testing this week could quickly find the company behind.
This does not mean making reckless decisions.
It means creating a culture where responsible experimentation is encouraged.
The Human Side of Leadership Is Becoming More Valuable
There is an interesting paradox happening.
As machines become better at performing tasks, the skills that make us uniquely human may become even more valuable.
AI can create a report.
It cannot replace trust.
AI can analyze customer data.
It cannot build genuine relationships.
AI can recommend a strategy.
It cannot take responsibility for the consequences of that strategy.
Strong leaders will need emotional intelligence, communication skills, judgment, creativity and the ability to bring people together around a common vision.
Technology can support leadership. It cannot replace leadership.
Leaders Must Decide What Should Remain Human
One of the most important questions executives should ask is simple:
Just because we can automate something, should we?
Companies should consider the customer experience before replacing every human interaction with automation.
The same applies internally.
A difficult employee conversation probably should not become an automated email.
A major client experiencing a problem may need a person rather than a chatbot.
A team facing major organizational changes needs leadership, communication and reassurance.
The winning organizations will likely create the right combination of technological efficiency and human connection.
Training Matters More Than Buying Another Tool
Businesses are already experiencing benefits from AI, but implementation remains uneven.
A 2026 Goldman Sachs survey found that 76% of participating small businesses reported using AI. Among those using it, 93% reported a positive impact and 84% pointed to increased efficiency and productivity as the main benefit. Yet only 14% said AI was fully integrated into their core operations, while 73% said additional training and implementation resources would help.
That gap is important.
Buying technology does not automatically create transformation.
Companies must teach people how to use it.
Leaders should create clear guidelines, provide training and identify practical ways AI can improve existing workflows.
The Leaders Who Win Will Be Adaptable
Every major technology shift creates winners and losers.
The difference is often not the technology itself.
It is how quickly people adapt to it.
The leaders who thrive in this next era will not necessarily be the people who know the most about artificial intelligence.
They will be the people who remain curious enough to learn, confident enough to change and disciplined enough to know where technology belongs—and where human leadership still matters most.
Because in an increasingly automated world, leadership may become more human, not less.
Innovation
How Leadership Changes When AI Becomes a Daily Coworker
Not long ago, artificial intelligence lived quietly in the background—powering search engines, automating reports, and optimizing supply chains. Today, it sits beside employees as a daily coworker, drafting ideas, analyzing strategy, and influencing decisions in real time. This shift marks more than a technological upgrade; it represents a fundamental rewrite of leadership itself. Managers are no longer leading teams composed solely of people—they are guiding hybrid workforces where human judgment intersects with machine intelligence. As AI moves from tool to collaborator, leadership is being redefined in ways many organizations are only beginning to understand. The question facing executives is no longer whether AI will change work, but whether leaders are prepared to change with it.
From Managing People to Managing Human–AI Collaboration
Gone are the days when leadership was solely about managing people and processes. The rise of AI has shifted the role of leaders from controllers to orchestrators. Now, leaders must harmonize human creativity with AI’s efficiency, leveraging data-driven decision-support systems.
Key challenges for leaders in this new model:
- Determining who does what: What should humans handle? What is best left to AI?
- Shifting focus from control to orchestration, blending human ingenuity with machine precision.
- Designing workflows that optimize both human and machine strengths.
Leadership is no longer about directing a single workforce—it’s about managing a dynamic collaboration between humans and machines.
Decision-Making in the Age of AI Assistance
In an AI-augmented workplace, leaders are not just relying on instinct or experience to make decisions—they’re now balancing intuition with algorithmic insights. With AI providing instantaneous data-driven recommendations, the temptation to follow these outputs blindly is strong. However, the challenge for leaders is to not simply trust AI but to question it, challenge it, and understand its limitations.
New leadership responsibilities include:
- Questioning AI outputs and ensuring they align with organizational goals.
- Balancing intuition with AI insights to make informed decisions.
- Maintaining critical thinking and not blindly relying on AI’s recommendations.
AI can assist, but leaders remain responsible for the final call.
Emotional Intelligence Becomes More Important, Not Less
As AI takes on more analytical tasks, the need for emotional intelligence in leadership only grows. Machines may excel at crunching numbers, but they lack empathy, understanding, and the ability to motivate human teams. Leaders must step up as emotional anchors, providing communication, trust, and psychological safety in a rapidly changing work environment.
Key emotional intelligence skills leaders need:
- Communication to clarify AI’s role and manage expectations.
- Trust-building to reduce employee concerns about AI.
- Psychological safety to create an environment where employees feel valued, not threatened.
- Conflict resolution to address concerns over AI integration and potential job displacement.
Strong leadership in this new AI-augmented world is defined not by technical know-how but by the ability to connect with and support people through technological change.
Redefining Skills and Talent Development
AI’s rise demands a shift in how leaders approach talent development. It’s no longer enough to focus solely on traditional skills. Leaders must foster AI literacy, adaptability, and creative problem-solving across their teams.
Areas leaders should focus on for skill development:
- AI literacy to ensure employees are comfortable working with AI tools.
- Adaptability to respond to ever-changing technological advancements.
- Creative problem-solving to encourage employees to think beyond AI’s capabilities.
- Continuous learning to keep teams evolving as new tools and technologies emerge.
Leaders must cultivate evolving capabilities, coaching their teams to leverage AI while honing skills that machines cannot replicate. The role of leadership shifts from being a manager to being a coach and capability builder.
Ethics, Trust, and Responsible AI Leadership
As AI becomes more integrated into the workplace, it also brings new ethical challenges. Bias in algorithms, privacy concerns, and the risk of over-automation are just a few of the issues leaders must address.
Ethical responsibilities for leaders:
- Establishing guidelines for AI usage to ensure fairness and transparency.
- Ensuring data privacy and protecting employee/customer information.
- Addressing biases in AI algorithms to prevent unintended discrimination.
- Building trust by being transparent about AI’s role in decision-making.
Ethical leadership isn’t just about protecting privacy or avoiding discrimination—it’s about creating a culture of trust, where AI is used to enhance human capabilities rather than diminish them.
The Leader as a Learning Partner with AI
In this new landscape, leaders are no longer the all-knowing authorities they once were. Instead, they must embrace a mindset of continuous learning, staying ahead of the curve by becoming proficient in AI tools themselves.
Shifting leadership responsibilities include:
- Learning AI tools to understand their potential and limitations.
- Modeling curiosity and an eagerness to experiment with new technologies.
- Fostering a culture of collaboration between AI and human expertise.
- Helping teams adapt to AI as a thinking partner, not just a tool to be controlled.
Leaders who adapt to this new dynamic will thrive by fostering an environment of mutual learning between AI and their teams.
Leadership in the AI-Augmented Future
The future of leadership is one where human intuition and AI-driven insights work side by side. As AI becomes an indispensable part of the daily workflow, leaders must evolve from traditional management models to ones that prioritize collaboration, ethical decision-making, and continuous learning. Success in this new era will depend on a leader’s ability to blend technological awareness with emotional intelligence, all while guiding teams through the complexities of an AI-augmented workplace. Leaders who embrace this shift, balancing human understanding with data-driven strategies, will not only survive—they will thrive in the AI-powered future.
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