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Working and Leading Across Generations By Deborah Gray-Young

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Deborah Gray-Young  is a former advertising agency executive who now serves as a trusted advisor to senior executives and SMB CEOs. Known for distilling complexity, challenging assumptions, and clarifying high-stakes situations, she brings candor, strategic insight, and a grounded perspective that helps leaders see possibilities and lead with intention. We talk a lot about generational differences, especially in the workplace. Sometimes so much so that it becomes a self-fulfilling prophecy. Labels like Boomer, Gen X, Millennial, and Gen Z can help us spot broad trends in values, motivators, and communication styles. But they can also lock us into assumptions and stereotypes that limit real leadership.  Over two editions, Leadership Axis will unpack the generational puzzle, without getting lost in the labels and stereotypes, so you can focus on leading people, not categories. We’ll unpack motivations, communication styles, and decode generational differences, some of the p...

Midlife Is Not the End – It’s the Boss Era You Were Born For by Conchetta Gibson

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Conchetta Gibson is an Empowerment and Lifestyle Coach for women 40+ who believe aging is not a  limitation but a glow up. Known for her Aging Fiercely movement,  Conchetta helps women reclaim  confidence, wellness, purpose, and joy in midlife and beyond. They say that midlife is when women slow down, disappear into the background, and just accept that  “this is as good as it gets.” But they forgot to tell us the truth. Midlife is not an ending. It’s a  reintroduction. We get to reinvent ourselves. Somewhere between raising our families, our relationships, and taking care of everyone else’s  dreams, many women lose sight of themselves and forget to put themselves on their “to-do” list. We wake  up one day and don’t recognize the woman in the mirror, not because she’s gone, but because she’s  been waiting. Waiting to be chosen. Waiting to be prioritized. Waiting to be free. I know this because I lived it. I didn’t write my first book until my 50’s...

BOSS Member Spotlight: Jada Samuels

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Jada Samuels is the founder and CEO of Jada Juice, a wellness beverage brand she started at 17 years old with a mission to create generational health through cold-pressed juices. Jada Juice continues to grow through online sales via Jadajuice.com and partnerships with local businesses, including Sip and Savor. What were some obstacles that you faced in the beginning process of starting your business or career?  I founded Jada Juice when I was 17 years old. At the time, I was a junior in high school, and the world was experiencing the nationwide COVID-19 pandemic. I had zero prior entrepreneurial experience, so starting a business was new territory for me. In the process of launching Jada Juice, I faced internal pressure and self-doubt. I struggled with navigating where to start and maintaining faith during this time of not knowing what was to come. What inspired you to break into your industry?  Growing up as a basketball athlete, health and wellness have always been a prior...

Your Next Chapter Requires You to Let Go of Perfection and Control by Monique Caradine-Kitchens

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In my last article , I shared a conversation between my best friend and me. We are two women in our 50s, both solopreneurs, and we’ve become accustomed to carrying the full weight of our businesses and our decisions. The conversation that day reminded us that operating this way for prolonged periods of time can hinder our growth. Since then, I’ve been thinking about something else that tends to hinder the growth of so many women: Perfectionism. Not the neat, organized, color-coded kind. I’m talking about the deeper kind that turns bold ideas into endless planning…the kind where big dreams turn into delayed action. For women who are leaders, professionals, and business owners, perfectionism often disguises itself as responsibility. We want to get it right. We don’t want to let people down. We don’t want to fail publicly. So we wait until we “feel” ready. All of which is rooted in a need for control as well as fear (that’s a whole topic for another day). But here’s the truth: you do not ...

The Mess You Leave Behind: You Can’t Take It With You by Tammecia Smith

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Tammecia Smith  is a monument dealer with over 17 years in the death care industry. She is the owner of Melanated Memorials, a diverse line of headstones and monuments featuring African American angels. She’s dedicated to transforming the memorial industry by offering high-quality memorials that honor memories while celebrating diversity.    As a follow-up to my previous post, I would be remiss not to share some of the most important information I’ve gathered over the years working in death care — specifically when it comes to “finding the money.” This isn’t about greed. This is about the next of kin who has to make funeral and burial arrangements — and discovers they need to come up with $15k by the day of service. Who has disposable income like that lying around in this economy?  How do you find the funds your secretive family member always told you were “in place,” but didn’t say where? Here are my tips for finding the funds — free of charge. 1️⃣ Employment &...

The Mess You Leave Behind: Things to Handle Before You Pass Away by Tammecia Smith

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Tammecia Smith is a monument dealer with over 17 years in the death care industry. She is the owner of Melanated Memorials, a diverse line of headstones and monuments featuring African American angels. She’s dedicated to transforming the memorial industry by offering high-quality memorials that honor memories while celebrating diversity.    I get it — life is hard, and death feels scary. Some people believe that discussing their demise is somehow summoning it. From years of experience in the death care industry, here’s the  honest truth: Death isn’t the enemy. Avoidance is. Avoidance protects no one — it leaves families overwhelmed and unprepared while grieving. In this line of work, we talk about death like it’s a regular Tuesday. Not because we lack compassion, but because compassion is the job. We see the aftermath — the arguments, confusion, and frustration that could have been avoided with a plan in place. What you do (or don’t do) today will continue to impact the...

BOSS Member Spotlight: Cheryl Monroe

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Cheryl Monroe is a highly decorated combat veteran, author, speaker, United Nations Peace Ambassador, and purpose-driven entrepreneur. As CEO of CK Management & Consultant Group and The Cleaning Advantage, she helps organizations build structure, scale with confidence, and turn opportunities into lasting impact through disciplined execution and leadership . What obstacles did you face at the beginning of starting your business or career? The biggest obstacle was transitioning from a structured military environment into the unpredictable world of entrepreneurship. In the Army, success is guided by clear systems and command. In business, I initially struggled with the lack of infrastructure. I also had to overcome being underestimated, particularly as a Black woman stepping into government contracting. But those challenges shaped the operational excellence and disciplined execution that define my companies today. What inspired you to break into your industry? I saw a gap in the comm...