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Diggin Deep

5

with
Gregg Diggs

There is surface-level music, and then there is the treasure buried underneath. Gregg Diggs, the sophisticated curator of "Diggin' Deep," is our resident musical archaeologist. Pictured in his sharp suit and headphones, Gregg brings a touch of class and decades of crate-digging experience to the team. He specializes in unearthing the rare soul, funk, and R&B gems that time forgot but the groove never did. Whether he is rediscovering a lost vinyl classic or tracing the original samples behind today’s biggest hits, Gregg Diggs ensures that the history of the music is treated with the respect it deserves.

Palette & Purpose
Diggable Abstract Artwork

For Gregg Diggs, a blank canvas and a young mind hold the same potential: limitless possibility. As the creative soul behind "Palette & Purpose," Gregg bridges the gap between fine art and life leadership. He believes that the principles of great design, balance, perspective, and the courage to make bold strokes, are the exact tools needed to build a successful future. Whether he is unveiling his latest visual masterpiece or offering critical guidance to the next generation of talent, Gregg is dedicated to helping others find their unique style. In this column, he explores how the discipline of the studio translates into the art of living.
Artwork art

Time Shift Painting (18 x 24)

Art artwork

SO, YOU MADE IT…NOW WHAT? THE IMPORTANCE OF MENTORSHIP 

By Gregg Diggs 

You’ve worked hard, incredibly hard, to sit behind that big fancy desk, to verbally caress that microphone, to stand in the musical spotlight, or maybe even to work behind the scenes calling the shots. But at what cost, and with whose help?

So many people strive for success in the entertainment industry, but once you’ve made it to that highly coveted “Power Player” position…NOW WHAT? Long after you’ve popped open that celebratory bottle of champagne, implemented your vision, marked your territory, and made a name for yourself, do you simply revel in the glory of your success, or do you think about ways
to help others achieve their goals and dreams?

I strongly believe that mentorship is extremely important, especially for African Americans navigating the competitive and sometimes biased music and entertainment industry. I know first-
hand how knowledgeable, insightful, and inspiring mentors can shape a career and a life.

The late great Gil Scott-Heron, the musician and poet behind “The Revolution Will Not Be
Televised,” was my first mentor, and my professor for a college creative writing course. I still remember him handing me back one of my short story submissions that I thought was perfect. “This is good, Diggs,” he said, “but I know and you know you can do better.”

That strong, firm challenge lit a fire in me and made me want to give my very best. He taught me discipline, structure, and the importance of striving for excellence, while also helping me recognize potential I had not yet seen in myself. Those lessons planted seeds that later grew into my book The Musical DNA of Gregg Diggs and other literary projects.

Although Gil Scott-Heron believed in my potential, radio legend Donnie Simpson gave me the opportunity to explore and utilize even more of it. He hired me, a club DJ with no radio experience, as his Music Director at WKYS-FM, a bold move that was revolutionary for the Washington, D.C. radio market.

Beyond teaching me radio strategies, on-air presentation, and the dynamics of music programming, Donnie embodied strength, integrity, and leadership. Observing and learning from him showed me that mentorship is not only about imparting information and wisdom, but also about modeling values and character that mentees can carry forward in their own lives.

Because I had such exemplary mentors who opened doors for me, I vowed that if I were ever in a position of power, I would follow their example and pay it forward. When I later had the opportunity to hire young professionals at Black Entertainment Television (BET) and later at Sirius XM, I looked for creativity, enthusiasm, attention to detail, and a drive for professional growth.

I encouraged my mentees to participate fully, ask questions, and develop their own distinctive voices. Seeing them take responsibility, make decisions, and flourish was a vivid reminder that mentorship is not just about teaching skills, it is also about nurturing talent and helping it reach its full potential.

Over time, their dedication, innovation, and hard work propelled them forward. Many went on to hold high-profile positions, shaping music and culture in meaningful ways. Their journeys illustrate how skill, preparation, and opportunity can transform potential into extraordinary achievement.

For many with ambitions in the entertainment industry or any field, mentorship can feel elusive and out of reach, yet it is often closer than it appears. Teachers, colleagues, or industry professionals already doing the work you aspire to can become mentors if you know how to connect with them.

Finding a mentor is not about waiting for someone to notice you. It is about preparation, persistence, and being ready when opportunity presents itself. By showing up, demonstrating your abilities, and remaining open to learning, you open the door to insight that can shape your career and your life.

Also, mentorship does not always arrive through formal introductions or polite channels, and sometimes it begins when preparation meets the courage to be seen. One music industry veteran once shared how a bold attempt to reach a mentor changed his career. During an internship, he sent a memo to the record label president outlining some of his ideas and what he would do if he ran the company.

His branch manager was outraged, but the next morning they discovered the president had read the memo and was very impressed. He offered that bold intern a position at his new label venture. That audacious move could have easily ended in catastrophe, but fortunately, in this case, it worked. I’m not encouraging anyone to send unsolicited memos to executives. The lesson here is that preparation, initiative, and thoughtful risk-taking can sometimes position you
for opportunity and advancement.

Mentorship can be a life-altering cycle. The guidance and wisdom we receive often return like a boomerang in ways we may not expect. Success is measured not only by what we achieve, but by the doors we open for others.

So, when you reach your position of influence and power, whether behind the mic, in the executive suite, or in the bright glare of the spotlight, don’t stop at the finish line. Look around, reach out, and pass the baton by mentoring someone, giving them the chance to run their own race. Don’t let your success end with you. Reach back, lift someone up, and be the mentor who helps the next generation find their voice, their path, and their destiny.