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‘Define Yourself’: Stedman Graham, Leadership Coach and Life-Partner of Oprah Winfrey, Tinsels Flagler Tiger Bay

December 18, 2025 | FlaglerLive | Leave a Comment

“When we talk about self-leadership, you can’t do that unless you know yourself,” Stedman Graham told the Tiger Bay audience.
“When we talk about self-leadership, you can’t do that unless you know yourself,” Stedman Graham told the Tiger Bay audience. (Tiger Bay)

When Stedman Graham – a management and marketing consultant, leadership guru, author of bestselling, motivational you-too-can-be-a-success books, and life-partner of Oprah Winfrey – spoke to the Flagler Tiger Bay Club Wednesday evening, he related a personal story from his early teens.

Growing up in Whitesboro, New Jersey – a segregated African-American community founded by his ancestor, George H. White – Graham had two hard-working parents and five siblings, including two younger brothers who had intellectual disabilities. Graham was 14 years old in 1965 when, he told the sold-out Tiger Bay audience, he began announcing to anyone who would listen: “I’m going to college!”

But an adult family friend Graham called “Mr. T.A.,” hearing young Stedman’s proclamation, replied: “You’re not going to college because your family’s too stupid.”

With Graham already stung by merciless teasing from his peers because of his brothers’ challenges, Mr. T.A.’s rebuke knee-capped Graham’s self-esteem even as the put-down made him both angry and motivated, he told an audience of 120 or so at the sold-out, holiday-themed dinner event at the Hammock Dunes Club.

This planted the seeds of two mantras that Graham would later elaborate in his 12 books, and which he related to the Tiger Bay Club audience: “It doesn’t matter how the world defines you,” Graham said. “It only matters how you define yourself.”

He also spoke on his concept of “Identity Leadership,” which he said is based on his philosophy that “One cannot lead anyone else until you first lead yourself.” The title of Graham’s latest book, published in 2019, is Identity Leadership: To Lead Others You Must First Lead Yourself.

Graham earned a bachelor’s degree in social work from Hardin-Simmons University in 1974. He then served five years in the Army, mostly in Germany, where he played in a European professional basketball league. (Even as a youngster, he said, “Basketball helped me believe in myself.”) While in the Army, he also earned a master’s degree in education from Ball State University.

After the Army, Graham landed a job with the federal corrections system, working his way up to become director of education at the U.S. Metropolitan Correctional Center in Chicago. It was in that city, Graham said, that he met an up-and-coming television producer and hostess of her own show: “You may know her as Oprah,” Graham said, the only mention he made of his life partner. (Though never married, the couple have been together since 1986.)

In 1988, Graham founded S. Graham and Associates, a management, marketing and consulting firm. Along with serving for a time as an adjunct professor at the Northwestern Kellogg School of Business, Graham penned such books as The Ultimate Guide to Sport Event Management and Marketing (1995), You Can Make It Happen: A Nine-Step Plan for Success (1997), Teens Can Make It Happen: Nine Steps for Success (2000), Diversity: Leaders Not Labels – A New Plan for the 21st Century (2006), Identity: Your Passport to Success (2012), and others.

Flagler Tiger Bay Club  President Jay Scherr with Graham. (Tiger Bay)
Flagler Tiger Bay Club President Jay Scherr with Graham. (Tiger Bay)

Graham was introduced by Flagler Tiger Bay Club co-founder and president emeritus Greg Davis, who called him “my very good friend.” Jay Scherr, current Tiger Bay president, told FlaglerLive that it was Davis’s personal relationship with Graham that led to Graham’s speaking engagement.

Graham opened his talk by approximately quoting lines from T.E. Lawrence’s Seven Pillars of Wisdom (Lawrence wrote them in the prose introduction to his book, but misattributions and faulty quoting has often transformed them into verse, as Graham did last night):

All people dream, but not equally.
Those who dream by night in the dusty recesses of their mind,
Wake in the morning to find that it was vanity.
But the dreamers of the day are dangerous people,
For they dream their dreams with open eyes,
And make them come true.

Lawrence wrote those words about the dreams of 20 million Arabs having their own nations (“I meant to make a new nation, to restore a lost influence, to give twenty millions of Semites the foundations on which to build an inspired dream-palace of their national thoughts”), not about individuals self-actualizing themselves. The evening of course was not about the right of Arabs to their own nations.

Early in his talk, Graham exhorted the crowd to “be interactive” as he leisurely paced back and forth in the room’s open circle surrounded by tables packed with patrons who had paid $80 or $90 to attend. (There was a limit to the interactivity: though Graham is in innumerable videos, photographs and recordings all over the web, photography, video or audio recording by anyone in the Tiger Bay crowd was strictly and inexplicably prohibited. The restriction accompanies, say, the speaking engagements of the prickly Clarence Thomas, the supreme court justice. It has never before cloaked a speaker at Flagler Tiger Bay. Media were exempt from the photography restriction, as was a publicist who photographed the event.)

“When we talk about self-leadership, you can’t do that unless you know yourself,” Graham said, getting closer to Montaigne than to Lawrence. He then asked, “What happens if you don’t know yourself?” to which various audience members responded in various ways, including one woman who answered, “You follow someone else.”

Graham noted that “there are 8 billion people in the world today, and how many can lead themselves?” He answered himself by saying, “99.99.99.99 percent cannot.”

Most people are so caught up in the drudgery of working 9-to-5, five-days-a-week jobs “that they forget to think, they forget to design their own future,” he said. “The world says it will define you, and it will define you by the color of your skin,” or define women as subordinate, Graham added.

He peppered his talk with other aphorisms: “You will never find freedom on the outside, only on the inside.” “The process of success is the same for everyone.” “The world’s going to try to take you down sometimes: ‘Why don’t you sit down, quit, give up. This time you can’t succeed.’ But you’re not a failure when you fall down – you’re only a failure when you what?”

To which numerous audience members responded in near unison: “You don’t get up.”

Scherr, the Tiger Bay president, said that part of the non-partisan club’s mission is “education, developing civic leaders and connecting the community.” That mission was aided by Graham because “his expertise is leadership, and what a dynamic and inspiring topic – especially his views on self-leadership.” Landing him as a speaker could no have been inexpensive for the club’s budget, though its monthly lunch prices are going up next year. ( Scherr declined to specify the amount of Graham’s speaker fee, but added his appearance would not have been possible without the financial support of numerous sponsors.)

The club continued its tradition of giving its Fang and Claw Award to the member who, during the concluding question-and-answer session, asks the question that prompts “the most illuminating response.” Joe Saviak, the club’s second vice president, and board member Trish Giaccone, named Monica Garcia the winner for her question about how to best coach others using one’s own experiences.

The event was attended among others by Flagler Schools Superintendent LaShakia Moore, Flagler County Commissioner Greg Hansen, Flagler Cares CEO Carrie Baird, Circuit Judge Joan Anthony, Volusia County Judge Chris Miller and County Judge Katherine Miller–who has just been appointed circuit judge–and other area judges.

Graham spoke earlier in the day to 250 students at Matanzas High School, a group that also included students from Flagler Palm Coast High School. At the event, he sold out of the books he and his publicist had brought along.

Graham signing books. He sold out. (Tiger Bay)
Graham signing books. He sold out. (Tiger Bay)
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