7 Ways Aspiring Millionaires Go Wrong, According To Self-Made Business Icon Diane Gilman
Written by
Gabriel Vito
Edited by
Amen Oyiboke
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Diane Gilman didn’t become a millionaire in her 20s. Or her 30s. Or even her 50s.
She hit her peak at 60, creating a line of jeans for middle-aged women and building a $150 million fashion empire. Now 79, Gilman is best known as the “Jean Queen” from her two-decade run on QVC and HSN. Unconventional and inspiring, her road to success was anything but easy.
She grew up in a violent household, had a scholarship stolen from her by her parents, and battled breast cancer in her 70s. Despite it all, she never gave up on her dream. In an interview with the Seeds of Success podcast, Gilman reflected on her journey and revealed the biggest mistakes she sees aspiring millionaires make.
Here’s what holds most people back, and how she says to break through.
Waiting for the Right Time
Gilman’s parents burned the letter informing her of a four-year scholarship. She didn’t find out until she was 52.
“I could have had a totally different life,” she said. “But I was their property.” So she struck out on her own at 17, with just a quarter in her pocket.
Her message: don’t wait. You’ll miss your moment if you’re waiting for ideal conditions or permission.
Believing It’s Too Late
Gilman didn’t start her most successful venture until age 60. That’s when she designed jeans that flattered aging bodies, something no one else was doing, and sold millions
“You’re the luckiest person in the world if you get to do something every day that you’re truly in love with,” she said.
Her rise came decades after most people retire. Aspiring millionaires often underestimate how long it takes and how much time they still have.
Comparing Themselves to Others
“If you’re going to play that comparison game,” she warned, “you are going to mutilate your peace of mind.”
Gilman says comparing yourself to younger, faster, or flashier entrepreneurs is a recipe for misery. Instead, focus on your vision and your own pace.
Ignoring Their Inner Voice
Gilman knew from childhood that she wanted to be a designer. Even when others mocked her, she never stopped dreaming.
“I was born this way,” she said. “From a very young age, I said, ‘I want to be a fashion designer.'” Aspiring millionaires go wrong when they ignore their instincts in favor of what’s “practical.”
Underestimating Struggle
Gilman has battled more than most poverty, rejection and cancer.
Before her first chemotherapy treatment at 72, she told herself, “Nobody likes a cranky, bitter old lady. I was going to have to be the best me I could be.”
Struggle isn’t a sign to stop. It’s part of the path. “Cancer was about the only thing that could stop me, or I would have just barreled through life,” she said.
Wasting Time on the Wrong Things
Ask Gilman what her most valuable possession is, and she won’t say money. She’ll say, time.
“How are you going to use that?” she asks. “How are you going to take care of that and nurture it, and get something lasting? Tomorrow’s not promised to us, and the past is the past.”
Aspiring millionaires often waste time doubting themselves, overthinking, or chasing the wrong goals. Gilman says every minute counts.
Giving Up Too Soon
“Most women give up somewhere toward the end of middle age,” Gilman said.
But she didn’t. She kept working, kept believing, and kept building even when no one else believed in her.
Her final advice? “Follow your dreams. Believe they can come true. And follow your dreams.”
When All Else Fails, Keep Going
Diane Gilman’s journey proves that success isn’t about starting early; it’s about refusing to stop. She didn’t have the right support, education, or timing. What she had was clarity, grit, and an unshakable belief in her dreams.
Whether you’re 25 or 65, the takeaway is the same: don’t wait for permission, don’t waste time comparing, and don’t give up when it gets hard. As Gilman puts it, “Follow your dreams. Believe they can come true. And follow your dreams.”
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