Understanding what makes you uncomfortable about selling is the first step to overcoming it. Is it fear of rejection? Worrying about being too pushy? Or doubting your product’s value? Pinpointing the root cause helps you address it effectively.
Real-Life Example: Barbara Corcoran’s Early Sales Anxiety
Barbara Corcoran, founder of The Corcoran Group and investor on Shark Tank, admitted early in her career that she was intimidated by the idea of selling high-end real estate in New York. She feared not being taken seriously due to her modest background. By acknowledging that fear and focusing on her deep knowledge of the market and personable style, she gained confidence and built one of NYC’s top real estate firms. Her self-awareness was key to overcoming sales anxiety.
Instead of viewing selling as “convincing someone to buy,” think of it as sharing your passion or offering solutions to problems. This mindset shift can make the process feel more natural and authentic.
Real-Life Example: Blake Mycoskie and TOMS
Blake Mycoskie, founder of TOMS Shoes, changed the perception of selling by focusing on storytelling and impact. Rather than just pitching shoes, he shared the One for One mission: for every pair sold, a pair would be donated to a child in need. This purpose-driven approach resonated with customers and created a global movement. Mycoskie wasn’t just selling shoes—he was sharing a cause, which led to rapid brand growth and deep customer loyalty.
Begin by sharing your product or service with trusted friends or small groups before expanding to larger audiences. This gradual approach can help you build confidence without feeling overwhelmed.
Real-Life Example: Melanie Auld Jewelry’s Grassroots Growth
Melanie Auld began her jewelry business by selling at local boutiques and pop-up markets in Canada. Starting small allowed her to test designs, gather feedback, and build a loyal customer base. As her confidence and demand grew, she expanded to e-commerce and opened a flagship store. Her gradual, community-focused approach laid the foundation for a successful and scalable brand
Rejection is a natural part of sales, but it doesn’t define your worth or your product’s value. Practice exposure therapy—such as asking for something unexpected—to desensitize yourself to hearing “no.”
Real-Life Example: Jia Jiang’s 100 Days of Rejection
Entrepreneur Jia Jiang undertook a personal project called 100 Days of Rejection, where he deliberately sought out situations where he expected to be turned down—like asking a stranger to let him play soccer in their backyard or requesting a “burger refill” at a fast-food restaurant. This experiment helped him overcome the fear of rejection and build confidence. His journey later became a bestselling book and TED Talk, proving how embracing rejection can lead to growth and unexpected opportunities.
Remind yourself why you’re passionate about your product or service by listing its benefits and successful outcomes for past customers. Enthusiasm is contagious and can boost your confidence during sales conversations.
Real-Life Example: Jamie Kern Lima and IT Cosmetics
Jamie Kern Lima, founder of IT Cosmetics, stayed deeply connected to customer stories—often reading letters from people whose skin conditions were improved by her products. This genuine passion fueled her confidence, even when facing rejection from major retailers. Her persistence paid off when she secured a live spot on QVC, passionately demonstrating the product herself, which led to a sellout in minutes. Eventually, she sold the brand to L’Oréal for $1.2 billion.
Real-Life Example: HubSpot’s Inbound Marketing Strategy
Track your successes—even minor ones—to stay motivated and build momentum over time. Recognizing progress helps reinforce positive feelings about selling.
Real-Life Example: Sara Blakely’s Win Journal
Sara Blakely, founder of Spanx, kept a journal to record her small victories throughout her entrepreneurial journey. Whether it was securing a meeting with a retailer or getting positive customer feedback, she celebrated each step. This practice helped her maintain confidence and perspective as she built Spanx into a billion-dollar brand. Blakely credits this habit as a key tool in sustaining her motivation during tough times
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