<p id=”par-1_74″>Long before fame, <a href=”https://www.cheatsheet.com/tag/taylor-swift/?swcfpc=1″>Taylor Swift</a> sought the opportunity to <a href=”https://www.cheatsheet.com/music/”>perform</a> for an audience whenever it presented itself. She entered karaoke competitions, became involved with musical theater, and sang the national anthem at sporting events. By the age of 12, she had the opportunity to sing the anthem at the US Open. A producer didn’t think she’d be a good fit, though. Years later, he still views this as the biggest mistake of his career.</p>
<h2 class=”wp-block-heading” id=”h-taylor-swift-lost-her-chance-to-perform-the-national-anthem-at-the-us-open”>Taylor Swift lost her chance to perform the national anthem at the US Open</h2>
<p id=”par-2_26″>Swift has known she <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-admitted-parents-embarrassed-early-ambition.html/?swcfpc=1″>wanted to be a singer</a> since an early age and did all she could to get in front of a live audience.</p>
<p id=”par-3_50″>“When I was 11 years old, it occurred to me that the national anthem was the best way to get in front of a large group of people if you don’t have a record deal,” Swift said, per <a target=”_blank” href=”https://whyy.org/articles/taylor-swift-sports-performing-national-anthem-pennsylvania-phillies/” rel=”noreferrer noopener”>WHYY</a>. “So I started singing the national anthem anywhere I possibly could.”</p>
<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/03/Taylor-Swift.webp?strip=all&quality=80″ alt=”Taylor Swift wears a white dress and stands in front of a microphone with a guitar.” class=”wp-image-3784474″><figcaption class=”wp-element-caption”>Taylor Swift | Jason Squires/WireImage</figcaption></figure>
<p id=”par-4_59″>When she was 12, she had the opportunity to sing the national anthem at the US Open. Ultimately, she didn’t perform that year because a producer thought she wouldn’t be the right fit. She was a <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-opens-up-about-leaving-country-music-behind.html/”>young country artist</a>, and she would have been performing in New York. Upon reflection, however, this was one of the producer’s biggest regrets.</p>
<p id=”par-5_55″>“Her father asked us if we’d put her on Arthur Ashe Kids’ Day, and we said: ‘She’s just taking off, she’s really country, we don’t think that would play in New York,’” producer Michael Fiur said on the <em>Served </em>podcast (via <a target=”_blank” href=”https://www.the-express.com/sport/tennis/149880/Taylor-Swift-US-Open-tennis-sport” rel=”noreferrer noopener”>Express</a>). “I do not share this publicly very often. Worst decision I ever made.”</p>
<h2 class=”wp-block-heading” id=”h-taylor-swift-said-she-tried-to-perform-at-every-opportunity”>Taylor Swift said she tried to perform at every opportunity</h2>
<p id=”par-6_20″>While Swift had some massive opportunities as a young singer, she said she was happy singing karaoke at that age.</p>
<p id=”par-7_20″>“Singing country music on that karaoke machine was my favorite thing in the world,” she told <a target=”_blank” href=”https://www.rollingstone.com/music/music-country/the-very-pink-very-perfect-life-of-taylor-swift-107451/” rel=”noreferrer noopener”>Rolling Stone</a> in 2009.</p>
<p id=”par-8_10″>She entered competitions and continued joining them until she won.</p>
<p id=”par-9_16″>“I sang every single week for a year and a half until I won,” she said.</p>
<h2 class=”wp-block-heading” id=”h-she-revealed-another-early-career-disappointment”>She revealed another early career disappointment</h2>
<p id=”par-10_20″>Not long after her thwarted attempt at the national anthem, Swift booked a job opening for Kenny Chesney on tour. </p>
<p id=”par-11_16″>“This was going to change my career,” she told <a target=”_blank” href=”https://time.com/6342806/person-of-the-year-2023-taylor-swift/” rel=”noreferrer noopener”>Time</a> in 2023. “I was so excited.” </p>
<p id=”par-12_28″>It was a major opportunity, but it soon fell apart <a href=”https://www.cheatsheet.com/entertainment/kenny-chesney-revealed-fired-taylor-swift-opener-tour.html/”>because of her age</a>. A beer company sponsored the tour, and they could have an underage Swift performing.</p>
<figure class=”wp-block-image size-full” id=”emb-2″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/03/Kenny-Chesney-Taylor-Swift-1-1.webp?strip=all&quality=80″ alt=”Kenny Chesney wears a cowboy hat and stands with Taylor Swift. He holds a cup.” class=”wp-image-3784477″><figcaption class=”wp-element-caption”>Kenny Chesney and Taylor Swift | Rick Diamond/WireImage</figcaption></figure>
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Taylor Swift Admitted Her Parents Were ‘Embarrassed’ by Some of Her Early Ambition </a>
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<p id=”par-13_20″>“[My mom] was weeping,” Swift said. “Her head was in her hands as if there had been a family emergency.” </p>
<p id=”par-14_14″>It was one of her biggest career disappointments at that point in her life.</p>
<p id=”par-15_5″>“I was devastated,” she said. </p>
<p id=”par-16_16″>Chesney felt so bad that <a href=”https://www.cheatsheet.com/entertainment/taylor-swift-billionaire-status.html/”>he paid her</a> for the tour even though she couldn’t perform.</p>