Meet Cynthia Usui, A Career Break Advocate & Chief Empowerment Officer of Sekaia Inc.

Savvy Spotlight is a monthly feature introducing foreign and Japanese women at the frontline of what’s successful, contributing, cool, unique and interesting in the city.

Born in 1959 into a Chinese–Filipino family in the Philippines, Cynthia Usui, Chief Empowerment Officer of Sekaia Inc., came to Japan in 1980 as a government-sponsored international student and graduated from Tokyo University of Foreign Studies. She once imagined a traditional professional path, but life took her across countries and roles, including a long period as a full-time homemaker. Married to a Japanese diplomat, she spent nearly two decades raising her daughter while living in multiple countries before eventually becoming a Japanese national and calling Tokyo home.

At age 47—when most people believe “it’s too late to start over”—Cynthia re-entered the workforce with a part-time cafeteria job. She began what would become one of Japan’s most remarkable second-career stories. From hospitality roles at major hotels, including ANA InterContinental Tokyo and Shangri-La, she went on to lead Tokyo 2020 hospitality at Coca-Cola. She later became a country manager in the hotel industry and then a manager at a major global IT company. Today, she serves as an advisor to an NPO that supports single mothers, while being recognized as a LinkedIn influencer and published author who advocates for career breaks.

Career Breaks by Cynthia Usui

Cynthia’s beliefs are rooted in lived experience. After a 17-year career break, she learned firsthand that stepping away from work is not the end of a career. It can become the beginning of a more authentic one. She calls herself the “Cinderella of stay-at-home moms,” not because she waited for the clock to strike midnight. But because she transformed “ordinary” and “unemployed” into extraordinary and unstoppable through curiosity, humility and persistence.

Her message is simple but radical:

“A career break is not a career end.”

Career pauses also create space for growth, resilience and new perspectives—qualities that enrich professional life later. Through storytelling, writing and mentoring, she now champions women who are restarting professional journeys after motherhood, caregiving, relocation or personal transitions.

What makes Cynthia inspiring is not only that she achieved senior roles. It is the fact that she began again when most people believe the window has closed. She has proven, through her own example, that it is never too late to reinvent oneself. Opportunity doesn’t fade with age, gender or circumstance. She stands for possibility, for second chances and for the power of saying “yes” even when your confidence says “not yet.”

Today, through Career Hub, her books and her platform on LinkedIn, Cynthia empowers a new generation of women to believe that every chapter counts—and that the time spent away from work doesn’t erase your potential. It expands it.

Cynthia’s Japan Recommendations

• Take the train and get out of central Tokyo to see how regular people live.

Visit Cynthia’s website for more information about her and her work.

Her books are all available on Amazon (Japanese language):

• 人生は、もっと、自分で決めていい (Jinsei wa, motto, jibun de kimete ii; “You’re allowed to decide more of your own life.”)
• ハーバード、イェール、プリンストン大学に合格した娘は、どう育てられたか ママ・シンシアの自力のつく子育て術33 (Hābādo, Yēru, Purinsuton Daigaku ni gōkaku shita musume wa, dō sodaterareta ka: Mama Shinshia no jiriki no tsuku kosodatejutsu 33; “How was the daughter who got into Harvard, Yale and Princeton raised? Cynthia’s 33 child-raising methods for building independence.”)
• 専業主婦が就職するまでにやっておくべき8つのこと (Sengyō shufu ga shūshoku suru made ni yatte oku beki yattsu no koto; “Eight things a full-time homemaker should do before getting a job.”)

If you would like to follow Cynthia Usui personally, you can find her over on LinkedIn, X and Facebook.

If you have someone in mind you would like us to interview for Savvy Spotlight, please leave a comment below with your recommendations.

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