Do you ever think about the paths you didn’t take?
A few weeks ago, I was reconnecting with a former colleague from my higher education days, and we started talking about our current work. At one point, she paused and said, “I love the path you’ve taken, but if you’d asked me 10 years ago, I would have said you’d definitely end up a dean somewhere.” Honestly, there was a time I thought so, too. For years, that path felt not only plausible, but likely. I loved universities: the intellectual intensity, the sense of mission, the complicated human systems. I was drawn to institutional leadership and to the challenge of helping organizations navigate moments of conflict, ambiguity, and change. I understood academia intuitively and knew how to function effectively within it. There was a version of my life that felt visible and coherent long before it actually happened. {"blockType":"mv-promo-block","data":{"imageDesktopUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/cupofambition.png","imageMobileUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/11\/cupofambition-mobile.png","eyebrow":"","headline":"\u003Cstrong\u003ESubscribe to \u003Cem\u003EA Cup of Ambition\u003C\/em\u003E\u003C\/strong\u003E","dek":"A biweekly newsletter for high-achieving moms who value having a meaningful career \u003Cem\u003Eand\u003C\/em\u003E being an involved parent, by Jessica Wilen. To learn more, visit \u003Ca href=\u0022https:\/\/acupofambition.substack.com\/\u0022\u003Eacupofambition.substack.com\u003C\/a\u003E.","subhed":"","description":"","ctaText":"SIGN UP","ctaUrl":"https:\/\/acupofambition.substack.com\/","theme":{"bg":"#f5f5f5","text":"#000000","eyebrow":"#9aa2aa","subhed":"#ffffff","buttonBg":"#000000","buttonHoverBg":"#3b3f46","buttonText":"#ffffff"},"imageDesktopId":91454061,"imageMobileId":91454062,"shareable":false,"slug":"","wpCssClasses":""}} Instead, my life unfolded differently. I left higher education, built a coaching and consulting