"She looked left, looked right, and realized most people in that room would not make the switch. Out of about 20 classmates, only three successfully transitioned."
Jen Tran bet on herself in her mid-thirties with doubt, limited support, and the pressure of who you think you are supposed to be at that age. This is the last guest episode of the season, and it closes out with the truth about career transition — the parts that rarely make it into the highlight reel.
In this conversation, Savan and Jen get into rejection, endurance over talent, and the messy middle after a boot camp ends — when confidence drops and the real work begins. They also talk about her path from HR and learning and development to UX, how anthropology shaped her empathy as a designer, and why something as simple as a workplace potluck can be a real signal of belonging.
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ABOUT JEN TRAN
Jen Tran is a UX designer who made a mid-career pivot from HR and learning and development in her mid-thirties. She studied anthropology, which became the foundation for her empathy-driven approach to design. Her transition story — through General Assembly, rejection, and the messy middle — is one of the most honest accounts of what career reinvention actually looks like from the inside.
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TIMESTAMPS
• 🕐 00:00 – Introduction and holiday greetings• 🕐 04:53 – The joy of workplace potlucks• 🕐 09:47 – Growing up in Orange County• 🕐 10:57 – Career aspirations and college choices• 🕐 14:08 – Transitioning from college to the workforce• 🕐 16:48 – The journey to Kareo and startup culture• 🕐 18:43 – Investing in personal growth• 🕐 22:10 – The role of HR and career pathways• 🕐 24:49 – Discovering UX and software engineering• 🕐 28:02 – The journey to UX: from support to design• 🕐 33:58 – Overcoming challenges in transitioning to UX• 🕐 40:15 – Skillsets for success in UX• 🕐 42:39 – Proud moments in UX design• 🕐 46:02 – Developing empathy as a UX designer• 🕐 50:06 – Reflections on education and career growth• 🕐 54:34 – Looking ahead: future aspirations in UX• 🕐 56:46 – Navigating the tech landscape and AI's impact• 🕐 1:00:03 – The role of leadership in corporate America• 🕐 1:02:54 – Handling difficult conversations in business• 🕐 1:10:31 – Dreaming big: future aspirations and opportunities• 🕐 1:16:37 – Reflections on past aspirations and current realities
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