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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of The Reboot Era, I reconnect with my fellow Bryant University alum Vivian to explore her unconventional career path — one defined by global adventures, freelancing experiments, and fearless reinvention.
After graduating in International Economics, Vivian skipped the corporate route to pursue a fellowship in LA, a cultural exchange in Brazil, and eventually five years of freelancing as a writer. She shares how she built a career on her own terms, the highs and lows of freelancing, and why AI ultimately pushed her to pivot again — this time into business development in New York’s electrical industry.
We discuss:
- Why freelancing can be both freeing and unpredictable
- How to build a personal brand on LinkedIn that actually drives opportunities
- The realities of AI’s impact on creative careers
- Why blue-collar entrepreneurship may be one of the most future-proof industries
- How to recognize — and act on — the right career pivot
📍 Connect with Vivian on LinkedIn: Click here
If you’re rethinking your career path or curious about freelancing, entrepreneurship, and AI’s role in shaping the future of work — this is an episode you don’t want to miss.
💼 Partner: Jobhire.ai — Apply to jobs while you sleep. 30% off in Sept. 2025 with code DRAY30 → jobhire.ai/job-matcher/?imutm=dray (you must use that link)
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Thanks for supporting The Reboot Era — every follow, share, and tip helps me keep making content for anyone navigating layoffs, pivots, and everything in between.
Everything shared on this podcast is based on personal experience and opinion. Unless explicitly stated otherwise, no content should be considered professional, legal, or career advice. Any mention of companies, products, or individuals is done in a personal capacity and does not represent the views or endorsements of those organizations or people. If a sponsorship or paid partnership is ever included, it will be clearly disclosed during the episode.
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