The episode covers Ali Sipher’s experience taking a 7-month career break. She discusses the importance of setting clear goals for the break, such as self-discovery and exploring new directions. Financial planning for 1.5-2x the intended break duration is recommended to avoid undue pressure. The initial months involved decompressing from the fast-paced work mindset and pursuing personal interests like getting certified as a phlebotomist. A major realization was how much time actually exists in a day without the constant urgency of work. The break allowed Ali to rediscover her core identity beyond her job and gain Clarity on her values and interests. She advises taking at least 6 months for a true mental reset, and beginning the re-entry process 1-2 months before the intended return date. Overall, an intentional career break can provide invaluable self-awareness and perspective.
Planning for a Career Break
Embracing the Break
Lessons from the Break
Re-Entering the Workforce
Key Takeaways
Ali Sipher: Ali Sipher is an accomplished product leader who loves complicated and unglamorous problem spaces (think: supply chain, healthcare, accounting). She’s delivered innovative products, unlocked new revenue streams, and optimized operations in leadership roles at Parsley Health, Walmart, and multiple startups. After taking a six-month career break, Ali started working as a product management consultant. This helped her realize how much she loves owning the day-to-day product work. Ali is actively looking for her next full-time role solving complicated and unglamorous problems. Interested in connecting? Reach out: alexandrasipher@gmail.com
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