29. The Art of the Sabbatical Career Break with Ali Sipher

The Estee Show - Product Management & Business Insights

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

• Set clear goals for the break - e.g. self-discovery, exploring new interests
• Financially plan for 1.5-2x the intended duration of the break
• Determine responsibilities to hand off or cover during the break

Embracing the Break

• Allow time to truly disconnect and decompress initially
• Pursue personal interests, projects, certifications
• Expect a mindset shift - days feel longer, less urgency
• Rediscover your identity beyond work

Lessons from the Break

• You have more time than you think for what's truly important
• Savor the mental break from constant urgency
• Gain self-awareness about your core values and interests
• Decide if/when you want to re-enter the workforce

Re-Entering the Workforce

• Start considering re-entry 1-2 months before intended return
• Don't wait until burnout to take a career break
• Plan for a bit more break time than you think you'll need
• Expect to miss using your brain for problem-solving eventually

Key Takeaways

• Career breaks allow valuable self-discovery and mindset shifts
• Proper planning (financial, responsibilities, duration) is crucial
• Be open to the break taking you in an unanticipated direction
• Decide when you're ready to re-engage based on your goals

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: [e-mail]