Key Insights

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1. Creative Roots Drive Legal Purpose.
Sarah identifies as a creative first; her legal career was initiated by a desire to protect her own creations (jewelry) through intellectual property law. This connection meant her practice was always aimed at helping creatives like herself.

2. The Non-Traditional Route to Startup Law.
Sarah joined Etsy as the first lawyer and 17th employee not through a formal posting, but by proactively identifying an area of business policy that needed tweaking. She pitched herself directly to the CEO, making a business case for her value-add over a marketing or engineering hire.
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3. Theater as a Solution to Attorney-Client Privilege.
The play Dirty Legal Secrets was born from the insight that lawyers are "privileged and voiceless"—they accumulate fascinating, funny, or vulnerable stories under privilege that they cannot share. The solution was to solicit anonymous stories and hire actors to perform them, offering a "four-dimensional," interactive experience that couldn't be achieved via a book or podcast.
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4. Overcome Perfectionism by Embracing the "Bad First Draft."
The biggest obstacle for aspiring writers, especially lawyers with perfectionist tendencies, is holding themselves to an impossibly high standard. The advice is direct: "You got to get the bad first draft out of your system". Do it poorly, focus on getting the story out, and worry about honing the craft later.
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5. The Entrepreneurial Path Requires the "Rejection Muscle."
Transitioning from an advisory role (GC) to a creative/entrepreneurial role (Playwright/Founder) requires enduring constant rejection. Success means actively putting yourself out there and accepting that rejection is a necessary part of launching ambitious projects.
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6. Prioritization Sustains the Creative Spirit.
To maintain a creative life while working a demanding full-time job, you must make a commitment. The only way to find time is to prioritize and put it in your calendar.

7. Closing Insight

Your legal career is a unique source of material that the world wants to hear. Don't let attorney-client privilege or professional perfectionism silence your stories; find creative vessels to share the human dimension of your high-stakes work.