Episode 68

From Litigator to Spin Instructor to Chief Legal Officer with Jasmine Singh

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Episode 68

From Litigator to Spin Instructor to Chief Legal Officer with Jasmine Singh

Cover of SpotDraft guide titled Building Smarter In-House Teams with photos and names of four professionals: Adam Becker, Akshay Verma, Tommie Tavares-Ferreira, and Kevin Cohn.
Here’s how Adam Becker at Cockroach Labs turned AI from experiment into daily legal ops power.

Summary

Key Insights

1. Burnout is Often a Breaking Point of Misalignment.
Jasmine's burnout was not caused by a single factor, but a combination of unsustainable hours, physical and mental toll, and a clear misalignment between her authentic self and the requirements of her job. She felt compelled to hide her "superpowers"—personality, happiness, spunk—which compounded the stress.

2. Core Litigation Skills Transfer Powerfully to Transactional and In-House Roles.
Moving from litigation to in-house commercial legal was possible because litigators are expert rapid learners. Jasmine successfully pitched herself as highly coachable and willing to master a new domain, proving that her fundamental skill was learning new subject matter quickly and thoroughly, a necessity in fast-paced transactional work.

3. Mission and Culture Outweigh Hyper-Growth Alone.
For long-term commitment and high motivation, mission and people/culture are paramount, sometimes trumping title or compensation. Jasmine requires a workplace where she can be her authentic self without "code switching" or "putting on airs," allowing her to invest fully in a cause she believes in.

4. The Power of a Sabbatical for Self-Discovery.
A career break (like becoming a spin instructor) can provide critical perspective. The spin instructor role was satisfying because it was inherently mission-driven (making a difference daily) and team-oriented, providing the exact qualities she realized were missing from her previous legal career.

5. Networking and Mentorship are Essential for Non-Linear Career Moves.
Breaking into a specialized role (in-house, from a year-long gap) is nearly impossible without a personal connection. Jasmine's job at 24 Hour Fitness came directly from a former law firm colleague who vouched for her, proving that advocates are necessary to get past initial screening barriers.

6. Closing Insight

Trusting your gut and prioritizing authentic leadership is not a soft skill; it is the ultimate strategy for unlocking your full potential and ensuring your career trajectory is one of sustainable, mission-driven success.

In this podcast, we cover

0:00 Introduction
2:39 Why Jasmine chose to become a lawyer
6:00 Knowing when to take a break
14:46 Teaching spin classes
19:18 Getting your first in-house role at 24 Hour Fitness
22:39 How to position yourself during an in-house job interview
26:40 Transitioning into tech counsel
32:31 Explaining Binti and it’s mission
38:10 Fulfilling a philanthropic mission with Dincert Movement
42:31 Tips for people who feel stuck at work
45:16 Rapid-fire questions
46:50 Book recommendations
50:20 What Jasmine wishes she’d known as a young lawyer

View AI generated transcript

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