June 29, 2026

Most lawyers perceive the start of an entrepreneurial journey as the moment they hand in their resignation letters. However, the truth often begins with a late-night spark of inspiration, a relentless idea, or a conversation that lingers in the mind long after the working day has ended. These are the real starting points for many lawyer-entrepreneurs, a conversation explored deeply in the "Notes to My Legal Self" series with legal professionals Netta Aloni and Jessica Nguyen.
The discussion veered away from the typical narratives about personal branding to delve into the realities of ambition, identity, risk, motherhood, and burnout. It highlighted a crucial misconception: the belief that legal training is incompatible with entrepreneurship. In reality, the skills honed in law—navigating ambiguity, balancing risks, and decision-making—are foundational for entrepreneurial success.
Jessica Nguyen pointed out a critical barrier: "All we’re taught is issue spotting and thinking about all the ways things can go wrong." This risk-averse mindset, while valuable in legal proceedings, can dampen creativity and initiative—qualities essential for entrepreneurship.
The real conversation about side hustles is not as glamorous as social media makes it seem. Netta’s story of managing her startup, Contract Nerds, alongside a full-time in-house legal role and motherhood sheds light on the sacrifices involved. Time becomes a series of tough choices, and every commitment means something else gets less attention.
Jessica’s experience resonates with many who juggle multiple roles: "I don’t really have a social life unless you are a parent on my kids’ sports team or I run into you at Costco. My house is always a mess." Her candid admission that "You can’t do it all" is a necessary counter to the prevalent myth of perfect balance.
An interesting evolution occurs when lawyers realize they can contribute more than just legal expertise. Jessica, for example, found her niche in startup leadership by leveraging her skills in growth, strategy, and communication, moving beyond the narrow confines of legal review.
Community building has also emerged as a strategic asset. What once was viewed as an optional social activity is now recognized as a crucial business tool. Communities serve as distribution channels, market intelligence systems, and trust engines. Netta's approach to prioritizing meaningful connections over superficial metrics exemplifies this shift.
Moreover, the discussion on acquisitions revealed insights into the psychological aspects of business negotiations, emphasizing professionalism and alignment over high-pressure tactics.
The conversation culminated in a powerful reminder for all professionals, not just lawyers: building public visibility and influence starts with generosity and genuine engagement, not the pursuit of monetization or fame.
Ultimately, every lawyer might not want to start a company or become a public figure, but there is undeniable value in building something personal and meaningful—be it a network, a specialty, or a community. These assets, developed quietly and consistently, form the backbone of a resilient career, adaptable to changes in the market or job status.
As Jessica advised towards the end of the discussion, "Just crawl. Just take that step." It’s a call to action for any lawyer hesitant about embracing their entrepreneurial potential, encouraging them to start small but start now.