Most lawyers think entrepreneurship starts with a resignation letter.
It usually starts with exhaustion.
A late-night idea. A LinkedIn post. A spreadsheet. A conversation that refuses to leave your head. Something you build after your children go to sleep because you cannot build it.
That was one of the most interesting undercurrents in my recent “Notes to My Legal Self” conversation with Netta Aloni and Jessica Nguyen. What emerged was not another polished “personal branding” discussion. It was a far more honest conversation about ambition, identity, risk, motherhood, burnout, acquisition strategy, and what in-house lawyers misunderstand about themselves.
And frankly, I think many in-house lawyers need to hear it.
Lawyers Are Already Entrepreneurs. Most Simply Refuse To Call Themselves That.
One of the biggest misconceptions in legal is that entrepreneurship is somehow incompatible with legal training.
It is not.
In-house lawyers spend their careers operating inside ambiguity, balancing risk against business opportunity, translating competing incentives, managing stakeholders, and making decisions without perfect information. That is entrepreneurial work.
The difference is psychological.
Many lawyers were trained to spot downside before they ever learned to evaluate upside.
Jessica put it bluntly: “All we’re taught is issue spotting and thinking about all the ways things can go wrong.”
That mindset creates excellent legal judgment. It can also quietly suppress creativity, experimentation, and initiative.
The irony is that some of the skills that make great in-house lawyers also make great founders, operators, advisors, and builders.
Not despite legal training.
Because of it.
Netta captured it well when she said, “I think that being an attorney makes you an excellent potential entrepreneur because law school trained us how to think and analyze, and working in-house trained us how to work with business partners and understand risk from both the business and legal side.”
The Real Side Hustle Conversation Nobody Wants To Have
The internet loves productivity culture.
Wake up at 5 a.m.
Build a company before breakfast.
Optimize your life.
Scale yourself.
Reality looks different.
Netta described building Contract Nerds while practicing full-time in-house law and raising children. The story was not romanticized. It was honest.
At one point, she stayed on an important business call while her baby cried in the background because ending the call would have damaged the relationship she was building. By the time the call finally ended, her husband had already put the baby to sleep.
That moment stayed with me because too many conversations about “building something on the side” skip the actual cost.
Time does not magically appear.
You choose where it goes.
As Netta said, “Time comes down to choices for most people.”
And every meaningful commitment necessarily displaces something else.
For many in-house lawyers, the issue is not capability. It is the willingness to tolerate tradeoffs without collapsing into guilt.
Jessica was refreshingly candid about that reality, too.
“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,” she joked. “My house is always a mess.”
Then she added something many ambitious professionals quietly feel but rarely admit publicly: “You can’t do it all.”
That honesty matters.
Because many lawyers assume everyone else has figured out balance while they alone are struggling to hold competing priorities together.
Most people are improvising.
Some are simply more honest about it.
The In-House Lawyer Identity Crisis
One of the most interesting parts of the conversation was hearing both women describe how their careers evolved once they realized they could create value beyond legal analysis.
That shift matters.
A surprising number of in-house lawyers still define themselves narrowly as legal reviewers rather than business contributors.
Jessica described realizing that executives valued her not only for legal advice, but for growth, strategy, communication, and go-to-market thinking.
“What companies really value is growth, revenue, and brand,” she explained.
That realization eventually led her into startup leadership, advisory work, and the scaling of a legal tech company from an early-stage startup to an acquisition.
What struck me was not the career move itself.
It was the permission structure behind it.
Many lawyers wait for someone else to tell them they are allowed to think bigger.
Nobody is coming to do that.
Why Community Became A Strategic Asset
Contract Nerds began as content.
Then it became infrastructure.
That transition reflects a broader shift happening across legal.
For years, lawyers treated community-building as an extracurricular activity. Something social. Something adjacent to “real work.”
That model is collapsing.
Communities are now distribution channels.
Market intelligence systems.
Trust engines.
Brand accelerators.
Netta understood this early when she began prioritizing email subscribers over vanity metrics.
“You could have a large following on LinkedIn,” she said, “but if LinkedIn shuts down one day, all of your contacts disappear. But an email address, you own it.”
That is not creator thinking.
That is operator thinking.
And more lawyers need to start thinking that way.
Acquisition Teaches You More About Relationships Than Dating Does
The acquisition discussion unexpectedly became one of the most revealing parts of the conversation.
Not because of the transaction mechanics.
Because of the psychology.
Netta described interactions with potential buyers that created anxiety, urgency, pressure, and emotional whiplash. Deadlines designed to destabilize. Negotiation tactics designed to manufacture scarcity.
Many founders mistake adrenaline for excitement.
It is usually misalignment.
I said during the conversation that acquisitions teach you more about love than dating does, and I stand by that.
Healthy long-term business relationships do not create chaos in order to force decisions.
They create clarity.
Netta reflected on how different the experience felt once the right partner emerged: “Everything was really smooth and professional and courteous from the very beginning, and that went a long way to making it feel right.”
That observation matters for in-house lawyers because many of us have been conditioned to normalize pressure and dysfunction as indicators of importance.
They are not.
Sometimes professionalism is the signal.
The Quiet Power Of Building In Public
One of the strongest themes from the conversation was generosity.
Neither Netta nor Jessica built influence by directly chasing it.
They shared knowledge.
Answered questions.
Taught openly.
Supported others publicly.
Built relationships consistently over time.
That approach compounds.
Too many lawyers approach visibility backward. They focus first on monetization, followers, speaking opportunities, or prestige.
The stronger approach is simpler:
Become useful first.
The opportunities tend to follow.
As Netta put it, “First think about what you can offer and give to people before you think about how much money you can make.”
Jessica echoed the same idea from a different angle: “There’s a lot of upside to building a personal brand, and I don’t think that is taken into account enough.”
The Most Important Thing In-House Lawyers Should Build
Not every lawyer should start a company.
Not every lawyer wants a public brand.
Not every lawyer should become an advisor, founder, creator, or operator.
But I do think every in-house lawyer should build something.
A point of view.
A network.
A specialty.
A writing habit.
A community.
A body of work.
A reputation for clarity.
A framework others rely on.
Something that belongs to you.
Because careers change.
Companies change.
Markets change.
The lawyers who remain resilient are usually the ones who have built assets beyond their job title.
And often, those assets begin very quietly.
One post.
One idea.
One awkward outreach message.
One step taken before you feel ready.
As Jessica said near the end of our conversation, “Just crawl. Just take that step.”
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
The post The Side Hustle Myth Lawyers Need To Stop Believing appeared first on Above the Law.
Most lawyers think entrepreneurship starts with a resignation letter.
It usually starts with exhaustion.
A late-night idea. A LinkedIn post. A spreadsheet. A conversation that refuses to leave your head. Something you build after your children go to sleep because you cannot build it.
That was one of the most interesting undercurrents in my recent “Notes to My Legal Self” conversation with Netta Aloni and Jessica Nguyen. What emerged was not another polished “personal branding” discussion. It was a far more honest conversation about ambition, identity, risk, motherhood, burnout, acquisition strategy, and what in-house lawyers misunderstand about themselves.
And frankly, I think many in-house lawyers need to hear it.
Lawyers Are Already Entrepreneurs. Most Simply Refuse To Call Themselves That.
One of the biggest misconceptions in legal is that entrepreneurship is somehow incompatible with legal training.
It is not.
In-house lawyers spend their careers operating inside ambiguity, balancing risk against business opportunity, translating competing incentives, managing stakeholders, and making decisions without perfect information. That is entrepreneurial work.
The difference is psychological.
Many lawyers were trained to spot downside before they ever learned to evaluate upside.
Jessica put it bluntly: “All we’re taught is issue spotting and thinking about all the ways things can go wrong.”
That mindset creates excellent legal judgment. It can also quietly suppress creativity, experimentation, and initiative.
The irony is that some of the skills that make great in-house lawyers also make great founders, operators, advisors, and builders.
Not despite legal training.
Because of it.
Netta captured it well when she said, “I think that being an attorney makes you an excellent potential entrepreneur because law school trained us how to think and analyze, and working in-house trained us how to work with business partners and understand risk from both the business and legal side.”
The Real Side Hustle Conversation Nobody Wants To Have
The internet loves productivity culture.
Wake up at 5 a.m.
Build a company before breakfast.
Optimize your life.
Scale yourself.
Reality looks different.
Netta described building Contract Nerds while practicing full-time in-house law and raising children. The story was not romanticized. It was honest.
At one point, she stayed on an important business call while her baby cried in the background because ending the call would have damaged the relationship she was building. By the time the call finally ended, her husband had already put the baby to sleep.
That moment stayed with me because too many conversations about “building something on the side” skip the actual cost.
Time does not magically appear.
You choose where it goes.
As Netta said, “Time comes down to choices for most people.”
And every meaningful commitment necessarily displaces something else.
For many in-house lawyers, the issue is not capability. It is the willingness to tolerate tradeoffs without collapsing into guilt.
Jessica was refreshingly candid about that reality, too.
“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,” she joked. “My house is always a mess.”
Then she added something many ambitious professionals quietly feel but rarely admit publicly: “You can’t do it all.”
That honesty matters.
Because many lawyers assume everyone else has figured out balance while they alone are struggling to hold competing priorities together.
Most people are improvising.
Some are simply more honest about it.
The In-House Lawyer Identity Crisis
One of the most interesting parts of the conversation was hearing both women describe how their careers evolved once they realized they could create value beyond legal analysis.
That shift matters.
A surprising number of in-house lawyers still define themselves narrowly as legal reviewers rather than business contributors.
Jessica described realizing that executives valued her not only for legal advice, but for growth, strategy, communication, and go-to-market thinking.
“What companies really value is growth, revenue, and brand,” she explained.
That realization eventually led her into startup leadership, advisory work, and the scaling of a legal tech company from an early-stage startup to an acquisition.
What struck me was not the career move itself.
It was the permission structure behind it.
Many lawyers wait for someone else to tell them they are allowed to think bigger.
Nobody is coming to do that.
Why Community Became A Strategic Asset
Contract Nerds began as content.
Then it became infrastructure.
That transition reflects a broader shift happening across legal.
For years, lawyers treated community-building as an extracurricular activity. Something social. Something adjacent to “real work.”
That model is collapsing.
Communities are now distribution channels.
Market intelligence systems.
Trust engines.
Brand accelerators.
Netta understood this early when she began prioritizing email subscribers over vanity metrics.
“You could have a large following on LinkedIn,” she said, “but if LinkedIn shuts down one day, all of your contacts disappear. But an email address, you own it.”
That is not creator thinking.
That is operator thinking.
And more lawyers need to start thinking that way.
Acquisition Teaches You More About Relationships Than Dating Does
The acquisition discussion unexpectedly became one of the most revealing parts of the conversation.
Not because of the transaction mechanics.
Because of the psychology.
Netta described interactions with potential buyers that created anxiety, urgency, pressure, and emotional whiplash. Deadlines designed to destabilize. Negotiation tactics designed to manufacture scarcity.
Many founders mistake adrenaline for excitement.
It is usually misalignment.
I said during the conversation that acquisitions teach you more about love than dating does, and I stand by that.
Healthy long-term business relationships do not create chaos in order to force decisions.
They create clarity.
Netta reflected on how different the experience felt once the right partner emerged: “Everything was really smooth and professional and courteous from the very beginning, and that went a long way to making it feel right.”
That observation matters for in-house lawyers because many of us have been conditioned to normalize pressure and dysfunction as indicators of importance.
They are not.
Sometimes professionalism is the signal.
The Quiet Power Of Building In Public
One of the strongest themes from the conversation was generosity.
Neither Netta nor Jessica built influence by directly chasing it.
They shared knowledge.
Answered questions.
Taught openly.
Supported others publicly.
Built relationships consistently over time.
That approach compounds.
Too many lawyers approach visibility backward. They focus first on monetization, followers, speaking opportunities, or prestige.
The stronger approach is simpler:
Become useful first.
The opportunities tend to follow.
As Netta put it, “First think about what you can offer and give to people before you think about how much money you can make.”
Jessica echoed the same idea from a different angle: “There’s a lot of upside to building a personal brand, and I don’t think that is taken into account enough.”
The Most Important Thing In-House Lawyers Should Build
Not every lawyer should start a company.
Not every lawyer wants a public brand.
Not every lawyer should become an advisor, founder, creator, or operator.
But I do think every in-house lawyer should build something.
A point of view.
A network.
A specialty.
A writing habit.
A community.
A body of work.
A reputation for clarity.
A framework others rely on.
Something that belongs to you.
Because careers change.
Companies change.
Markets change.
The lawyers who remain resilient are usually the ones who have built assets beyond their job title.
And often, those assets begin very quietly.
One post.
One idea.
One awkward outreach message.
One step taken before you feel ready.
As Jessica said near the end of our conversation, “Just crawl. Just take that step.”
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.
The post The Side Hustle Myth Lawyers Need To Stop Believing appeared first on Above the Law.
