Children's book author and freelance lawyer Jill Diamond. Courtesy photo.

Most clients would probably consider a lawyer who spends a sizable portion of her day dreaming up adventures for a pair of pint-sized detectives to be a cause for mild-alarm, if not a a stricter interpretation of term “billable hours.”

Not to worry. Corporate attorney and litigator Jill Diamond isn't stealing company time, just taking it out in installments. She left her full-time job at a law firm shortly after giving birth to her now preschool-aged son. In between dropping him off at school and churning out installments in her children's novel mystery series “Lou Lou and Pea,” Diamond reviews, drafts and negotiates non-disclosure agreements for venture capital clients on a freelance basis.

“Obviously, I am not on track to be a partner at a Big Law firm or climb the ladder in a traditional sense,” Diamond said. “However, I think my law-writing-life balance is beneficial to my attorney work. I don't feel burned out on the law and I am able to approach legal work with enthusiasm and dedication.”

The classical and not-so-secret origin story for a lawyer/author hybrid begins with a mom who was a elementary school librarian and ends with a cloud-based legal technology company. Diamond started writing children's fiction early in her career as an attorney and polished off the first “Lou Lou and Pea” story while caring for her mother during an illness.

She loved the collegiality of the law firm environment and its revolving door of new and diverse clientele but had just delivered a baby and a paperback in fairly short succession.

“At this time, I already had a publishing contract for the 'Lou Lou and Pea' series, and there didn't seem to be enough hours in my day for full-time legal work, my author career, and caring for an infant,” Diamond said.

However part-time legal work was still very much on the table. Diamond came across InCloudCounsel on a Facebook group for San Francisco parents. As the name suggests, the legal service provider utilizes the cloud to facilitate connections between clients looking to put a dent in a backlog of routine legal document work and attorneys who enjoy taking a gig economy—or freelance—approach to the practice of law.

Diamond, for instance, can slot her disclosure agreement projects wherever they fit best into a given day (usually after she drops her son off at school and then again once he's in bed for the evening). Once InCloudCounsel has arranged an introduction, she'll receive the rest of her assignments directly from the client, who can then track the progress of their documents on the cloud-based platform.

“I work hard to prioritize what needs my attention the most at any given moment: a legal project, writing [and] book-related work, or my three-year-old, so my days are quite varied.” Diamond said.

It's not entirely clear if it's the lawyering or the children's books that are her side hustle at this point, but the two disciplines compliment one another better than you might think. Both engage different aspects of Diamond's creativity, whether it's a drafting a compelling legal argument or a fictional narrative draped in kid-friendly intrigue.

Diamond could see a future where there are more attorneys making a living using platforms like InCloudCounsel, chasing passion projects while standing on the back of the gig economy.

“The project-based approach also seems to work well for clients. I think there will always be a place for the traditional law firm, but there is no reason that the two models can't coexist,” Diamond said.