Gilliana (Jill) Shiskin

Gilliana (Jill) Shiskin


Being a second-career, mature new lawyer, taking an non-traditional law career path led to an unexpectedly satisfying, and successful career.


When Jill Shiskin was in law school, if you’d told her she would become a happy and successful criminal lawyer, she never would have believed it.  Jill entered law school in her late 30s with the goal of working in-house in oil & gas, or in employment and human rights law, or in regulatory law – or really in any area of law other than family or criminal law. In her final year of school, she was hit with the reality that as a second-career law student, and as a middle-aged woman, options for articles are limited. Disappointed, but determined, Jill took an articling position which was going to be a combination of criminal defence and regulatory law. She knew she would enjoy the regulatory work. Her plan was to get through it and then focus on the regulatory side, or move on after passing the bar. She never expected to fall in love with criminal defence.

Jill was considering law school right after undergrad. When she brought up the idea of law school with her family, her dad told her happy lawyers don’t exist. To drill in his point, he had his lawyer friends call Jill and tell her not to choose this career. Convinced that a legal career would be miserable, Jill began a journey towards a PhD in philosophy, planning to become a professor. 

Jill felt that something was missing while completing her Master’s program. She liked philosophy, but did not have the same passion for it as did her fellow grad students. Jill switched gears and started working in customer service/sales and then fell into recruitment and human resources. She enjoyed a 10-year career in recruitment and HR, including with a senior executive international search firm, and with a major international oil and gas company. The O&G company had an in-house legal department. Jill’s interest in law was sparked whenever she would work with the legal department. She would joke– “why can’t I just transfer from HR to the legal team?”. The reply: “You can. You just have to get a law degree!”

A decade into her career, Jill struggled with the decision to apply to law school this “late” in life. Eventually she came to the conclusion that “I can be 40 and be a lawyer, or I can be 40 and not be a lawyer.” 

She took the leap and went to law school. And loved it.

Jill thought that after law school, she would be well-positioned to return to the oil and gas sector, employment law and HR, and/or regulatory work.  Unfortunately, the sector went into downturn in the years she was studying, many of her dream opportunities had disappeared. Jill was not an A-student and was a woman over 35. She got the message, through indirect sources, that employers thought because she was not 24, she would be less coachable, difficult to mold, and in the back of their minds, they would worry she would soon leave or take time off to raise a family. Although age and family status should not be factors in considering a candidate’s suitability for a job or corporate “culture”, she realized it might be naïve to believe these factors were entirely absent from the minds of the hiring committee. Jill’s search for articles during her law school years was depressing. 

Shortly after graduation, Jill finally got an articling position offer at a criminal defence firm. A caring and empathetic person, Jill was certain that criminal law would be too emotionally overwhelming and draining for her. She was surprised that she fell in love with criminal law because of the emotional aspect. Jill found being able to help people during the most difficult times of their lives was indeed emotionally overwhelming at times – in both a exhausting way, but also in an intrinsically rewarding way. 

Jill was lucky to be exposed to many aspects of criminal law during her articles. She was introduced to appellate work very early on and it changed everything for her. Jill loves appellate work because she finds it more abstract, clinical and academic than trial work which involves a lot of multitasking between conversations with clients, their family members and support networks, social support agencies, housing and treatment centres, Crowns, and courts. Additionally, she thrives on deep disclosure review for disclosure-heavy trial files. These types of work allow her to focus intensely on one or two big projects at a time, while most trial lawyers love the action, diversity of tasks, cases and clients that come with criminal defence trial practice. 

Both kinds of work are important, and meaningful, but as a self-described “cave troll”, the independence and intensity of “locking down” for hours (or days, or weeks) to focus solely on the disclosure and research work for a single project - appellate work, or trial prep for a disclosure-heavy trial file - is a better fit with Jill’s character. She admits it can be a struggle to balance both types of high-volume trial work with high-focus research and written work. 

Having a lot of files on the go and being in court daily is exciting for a lot of lawyers. For Jill, it is not something she could do every day of every week. Appellate work and disclosure-heavy trial prep allows Jill to focus on one file for a long time and work outside of regular court/normal people hours. She is not a morning person and often starts her days after 10 AM. She loves working late and into the wee hours of the morning because she can focus better once everyone has left the office, and the phone calls and emails stop coming. Jill also enjoys “locking down” at her home office - with her purrralegal Wally (pictured) by her side.

The day after Jill was called to the Alberta bar, Jill became a sole practitioner and “partner” at the association of independent practitioners, Craig Hooker Shiskin, which is her “firm”. Being in this position comes with a lot of perks, like the freedom to make her own hours, choose her clients and select cases in her areas of interest. There are also drawbacks. 

As a new call, Jill was learning the business side of running her practice, while learning how to be a lawyer. If she could do it over again, she might take things more slowly. She suggests others think carefully before jumping into a partnership or management position. 

Based on what she knew about criminal law prior to doing it, Jill had excluded herself from practicing in this area. Being open to possibilities and challenges, Jill found her perfect practice in an unexpected place. She realized being an empathetic person does not mean you can’t work in emotionally-charged areas of law – but recognizing your own personality and capacity is crucial to identifying and building the appropriate balance of work in your practice. Most importantly, she discovered, being a second-career, mature new lawyer, taking an non-traditional law career path in an area to which she was initially disinterested can lead to an unexpectedly satisfying, and successful career.