How a Flexible Mindset Took Her From Bankruptcy Law to Legal Tech with Ivy Grey (TFLP 085)

Ivy Grey moved from IT to advertising to law, before landing at a legal tech company WordRake, a Microsoft Word add-in, which edits legal documents for clarity and brevity. 

On this episode of the podcast, Ivy shares how her flexible mindset, a hobby, and her skillset beyond her law degree led to a complete career transition into legal tech.

Law School Was Miserable 

Ivy just never felt like she “got” it. Others seemed to thrive in law school while she couldn’t seem to work hard enough to get the results she desired. 

She wanted to give up, but then she realized that she was just playing a particular type of game, the law school game, and she just needed to learn the rules. 

After hiring a coach, Ivy set benchmarks for herself, and learned how to “play the law school game better”, meaning she learned how to play it in a way that was useful for her. 

This is important because many lawyers leave law school and enter into legal practice and are surprised by how different the rules of the game are. The key is to learn to play in a way that works for you, much as Ivy did in law school. 

“The” Way Is Holding Lawyers Back From Other Careers

During Ivy’s law school days, she had an important realization that there was no one way to do law school. While others were linear learners, she decided she needed diagrams and flowcharts to learn. While others seemed to excel, she found coaches and tools to make law school work for her in her own way. She recognized that there was no “one” way, one environment, one path to being a lawyer. 

This is a critical lesson for all lawyers as we tend to hold ourselves back from exploring other career options because we think there is only one way. There is no such thing as “the” way. 

Big Cases Weren’t So Great

After graduating from law school, Ivy practiced bankruptcy law for a few years before deciding she wanted to aim for more. She moved to NYC, got her LLM, and began working on high-profile cases. 

The problem with aiming for something we think we should aim for, like the high-profile cases, is that we forget to think about what our lives will be like when we’re doing that thing. Ivy was miserable working 7 days a week while knowing there was more to life.

It’s All Mindset

Ivy decided to make a plan. She knew she couldn’t continue her work-heavy lifestyle, so she got to work to change it. 

The first step was falling back on her flexible, open mindset. Ivy knew she was capable. She knew she could understand large quantities of information, could learn quickly and knew she could find something related to what she enjoyed. It took the right mindset to see things clearly. 

Building The Plan To Leave Law

The next step in Ivy’s plan to leave had a few pieces. She cataloged her skills and what she enjoyed. She participated more on social media to network and stay connected. She read more about different industries and did cross-training with other areas. 

She knew that if all she knew was law, she was always going to filter things through a legal view, so she learned more about business and client problems and the broader world so she could be ready to do something other than think only like a lawyer. 

Ivy also saved money because she knew that it could take a while to make the change that we wanted and she would be sucked right back into the sort of thing she didn’t want to do if she didn’t have a financial cushion.

The Legal Tech World

Thanks to her planning, Ivy was ready when an opportunity landed in her lap, through swing dancing. She had picked this up as a hobby and one of her dancing buddies happened to be the founder of PerfectIt, another Microsoft add-on for proofreading. He asked her to try the product and she didn’t love it. In response, she gave him pages and pages of feedback and in return, he asked her to join him in building a better tool. 

Ivy’s time in legal tech had begun. 

Marketing To Lawyers

In this new world of legal tech, Ivy needed to learn some new skills, including marketing to lawyers. She had to cultivate a marketing mindset, figure out where her customers were, and bring them up from there. This is such a unique marketing field because it includes not only more educational components, but you’re also speaking to people who don’t think what you offer is important. 

You have to show that what is being done now is problematic (even if it’s not recognized as an issue) and that there is a solution. For those of us that have practiced, or practice, law, we’re not looking at the way we do things, we know it feels tiring and off, but we don’t think about our process. 

One of the ways Ivy suggests we can open our mindset around this idea that our processes and tools could be improved is by speaking with more people to learn what they do and how they position their products so we can embrace that way of thinking. We can’t apply our legal brain to everything, in other words. 

From Lawyer To Wearing Many Hats

Beyond expanding her marketing mindset and skills, Ivy shares that in her legal tech job with WordRake, she now wears many hats. There is no typical week for her. She works on the operating budget, manages many people in the company, stays on top of trends, manages social media and UI (user interface) for new features  – it’s a lot of stuff!

How Self Talk Led To Embracing Legal Tech And New (And Old) Skills

All of this change in work and mindset for Ivy came from self-talk. Instead of focusing on what she didn’t know or couldn’t do, she focused on her skills and the tools she had to get things done. She didn’t focus on building “legal tech skills”, she did what she needed to get her work done. 

In fact, some of her most useful skills came from her teenage years, when she was helping her mother illustrate patent applications on the computer and her diagramming days of law school. 

She didn’t look myopically at just what she had been doing in her job as a lawyer or what she had studied, she looked at all the skills she had. That’s really what helps us figure out what’s next, as we learn to understand ourselves better and what we enjoy – which sometimes does not sound as exciting as figuring out the perfect next job – we learn our unique skills and strengths, change our story about ourselves, and are able to see other options for our future. 


One thing Ivy shares with us is to not be embarrassed by background. Much like we never know which skills will prove useful, we never know which aspects of our background will help us. She encourages us to not write off our background as useless or something that’s going to hold us back. Your background is a unique superpower that makes you you, and that makes you able to do something that other people can’t. And you should embrace that.

An aspect of this we often see in the legal world are those obsessed with prestige. But prestige is actually not a particularly good guiding light to rely upon in making your career and life decisions. In fact, it is one of the things that tends to result in a great deal of unhappiness, which is also a common pitfall that lawyers fall into when they’re thinking about these issues.

Getting Into Legal Tech

Ivy has simple and effective advice for those looking to get into legal tech: catalog your skills and figure out what you are willing and excited to build on. If you are good at something, but you hate doing it, don’t build on that one. 

Using A Flexible Mindset To Your Advantage

Additionally, Ivy shares the advice that a flexible mindset will take you to wherever it is that you need and want to go, even if you decide to stay in practicing law. 

Learning to understand problems and come up with creative approaches to solving them that aren’t necessarily legal or from a textbook is critical. Thinking more creatively may help you find happiness in law, and even if you don’t find happiness in law, this creativity will help you start to reevaluate your skills and see where else you can be successful and happy. 

Connect With Ivy

Mentioned In This Episode: 


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