From Cults to Law to PM: How I Found My Way to Product

As with most product professionals, I didn’t set out to become a product manager. In fact, when I went to undergrad, I didn't have any idea what a product manager was. To get to product, I took a meandering path through a wide array of careers and disciplines marked by trying things, learning quickly, and continually moving toward what energized me. Here’s the winding route that brought me to product—and what I learned along the way!

If you’re just here for the takeaways and not the story of how I got to product, jump straight to the end!

Undergrad: Abandoning the Practice Rooms and Discovering Cults

The story of my journey to product starts in undergrad. Going to undergrad at all was a feat for me. I loved school and learning, but I had my heart set on being a singer right before I started college. I thought a better use of my time would be waiting to start college to give myself time to try and make it in a band with my friends. My parents were a little less than enthused with this idea and, after much encouragement from them, I started at Truman State University with a plan to double major in vocal performance and French.

Within a month of starting, I was awakened to the harsh reality that faces a vocal performance major: practice hours. Vocal performance majors had to spend 20-30 hours per week logging practice sessions and honing their craft and it was all focused on classical singing. I gave it the good old college try (literally), but saw myself drifting closer to opera singer than pop star and that wasn't what I had envisioned. I didn't know what was next, but I knew that vocal performance wasn't it.

I spent a lot of time wandering the campus solo and exploring the secrets the old buildings held on the inside. The library was a particularly fun place to try and get lost and one day I happened on the film section. In retrospect, I'm not sure why it struck me as weird, but at the time I was shocked to learn you could check out up to 10 movies at a time (like free Blockbuster!). I started binging all kinds of films and got especially interested in educational neurosurgery videos (strange, I know. I just thought it would cool to learn how brain surgery was done - and it was). My interest in them gave me an idea: maybe I’d go to med school.

After doing some quick research on what it would take to be a doctor and get into med school, I switched to chemistry as a major. Despite again giving it a good attempt, I eventually had to drop my first chemistry class. My grade had started to slide from an A to a C and I knew I'd need excellent grades to get into med school. If I wasn't capable of crushing my science classes, it was time for another pivot.

This pivot led me to psychology, thinking I might become a clinical psychologist and stay adjacent to the neurosurgery that had interested me so much. While I got to do a lot of interesting things, including research on whether hypnotism could help boost athletic performance, I again found myself unengaged.

Through all the change, I had held a steady minor in philosophy and religion. My professor for an Intro to World Religions course, Dr. Ashcraft, quickly became my favorite professor and inspired me with his passion for belief systems. I took a few more courses with him, and I learned that he was one of the world’s experts on New Religious Movements (“NRMs” - the academic term for cult groups). His passion for the subject rubbed off on me and compelled me to switch my major for the last time.

My cult classes captivated me. As a field of study it was a fascinating blend of philosophy, religious studies, anthropology, sociology, psychology, and law and I spent a lot of time trying to understand what motivated people to join religious groups that didn’t seem to have a lot of credibility to outsiders (If you ever want to get me talking, ask about my favorite cult groups. There are lots.). I went all-in and learned as much as I could about the subject, but, in the back of my mind, the question of what I was going to do with my future lingered. Enter: Diane Lockhart.

How Glenn Close and Christine Baranski Took Me to Law School

Early in my Junior year, I started focusing more on the future and trying to decide what I ought to do with my life. My degree didn’t seem the most practical unless I wanted to be a professor or start my own cult - neither of which was part of my short-term plan.

At the time, I had started binging a couple of legal dramas: Damages and The Good Wife. Both shows had strong female leads (Glenn Close and Christine Baranski, respectively) that took on large-scale class action work against large companies while generally being chic and amazing in every way. My favorite character was Christine Baranski's Diane Lockheart. She was powerful, worked on exciting things, and tried to use the law to both make money and move toward a greater good. Inspired by a fictional character, I decided I’d start researching what it took to be a lawyer.

After some research, I learned that all you needed to do to go to law school was take the LSAT. That felt a lot more achievable than the litany of prereq classes you had to take to go to med school, so I decided to give it a go! I made a deal with myself: I’d focus full-time on studying for the LSAT for three months. If I did well and got a good scholarship, I’d take it as a sign I should go to law school. If I did poorly, I’d figure out something else.

I spent the next three months focusing for a minimum of 40 hours per week on LSAT studies - everything else (school included), took a backseat. I simulated test conditions, took hundreds of practice tests, tracked misses by question type, and learned how to be better.

I took the test in February 2014 and I ended up in the 98th percentile for my testing year - high enough to have my choice of law schools to attend, likely with a full scholarship. After an application process that was equal parts stressful and exhilarating, I chose Washington University in St. Louis School of Law, partly because they offered a full scholarship and partly because it was close to home for me (Kansas City).

Law school was rigorous and high-stress. All classes are based on the Socratic method, where students are cold-called and expected to answer questions and hypotheticals about the case law that had been assigned. It’s a great way to learn, but definitely stressful. I did well in my studies, but one semester in, I had a creeping realization: if being a lawyer feels like law school, I might not want this. It was academic and heady and I loved that part of law school, but it didn’t feel as “cool” as Diane Lockheart had made it seem.

Your first year of law school is all about getting the best grades you can and trying to get a first summer internship that will ideally convert into a full-time job after school. Most of the students at WashU were BigLaw (the largest law firms in the world, which pay extremely well) bound and I assumed I would do the same, but I got a wildcard opportunity that was too good to pass up. A family friend was the named partner at a small mass action firm handling huge multi-million and multi-billion dollar cases. This was the exact type of work that had inspired me to go to law school in the first place - the exact type of work Glenn Close did on Damages. He offered me a spot as a law clerk at his firm and I took it.

When I joined, the firm had four lawyers and two paralegals. That size afforded me the chance to engage in high-stakes work and own some cases more or less independently (again, ask me sometime. I've got loads of interesting stories), giving me a great picture of what a life in the law would be like. I also learned the cost of a life as a complex litigator: the draining hours, the constant demands of the court, and the immense emotional load of working with people who’ve experienced tremendous loss. I stayed with the firm and did work for them on and off through law school and after I graduated, but I knew it was going to be too heavy for me long-term. It was time to figure out what else I might try.

A Pilgrimage of Self: Los Angeles

My 2L (second year) of law school, I came out as gay and decided to move to Los Angeles. I worked out an opportunity to be a visiting law student at UCLA. I had never been to LA before moving there, I just knew I needed a place where I could find myself and I had heard there were gay people there because of influencers on Youtube (I’m not kidding - that was the extent of the reasoning for picking Los Angeles).

While at UCLA, I focused on entertainment law and venture capital law courses, thinking that might be a less taxing field of law than litigation, but I came up empty. I did get to help a company attain regulatory approval for their new shelf-stable breast milk product, which was very interesting! But I ultimately found the corporate side of legal work even less compelling than litigation.

To stay in LA for my final semester of law school, I found a semester-in-practice role at Lambda Legal, an LGBT rights constitutional litigation organization, where I could work full-time and earn credit toward my JD. We worked on highly impactful cases during my six months there: the trans military ban (post-Trump election), LGBT parentage and social security benefits issues in conservative states, and the Colorado cake baker case (with the ACLU). I got an offer to return full-time after my semester there, but I’d made up my mind after exhausting a variety of options: I didn’t want to practice law.

Forging My Own Path: Legal Recruiting

By complete happenstance, I met a former solicitor from England who’d become a legal recruiter. How this meeting happened is a bit of a long story, but it involves a matchmaker and a British boxing instructor (ask me sometime). She didn’t sit for the California Bar (which I was preparing to take) and mentioned that she now worked in legal recruiting. As she described it, the compensation was competitive with BigLaw and the lifestyle was much better. I was sold and lined up an opportunity with a legal recruiting firm. This put me decidedly out of step with the ideal outcome for a graduating law student (I was the only one in my class going into a field that didn’t require or preference a law degree).

My job as a third-party recruiter (headhunter) was to call BigLaw associates and partners to see if they were happy or looking for new opportunities and then represent those candidates in their moves to other BigLaw firms. If I placed a candidate, I would make a commission on the placement from the law firm. I learned a lot by doing while I was a legal recruiter: the dynamics of BigLaw firms, the differences between practice groups, and how to coach people through major life decisions. I gained skills I still use to this day too, developing my sales abilities, but I ultimately learned I wanted to grapple with more intellectually dense ideas in my work than recruiting offered.

Learning to Code: Making Ideas Manifest

While working as a recruiter, I started teaching myself to code on the side. I’m not really sure what inspired me to start - I had never taken a computer science class and knew nothing about software engineering. As I dove into coding, the thrill was instant: take an idea, make it real, see it running in front of you, manifesting a real product, website, or application.

Riding high on the thrill of creation, I took the GRE, applied, and was admitted to get my Master’s of Computer and Information Technology at the University of Pennsylvania. The program was designed with four foundational classes equivalent to an accelerated Computer Science bachelor's degree, followed by six master's level electives which I focused on AI and machine learning. I got started with my studies soon after the pandemic started, a serendipitous timing that made stepping away from recruiting less risky as candidates were no longer moving jobs, so I didn’t really have much to lose by quitting my job and going all-in on school. Going back to school as a 28 year-old lawyer certainly wasn’t traditional, but I was excited by the newness of it all.

Once I was in my program full-time, my philosophy was simple: I could either pay to learn by staying at Penn full-time until my degree was complete or get paid to learn by getting a job and doing school on the side. Eight months into my degree, after grinding LeetCode problems, building out my portfolio with side projects, and sending out hundreds of applications, I landed a software engineering job at a tiny marketing tech startup. The path to that one yes was fraught with rejection (I had a success rate of less than .05%), but I kept at it and eventually landed a job that would help me learn more about the real-world experience of being a software engineer.

Startup Engineering: Building Without a Product Org

The company I joined was about 10 employees at the time—a seed stage startup with a few customers. There was no product, UX, or data organization. Because there was no formal product structure, engineers (including me) had the privilege of pitching what we thought should be built next and why we thought it would drive the business forward. I relished getting to flex some strategic thinking muscles and balancing those with my understanding of our customer base, our strategic direction, and our platform’s technical capabilities. It felt like magic to go from idea, to building consensus around it, and then implementing it. One day, it didn’t exist. The next, it was in the application and real customers were using what we had built.

Inspired by the engaging nature of the product work I had started to take on, I began targeting product management roles to combine my technical skills with my newfound love of inspiring others to build amazing products.

The Ontra Connection: A Long Callback

Years before my pivot into product management as a career, during my legal recruiting days, a candidate I was working with had mentioned InCloudCounsel (now Ontra) could be an interesting place for me to look to leverage my law license in a part time capacity, helping negotiate routine documents. I looked into joining the company as a lawyer at the time, but ultimately decided against it.

Fast-forward: I saw a product role open at Ontra that seemed to cater perfectly to my background in law, tech, and AI. I applied and got a call within hours. The hiring manager joked they’d been discussing posting a role for a hybrid lawyer/technologist, and my resume looked so perfectly aligned they thought someone submitted it as a prank. It wasn’t a prank. I interviewed for the job and got pulled in as an associate product manager, and kicked off a career I am confident I’ll stay in for the rest of my working days.

What I Learned on the Road to Product

The journey to becoming a PM was a long one, made up of lots of disparate phases that, at the time, seemed like they would never connect in a meaningful way. Through it all, I took away a few lessons that I still apply to my work and personal life today.

• Just Commit and Do It
  • Don't get stuck in analysis paralysis. I'm a big believer in doing something being far better than thinking endlessly and doing nothing. If you make a wrong choice, you'll quickly figure out that what you've picked isn't for you. No choice is "final" - with enough hard work, you can always move on to something different. I bounced between majors, went to law school, became a lawyer, tried public interest work, jumped to recruiting, learned to code, and found product. You only figure out your ideal fit by doing and pivoting when something isn't working.
• Follow the Passion of the Moment
  • If you're passionate or curious about something, go all-in and try it! If the passion has staying power, it'll stick around. If it doesn't, it won't. But as with my first learning, the only way to figure out what works for you is to go all-in on what excites you.
• Prioritize Ruthlessly So You Can Focus
  • If you're going to try something, try it and go all in! To go all in, you need to say "not right now" to other great opportunities. When I was studying for the LSAT, that test was the most important thing at the time, so I studied for it to the detriment of other important things - school, social activities, and more. As with product management, life is really about prioritizing what’s most important at any given time and intentionally making choices about what comes first.
• Be Unafraid of Failure and Fail Well
  • Trying new things means that there's a risk of failure and you'll have to get good at not being good at some things. When you're faced with not being good at something, you can either take the failure, learn from it, and improve yourself for the next time or choose to pivot away. I've done both! I was failing in chemistry and took that opportunity to pivot away to something new. But I also failed at tons of coding interviews and LSAT questions and chose to take the learnings from those failures to improve my performance on those tasks the next time I tried. Knowing which to do is really a matter of preference and passion, but either way, taking the learnings from failure is a must. The only true failure is failing to learn.
• Be Willing to Take a Step Down
  • If you're going to try new things with your career, starting lower on the ladder is often the price of entry. When I went from recruiting to software engineering, I took a massive cut in pay and level. I knew I could quickly learn and climb my way back up once I got a foot in the door, but getting a foot in the door required a step back. To do new things and embrace change, you have to be humble enough to admit when you're new to something and be willing to start as a beginner and grow in that new discipline.
• Nothing is Wasted
  • When you go from thing to thing, it's tempting to think that prior pursuits were "a waste of time": resist that urge. There is almost always a way to apply learnings from another arena to a new pursuit. Studying cults taught me psychology, sociology, human interaction, and frameworks of thinking about how people relate and get their fundamental needs met—relevant to user motivation, behavior, and influencing without authority. Law taught me structured thinking, better communication, and negotiation skills. Recruiting, my first sales-type role, taught me how to sell well and be a thought partner. Engineering and my CS master’s gave me a wide array of technical fluency and a bias for building. In my role as a PM, I apply all of these skills frequently and think I'm better for my array of cross-functional disciplines.
• Be Ready
  • If you're looking to pivot into product or any other career, be ready when the time is right. All of your prior lives have brought you to that moment, and when it comes its your time to shine!

Why Product Stuck

Product management gives me the best parts of what I loved along the way: complex problems, human behavior, multiple disciplines in one, high ownership, collaboration with brilliant people, and the joy of making something out of nothing. I wouldn’t have found it without trying, pivoting, and refusing to treat any step as wasted.

If you’re on your own winding path to product—or wondering whether to make a leap—try it! You can always pivot. And if you’ve made the jump, I’d love to hear your story!