Introduction

When I first tell someone I’m in law school, I’m often surprised by how many people are considering it too. Maybe as a next step or a someday plan, usually accompanied by a healthy dose of uncertainty. 

When I ask them, “Why not?, their answers are often verbatim what I was weighing before deciding to go. These conversations inspired me to reflect on what my decision-making has looked like over time, and sketch out the imperfect process so far. 

I used to stay up late watching many more “Should I go to law school?” type YouTube videos than I’d like to admit. They were not particularly helpful. So, I won’t try to list the general law school pros and cons here. And I could never try to suggest the right decision for anyone else. What I can do is outline from the moment I wanted a career change to deciding on law school. So if your Google search history looks like the graveyard of midnight career research that mine often was (and sometimes still is), this article may be for you. 

Disclaimer About “Why”:

I’ve focused on the “how” of this process first, which leaves an obvious gap near the beginning where my “why” should be. Why keep fumbling around at school or work to try and offer something up to the void in the first place? And is that “why” robust enough to keep me going when the going gets tough? I hope to dive into that subject in another article.

Additional Context: Why I First Left Tech

Note: Skip over to stage 1 for the more practical parts of this article.

I’ve met plenty of people who appear to have been assigned lawyers at birth. Maybe their parents even met in law school, and that’s always been an obvious option for their kids. I can’t relate to that. Practicing law had little to no appeal to me until my mid-20s. 

I first worked for a few tech start-up companies and loved a lot about it. Particularly the environment and teams I got to work with and learn from. There was only one problem, I couldn’t sleep at night. We were focused on solving problems I felt I had little personal investment in, and it was beginning to wear me down. Yes, that’s an incredibly idealistic reason. In retrospect, I could have stayed for many more years, building enough career capital in that industry to eventually move on to something more aligned later in my working life. That could have been a reasonable path, but luckily, I was at a point in my life (and still am, to some degree) when I could afford to take on more risk. I chose to make a change and see what happens, rather than always wondering. 

I think some of what I realized at that time is best described as concerns of technological solutionism. The problems I was interested in didn’t have apps for solutions (and believe me, I tried to convince myself they did). 

Feeling a bit disillusioned, I can now see that I was beginning the first stage of my decision-making process.

Stage 1: Getting Involuntarily Humbled Enough To Let Go Of What I Thought I Wanted to Do & Opening Up to Different Possibilities

At first, most of my interests appeared to point toward a career in social work. As I started to daydream about it, build a plan, and set off to start my social work program, this option had crowded out any others in my mind. I loved how certain that felt. It was relieving to think I’d soon be out of this period of career uncertainty and back onto the firm ground of a set plan. 

But after the first few months of my social work program, that certainty started to run out. I hated being there and was slow to admit it. There was no hope of trying to force it, either. I realized I was not about to learn the types of skills I was interested in offering as a service in my future career, even if it was connected to my main interests, and I could likely be good at it. 

This was followed by a micro existential crisis. I had spent so long thinking about this change, just to be flat-out wrong. I spent some time double-checking why social work was not a fit for me, dropped out of the program, and never looked back.

This stage forced me to loosen my grip on what I thought I was certain my next steps were. Not knowing is an answer in itself, but an uncomfortable one that I had tried to fight off with a quick answer. Now, with an open mind, I got to work thoroughly considering other options in a new way.

Stage 2: Abandoning “Just Follow Your Passion!” as a Decision-Making Strategy

Around this time, I realized that “just follow your passion!” is terrible career advice. Even when I heard it from people who were (by my standards) highly successful, it didn’t even appear to be what they had done. There was a lot more to their career evolutions. 

I had recently tried following another passion of mine, photography, and decided to monetize it. This managed to quickly squeeze any living passion out of it. (Don’t worry, it’s since been revived). I was not looking to repeat that experience.

Today, I know that the number one book I would have benefited from reading at this stage was Cal Newport’s So Good They Can’t Ignore You. (Wait, how many of my articles are just disguised reviews of Cal Newport books? Okay, fine, a couple). 

So Good They Can’t Ignore You outlines why chasing your passion is indeed awful advice. Instead, it suggests focusing on providing value and outlines Newport’s Career Capital Theory. In short, by first focusing on providing value, I can build career capital based on rare and valuable skills and, over time, trade them for more aligned work. In doing so, I can increase the three main factors Newport thinks everyone wants most in their work: creativity, control, and impact. This book is essentially an archive of how Newport developed his own career decision-making process as it first unfolded (and in my opinion, it is the best of his books).

So, at this stage, I stopped picking apart all my passions, looking for the next one I’d milk to make an income. I started focusing on the value I’d like to bring. What would that value look like? What form could it take? Inspired by my time with start-ups, I also drafted my extremely vague mission statement, centred on providing value instead of anything to do with passion.

Stage 3: Deciding If I Should Continue in School

Next, I had to consider how I wanted to learn to provide value in this new (and, so far, vague) way. I knew there were different paths I could take, which did not all include institutionalized schooling. I began by sketching out what I did know as a starting place made up of my more “fixed” puzzle pieces:

• I wanted to spend more time learning about the areas I was interested in, before trying to work on them
• There were university programs aligned with my interests (which I believed I could learn adequately enough from) 
• I had a feeling I’d enjoy the structure of a set school program (even if I also resisted it at other times)
• I didn’t find any non-traditional or non-accredited type programs I was interested in
• Grad school seemed like an interesting self-directed learning opportunity (but I would first need an undergraduate degree)
• I learned there were more bursaries, grants and scholarships available for tuition than I had anticipated, should I go the institutionalized schooling route 

I Balanced This Against What I Didn’t Know And/Or Worried About:

• Exactly which undergraduate degree would be the best fit
• How I would pay for it. I had watched Hassan Minhaj’s Patriot Act episode on the racket that is the US student loan industry, and wrongfully assumed Canada’s industry must be similar
• The opportunity cost of not having an income or building work experience for an extended period

I tried to logically weigh these factors for some time, but ultimately failed to arrive at a conclusion that way. Instead, I trusted my gut feeling leaning toward school and decided to take a bet on the possibilities it could bring, rather than focusing on (albeit genuine) concerns about the negative consequences. Again, I was in a position where I figured I could get away with taking on a bit more risk and decided to do so. And, spoiler alert, I don’t regret it (so far, at least). 

This is how I went from “I have no idea what my next steps are” to “This is the working mission statement I’m running with. I want to provide value for my community in this way and return to school, because I think I might want to continue to graduate school, and at least this gives me space to learn more about the issues I’m interested in”. And off I went. Having an incomplete, “bad” plan to begin the iterative process of adjusting as I continued was much more valuable than no plan at all. 

Stage 4: Digging Into a Couple of the Best Blog Posts on Careers I Could Find 

First, I Read The 80,000 Hours Career Guide (And Disagreed With Lots Of It, But Was Still Inspired By Lots More)

80,000 Hours is a career resource with a full how-to guide on their website, blog, and podcast. Its name points to how we have about 80,000 working hours in our careers (40 years x 50 weeks x 40 hours). It focuses on how if we want to make a positive impact with our lives, choice of career is probably the best opportunity to do that.

Their career guide offered plenty of ideas and a framework to steal from, as I built my approach to deciding on the next step in my work. I also appreciated that, on balance, it was well-researched, rigorous and rational in its advice. It’s the furthest thing from “just follow your passion!” I could find, and I needed a palate cleanser. 

However, it’s worth noting that the organization’s underlying mission is to push the philosopher Peter Singer’s doctrine of “effective altruism.” While the guide offers useful examples of analytical reasoning through this problem from multiple angles, some of their conclusions appear biased towards trends in the effective altruism movement.

For example, the most pressing problems they suggest everyone focus on are limited to mitigating existential meta-risks like AI, bio risks and climate change. I’ll give them credit for the fact that they listed global infectious pathogen response as a top concern for years before COVID-19. But the areas I’m looking to focus on aren’t high on their list of suggestions. I’ve decided not to discount the power of intrinsic motivation, especially not just because Peter Singer says I should.

So I took what I liked from their guide and blog posts, remained aware of its biases, and left the rest.

Bonus: I liked their recent article on deciding to go to law school, which specifically translates well to a Canadian context.

Then I Read Tim Urban’s Wait But Why Article on Picking A Career & Loved It

Now that I had more structure for approaching my decision-making from 80,000 hours, I started digging deeper into my career options on the table.

I had been a long-time reader of Tim Urban’s Wait But Why, and in 2018, exactly when I was toiling with this the most, he released his article on picking a career path. To this day, it has been the most helpful tool for visualizing and conceptualizing this process.

I read the article a few times, loving it more each time. Then, one night at the surprisingly tired age of 24, I braced myself and filled out all the post’s accompanying worksheets in one sitting.

On the “Denial Prison” page, which asks, “What are you curious about in passing that you’ve never really dug into?” out popped onto my sheet – law. It was preceded by political science, comedy, music and writing, which were all much more obvious to me. But, law? I could barely admit that to myself in the moment.  

Next in the exercise is the “Want Box,” where I carried my “law” answer forward from the previous page.

When it came to drawing all the career paths from my “Want Box” on a timeline from my current position to success (however I define that), in retrospect, I really could have researched my answers a bit more. I listed “lawyer” as having the longest career arch from start point to success of all my options. I defined success in that field as just passing the bar. (Talk about a low bar. Sorry, had to.) I gave it a ballpark estimate of taking ten to twelve years from beginning to passing the bar. Suffice it to say, that may as well have been 100 years at the time, and “law” didn’t make it onto the next worksheet. I felt unsatisfied as I finished the worksheets with the other options in my “want box,” but this was the night that a lingering question of “why not?” about law slowly started to grow in the back of my mind. 

Stage 5: Chipping Away At My Running Note Entitled “Official Process of Elimination”

So, neither of these helpful, clarifying processes revealed a concrete career choice in the moment. However, I was left with solid options and limiting factors to move forward with. Again, these were the fixed puzzle pieces I had collected at the time:

• Still, that vague mission statement of the value I’d like to bring and a bit of why 
• Accepting that I wanted to go back to school
• and that I’d likely want to continue to grad school 

From then on, every next step helped illuminate the next one. That cheesy saying that you can make it from one side of the country to the other with only what you can see in front of your headlights kept coming to mind. And it was true.

I started a running note with a list of undergrad degree options and careers I was researching. I left no stone unturned; I even added the middle-of-the-night ideas that made little sense in the morning. I needed to get them all down as options to parse through individually and ensure I wasn’t missing anything. I lived with a persistent worry that I might be missing some perfect choice right before my nose, so this process helped me systematically cover everything I genuinely thought could be an option. 

The undergrad degree options on my list were under health care, social science, or creative sub-categories. Followed by long lists of pros and cons, and ideas for how I could slowly try each of these options “on.” I could research online, talk to someone working in that field, journal about it, and more until I felt I had an answer to move forward with for the time being. Even if I realized later that I had made a wrong turn, I figured I’d at least have a written record of the flaw in my reasoning that I could return to as I reset to try again or make a change. 

Then, finally, for my undergraduate degree, I landed on:

Health Science

• Main pro (among others): I genuinely enjoy helping and caring for others, and health care can be a political act of compassion
• Main cons (among others): Am I interested in being employed by a healthcare system that’s not aligned with my values? Are there enough opportunities for change?

With enough of a next step, I set off to complete my Bachelors of Arts in Health Science. I was still considering grad school, but continuing to study something like health policy was sounding less and less interesting to me by the day. However, my notes list continued with graduate school and/or career options for post-graduation.

Thankfully, this is when I was properly reintroduced to law in one of the health science courses of my last year. My school’s dean of health science was also a lawyer and offered a lecture series on law. Finally, I had a big light bulb moment, like I had heard long heard about and given up on ever happening to me. 
The more I researched this option, the more I saw it as a craft worth learning to offer as a service in the future. A new framework for looking at my existing interests. My pros and cons list finally balanced toward the pros, and I had no other options left to work through. After a long process of elimination, I was left with a strong enough “Why?” and not a single (or cumulatively) convincing enough “Why not”. 

Looking back, regardless of how much I felt this was a streamlined, rational process I worked through for myself, I didn’t. Ultimately, the lucky and unplanned variables of who I met, what I was exposed to, and what I was inspired by along the way shaped and continues to shape this process the most. Now I try to remember to leave the door open enough for these happenings to unfold while I’m busy working away on what I think will yield the “real” answer. 

Conclusion

In the end, that 12 years I was certain it would take just to pass the bar is working out to be an estimated (*knock on wood*) about six years. While I may not have been that wildly far off with my initial estimate, I was surprisingly short on estimating how personally satisfying and enjoyable this time in my life would be. To an uncertain 24-year-old, 10+ years just to get to a starting line may as well have been 100 years. But now, as a 30-year-old, being ~2.5 years from (hopefully) passing the bar and just beginning on this path feels fresh and energizing. It’s been far from easy, and it’s far from over. But it’s a starting place that, in hindsight, I think I had wanted to land on for quite some time. 

So, in case your own messy, confusing, tiring process of deciding on your next career step is wearing you down, keep going. I’ll try to continue this series of posts as I keep going, too.