In my experience, most people find their way through their careers by default.

It goes something like this: 

You take a look at your high school grades and pick a post-secondary program that felt doable, marketable and had validation from those around you (e.g. family, friends and perhaps career counselors). As you progress through school, you acquire skills and credentials that can be applied toward a job that at least on the surface, is prestigious, stable and pays a lot. Once you're done your education, you begin working, move around a couple of companies and take on more responsibilities that come with a higher reward (title and compensation). 

Before you know it, you are the {{Insert_Fancy_Title}} of {{Something_That_People_Recognize}} at {{Company_That_Everyone_Knows}}. 

You're probably confused because you were never interested in {{Something_That_People_Recognize}} or the mission behind {{Company_That_Everyone_Knows}}. 

I personally found myself caught in this cycle where as long as I worked hard, I'd have a fairly predictable career that rewarded me well. The choices I make would have been a function of prestige and compensation. 

As I rethink how I make career choices, I've tried to understand why a lot of people end up in a position where there's a strong misalignment between what they're truly passionate about and the work they spend most of their life doing. 

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What Does A 'Career' Mean? 

The Webster definition for a career is "an occupation undertaken for a significant period of a person's life and with opportunities for progress."

The above definition has a few problematic implications: 

• A career defines who you are ("I am a {{Insert_Cool_Occupation}}")
• It has a clear progression plan
• It is commonly understood - people understand your story 
• It takes a long time before you get to reap the rewards of your work (e.g. X years of education, X years of work with low pay) 

A lot of people who have managed to align their passion and day-to-day work didn't portray the characteristics above. Yet, our education system is structured in a way where we explicitly and implicitly push people in the direction of selecting a career path. 

Here are some examples of how our education system is designed to perpetuate the above career framework: 

Career Fairs: A lot of career fairs are designed to showcase certain careers over others. In business school, I was exposed to large companies that had focused streams of work (often in the form of rotational programs or structured positions such as accounting at the Big 4, investment banking or consulting). I wasn't exposed to opportunities at tech companies or the various roles that exist within a startup. 

Career Centres: Post-secondary counselors are often structured by function and don't allow students to be exposed to interdisciplinary learning opportunities. As a business student, it would have been very hard to understand how I could pick up skills that were normally saved for engineers (and vice versa). Moreover, the type of information that is exposed by career centers is largely around progression and compensation - not the actual work that gets done and the skills you'll develop. 

High School Courses: We tend to structure high school courses around subjects that can be easily rolled up to various university programs. It isn't designed in a way that allows students to see how the things they learn will be applied in the workforce. This perpetuates a system where the main goal is to maximize for post-secondary enrollment - not true student enrichment. 

Undergraduate Degrees: Similarly, undergraduate degrees are designed in a way where each of the courses relates to a skill that you'll see on a job description at a company that the university/college has historically placed students into. This again is very problematic as undergraduate programs are designed to maximize job placements among a select group of companies/professions. 

Our education system misses out on a few key points that people tend to learn much later in their careers.

1. There's an extremely broad range of career options. You can even create your own path!
2. You don't need to decide what to do right away - it's okay to take your time. 
3. You can change your mind or even go down multiple career paths.  

Seeking Productive Discomfort 

Before I explain my take on what we can do to combat the problems, I'd like to set parameters around the concept of risk and uncertainty. The top-level difference between risk and uncertainty is that risk is not truly uncertainty. Risk is when you are certain about the range of outcomes you will encounter and you just don't know what the actual outcome will be. On the other hand, uncertainty is when you're not even clear on what the outcomes could be. 

This feeling of uncertainty is extremely uncomfortable. The best way to describe this feeling is when you're given a task that you have no idea to do and you decide to google the task out of desperation that someone before you has solved the problem. 

While the system above trains you to try and avoid these situations through a well-defined career path, I'd argue that people should seek these moments of discomfort. I'm willing to be to bet that more often than not, this feeling of discomfort forces people to look in new places for new information, change their minds about things that aren't working and interact with people in ways that help them get the job done. I believe that, as humans, this survival instinct is deeply embedded in us. 

However, the problem is that our institutions and culture spend ~20 years of our life to instinctively avoid all sorts of discomfort, regardless of whether it's good or bad.

My Personal Evolution

While there are large systemic changes that need to be made to help future generations realize their full potential, I believe that we can all collectively do a better job of seeking productive discomfort. I also think that this mindset will implicitly allow people to converge their passion with their day-to-day work over time. 

Personally, I have always wanted to go down the path of entrepreneurship. It was a path that I felt like I deeply understood as I had the fortune of working with my parents as they started their own business. 

Following the path presented by those around me and the incentives of the education system, I found myself having completed business school with work experiences at well-known companies. However, I also realized that I wasn’t nearly prepared to start my own business.   

Since then, I have sought uncomfortable opportunities starting with an early-stage role at GrowthGenius doing things that I’ve never done before. This mindset also led to my decision to leave GrowthGenius and start all over again at Knowledgehook in a completely different area of the company. 

The rewarding part is that I’ve felt like I’ve done more work to prepare myself toward the path of entrepreneurship in the past two years vs. the prior eight years (working during my time at university, Rogers and Walmart). 

This isn’t a call to start changing your job and make drastic moves. However, I do think it’ll be helpful to proactively seek moments of ‘productive discomfort’ vs. shying away from them.