An Essay on Nonlinear Career Paths

A pet project of mine as of late is researching complex systems of nonlinearity, better known as Chaos Theory. I’ve always been fascinated with interconnectedness, feedback loops, and interdisciplinary study and always been considered a “Jack of all Trades” kind of person. But selecting a career can be discouraging to many like me.

It’s discouraging in career selection when you’re told to major or specialize in a discipline, get a job in that field, climb up the corporate ladder, and retire. A path with very little winding or turning, and is set for life travelers from the time they are 17 until 67. This isn’t how life works.

This has become so much so a status quo that we second guess at hiring people from what is deemed, “non-traditional backgrounds”. I’ve encountered this first-hand as I hold a B.S. in Recreation, Sports, and Tourism Management. The most non-traditional of backgrounds one can have.

Regardless of this, I’ve been able to contribute to fields such as Venture Capital, Solar, WiFi, Machine Learning, Media Production, Non-profit Organizations, Health Care, and Political Campaigns.

In the last two years alone I’ve held three different roles at my current place of employment; Trading and Technology Support, Product Manager, and now Trading Associate.

I want to advise college students graduating with a major they hate, but can’t imagine getting a job not in their field. To the mom who lost her job during COVID-19 and looking to make a career switch to benefit her family. To the human resource manager second-guessing hiring that mom who’s never worked in the field.

Innovation occurs from small, calculated risks that results in disruptions at bringing forth new thought.

One hire, one course, one interview, one decision is all that it takes to make a great impact on your life. Here are frameworks that I’ve used to make these decisions and why I encourage you to take that leap.

Tarzan Theory 

I’ve always looked at my life like I’m Tarzan, King of the Jungle. Swing from branch to branch, always anticipating and preparing for the next branch – but not jumping off the current one until the next has materialized.

Success occurs when opportunity meets preparation

Zig Ziglar

In 2017 I started teaching myself to program. I was still exploring start-up opportunities and what gearing up to fly to China to build hardware in Shenzhen. I took a CS course in undergrad but hated it, but I always knew the code would someone how to be in my future. Though I was holding on to business management and entrepreneurship, I was anticipating and preparing for what that next branch could be.

In the Fall of 2018 – that next branch came. It required that I passed a coding challenge and interview to grab on to it. That branch was PEAK6.

In my first role at PEAK6, I anticipated a need for Product Management. Again, I prepared and anticipated, and in 2019 I moved into a role in Product Management.

Finally – I reached out to members of our trader education team expressing interest in learning more about trading. I began to take courses and reading books about its theory. In 2020, a branch came for me to become a trader, and I jumped. I guess I’m quite literally a, “Jack of all Trades” now. Though I plan on holding on to this branch for a while, I’ve yet to see a 67-year-old trader.

Moral of the story: Execute your current role with the best of your abilities, anticipate shifts in your life and the world, prepare for unknowns, and don’t forget to jump!

Interconnected Mentors

In each industry that I’ve worked in, I’ve had a separate mentor or coach. When I played football, my coaches were completely different than when I was in venture capital. It is important to seek experts within your field or your anticipated field to get a perspective of what the grass looks like on the other side. It is now always greener.

At a point in my life – I considered law school or business school/project management. My mentor at the time happened to have a JD-MBA. He shared a story with me of how he was the Project Manager for the construction of the famous Chicago Cloud Gate. It was a miserable experience with long hours and OK pay. I did not want to be a project manager.

I then asked a practicing lawyer for start-ups and entrepreneurs in the area surrounding law school. He was an older gentleman that had to have been practicing law longer than I been alive. His eyes were aged with wisdom and he sat me down and looked me square in the eye and said, “You do not want to be a lawyer, trust me”.

A mentor is someone who leverages their hindsight as your foresight

O.K. Arowolaju

My dad always told me to learn from the mistakes of others, because I’ll never live long enough to make them all myself.

Self Organization

On one of Naval’s most famous threads me a statement that stuck with me hard.

I am very cautious around telling people to pursue their passions, but I strongly encourage people to think about career stamina. At a young age I knew that technology was an area I could be in long term. Then finance began to creep in purview. And ever since, I’ve found myself at the intersection between the two.

Self Organization is about figuring out what problem in society you want to dedicate your life to solving. Along the way, you’ll find others actively chipping the way and coming up with solutions that you will have an opinion about.

Sooner or later, you’ll self-organize into careers, networks, societies, and institutions of individuals in which you can be your authentic self. But the requirement of this is to be your authentic self at all times.

Complex systems have a way of determining false positives and faking it will eventually throw red flags.

If people love you for who you aren’t, they’ll eventually hate you when they find out who you really are.

I’d rather people hate me for who I am than to love me for who they want me to be.

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