Why I Broke Up With My Dream Job

Working in tech was lucrative, but it narrowed my perspective.

I didn’t stumble upon my dream job by accident. After a few years in the non-profit world, I was tired of feeling like no matter how many people we helped, more people were just streaming in the door behind them. I wanted to get more at the root of the issues I was seeing. And, like a typical millennial, I was ambitious, idealistic, and impatient — I wanted to reach as many people as possible as quickly as possible. There was no better way to do this than to be in the “education technology” space.

I went to business school to help me make this transition. While there, I was surrounded by people who saw working at Amazon, Google, McKinsey, or Goldman Sachs, as the ultimate dream. I started to wonder if maybe I had been wrong about my chosen path after all.

Thankfully, I fought off those doubts and followed my gut. This led me to an ed-tech startup that didn’t just address all the issues I was passionate about — mental wellness, diversity and inclusion, financial literacy, substance abuse prevention, and digital citizenship — it also had some traction and an awesome team. It was exactly the mission I was looking for, and as fate would have it, they were looking for someone exactly like me.

I joined the company to lead their first international expansion, and while I was there, I wholeheartedly believed that, of my whole Ivy League MBA class of 750 graduates, I had the best job.

For five years I devoted myself to the teams that I managed and to the company’s mission. Together we developed and distributed online educational games that reached millions of students. We built and maintained partnerships that allowed us to offer these products for free to schools. I worked over time every day with the hope that the generation of students we touched would be a little more compassionate, a little more balanced, and a little better prepared for the future of work and the challenges of adulthood than my generation was.

And then I just couldn’t do it any longer.

Don’t get me wrong, this isn’t an exposé about why the job or company sucked. The job was challenging, rewarding, and meaningful. It allowed me to travel to my favourite cities around North America whenever I wanted to. It introduced me to so many incredible humans from around the continent. I had a kind and supportive boss who I respected. There was nothing ‘wrong’ with it.

Many people, especially my team members and peers, thought I was crazy for not just quitting a great job, but quitting without a plan. It reminded me of the reactions I would get in my MBA when I didn’t go to corporate recruiting events. It didn’t help that I couldn’t articulate clearly why I decided to quit (that’s why I wrote this, one year later).

Though I timed my departure to minimize disruptions to the team as much as possible, I still felt guilty for leaving my boss and the people I managed. Like in my MBA, I wondered if maybe my gut was wrong. But it has become more and more clear to me over the past year that it was as wise a decision as the one to join the company in the first place. Here’s why:

Change scares me, but comfort scares me more

I knew it was time to leave precisely because change was starting to feel really scary. I knew all our systems, tools, and policies inside and out. I had strong relationships with key decision makers in all departments. I knew how to get things done and how to help others navigate bureaucracy. And I’d think to myself “wow, it would be really tough for me to get this good in a new environment.” That thought scared me.

I had 21 jobs between the ages of 14 and 25 (for comparison, my brother over the same age range had 3). I worked at a donut shop, a call centre, a liquor store, a pizza parlour, a doctor’s office, a nursing home, a food bank, a mental health centre, a foster care agency, a bank, an anti-poverty advocacy organization, a federal government agency, and an independent film distribution company, among others. I babysat, I tutored, I took notes for college students with disabilities, I collected census forms, I even helped revamp teacher training programs in the continent’s biggest school district. (For what it’s worth, not once did I quit or get fired from any of these jobs — they were all either summer, semester-long, or contract jobs.)

Every time I started a new job, I was terrified. I didn’t know anyone, I didn’t know what I was doing, and I certainly didn’t know how I was supposed to act in a new environment. But every one of these jobs exposed me to a world that made me a better person.

I gained intimate knowledge of what it was like to live with limited mobility, or schizophrenia, or arthritis, or a foster family. I befriended regulars who were truckers, farmers, nurses, and construction workers. I was exposed over and over, through coworkers, customers, and clients, to the injustices and constant obstacles that people living in poverty face. I too lived below the poverty line.

Despite all the change, one thing was constant: with every new job, my perspective grew.

In my teens, I used to study the faces of people on the street on my long solo bus rides to school. I had the actual dream of really knowing every person in my hometown, population 700,000. Working in a variety of jobs brought me closer to that goal. Each person I met added fuel to the fire. “I was within and without, simultaneously enchanted and repelled by the inexhaustible variety of life.” One of my favourite literary lines ever, from the Great Gatsby, captured my dream almost perfectly. Except I wasn’t repelled, I was enchanted and hungry for more.

And then I got a job in “tech”. The dream job. I went from averaging two jobs a year, to keeping one job for five. I paid off all my student debt and watched my savings account grow. I felt a sense of pride that I hadn’t known in my other jobs. It was very comfortable.

That is, until I noticed that my world was slowly starting to narrow. I became more and more aware that everyone I interacted with was like me: young, university educated, high income, and for the most part, white. The diversity of perspectives and experiences that I had so loved in my other jobs was virtually non-existent in tech. I realized how much I missed that side of me that worked two jobs to make ends meet, that joy of getting to really know a stranger with a completely different perspective, that cameraderie I felt with people who weren’t like me.

So, just like my gut told me exactly what I wanted to do after my MBA, it told me it was time to take another leap of faith, to step out into the scary unknown again. It was time to try something completely new.

Without a plan, I just started following my interests. I found myself, for the first time ever, meeting filmmakers and freelancers. I started to mingle with the artists and authors of Brooklyn. My life became richer and more joyful. It deepened my sense of interconnectedness, of shared humanity.

I still don’t really have a plan, but I’m ok with it (as we’ve seen with this pandemic, planning is overrated anyway). I’m not just ok with it, I love it. Over and over, life has rewarded me for moving away from what is comfortable and leaning in to what scares me. I know that doing the things that scare me may not help me accumulate any assets, but at the end of my life, I know I’ll have a better understanding of this world and its people, and that’s what really matters to me.

It’s taken me one year to finally be able to articulate why I left that dream job, and one year to see that I didn’t break up with my dream job after-all, I actually rediscovered it.

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