Chasing My Dream Job


My family moved to Canada when I was 15. Until then, my life had revolved around academic achievement, music, dance, and family. When I started high school in Canada, I learned that many of my classmates had money of their own. They worked at coffee shops and fast food restaurants. They made money, and usually spent it all on food and shopping while hanging out with friends at the mall. 

I went home one night and announced to my parents that I was going to apply for a job at Tim Hortons. This was my dream job, because it meant free Iced Cappuccinos every day. My parents shot this idea down pretty fast, and rationalized to me that my time was worth way more than whatever money I would make. I sulked for a few days, and eventually got over it and just got back to kicking ass in school. I graduated high school with the highest average in my year, and got into a competitive math/accounting undergrad program at a well known university in Canada. 

Fast forward a couple of years and while in university at age 18, I told myself that my actual dream job was to work as an auditor for a Big 4 public accounting firm. I was enrolled in a co-op (intern) program, which meant that I had to find myself a job at the start of my second year in college. I attended a million networking sessions, stood around in uncomfortable heels for hours on end, and struggled to make a lasting impression on the campus recruiters. There were three hundred students competing for 30 open positions in the Big 4 firms. What chance did I have, as a shy and nervous girl that could barely speak up loud enough to be heard?

This was Fall 2008, at the peak of the financial crisis, and every accounting firm in Downtown Toronto was scaling back their hiring. Through sheer luck, I managed to connect with the head of campus recruiting at one of the firms during an event. I had simply reached out to her asking if there were any vegetarian food options that evening at the event, and we ended up having a 20 minute conversation about her journey to vegetarianism. If you've never been to one of these networking sessions, you should know that 20 minutes with the head of recruiting is like manna from heaven. That one conversation helped me get into their summer leadership event, which then got me a job offer. I had finally landed my dream job!

This job was at once the most intensely challenging and most rewarding learning experience. Public accounting is like bootcamp for accountants. Whatever is thrown at you, you learn to grit your teeth and just get it done. Grit, it's a powerful thing. Fast forward to age 24, I realized that my dream job had turned into a nightmare. 80 hour workweeks, lack of sleep, non-existent work life balance and all for what? $67,000/year in salary, with the potential for some career growth over the next 10 years being the carrot dangled in front of me. Always in front of me, but just out of reach, like a mirage. 

To hell with that. I decided the money wasn't worth it. I started interviewing for accounting jobs at tech companies in San Francisco. The offers of unlimited (untracked) vacation time, and free lunch and dinner everyday at work made me starry eyed. I had finally figured out my one true dream: land an accounting job inside one of Silicon Valley's darling tech companies and enjoy a life of luxury and bliss. 

I had competed with 300 others in my college in Canada, but here I was in San Francisco, competing with 3000 others for a single job. I failed my first phone screen, and re-applied for the same role at the same company 6 months later. This time I did much better on the phone interview, and I got invited back for 4 more rounds of interviews before they made me an offer. In my excitement, I didn't even think to negotiate a better offer. What an idiot. 

The first six months were hellish. The team was dysfunctional and filled with cliques of people that couldn't stand each other. Everyone had some complaint about everyone else, and I was so lost. On top of this, learning the products and business, along with learning my job responsibilities was mentally exhausting. I would sit through a 2 hour meeting with 30 people in Finance and Accounting, and half the things that were being said went right over my head. If you had asked me how I was doing at my dream job, I would have been too embarrassed to answer. 

At the 6 month mark, something magical happened. I started reporting to a new manager, and for the first time in my career, I was reporting to someone who actually cared about me. She asked me what my career goals were and I responded with a blank stare. This conversation was an inflection point for me. I realized that chasing a dream job was a futile exercise. I had a killer opportunity right now, and I needed to start hustling if I wanted to have any kind of impact on the company and on my own career.

Well, it turns out that all I needed was a kick in the butt. Once I started hustling, I gave it my everything. I worked through every problem that came my way, built up the courage to reach out to strangers in the company for help, kept my head above the water even when everyone else was drowning under the pressure to perform, and stayed the hell away from all office politics. After about a year of hustling, I applied for a manager role within my team. I got the job, and got a nearly 50% increase in pay along with the promotion. This role gave me a ton of autonomy, allowed me to build my team from the ground up, and I worked on things that had a lasting impact on our team and the company.

I chased my dream job for years, and it always eluded me. I quit that search for greener pastures while I was busy hustling, and magically, it came and fell on my lap. 

As I reflect on this journey, a few things stick out to me. Money is a lure, but money alone is never enough to keep me motivated and happy. Building genuine relationships with people matters. Don't try to fake it, because people can tell. The grass is always greener on the other side. Try to fix things on your own turf first before you reach for the next cool and shiny thing. Keep hustling. It doesn't matter if someone's watching. It doesn't matter if you don't see the carrot dangling in front of you. 

Don't chase your dream job. Chase the hustle, and watch your dream job chase you.