This post may contain affiliate links. Read my full disclosure.

Before I became an entrepreneur, I fought for an accounting career. It started off as an underdog story with 3 important failures.

I was raised in a modest, middle-class family that nurtured education and well-roundedness. I was encouraged to pursue a professional certification, and find a steady job in the corporate world out of a desire to create financial stability in my career. That way, I’d always be in demand in the job market, and higher salaries would enable me to live comfortably.

All of that sounds fine and dandy when you’re young, and life has been relatively smooth sailing. After all, I was lucky to have a roof over my head, a warm bed to sleep in at night, and didn’t have to wonder where my next meal was coming from, so I never had a reason to question it.

But the universe has a funny way of shaking things up when you least expect it.

I Started on a Safe Path

Growing up in a family of academics and professionals, I had always assumed I would walk the same life path forged by other children from typical middle-class families: Go to a good school. Get decent grades. Land a sweet job after graduation. Work hard and climb the corporate ladder. Get married. Have kids. Relish in the occasional material indulgence – maybe a vacation or two every year. Rinse and repeat… Retire.

Every summer, my parents sent me to camp so that I could be exposed to a whole plethora of skills and life experiences, from horseback riding, to art, to computers and basketball camp. During the school year, I took piano lessons, swimming, ice skating, and even got to brown belt in Shotokan karate. All in all, I was a healthy and well-rounded individual who stayed out of trouble.

When I started undergrad at University of Toronto, I still felt like I couldn’t commit to a career choice, but I knew a business degree would give me some options. I became involved in student government, where I met alot of ambitious, type-A friends and had a little too much fun on weekends, all while holding down part-time jobs working at the mall.

At that time, many of our student mixers were sponsored by one of the “Big-4” major accounting firms, who also happened to actively recruit Commerce undergrads for jobs after graduation. It wasn’t hard for a starving student like me to be seduced by the glamorous lifestyle featuring open-bar events held at poshy downtown venues. If I could keep living a swanky lifestyle on my own dime after graduation, I was pretty sure that accounting was a solid career path… why not, right?

A Fight For Face Time

Nailing that elusive internship wasn’t easy. The recruiters at networking events were like local celebrities on campus – everyone fought for face time.

Most people just cared about showing off their academic achievements and sexy résumés, forgetting that these recruiters were human beings with real-life interests outside of work.

I discovered I had the natural ability to keep conversation casual (especially after a few drinks), and would rather talk about my recent snowboarding trip, or summer travel instead. That (along with my chopped pixie hair à la Shannyn Sossamon circa. 2002) was what made me memorable.

I was lucky to land an internship at one of the “Big-4” accounting firms, which was a feat in itself after fierce competition and multiple rounds of interviews. After an amazing summer in the Assurance & Advisory group, I was offered a full-time position at the firm after graduation.

Life was good, I was on top of the world.

The Rigorous Exams

The Canadian Chartered Accountant (CA) designation – now called the Canadian CPA – has one of the world’s most challenging and rigorous qualification processes: 3 multi-competency-based exams, and strict articling and professional experience requirements. Working at a big firm, we had the advantage of prep courses and paid time off to study. Everyone in my peer group was going through the same challenges, so study buddies were everywhere.

However, one of the drawbacks of going through the process together, was that if you couldn’t keep up, you would get left behind.

Triple Failure Smackdown

Results of each exam were posted online, and the names of all successful candidates were posted on a single website that you had bookmarked, refreshing 1000 x on results day, and praying that you would see your name on the page.

I had always done relatively well in school, but apparently, standardized exams are a different beast. Lady Luck didn’t carry me as far as I had hoped.

Over the next two years, I ended up failing ALL THREE EXAMS on the first attempt.

My first failure wasn’t too bad… I blamed it on the fact that the exam was multiple choice, so I studied one more time, and passed it.


The second exam also ended up in failure… ok it’s starting to get a bit embarrassing now, maybe I just had to work a bit harder? I had a year to regroup and get myself back on track, and I passed it!

2 down, one to go.

Third and final exam, ended up failing AGAIN.

Seriously now, WTF is wrong with me?

Admitting Defeat

By this point, my confidence had taken a severe beating. Another side effect was experiencing crazy feelings of inadequacy and major jealousy when I saw celebration photos of my successful friends at the results parties I couldn’t go to – and that happened 3 times over 2 years, by the way.

It was a dark time in my life when I had to continue seeing the same friends at work and lunch dates. Although I was genuinely happy for them, I could sense awkwardness in the air when they had to refrain from talking about their achievements with me around.

I felt bitter and ashamed around my accomplished family, and withdrew from conversation at gatherings.

I became SUPER self-conscious, confused, and started questioning whether I was really cut out for this profession. Although I was a high-achiever at the office, I started questioning my professional abilities too.

To add fuel to the fire, my firm had also instituted a policy that if any candidate failed an exam twice, they would no longer be employed.

I was walking on thin ice every day from the pressure.

It felt like a miracle that I passed the first 2 exams on the second try, because I never walked out of the exams feeling like I nailed it. Having no gage over my performance made every attempt feel like a shot in the dark. When it came time for my second sitting at the Uniform Final Examination (UFE), the most intensive exam, I knew I needed a fundamental shift in my mindset.

Everything that I had strived for in 4 years of school and 2 years at work were on the line, and if I lost my job this way, it would all be in vain – I couldn’t just hope for a Hail Mary.

Eye of the Tiger

This is where my Rocky-esque training montage begins.

The strategies taught in our prep courses were meant to be applied as-is because they delivered results.

One of the most important aspects of the approach was to study from 9-to-5 like it was a job. After 5pm, you shut your computer and you go relax. You go out and have a life.

It made NO SENSE to me at the time.

I was bred to believe that studying longer was better, and that all-nighters = increased chances of success. But that thinking actually led to major burnout and failure. So this time, I just had to do what I was told, and nothing more. No gaming the system. No trying to outsmart a method that was already proven to work.

For the first time in my life, I had no choice but to trust the system.

So against every grain in my body, I worked hard and played harder that summer, and a funny thing happened.

I started to loosen up, visualize my success and actually believe it was possible.

Game Day

I walked into the exam that day like a fighter before a big match. I felt nervous, but well-rested with my headphones in, listening to battle jams. Psyching myself up.

Hundreds of people along rows of desks typing furiously away on their laptops didn’t bother me.

I was ready.

The exam took place over two days, 4-hours each day (barf). I didn’t walk out on day 2 feeling particularly victorious, but I knew deep in my heart that I gave it my 110% effort this time.

There was nothing I could have done better.

No matter what happened – pass or fail – I could live with it.

The Defining Moment

On results day, I locked myself in my room all morning and online-window-shopped until I was thisclose to carpel tunnel.

At 11:59 am, I loaded the results website and stared in disbelief, as names already appeared on the page… a minute early.

I scrolled down in a cold sweat and saw my name… making sure that every letter of my first, middle and last name were spelled correctly.

HOLY S**T – that was me. I finally passed.

I remember running down the stairs and screaming at my mom in pure joy that I finally got over one of the biggest hurdles EVER. Even in the euphoria of that defining moment, I didn’t really care about what getting my CA designation meant for my career.

To me, the real joy was overcoming this emotional and psychological hurdle, and proving to myself that I could win.

Failure is the best thing that ever happened to me.Click To Tweet

I don’t fear failure anymore. In fact, it makes me stronger.

The bitterness of previous failures only made success taste a million times better.

Perseverance and grit helped me stick it out to the end, even though I wanted to give up a million times. This feeling of triumph affected me so much to the core that I carry it with me every day.

Little did I know that my first taste of failure would light a spark that would eventually end a very promising career… but that’s for another story.


Failure is a rite of passage for many entrepreneurs… Have you ever experienced failure that felt like a near-death experience? How did you overcome it?