The Story of My Radical Career Pivot into Analytics & Technology

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This is a story of incredible personal growth, shameless risk-taking, and success. But I’d feel fraudulent if I made any of it appear “easy”. The truth is that any level of personal growth worth pursuing will come with costly sacrifices. And I made many. Over the course of transforming my career, life and relationships I came to terms with the best and worst parts of myself. And let me tell you, this was tough.  During the course of my adventures, I picked up some heavy baggage loaded with suffering, anxiety, uncertainty, stress, and sadness. All of which I hadn’t fully anticipated. But taking this leap of faith as I did throughout 2019 was the best decision of my life. It was also the hardest. As scary and incredible as my year was, the thought of possibly never taking such an opportunity for growth, self-discovery, self-improvement, and adventure is the scariest of them all. 

In the end my intuition had guided me in the right direction. Within a year I nearly doubled my salary, moved to the “big” city, landed the best job I could have imagined at this point in my life, pivoted my career from government administration into information technology, banking, finance, and analytics, travelled around the world (Cuba, California, British Columbia, Myanmar, Thailand, Laos, China, Croatia, Bosnia, Poland, Montenegro), reconnected with the most important people in my life, built new relationships and met dozens of new friends, acquaintances and wildly inspirational people. I also learned things I’d have never been exposed to otherwise, started projects that energized me, persisted through new technical skills and lots of self-directed learning, and became a better human. In sum, I completely altered the course of my life. I replaced any doubt, negativity, and sadness with confidence, accountability, and gratitude. And to think that I could be still sitting in my old office wondering why I was becoming unfulfilled?

November 2018: I took this photo from my office in Ottawa, Ontario overlooking Parliament and the downtown area just two weeks before I would leave not yet knowing the adventures to come. I moved to Ottawa in 2014 with just a backpack and slept on my empty apartment floor for 3 weeks while working as a waitress at a Scottish bar across the road. I was hired as a bar manager in the evenings and went to school during the days before starting a career in international policing and later, foreign and corporate statistics. By 2019, I’d experienced so much growth living in this city and had taken advantage of all that it offered, that I will remain eternally indebted and grateful to have lived here.

The Decision To Leave My Job, My City, & My Friends

The Pros: By all accounts, I was doing well in my previous role. I worked as a financial economist/data analyst for the government of Canada and I adored my management, my team, and the work I was doing. Importantly, I felt gainfully employed as a recent graduate – I was utilizing everything I had ever learned over the course of my three degrees and putting the majority of my skills to use. In addition, the nature of my subject matter expertise couldn’t have been better suited to what I was doing: I was working with relevant statistics, publishing new research, and leading interesting projects that further developed my skillset. All around me, many of my peers were comfortable, happy, and insisted they had “made it” at our jobs. 

The Cons: But I wasn’t working in an industry that inspired me and I didn’t want any of the jobs held by upper management, so where was I going? I could feel the utility of my skills becoming “capped” out and slowly I feared my own value would depreciate in time as technology was rapidly evolving around me. I had started to feel like my life was being decided for me, rather than the other way around. In terms of compensation (because this is extremely important as well) I was paid well, but by no means competitively at an industry-standard for many of the skills I was qualified for and this made me feel extremely left out. I had also started to wonder if the opportunity cost of my staying in a role that didn’t have a capacity for experimentation, risk-taking, and learning invaluable new tools and technologies was too high given that I was still so young and eager to improve myself. I’d also discovered that internal promotions were rare and the development of internal talent was too sticky to wait out five years for the sort of promotion I landed myself less than a year later. Ultimately, I knew that if I stayed, I would be making the biggest career blunder of my life. 

September 2017: A solo trip to Boston (Harvard & MIT) seeded a new ambition in me: I discovered that I was passionate about learning and adventure. I discovered machine learning in finance and marketing which gave me new ideas I’d never considered before. It was here that I also decided I wouldn’t pursue a PhD, but rather, a career that allowed me to continue fascinating life-long learning and application of my skills.

Apart from recognizing that it was my responsibility to safeguard my income earning potential, there were in effect two deterministic reasons motivating my move: 1) I wasn’t ready or informed enough to make the decision of staying permanently in my job, industry, or city and 2) it was causing me immeasurably suffering knowing that I hadn’t yet given myself the opportunity to explore new avenues for personal and professional growth. I felt that I hadn’t yet experimented in my own life or challenged myself to move outside of my comfort zone!

Yes, I had always taken some degree of risk at the professional level – I am known to be swift and decisive with life-altering decisions – but all of my most significant life choices had been carefully calculated and well strategized. I had done so much “of the right thing” – always studying, working, volunteering, training, etc, that I wondered, could I be selfish enough to take risks and without predictable outcomes? Could changing my entire operating procedure offer radical new improvements and potential success? Fortunately, I was curious and desperate enough to find out.

Recognizing That I Was Ready For "The Difficult Stuff"

The truth is, life got really hard for a while in 2017 and 2018, as it invariably will at some point for each of us, and it was during my most difficult times that I came to recognize my own personal strengths. Most of this had nothing to do with whether I had learned to code or build machine learning algorithms. What mattered most at this point is that I had started to believe in myself. I learned that I was perseverant and had an inordinate amount of willingness to overcome setbacks, I could work relentlessly toward my stated goals, I did not fear the challenge of solving complex problems, and above all, I was exceptionally resilient amidst crisis with a deep-rooted commitment to personal and professional growth. Equipped with this understanding and my new found self-awareness, I had started to imagine new possibilities for myself that stretched beyond my current circumstances. This confidence became the only assurance I needed to build out the new life trajectory I imagined, on my own, with determination and strength.

November 2019: This photo was taken by a couple in Montenegro where I went solo back-packing and hiking through Croatia, Bosnia, Montenegro and Poland before starting my new job. I felt giddy throughout my travels and met incredible people along the way, in my heart I knew I was on the right path even if I had no idea where I was going. 

A Year of Travel, Discovery, Learning, and Becoming

I don’t think anyone who takes the sort of leap that I took jumps immediately into exciting new ventures. In my case, it took me a while to figure out what I was doing and what I wanted. Operating without any clear roadmap, my only rule had been to “keep moving forward” and to work hard. At times it felt like I was accomplishing nothing as I had no clear metrics for productivity; my day was no longer measured by the completion of work-drawn tasks or hours spent at the office. 

I had to redefine everything I’d thought I understood about productivity, value, and improvement. I quickly realized that investing in the unknown could have better returns than if I just kept repeating the same old behaviours and tasks as I had in my previous role. So I decided to get involved in entirely new lines of thinking and learning. I started web development, coding courses, content marketing, digital marketing, marketing research, startup organization, big data analysis, data strategy, data science, and cloud computing. I spent hours in online courses, watching Youtube videos, in meetups, at conferences, and even in classes. I spoke to everyone, everywhere, and tried everything! I started to read software documentation, magazines, books, you name it! I allowed myself to learn the minutia around random topics of interest in the field of technology and marketing without any concern if it was immediately impactful. I simply had to immerse myself in new knowledge before I could make any assertive claims or conclusions about what I’d wanted and where I could build a life. 

Sometimes I felt overwhelmed and lost, for sure. But I had also given myself the time to “waste time,” to err and to make mistakes. This prevented me from backing out of my plans in a panic. I had essentially given myself permission to fail! I had drawn a clear line in the sand so that if in a year if I found myself hopeless, broke, worse off and without a clue in the world, I’d admit defeat and start acting “sensibly.”

While I don’t advocate this approach to everyone, I had done enough soul searching in 2017 and 2018 to know that perhaps what I needed most was to defy everything I had ever known about myself and to shock my own reality with a completely open mind and new way of doing things. I listened to the cues of what was causing me bitterness and resentment and decided to act in way that solved for those issues.

 I had always been strategic, careful, calculated …. and successful. But I knew my happiness was dwindling and I had outgrown my current state. I knew that I needed to take some big risks to uncover my inner truth and uncover my next steps. And it worked!

By the summer of 2019 I had finally made the decision: I knew who I was and what I wanted – my personal and professional life was to be intertwined and above all, I wanted to work at a tech startup in downtown Toronto. I wanted to brave, adventurous, and wildly independent in accomplishing the dreams I set out for myself. I was ready to totally level up in my life. 


April 2019: Scuba diving at Sail Rock, Koh Tao, Thailand. At the beginning of my adventures I had outlined some pretty aggressive goals. One was to travel to Thailand and get my scuba diver’s certification. I did it! This was the last dive and the completion of my certification at the famous dive spot. It was one of the most terrifying experiences of my life because up until this point, I had never swam in open waters or put my face underwater!

Getting Clear On My Next Steps

I had taken the time to uncover what I wanted and who I was and I believe that this was the single most valuable gift of 2019. By taking extreme accountability for my actions, I stopped living in shame or guilt or regret for not being “enough” or “perfect” or “talented” and instead adopted a bias for action and implementation. I accepted that I am a human on a lifelong adventure of growth, learning, and improvement and that I while I was starting from ground zero, I could significantly improve my life with micro activities that I practiced consistently.

From here, I decided that what I wanted was to work at a tech startup, in an analytics capacity, surrounded by data scientists and data engineers, digital marketing professionals and developers in a tight-knit community. I wanted the perks of startup culture, and the pace that went with it. I wanted to work in a location that inspired me daily and I was excited to be in. I wanted challenge, energy, motion, and continuous learning and development. I wanted exposure to technology and new ways of working. I wanted dynamic teams and responsibilities. I wanted creativity and experimentation. I wanted to work extremely hard and learn everything that I could in the area of digital transformation and data strategy. I also wanted to develop critical business acumen, corporate strategy and execution. I wanted flexibility, benefits, and fun. I wanted to work with big data and customer insights. I wanted to be an “insights architect” a self-ascribed title that incorporates all that I love about technology and analytics.

Can you believe this is exactly what I got?

September 2019: Coronado Beach, California. If you can’t dream, how can you achieve? I’ve always wanted to visit Coronado and San Diego. I believe this was the only time I went outside during the entire month due of September due to job applications and work. I walked for hours every day and explored new areas while also attending a data science conference and meeting amazing people.

Going For Gold

If my year started off in ambiguity, then you’ll understand that making the decision to get very specific about the job/life I wanted for the next chapter was terrifying to me. Had I known it all along? Was I avoiding my own truth? Was I finally accepting what I wanted and who I was? Saying it out loud meant that I could fail. I could fail to achieve my dreams and discover that I wasn’t “good enough” or “qualified enough” to lead the life I really wanted.

Fortunately, when I felt hopeless or scared my support system backed me up. My parents and friends were the first to remind me that I was going to accomplish my goals and it was a matter of patience and perseverance. I treated the job hunt like a new adventure where I would need to harness every skill and strength I’d developed over my lifetime.

The Painful Process of Job Applications

I didn’t immediately rush through job applications as I still had room left in my year before I “failed myself”. So I continued to prioritize my learning and when I found the time, I would write a few cover letters and send out some resumes. I spent the better part of 2019 learning, experimenting, creating, and travelling. But that’s not to say this is a blueprint for success. For others looking to pivot careers and land dream jobs, I might advocate a strictly more disciplined approach. To accomplish this I’d also consider gamifying the entire endeavour so that you’re less likely to chronically avoid the job applications and networking requirements. 

 The most depressing aspect of my job search was in finding jobs that inspired me. Having never worked in this area before, I wasn’t entirely sure that the job I wanted existed or was available. Then, whether or not I’d find it, if I was qualified, get an interview, or land the job…. oh, my, god… I was terrified. 

Needless to say, I think I submitted far fewer applications than is normal given that I was getting very specific early on in what I was looking for. After all, I hadn’t gone through a year of risk-taking and personal development to start a career that didn’t align with my new-founded goals and beliefs. 

Because I was pivoting industries and my entire career, and I had no contacts or network in the industry and no perfectly matched experiences.  It often felt like the odds were disastrously stacked against me. Nevertheless, I kept hopeful that given the industry’s demand for analytics professionals and the hard work I’d put in developing my skills, I’d find some traction in the process and squeeze through in some way by translating convertible skills and demonstrating my value.

The Strategy Behind Job Applications

The interviews I landed all followed a similar pattern: I’d apply for a role that was aligned with my skills and interests while still allowing room in the specifications for my own professional development goals. What I mean is, I’d attack job applications where I’d felt at least a 75% goodness of fit at the technical or experience level. After submitting my resume formally, I would then research individuals in the organization or the recruitment team and reach out to state that I’d put in my application and I’d be keen to talk about the role in greater detail.

From this alone, I had multiple responses and wonderful conversations with the business. This would follow up with another round of interviews, take home assignments, tests, and later, more interviews. The process was gruelling but I learned a lot and sacrificed an entire summer doing the work that was required for it all. For example, I spent my 29th birthday weekend doing an assignment which didn’t materially translate into a new opportunity.

To say that job applications is a “full-time job” is an understatement. Requirements can be rigid and preparation is paramount for tests, assignments, and interviews. Very few discuss the emotional toll it takes which feels equivalent to a multiple tonne elephant sitting on your back at all hours of the day, I assume. Sure, it would be easier to avoid all of this and be handed a new job from a friend or contact, or to simply stay in your current role until a promotion is offered up, or to make inroads with a network and transfer over to a new company, but this isn’t my story, and I’m not sure any of these paths would bring me the transformation that my life craved. I needed to know that I could do it, and to discover myself in the process.

The manual labour of job applications is extremely humbling and uncomfortable. It challenged all aspects of my self worth and well-being. At the beginning, I was optimistic and painted a pretty picture of the process long before I entered the ring. Now, my experiences interviewing with fast growing or large tech companies has me more informed. These guys are vetting candidates carefully at every round which means you’re putting in a lot of work with no guarantee of success. My first interview was such an epic disaster I can only cringe at how novice I was at the beginning. And still, it was a fantastic learning opportunity.

The truth is, I’m amazed at how much I learned about technology and startups by simply interviewing with them. The data sets that were shared were so much fun, I was delighted just being able to get that close and personal to the job. From this perspective, I now feel that job interviews are interesting avenues for learning and research and I’m much less fearful of them.

The Final Offer

The job offer I received was nothing short of a perfect match. I loved everyone I met, felt great about the company, and got along well with the team. I hadn’t felt judged or criticized as I had in previous interviews which always made me question if I’d even wanted to work for those teams. In this case, everything was different. I was as ecstatic for the role as I hoped they were to have me and even though I had ongoing interviews, I didn’t hesitate to accept the offer. 

It all played out wonderfully and in the end I feel a little silly for all the anxiety and pressure I put upon myself in the final months. That being said, I couldn’t have accomplished any of my successes of 2019 without taking a few risks, making bold moves, inviting failure and wildly pursuing my own life transformation. It was a significant year for me and one I am incredibly grateful for.

November 2019: Less than a week after my final job interview and where I accepted my offer, I went solo-travelling through Croatia, Bosnia, Montenegro and Poland where I spent the majority of my time hiking everywhere! This is a photo outside the Fortress of Kliss, along the Adriatic coast in Croatia.

The Biggest Lessons of 2019

I stopped making excuses, I took extreme accountability for my actions, I became responsible for my outcomes, I got comfortable with discomfort, I challenged my limiting beliefs, and I practiced hard work in multiple areas of my life. I’ve proven to myself that the greatest achievements are earned and start within. 

I also experienced new modalities of being by questioning and testing old habits, behaviours, and responses to triggers, challenges, and setbacks.  I had to unlearn a lot which I hadn’t recognized was necessary in order to create the space I needed to become a better person both personally and professionally.

Growth and transformation are non linear but you have to maintain belief in yourself, regardless of how others make you feel! Because some days are good and some days are bad. In one moment you may accomplish something new and feel great, and in another you may feel hopeless and confused by another problem. 

There will always be spectators who observe a short frame of your transformation and generalize their conclusions about you. Unfortunately for them, their opinions don’t matter at all. What matters is that you stick through your goals and stay committed to betterment, even if it doesn’t always feel like you’re getting there.

Recover fast. Failure is good if you’re willing to grow from it. The same is to be said about rejection. What matters most is that you acknowledge how you feel, allow yourself space and compassion to recover, learn, and move on. Recovery is also non-linear, some days are easier than others.

While I finally got clear on what I wanted in 2019, I believe my pivot started far earlier, maybe even as early as 2017 when I visited Boston during a trip to Harvard and MIT. In that sense, my overnight success was a process that took me two years.

I had never focused exclusively on the job hunt. At the end of the day, I’m choosing a life and career, not just a job. And when you break it down, all of it is meant to bring meaningfulness, purpose, happiness, and fulfillment, with a healthy does of challenge, growth, and change. When I got clear on what all of this meant for me, and what it entailed, I did the only thing I knew how: try my best to figure out the best path forward.

Oh, and its always okay to try new things and to change your mind. 

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