
It only took me five major career pivots and ten years to get to Twitter and secure one of the most interesting jobs in tech as a marketing strategy and operations manager. When I was an aspiring accountant in college, moving out to San Francisco to work in marketing and tech was the last path I would have picked for myself. I thought I had it all planned out and enjoyed the clarity I had provided myself.
Yet when I applied for the Twitter role, I had found myself in the Bay Area with a resume that read like the stereotypical indecisive, lost Millennial that always gets called out:
- Supply chain and IT consulting at a major management consulting firm
- Starting an MBA admissions company
- Getting an MBA at Michigan
- Financial planning at the world’s largest company
- Growth marketing at a ten-person edtech startup
My carefully planned life had given away to my curiosity and instinct to follow my gut. Little deviations like choosing management consulting over accounting after graduation gradually became larger pivots as I worked to refine my definition of what an interesting, fulfilling career could be.
Before I found my role at Twitter, I must have been rejected over 30 times for standard business roles that require deep experience in a focused area. Most structured companies avoid career switchers that aren’t developed internally. What I did discover throughout my journey is that for frequent career switchers like me, there will always be a few non-traditional roles that require unicorns and multi-talented athletes. However, they are almost impossible to find in a standard job search process and instead require robust networks to uncover.
Now let’s backtrack for a second so I can explain why it was so strange for me to end up so far off the beaten path.
I graduated during the 2009 global recession which should have steered me towards a path of job security and living a life of risk aversion. After all, many of my classmates were graduating without jobs while thousands of other workers were getting laid off every other week. It was an incredibly tough time to be going into the job market and becoming a certified public accountant sounded pretty good because as the saying goes the only things certain in this world are death and taxes.
However, something in my gut told me that I would end up unhappy and unfulfilled if I took the safe route so I turned down a guaranteed job at a major accounting firms and instead made a big bet on landing a highly competitive management consulting job…during a recession…from a school that consulting firms did not recruit from. My odds were pretty bad but somehow luck ended up on my side.
This is where my story should have ended — I had an exciting and lucrative path to partner at a major consulting firm. As a son of Asian immigrant parents, I had fulfilled my duty to secure financial prosperity and gain respect for the family name. Smart money would have said time to engage career auto-pilot, and I will see you on the other side in thirty years.
But I still couldn’t shake that itch. After four incredible years in consulting, I came to the conclusion that life was too short to get buried under all those status reports and be spending my life in airplanes and hotels.
During my two-year business school hiatus, I made the conscious decision that I would not let myself get caught up on climbing a corporate ladder and take the easy way out. I wanted to find a career that could be defined by purpose and fulfillment even if that meant making less money or stalling my trajectory in the short term.
With this goal in mind, I took an approach of conscious pivoting to give myself opportunities for self-discovery and growth in areas that I found inspiring and motivating. I carefully casted a wide net to collect a variety of experiences to refine and hone in on what mattered to me.
Each pivot brought me closer to identifying the work that I was passionate about like growth marketing and user acquisition as well as the type of work I didn’t enjoy like financial planning, supply chain operations, and brand management. I experienced what it was like to work in different sized companies with varying levels of maturity to discover if structure and process brought me enjoyment or frustration and how I would actually handle ambiguity and autonomy.
Most importantly I identified which aspects of a career motivated me and made me happy. Money, title, and prestige became less relevant to me despite my parents’ and society’s valiant efforts to convince me otherwise. What mattered more to me were roles that challenged me and allowed me to create and experiment and being able to work for mission-driven companies that are solving important social issues with tech.
There was no quiz or self-discovery exercise that would have gotten me to reach this conclusion. Trust me I’ve tried them all. Deviating from the beaten path was the only way I could get the exposure that I needed to find clarity and direction.
Now another pivot begins. I recently followed my gut again when I decided to leave the incredible setup I had at Twitter for a startup called Jobcase despite the amazing culture and strong professional momentum I had established at Twitter over the last two years. It meant leaving one dream job for another, and it was one of the hardest career decisions I had ever had to make.
I am a firm believer in the ethos that you only get one shot in this life to make a difference. I told myself that if I ever came across a professional opportunity where my skills and knowledge could be utilized to help millions of people live better lives that I would take the leap and never look back. I found that rare opportunity when Jobcase reached out and asked if I would lead their community and growth initiatives. It felt as if the stars aligned and the last ten years of wandering had led me to this very moment.
In many ways, Jobcase is a lot like me. It was a company born out of the 2009 recession and has survived by pivoting multiple times. Now it is a tech company that is focusing on finding job opportunities and resources for the millions of people out there that are not in a traditional corporate career. Many of its employees share my story of survivor’s guilt having made it out of a small, rural town to have successful careers but then not doing enough to support those who weren’t fortunate enough to have similar opportunities.
I knew this was the right thing for me having seen so many other green pastures from my experiences. In reflecting back on my time I also determined that had I followed my original plans for a conventional corporate path this opportunity would not have been possible. Why?
Well, I needed to start my own business to discover my love for marketing and learn how to be scrappy. I needed my experience at Walmart to develop greater empathy and understanding towards a workforce that is much different from the world that I had come from. I needed to run growth marketing at a ten-person startup to give myself a crash course in growth and community. I needed to get laid off of this startup in order to discover Jobcase in the first place. Finally I needed my time at Twitter to learn the intricacies of how different types of marketing teams in a mature tech operated and learn the nuances of conversations between strangers from our product team. Everything in my past had brought me to this moment.
I’ll summarize and end by saying that you will never find a blueprint that tells you where to go with your career. If finding purpose and fulfillment in your work is important, it requires significant trial and error in a carefully directed way to get there. I call it falling forward and being directionally correct until you finally reach your destination. For me, taking the road less traveled has brought me so much peace and clarity as well as opportunities that I could have never dreamed of. Go take that leap.
