Is This My Flop Era?

Making the difficult decision to leave the tech industry and my 6 figure salary that came with it.

Photo by Daniel Thomas on Unsplash

If you’re like me, you’ve devoured the multiple dramatic narratives that surround the tech start-up industry. Films like The Social Network that all but called out the Founder and CEO of Facebook Meta, labeling him a selfish, patronizing jerk who cares more about building a personal legacy than forming meaningful relationships; or the various mini-series available on every streaming service about the rise, fall, and rise again of well-known start-ups like Uber and WeWork; and of course I can’t highlight the problematic start-up ideology without vividly thinking about the aesthetic and sound of the infamous Elizabeth Holmes from Theranos. 

The reality is that the interest in tech start-ups is just as much about the behind the scenes drama as it is about the curiosity of the seemingly adult playground. Seeing images of offices with brightly coloured walls, open concept workspaces, refrigerators full of snacks and alcoholic beverages  — alongside foosball tables and bean bag chairs — seems like a fantasy land. Not to mention having the ability to have a boss who presents themselves more like your cool cousin or rich uncle instead of an out of touch, by-the-book parent. Although it feels like an inconceivable fictional version of a job, it is very real and only a select few of us were provided the unique opportunity to be a part of it. And once that opportunity has been bestowed upon you, it is very difficult to make the decision to ever leave.

It’s no secret that this sort of fantasy land comes with extremely long days and nights as well as toxic work environments and problematic leadership. Start-up employees have complained publicly as well as commiserated within whisper networks (literally just browse GlassDoor or google ‘working at a start-up’). But I'm sure if you check on your start-up friends, it wouldn’t be surprising if they were still at the same place they were lamenting or that they’ve moved to another tech company (myself included DRAG ME). There is something about the intrinsic promise of a tech start-up that has a firm grip on people like me that is far more meaningful than the visual fantasyland purported by their well-established PR teams. 

Innovation

Inclusivity

Opportunity

Community

Influence

With these value propositions in mind, of course you’d want to see the business succeed … by any means necessary. What’s a few late nights when you’re moments away from changing the way the world does X forever? What’s a few more brainstorming meetings that have nothing to do with the role you were hired for when you continue to close the gap between the have and have nots? What if your professional existence is your personal?

It was difficult enough for the average person to get inside the brightly coloured gates and for me the access seemed even that much harder. Reportedly Black women make up approximately 2% tech workforce in Canada — and even less when you consider the US and the UK. So the stakes felt extremely high for me when almost a decade ago I got the opportunity to intern for a well-known Canadian based start-up. The concept of being a part of a company whose values were so deeply aligned with my own, and in an industry that felt extremely exclusive was unbelievable. 

After 1 online application, 1 phone interview, and 2 in-person interviews I secured the highly coveted, temporary role, at the very bottom rung of the career ladder, with zero guarantee that it would be anything more… and I was elated! I committed to the 40hr work week required for the internship, alongside my part-time job, and my weekly post-grad classes — all in the hopes that their limited investment in me would turn into a full-fledged long term commitment. 

Even though my trust in the process paid off and in less than 10 years I went from intern to leadership, I was beginning to feel like the total investment I was making and the responsibilities I was continuing to take on were significantly unbalanced to what I was getting in return. Furthermore,  when I began comparing notes from my peers and other colleagues it was clear there were some individuals getting a lot more for doing a lot less.  I realized that as much as I hopelessly devoted myself to the business, the business was hopelessly devoted to mentions in flashy publications, revenue growth, and the mere perception of their value propositions over any tangible actions. The dramatized narratives I had devoured about tech start-ups were dangerously close to becoming my reality: I was moments away from being one of those lamenting tech employees and just completely burnt out. 

I felt desperately like I was drowning when seemingly out of nowhere I began receiving job offers that sporadically appeared in my inbox like possible life rafts. One in particular stood out with an offer I felt I just couldn’t refuse. However, I wasn’t completely certain whether this was the shift I needed or the change I wanted. I knew it was time for a change and this company had been aggressively trying to recruit me for months, answering all my questions, pacifying many of my concerns, and meeting a slew of my demands. So I couldn’t understand why I still had reservations about moving onward and upward.

Taking this new job meant all the education, multiple internships,  years of work experience, and past professional frustrations were worth it. I was finally  inching towards the 1% - making 6 figures with a fancy new title in a booming industry at a time when the rest of the global workforce seemed to be struggling. I couldn’t seem to reconcile this with my hesitation even though this is exactly the kind of opportunity I worked so hard to achieve.  

I grew up in a single parent home with little to no guidance on how or why to get a job that was more than merely something to pay your bills and keep you content. With this new job I would still be in the thriving start-up industry while having complete financial freedom and the ability to begin planning my future as a homeowner and jet-setter extraordinaire. For all intents and purposes, once I signed on the dotted line I would be ‘my ancestors wildest dream’. Once that all set in, there was no turning back - Signed, sealed, delivered, I accepted!

While I was a little overwhelmed with new processes, overload of information, and varying personalities, after the first few weeks I was still brimming with the excitement of possibilities. I felt a kinship with my new colleagues and was interested in how we would come together to see this business grow. However, as time went on I couldn’t help feeling that, personally and professionally, something was off. 

On the heels of the pandemic, more and more offices were resorting to working 100% remote and I knew that would be my reality. But what I didn’t realize was how much I relied on the social aspects of my previous work environments. Even during the peak of the pandemic, I would schedule park walks and outdoor distanced meals with colleagues so we could connect on projects and catch up on our personal lives. However, my new coworkers all happened to be located in parts of the US and Europe and therefore there would be no occasion in the near or distant future where we could connect in person. 

Although not being able to build meaningful relationships with my new colleagues was a bit of a hurdle for me, I didn't realize how much of an impact it would be when entering into a new medium; I was still firmly in the start-up space but the product and platform were quite different.  The type of support I realized I needed wasn’t readily available to me — and I wasn’t convinced it would be any time soon.

Lack of support on a practical and interpersonal level started to become a thread in my new work experience. Upon my arrival we discussed that the team would be small and I wouldn’t yet have any support from entry level employees. But the company was quickly growing and with the help of my guidance I should expect changes and support soon. Days turned into weeks, weeks  turned into months, and the work continued to pile up with no help or end in sight. I started to be tasked with more menial administrative work and less high-level thinking and strategic planning. In start-up land it is par for the course to take on a little more than your role requires and I’m very much a team player; but that feeling of imbalance was rearing its ugly head again along with a few other concerns. In addition to a variety of red flags that eventually came to the surface, the realization that I unknowingly and naively took on exponentially more work and significantly less support was extremely disheartening. And my feeling of burnout from my previous employment only exacerbated. 

Furthermore, many of the things the recruiter and I discussed early on about my passion for diverse representation and inclusivity as pillars to building a business no longer seemed to be at the forefront of our focus. I began getting the sinking feeling that again in my career I would be one of very few WOC that would have to defend and educate individuals on what was problematic, what was a true act of inclusivity and the value of representation or the lack thereof. Once the sinking feeling started to become a reality, it was setting in and leaving me to question if this was the role for me in the end. 

Before I made my decision final I did what every millennial woman does - I called on friends, family, therapists, financial advisors, tiktok takes and instagram memes to help me ruminate on the pros and cons of my position and the company overall. Nonetheless, I still wasn’t confident about my final resolve. Although there were some difficult moments in my past start-up experiences, the friends and connections I’ve made were incomparable. From my old bosses to my team who reported into me, these are people I see as a part of my life forever. For me, that was the trade off from everything else that comes with the rollercoaster start-up experience. 

Not to mention I was making a decision that would drastically change the financial situation I’d worked so hard to secure. As a single woman living in an increasingly expensive cosmopolitan was now the right time to walk away from a regular pay cheque? How much was my physical, mental and emotional health worth?

I can’t help but wonder … Will this life changing decision be exactly what I need or is 2023 going to be my flop era?