Two years ago I was packing up my stuff and saying farewell to my good friends in Waterloo. I was off to start a new adventure down in Seattle, working for the infamous Microsoft. If you had talked to me back then, and even in the first year and a half that I worked there, I would have told you that living on the West coast and working at Microsoft was amazing and I had no intention of ever returning to Toronto. Yet here I am, two years later, looking for a place to live in Toronto and working at ShopLocket (www.shoplocket.com), my friend’s startup.
I went from living on the West Coast with a well paying job, amazing friends, easy access to the mountains with gorgeous hikes, climbs and skiing; to selling almost all of my belongings, taking a huge pay cut and sleeping on an air mattress because I am currently “homeless”. At first this seems like a crazy move to have made, but what surprised me most is that when I told the world what I had done no one seemed surprised.
Microsoft was my first real foray into the software industry. Being a Waterloo Mechatronics Engineering grad, I had my fair share of co-op jobs, but none of them were at a large software company. As such, I wasn’t really sure what to expect from working at Microsoft. When I had first met the recruiters I was really excited about the job description; everything about the job seemed to look good on paper. I was going to help design software that would be used by billions of people.
When I received my Microsoft offer it was late November of my final year. I was still in school and had more than a term left, yet here I was being forced to make a decision about what I wanted to do with my life post graduation. I had also received job offers in the Toronto area, which made the decision even harder. I had to choose between living in a city I knew and felt comfortable with, with friends and family close by and moving to a new country, on the other side of the continent, where I knew no one.
After talking it over with my parents and my mentor, I realized that working at Microsoft was an amazing opportunity and if there was ever a time in my life to uproot myself and try something new and different, this was it. Sure it was more than a little scary, but above all else it was exciting. So I signed the offer letter and waited to graduate so I could start the next chapter in my life.
My first year at Microsoft was great! I was designing cool new features, and would wake up every morning looking forward to going into the office – life was amazing. Outside of work I had made an amazing group of friends. Over the years some of these people changed, but one thing remained constant, I never lacked great people to hang out with. I used to spend my weekends climbing, camping, hiking, mountaineering, skiing, going to concerts, festivals, and just about everything else in between.
This euphoria lasted about a year. Then I slowly became more and more unhappy with my life and the culture at Microsoft.
1. You Get Rewarded For Visibility, Not For What You Actually Contribute
One of the pieces of feedback I received during my time at Microsoft was that I needed to send out more status updates. It wasn’t that I wasn’t doing enough work; it was that I wasn’t being vocal enough about it. I had weekly meetings with my Manager, my office door was always open in case people had questions, and we had weekly team meetings where people could talk about what they were working on if others on the team needed to know. I very strongly believe that people should be aware of what is going on, but I like to limit that to people whom it concerns. By the time I left, I had thousands of unread emails in my Inbox because I was constantly being bombarded with useless status emails and updates about areas I did not own, did not care about, and had no actionable items for me to take on. The real kicker – these noisemakers were the people that we were being told to look up to.
2. “Be like a robot” – no thanks!
(Note: This was one of my favourite pieces of advice I was given from upper management, and was another giant red flag that I was clearly not in the right job)
The last couple months at Microsoft were by far the hardest for me. The fun part of the cycle was over, we had designed and spec’ed out the new features for the next release, and now it was time to bug bash and fix everything we broke. I can appreciate that triaging bugs is an integral part of the software development process, but at Microsoft this part lasted upwards of a year and was too painful to handle. In an era of agile software development and pushing out periodical updates, I was still stuck working in an organization whose release cycle spanned several years. I found myself in my office, day after day, triaging bugs that existed because of legacy issues that had long been forgotten about, or bugs based on feedback from self-proclaimed UI gurus. When I talked to skip level (my manager’s manager) about my frustrations and why I was having a hard time being excited and motivated, he understood where I was coming from, but there wasn’t much that could be done about it. I was told about the History of Office and how it had always attracted a certain personality type – particularly people that are not very warm, open or friendly, who can churn through processes and data and focus only on the bottom line. In short, he actually compared this optimal personality type to a robot. I walked out of that meeting in disbelief, I was pretty sure I was just told that I wanted to succeed, I needed to operate more like a robot :/. When I spoke to my manager about this, he “assured” me that his personality was similar to mine, and operating the “Office way” was not something that came natural to him either, but after many years of practice he was able to operate that way so that other people were happy and he fit in with the Office working style. Looking back, I am so glad I got out before I lost my personality; I still shudder at the thought of trying to conform and be like a robot.
3. Annual Reviews
Every year there is an annual review as well as a midyear check-in. The annual review cycle takes up four months. Seriously. Four months. There have been several stories on why employees hate annual reviews, and I can assure you all that I am amongst one of them (thankfully now as a former employee). The biggest disappointment to me was when I first started. I was told that as a new hire I would essentially be guaranteed ranking of 3. They understood that people need time to adjust so on our team, and in Office in general, it was common practice to rank new hires as 3s. Management liked to think that this would make new hires feel less intimidated by being, well, new. In reality all this did was stifle my desire to outperform and be great. Annual Reviews guaranteed that your team would have someone fall into each ranking, it felt like there were essentially unspoken waitlists for who should be getting what level based on how many years since their last promotion. As a newcomer to the company, I felt that I was set up for mediocrity - I’ve never settled for mediocrity in life before, and I didn’t feel ready to do start doing that now.
4. I loved my team – but they started disappearing
The one thing that I did love about Microsoft was my team. I worked on a team that was full of people that were young, full of life, and were just generally fun to be around. I enjoyed going to lunch with them and many of them I hung out with after work. Then one day, one of them left. Then another one disappeared. And so the trend continued. Soon, the team that I once loved being on, had turned into a toxic environment. People were slowly being pulled from one project to start working on another secret more exciting project. The people left behind were told not to worry or think about anything else, eventually everyone would get the opportunity to work on the shiny new thing. I was one of the ones left behind to clean up the mess of the old project and it was terrible. Upper management was too distracted with the new thing to pay attention to anything else. The hallways were constantly empty as managers would be at secret meetings offsite. The few of us that were left working on the old project were essentially abandoned while everyone else was off having fun – it was awful.
5. I like to do things – Microsoft likes to talk about things
When people ask me what finally made me decide to leave, I always tell them that it was a variety of factors. There was, however, one tipping point that I can trace it all back to – the argument over text casing for User Generated Content strings. While people were trying to solve ship-blocking issues, here I was in a never-ending debate over whether or not a string that would sometimes appear in the status bar of one of the Office Apps should be using Title Case, Capitols or Sentence Case. There were numerous arguments made for each of these designs, endless mockups were created and discussed over tediously long emails and meetings. People were brought in from several partner teams to weigh in on the issue, but never actually help drive to a final decision. Several weeks later I was finally able to close on it and get buy in from all the partner teams, only to have my Manager come in to my office and tell me he wasn’t quite sure about the final design direction. It was at this point that I had had enough. If he wanted to revisit the issue he was free to do so, but I had wasted enough time, effort and brain power on it. I was done. Several weeks later, after I had quit, I received an email from a friend letting me know that this dilemma was still being discussed. I couldn’t help but smile as I sat in my chair thinking about long-term strategies for potential partnerships, instead of the proper casing for a hidden string.
6. I Stopped Learning and Started Resenting
It finally dawned on me that instead of learning how to change the world, all I was learning was how to deal with crap. I was often told to do things, but I found that I didn’t want to do them not because I couldn’t but because I just didn’t believe in what they stood for. The number of times I was told to reinvent a process started to get ridiculous. It became very apparent to me that the way to solve a problem at Microsoft was not to fix it; it was to develop a process on how to vocalize the issue so everyone around you knew that you were aware of it. The attitude wasn’t “get things done” it was “create a process”. Not learning has always been a deal breaker for me in life – the moment I stop learning I know something needs to change.
All of this said, it took me nearly two years at Microsoft to realize I had to move on. This June I was heading home from the bar after my 25th birthday and thinking to myself “Wow, 25 seems old, what am I doing with my life?” I thought about where I would be in 7 years if I were to stay at Microsoft. More than likely I’d become a manager. When I thought about my manager and tried to picture myself in his life I panicked. I wasn’t sure exactly what I wanted to do or be, but the thought of ending up in a 9-5 job without ever really making an impact on the world terrified me.
I finally reached a point at work where I felt like I had had enough, so I did what any frustrated person would do – I booked a one-way ticket to San Francisco. Having worked in the software industry almost two years, not to mention the five years I spent in school and on co-op terms, I was ashamed to admit that I had still never made it down to SF. I just needed a break, and what better way to get my mind of the annoyances I was experiencing at Microsoft, than to immerse myself in the tech hub of North America.
I have a few friends down in SF, some even former Microsoft employees, so I was able to find a place to crash while I took my mental leave from the dark cloud of the software giant. While in California I met with people who worked at some well-known companies down there and I was introduced to their recruiters. I also timed my visit so that I was able to meet up with my old friend Katherine who was in town for the C100’s 48 Hours in the Valley. She was attending for her new company ShopLocket as one of 20 Canadian startups. Since her co-founder was unable to make it I was even able to join as her +1. The conference was great, it allowed me to catch up with a good friend, and reminded me that there was a life was like outside of the Microsoft bubble – and it was a really exciting one!
During my week down there I thought long and hard about why I was so unhappy with my life. On the surface everything seemed great. I had a great job, great friends, and great hobbies. My weekends were never the same. Heck, even my weekdays were rarely identical. One day I might be backpacking on the beach along the coast of the peninsula with ten of my closest friend’s; and the next I’d be driving on the highway in convertible with the top down and sun shining as I headed to Exit 38 to get in some climbing. My life definitely had its upsides, yet here I was incredibly unhappy.
The idea of finding a new job in SF and working at a software company had always seemed appealing, but I started to question how different this would really be from my current life, living in Seattle and working at Microsoft. I realized that if I followed this path I would more than likely end up in a role similar to the one I currently had, the only difference would be that I would be living in San Francisco instead of Seattle. This definitely was not the worst thing in the world. Being in a different space (i.e. not working on Outlook) would definitely mean that I could start learning new things again. I had friends in SF and in my short period of time there I had fallen in love with the city. Any company I might consider working for there would no doubt be smaller than Microsoft so I definitely had a better chance of making an impact. But at the end of the day, those changes were still incremental at best.
The other option that presented itself to me was to join my friend’s startup, ShopLocket – an e-commerce platform that makes selling online easy and social. They were just finishing up with raising a $1 Million seed round and were looking to hire someone for Business Development. The idea of working at a small company (the team was only three people at the time) was something I was excited by. The only downside* that I could see at the time was that it was in Toronto, and I had just fallen in love with San Francisco. I spent a while dwelling on this fact and finally came to the realization that San Francisco would always be there, but the opportunity to gain experience working in such an early stage startup doing something I truly believed in and being able to make a huge difference, was not something I was ready to pass up.
*Note: I had friends read this article before I posted it and they asked me if I even considered the obvious downsides to joining such a small startup. Concerns such as “what happens if things don’t work out…”, “aren’t you worried about working for a friend…”, and “do you realize what you are giving up at your current job at Microsoft…” I can honestly say that none of these really fazed me. Although I would never be downright irresponsible with taking risks, for the most part they just excite me!
My trip to San Francisco was coming to an end and I realized I had to eventually fly back to Seattle. I finally booked my plane ticket Thursday morning while I was sitting in a VC office on Sand Hill road with Katherine, waiting for her to give a pitch. I flew back four hours later, knowing my days in Seattle were now numbered. That Friday was possibly the hardest workday I have ever had to sit through. My head was thinking about Toronto, my heart was still in San Francisco, but for the time being body was in Seattle and it was expected to triage bugs. That weekend I received the “formal” offer from ShopLocket to come join Katherine and the rest of the now four-person team at ShopLocket. Monday morning I sat down in my Manager’s office and told him that I would be around for three more weeks, and that I was off to do big things.
I do still miss the West Coast and all my friends, but Seattle and San Francisco will still be there when I want to visit and in the meantime I am starting to fall in love with Toronto all over again.
Despite being homeless, sleeping on an air mattress and living out of a carry on suitcase, I couldn’t be happier. I found my passion again and I haven’t looked back since.