The cost of underselling

Some people who have worked with me or have a closer relationship with me will know that I have been working 18~24 hour days for the last few years. 8 of those hours have been at a full-time job, or doing freelance work while in class. Ever since I left school, it’s been 8 hours at a day job, with 10~16 hours of freelance right after.

During this time, I have had the fortune to establish great relationships with some great people. On a few occasions, these relationships have forced me to overcome my anxiety when it comes to public speaking, and have an audience of 200+ listen about my (boring) work and (faulty) advice. Yet somehow, the confidence I established by producing consistent and high quality results for clients have failed to shine through my interviews for full-time positions. I have been massively underselling myself.

“If you can get 99%, why can’t you get 100%?” tweet

You see, despite my mixed heritage, I grew up with an Asian mother in an environment where 99% was a horror. All my life, I have been competitive. Not in the sense that I was smarter than everyone else, but in the sense that I just had to win at everything. It no longer became something that was expected of me, it became something I expected of myself.

When I was 9, I placed 2nd in the Canadian National Chess Competition U-12 Division (2001). That’s amazing, wow! Was the reaction when adults found out. To me, it was a failure. A big black mark on my perfect scorecard in this life that had just begun. In that same year, my soccer team placed 1st in the B.C Junior Boys Soccer U-12 Division. Surely I was happy? Nope, I expected this of myself, and all I had done was accomplish what I should have. A few years later when I moved to Taiwan to learn Mandarin, it was dreadful. I didn’t know the alphabet. Yet these adults placed me in 5th grade. “You should be grade 5 in Canada, there’s no point starting from scratch again”. This was the time where I first learned how to fail, and hard. As a 10-year-old kid, I was already studying late into the night, till around 2~3 AM everyday. Still, my marks barely hit 60%.

If I remember correctly, this is the time where I transitioned from a somewhat energetic, outgoing, and chubby kid, into someone who was anxious, shy, and not-so-chubby. I was a failure. The marks that were commonplace were impossible now. I begged to return to Canada. To this land where I could feel normal and at home again. To this land where being 50% white did not make you look like an alien to other Asians. But it didn’t happen. I was to stay in Taiwan indefinitely. Eventually, I did get my report cards back to 100%, and I returned to shrugging off being 1st in a competition, and I returned to Canada, but I was no longer that smiling, outgoing kid.

Back in Canada, the friends I had in elementary were now also in high school. But they didn’t remember me, they had their own group of friends now. This was also the time I touched a computer for the first time. And despite judging myself for every imperfection, this thing never judged me. It let me experiment, it let me break things, it let me fail, anonymously. I spent huge amounts of time learning how to will this thing to life. At one point, I got involved with the “wrong” community of internet users, but that’s a story for another day. I was later introduced to my co-founder. This would be the first person on the internet who knew my real full name. Even during the early days of Windows7Center, no one knew my name.

3 years later, due to personal difficulties, I left Windows7Center. A few months later, my co-founder shut it down. Once again, I had failed. I’ve worked on this thing for 3 years, and we ended up shutting it down. I wrote it off as a failure, hidden away from everyone in my personal life, and tried to move on. But instead, I went back. I went back to my pseudonym. The handle which many more people in certain communities have come to recognize. The handle where I already had somewhat of a reputation, and a few people who looked to me for advice. They didn’t need to know my age, where I lived, or my name. All they needed to see, were the articles I had written, the tools and experience I brought to the table. The late nights breaking things, and learning how things really worked. It was all exhilarating, and comfortable.

Then I realized the path I was heading down had no great future for me. Sure there were successful people who shared a similar past, but how many of them ended up staring at the same 3 walls day in day out? As much as I hated to, I decided to leave it behind, and cut off any contact with people who may tempt me to go back, or bring back exciting memories. I focused on finding some part-time jobs to make me more employable, school, and instead of freelancing under a pseudonym, using my real name.

I still remember getting my first full-time job in this field. Some major software company with 3 letters. I remember how hard I tried, to show what I knew. To show the value I could bring to the table. But all that went through my mind was how to not let slip the things I worked on before. The 3 year long failure that was Windows7Center. A few exciting but frightening encounters with the law. My sweaty palms and my stuttering. Oh and “don’t forget to smile!” the interview prep articles advised. I went home knowing I had bombed it. Once again, I had failed…
I still got the job. From what I later learned, one of the people who interviewed me saw a lot of similarities between myself and him a few years prior.

My contract was to end after 16 months, and I was ready to move on. At that time, a few clients knew I was on a job hunt and offered me some positions. I was happy to work with them as a freelancer, but I wanted something new and different for my full-time job. So in the last 3 months working there, I applied to a lot of companies I was interested in. What made me special compared to all the other talented applicants? Nothing. Windows7Center was a failure, so I left that off my resume. The experiments and projects I worked on before that was something I was ashamed to be associated with. Freelancing was included, but I was unable to disclose many of my clients due to NDAs. Essentially, my resume told the story of how I am an average person who wants a job but has nothing to show. No one called me in for an interview.

Well then, I guess I’ll just return to school and figure it all out later. So up until the last week upon leaving my job, I had no plan. Returning to school was only a temporary solution, and an escape. If having recommendations from my co-workers and clients could not get me a job I wanted, I would still face the same problem once I leave school again.

At this point, a friend from one of the teams I worked with as a freelancer brought up the name of this one company in Palo Alto. He seemed to have quite a few good things to say about them, and he was definitely someone skilled, someone I trusted. After doing some research, I decided that company would be an exciting place to work. But my problem still persisted. If none of the major companies I was interested in even wanted to interview me, there was something I needed to change. I was underselling myself on my resume.

After 16 months at the 3 letter company I worked at, I noticed some people who sell themselves really well, even oversell their skills and accomplishments. People would gravitate towards, and support these people without any hesitation. There was no proof of their skills, no indication that these accomplishments they brought forward were true. Yet people embraced it and, for some of these over-sellers, their claims (lies?) became a self-fulfilling prophecy. For me, I feel like over-selling is the equivalent of lying. However, I didn’t have to oversell myself. What if I presented myself and my experience more accurately?

I decided to ignore all the insecurities I had about putting my 3 year long failure of a start-up on my resume. Since it was already the last week before I left my company, and had already registered for classes as a backup, I gave my job hunt one last try, having my mind already set on returning to school. I found 4 more companies that interested me (along with the one in Palo Alto) from Stack Overflow Careers 2.0, and applied. 3 out of the 5 companies ended up interviewing me and giving me offers. Surprisingly, what I thought was a major failure was one of the topics they were most interested about. We spent more time talking about my work on Windows7Center than almost anything else (aside from technical tests). 1 of them turned out to excite me a bit less in terms of the culture and work, but the other 2 (including the one in P.A) were very exciting to me.

Despite wanting to try something new and move to Palo Alto, I ended up picking the other one. The product they wanted me to work on just happened to be similar to an idea I had been giving some thought lately, and so I was willing to take a pay cut (compared to the other) and join the team.

After that week of interviews, I realized the value in my experience with Windows7Center. The qualities and knowledge I took for granted were not as plain and common as I had imagined:

  • to continue with something that showed no results after 8 months
  • to work on a project for 3 years, not jump to something new and shiny
  • to identify what is most important to users, and put that on the forefront
  • to monetize and live on a project
  • to drive down costs
  • to grow a project and find ways to sustain that growth
  • to connect with users and to develop closer relationships with them
  • and much more…

We all have valuable experiences and skills that someone, somewhere needs. Underselling is not only detrimental to yourself, it can be a major loss for many many people around you, including those you haven’t met yet. Do everyone a favor and don’t undersell.

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