How I went from a Janitor & Dropout to Earning Six-Figures & Master’s Degree

By Shawn Dexter / December 6, 2016
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I write this post with hesitation & unease. Perhaps it's because I'm about to reveal what very few know about me. But since I was recently advised to write about that which I’m afraid of — here I go:

The Tragedy

I come from a poor background in India. My father’s resilience and tenacity allowed us an escape. We moved from an impoverished neighborhood in Bombay to Canada. I complained at first —  since I had lost all my friends. But it finally seemed that I had a future to look forward to.

Abruptly things took a turn for the worse. In 2005, a tragedy took us by storm. A freak accident had my brother hurtling through the roof of a two-story building in India. His spine crashed through a clutter of steel chairs and desks. He landed into an empty children’s classroom.

how to become a product manager

I was in the living room with my mother when the phone rang in Canada. The doctor informed us that he was paralyzed from the waist down. We were stunned.

To help pick up the pieces, my family pulled me out of school and packed me off to India. Being uprooted from my life for the second time sucked. But I couldn’t complain. How could I? My brother go through something magnitudes worse.​

Lesson Learned:  As bad as you may have it, someone somewhere is going through worse.​

The Fight ‘Back’ & Getting Rejected

We had lost everything at this point. And after multiple surgeries, we drained most of the savings. My dad said Canada was bad luck and didn’t want to go back.

After around 3 years and a lot of ‘fighting for it’, I managed to make it back to Canada. (I'll need an entire post to expand on that). My family stayed behind.

Getting Rejected - How To Become A Product Manager

Alone as I was, I still believed everything could go back to normal. I approached a high school to continue where I left off. They turned me away. "You're too old to go here" said the administrative assistant. She spared me a single glance as she handed my application back to me.

I was 19, and they didn’t accept adults. Gah! It was fair, though. Adult High School was still an option. But the one I approached limited you to one course at a time! (At the time, I thought they were all like that) So I decided to do some additional digging.

Lesson Learned: It may take time. But there's always a way to hit "reset".

Getting into University Without a Diploma

It turns out, in Ontario, you can get into a University Program without a diploma — as long as you have the required grades & courses. I was always terrible at school, but I was good at Math. So I played the cards that were dealt to me. I aced all the Math courses required for the Math Major and sent in my application. A few weeks later, I received an acceptance letter! I was ecstatic.

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Going to university was a pretty big deal to me. A few years prior to this, I felt like my entire world was crashing down. Jesus, I hadn't even completed high school. But there was a catch. There's always a frigging catch. They put me on probation. If I were to fail even a single course, I’d be kicked out of the program. Uh oh...

Lesson Learned:   There’s always another way. Look for solutions.

Mopping the University Floors

It then dawned on me — that getting into University was only half the battle. Now, I had to figure out how to pay for it. So I applied for a job as a night-shift janitor. 

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Turns out, it was for a janitorial position in the engineering building of the same University I went to. Oh, the irony.​ Cleaning the floors at night, studying on the floors by day.​

I never did make it for my early morning classes, though. In fact, I rarely made it to ANY of my classes. I self-studied at home — but I still felt a stronger connection to that building than most of the students.

Lessons Learned: There’s a silver lining to everything.​

Getting Fired While Self-Learning


The pressure of probation & getting kicked out of school forced me to keep my grades up… really up. But I didn’t see a career in Math. It was a means to an end. Software always intrigued me. So I began using my spare time to learn how to program and requested a transfer to the Computer Science degree.​ 

Balancing my grades and working was hard enough without trying to learn how to code. So I tried to work “quicker” with the mop. I used the gained time to watch coding videos on my phone. 

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I remember the first time my manager caught me in the act. My feet were up on a table, as I leaned back on a chair holding my phone in front of my face. He wasn't pleased. I tried to be stealthier moving forward — but he always had one eye one me.

​The final straw was when he found me in the washroom cubicle. I had a Calculus textbook open on my lap. (I taught I had the damn door locked.)  He fired me at the end of that shift.

Lessons Learned: 1) Having your back to the wall can bring out the best in you. 2) Always 'make time' to move up. Take risks if you have to.​

All Was Gravy

At this point, though, I had secured a summer job as a Software Developer, so things weren’t too grim. In fact, for the first time in around 4 years, things were looking bright!

Working as a Software Dev now was great. But I felt something “missing”.  ​ I wanted to feel involved in the other aspects of the company. I enjoyed the technical aspect of Software Development. But I also wanted to talk to customers and discuss product strategy. That’s how I stumbled upon Product Management.

Lessons Learned: Don’t wait to ‘find what you love’. Just take steps, you’ll figure it out along the way.​

Finding a mentor & Self-Learning

Stumbling upon Product Management wasn't enough. I needed direction & guidance. So I found a mentor. 

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This was by far the single best thing I did for my career & personal growth! I probably avoided a thousand missteps because of his guidance. All my peers were improving their Software skills in their spare time. I, however, read about Product Management and practiced any associated skills .

Virtual Mentors & Self-Learning

Developing a relationship with a mentor within your network takes time. Eating into his time too much would be selfish. Fortunately, there were a few people on the internet who took it upon themselves to help people grow.  They post several YouTube Videos and Blog Posts that I was able to consume over the years. I like to call these guys "Virtual Mentors".

 Some of the most influential Virtual Mentors I've had was John Sonmez from SimpleProgrammer  and Sal Khan from KhanAcademy.  John Sonmez is one of those "I want to have it all" guys which was something I could resonate with strongly – but I always felt guilty for want it all – until I came across him, of course. If John could be a successful programmer, entrepreneur AND have a shredded/muscular body, why couldn't I?  Over the years John has inspired me to be everything I want to be and never settle.  A virtual mentor who didn't know I existed. 

Sal Khan was my "professor" for every class I missed. And I missed a lot. What Sal is doing with KhanAacademy – providing affordable & free education for students across the world has influenced SkipMBA as well! (To this date – even after an MSc in Comp Sci – I still use Sal's videos to brush up on my self-education. You're never too educated to learn the basics)

While the connection isn't as quite deep as it can be with a traditional mentor, there are advantages to a virtual mentor. YouTube Videos and Blog Posts can be referred to again. You don't feel "guilty" for asking the same question. You can even refer to the same content years later to reassess yourself.

'Making' time to 'Move Up'

I was essentially making time to “move up” instead of trying to excel at my current job. I had realized how important this was. If you have the ambition to move up, you have to focus on learning for the next job.

It’s not just your “spare time” that gets influenced, but also the ‘battles’ you choose to fight. For example, I would put a lot more effort into presentations & business classes than my friends did. I would choose to skip certain classes over the other. These little things added up over the years.

Lessons Learned: Long gone are the days when companies invested heavily into your self-improvement. Take your own measures to advance.

Using my Master's to Self-Improve

When I finally graduated, it felt pretty surreal. It wasn't too long before then when I had almost resigned to flipping burgers for the rest of my life. (I honestly saw no shame in that, I just needed to make a living.) And now I was suddenly on stage, receiving my BSc in Computer Science without a high school diploma. You can imagine how I felt...

If not, here's a shaky video of the moment:

​I promise you, this was not planned. It just... happened.  As you can see, I completely forgot to shake hands with the Dean etc. Oh well...

Due to my grades, I received a full scholarship to do my Master's degree. I was able to deepen my knowledge in the field. But also I used these two years for a lot of self-improvement (non-tech related). Towards the end of my Master's Degree, I realized how much I enjoyed presenting & speaking. Because of this I started teaching fellow colleagues on the basics of public speaking & presentations.

The Interview...

After graduating I landed a pretty high paying job as Software Sales Engineer. Toward the end of the year, a recruiter contacted me. It was for a potential Product Management position at a Fortune 500 company. She said the base pay was 100,000$! Wow! I was pretty excited.

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She then went on to say that I’d be going up against candidates that have 8 - 10 years of experience. My heart sank. I knew what this was. I was one of those “filler candidates”. The recruiter didn’t sound too enthusiastic either.

"Don't get your hopes up." she said in a thin voice.

After some deliberation, I decided to go forward with the interview. Worst case scenario I’d come out with some PM interview experience.

I got through the first round, which was super! At the second interview, though, my interviewer held a poker face the entire time. I couldn’t gauge whether my answers were sitting well with her or not. She was impressive — I'm usually great at reading people's faces.

​After the interview, they said I’d get a call latest by the end of the week. I didn’t get a call.

The Offer

I felt bummed — but only for a few minutes. I went on to enjoy my weekend — I had learned to appreciate to good things I had.

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The following Monday the recruiter called. I expected bad news. Turns out it was good news...great news actually. I thought I was going to round 3. But she said that the company decided to offer me the job and that they’d cancel the third round of the interviews if I accept.

After some negotiating and haggling, I accepted the offer.

Lessons Learned:  Pick up the bat, go up to the pitch... and swing. If you miss — whatever. No one's watching anyway. But what if you hit a homerun?

What’s Ahead?

Back in 2011,  I detailed wrote a 5-year career plan. The plan was to pursue my MBA in Fall of 2016 to help me break into Product Management.  Well, 2016 rolled along and I was already a Product Manager. I questioned whether it was worth going into severe debt to pursue an MBA.

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Looking back at my entire journey, I realized that most of my success came from self-learning. Education is important. But the degree not so much. So I decided to skip the MBA .. and self-study.

I read & study around two books a week. I do book summaries, case studies, and document it all on a blog. This helps me crystallize my knowledge.  I’m teaching everything I learn on it on this blog. I co-ordinate with my friends who are doing their MBA. And in contrast, I’m learning practical material at a faster pace. (And I’m saving a ton of money)

Major Lessons Learned: You may not have much. But you definitely have more than someone else in this world. Recognize that advantage, and LEVERAGE it to improve and advance. Don’t feel sorry for yourself and compare yourself to those who "have".

A quality education has never been as easily accessible as it is today.

Mark Twain: “I never let my schooling interfere with my education”


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About the author

Shawn Dexter

Shawn Dexter is a Product Manager, Entrepreneur & Software Developer. He is passionate about innovation management & technology.

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