I quit my $192K Microsoft job and moved to Canada – then almost everything I owned was stolen. I am learning to rebuild from scratch.

• David Chong quit his $192,000-a-year Microsoft job last year to build an AI startup.

• Weeks later, most of his belongings were stolen while moving from New York City to Toronto.

• He shares how he’s trying to bounce back — and why he doesn’t regret going into entrepreneurship.

This essay is based on a conversation with David Chong, a 38-year-old startup founder from Toronto. He worked as a senior software engineer at Microsoft until his resignation last September. The following has been edited for length and clarity.

I resigned from Microsoft in September 2025. Less than a month later, I lost almost everything I owned.

On my way from New York City to my hometown of Toronto, the trailer transporting my belongings was stolen in the middle of the night. The trailer was eventually recovered, but none of my belongings.

Resigning from Microsoft set me down this unfortunate path, I think leaving Big Tech was the right move for me. I had to learn what Zen monks preach about giving up your worldly possessions to attain enlightenment.

I struggled to get promoted at Microsoft

In 2016, I moved from Canada to New York City on a work visa. Before joining Microsoft, I worked at a small tech company for about seven years, starting as a junior employee and working my way up to a leadership role as a principal product engineer.

When I joined Microsoft in 2022 as a senior software engineer, it felt like a bit of a backtrack to the title. I thought it would be easy to get promoted back to the top level, but it certainly wasn’t; I stayed in that position for about three years.

At my previous employer, it felt like your work spoke for itself, but at Microsoft, it felt like I had to develop the skill of “promoting”—doing a lot of internal self-promotion to make sure my work was noticed outside of my immediate team.

From what I hear, the need to actively self-promote in order to move up is a pervasive trend in Big Tech. It seemed very non-transferable outside the Big Tech world, so I wasn’t very interested in developing it.

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Even though it meant leaving America, I began to think about leaving

During my last few years at Microsoft, the company went through several restructurings that moved me to different teams. In the most recent round, some of our managers were fired.

Job security didn’t worry me too much, because my department seemed starved for engineering talent. However, I was getting frustrated with the slow promotion timeline.

Companies are also seeing increased expectations around productivity and working from the office. The message from leadership seems to be that we need to ramp up and adjust because times are changing.

Another thing that made me consider quitting was that I wasn’t learning as much as I wanted to, partly because I was the most senior person on my team.

In early 2025, I started thinking seriously about leaving Microsoft and the next step in my career. It was a very difficult decision. I was working on a TN visa, which was tied exclusively to Microsoft, and resigning meant returning to Toronto and committing to a future outside the US, unless I could find another company willing to sponsor me. I came to America thinking of staying here for a long time. Microsoft has already started the green card process for me, and giving up means giving up on that too.

Last April, a friend opened my eyes to the possibilities of entrepreneurship. I became more interested in that path and started doing a lot of research on how to build a business. I decided that if I left Microsoft, I would pursue entrepreneurship.

In September, I resigned from Microsoft. I wasn’t too worried about giving up my $192,000 a year salary because I consider myself very risk-tolerant. I have saved enough of a buffer to go without income for several years, and I have no dependents.

The theft of my luggage forced me to delay my plans

Losing my stuff during the move definitely hurt my productivity, forcing me to delay my startup plans by a few months.

Everything I owned, what I had packed for the flight in my backpack and carry-on bag was all that was left. I landed in Toronto without winter clothes or bedding – I had to sleep in a sleeping bag on the floor.

I focused on solving the move problems: trying to figure out what happened, contacting the police, and dealing with the insurance claim. I unfortunately received the lowest insurance rate for my move, so the insurance payment was even less than what I paid for the moving service.

And of course, there was the economic effect of replacing everything. So far, I’ve spent about $12,000 on essentials like a sofa, bed, air fryer, instant pot, and clothes. Since everything is stolen, I’m starting from scratch in more ways than one.

However, I have made progress in recent months with my AI sales agent business, Falco. It’s still in development and not yet ready for customers, but it’s launched publicly.

When it comes to building a startup, I don’t think the idea is as important as the execution. I’m hopeful that if I go all in, go fast, and constantly test my ideas, I’ll be fine. I plan to spend about three years in entrepreneurship. If all else fails, I will return to the job market.

My advice for others weighing a big career move

My advice is to try to put yourself in their shoes five to 10 years from now. When I do, I look back at the decision I’m facing and ask myself, “Would I regret not doing this?”

If the answer is yes, I try to do something that I won’t regret. I often hear older people regret not taking more chances than they did.

In hindsight, I think this mindset helped me decide to move to New York and join Microsoft—two decisions that had their pros and cons, but I don’t regret it. My first job in New York helped me build the experience I brought to Microsoft, and Microsoft gave me the opportunity to grow my skills and meet some very interesting people.

For me, leaving Microsoft to start a business is a decision I don’t think my future self will regret, even if I fail, so I’m going into entrepreneurship.

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