This as-told-to essay is based on a conversation with David Chong, a 38-year-old startup founder in Toronto. He previously worked as a senior software engineer at Microsoft until resigning 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.
During my move 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 were.
While resigning from Microsoft set me down this unfortunate path, I believe leaving Big Tech was the right move for me. I’ve had to learn what the Zen monks preach about letting go of your earthly possessions to reach 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 smaller tech company for nearly seven years, starting as a junior employee and working my way up to a leadership role as a lead product engineer.
When I joined Microsoft as a senior software engineer in 2022, it felt like a bit of a backtrack in terms of title. I thought it would be easy to get promoted back to a higher level, but it definitely wasn’t; I held the same position for nearly three years.
At my previous employer, it felt like your work spoke for itself, but at Microsoft, it felt like I would have to develop a “getting promoted” skill — doing a lot of internal self-promotion to make sure my work got noticed outside my immediate team — to actually move up.
From what I heard, the need to actively self-promote in order to move up is a broader trend across Big Tech. It seemed pretty non-transferable outside the Big Tech world, so I wasn’t very interested in developing it.
I started thinking about quitting, even though it would mean leaving the US
In my last few years at Microsoft, the company went through multiple restructurings that moved me to different teams. In the most recent round, some of our managers were laid off.
The layoffs didn’t make me too concerned about my job security, in part because my department seemed starved for engineering talent. However, I was growing frustrated with the slow promotion timeline.
There also seemed to be rising expectations at the company around productivity and working from the office. The message from leadership seemed to be that we needed to ramp up and adjust because times were changing.
The other thing that made me start considering leaving was that I wasn’t learning as much as I wanted to, partially because I had become the most senior person on my team.
In early 2025, I started thinking seriously about leaving Microsoft and figuring out my next career move. It was a very difficult decision. I was working on a TN visa, which was tied specifically to Microsoft, and resigning would likely mean moving back to Toronto and committing to a future outside the US, unless I could find another company willing to sponsor me. I’d come to the US thinking about living here long-term. Microsoft had already started the green card process for me, and quitting would mean giving that up as well.
Around last April, a friend opened my eyes to the possibility 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’ve saved up enough of a buffer to go without income for several years, and I don’t have any dependents.
Read more about people who’ve found themselves at a corporate crossroads
Having my belongings stolen forced me to delay my plans
Losing my belongings during the move definitely hurt my productivity, forcing me to delay my startup plans by a few months.
Of everything I owned, all I had left was what I packed for the flight in my backpack and carry-on bag. I landed in Toronto without winter clothes or a bed — I had to sleep on the floor in a sleeping bag.
I focused on resolving the move issues: trying to figure out what happened, contacting the police, and dealing with the insurance claim. I’d unfortunately gotten the lowest insurance rate for my move, so the insurance payout was less than even what I paid for the moving service.
And of course, there was the financial impact of replacing everything. So far, I’ve spent around $12,000 on essentials like a couch, bed, air fryer, Instant Pot, and clothing. Since everything was stolen, I’m starting from scratch in more ways than one.
However, I’ve made progress with my AI sales agent business, Falco, in recent months. It’s still in development and isn’t ready for customers yet, but it has launched publicly.
When it comes to building a startup, I don’t think the idea necessarily matters as much as the execution. I’m hopeful that if I just go all in, move fast, and constantly test my ideas, I should be OK. My plan is to give myself about three years to pursue entrepreneurship. If all else fails, I’ll go back into the job market.
My advice for others weighing a big career move
My advice is to try to put yourself in your own shoes five to 10 years from now. When I do that, 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 the thing I’d regret not doing. I’ve often heard that older people regret the chances they didn’t take more than the ones they did.
In hindsight, I think this mindset is what helped me decide to move to New York and join Microsoft — two decisions that had their pros and cons, but that I don’t regret. My first job in New York helped me build the experience that landed me at 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 all in on entrepreneurship.
