Reddit’s former CEO on surviving Silicon Valley’s dotcom crash—and his advice to those facing tech layoffs today

An abandoned office in disarray, with papers on the floor
As Yishan Wong entered the tech workforce, some 200,000 jobs were cut in Silicon Valley.
Bill Varie—Getty Images

It was the year 2000 and tech intern Yishan Wong, who later went on to lead online discussion site Reddit, was unknowingly experiencing the peak of the dotcom boom. 

“I was getting paid a huge amount of money at the time and I had three other offers for internships,” Wong said in a call with Fortune

Just one year later, as Wong celebrated graduating in computer science from Carnegie Mellon University, some 200,000 jobs were cut in Silicon Valley.

The dotcom bubble had burst.

“Everything crashed,” Wong said. “There are these huge layoffs every so often, right? It’s nothing new, but it was my first time seeing the professional effects of a huge macroeconomic downturn.” 

Having landed a job at the then startup PayPal, Wong watched a generation of tech workers get spat out by the industry. 

His early experience at Silicon Valley closely mirrors the headwinds at play today. Amid hundreds of thousands of layoffs with more predicted to come, many tech workers don’t know how secure their roles are.

Yet not only did Wong survive the chopping board, he also thrived.

During a period of upheaval Wong went on to join Facebook in 2005, before taking the helm at Reddit in 2012 —and almost founded a WeWork rival in-between. Today, he is the CEO of his own climate venture, Terraformation.

Although Wong was “pretty lucky” to get his big break during the crash, he revealed two pieces of advice for tech workers in the current climate: Stop planning and get into A.I. 

 1. Turn to A.I.

Despite Goldman Sachs predicting that 300 million jobs could be lost to artificial intelligence, the development of large language models could also provide a lifeline to some, Wong insists.

“It feels like a hype train, but actually there’s an enormous amount of value overhang,” he says.

Even if Elon Musk, Apple cofounder Steve Wozniak, and thousands of other tech leaders manage to convince companies to hit pause on their A.I. developments, Wong claims that a decade’s worth of innovation has already been released in the past few months.

Instead of mulling over the likelihood of a layoff, Wong suggests candidates should look at sidestepping into A.I.

“You don’t need an enormous amount of technical skill,” he insists. “Nontechnical people can build pretty valuable and novel applications on A.I. There’s this enormous amount of leverage that an individual can have.”

2. Stop career planning

Benjamin Franklin, Winston Churchill, and many leaders have recited some variation of the phrase: “Failing to plan is planning to fail.”

It’s why there’s advice aplenty on how to plan every aspect of your career and land that dream role. 

But perhaps it’s time to take a leaf out of Wong’s book.  

Instead of creating a five-year plan and giving himself an annual personal performance review to stay on track, he insists he “randomly moved around” in his career and worked “really hard” wherever he landed.

He believes that not focusing on where you want to go next makes you more grounded in the job you’re actually doing—instead of dreaming about the next big thing and scraping by in your current role with little energy.

“If you’re really good at whatever you’re doing right now it creates a foundation and gives you a lot of option power for whatever comes next,” he says, while adding that it may even open up paths you would never have planned to take. 

“Make sure you’re really good at the time, wherever you are,” he repeats. “It doesn’t matter if you don’t know what the music is going to be. If you’re a good dancer, you can adapt.”

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