- Amazon CEO Andy Jassy tells Gen Z to stop worrying about knowing what their career will look like in their twenties. Instead, he encourages young people to focus on learning what they want to do—a lesson that paid off well for Jassy. Before starting his now nearly 30-year career at Amazon, he tried out jobs like sportscasting, soccer coaching, and investment banking.
Few topics spark as much debate as what your twenties should look like. Some see the decade as a chaotic struggle, while others view it as a rare window of opportunity.
But from Amazon CEO Andy Jassy’s perspective, Gen Z should take the pressure off themselves and realize they don’t have to have their entire life planned out by their twenties.
“I have a 21-year-old son and a 24-year-old daughter, and one of the things I see with them and their peers is they all feel like they have to know what they want to do for their life at that age,” Jassy said on the podcast, How Leaders Lead with David Novak. “And I really don’t believe that’s true.”
And while figuring out what you want to do in your career can feel existential—especially during a time when AI is completely reshaping the job landscape—Jassy knows the struggle firsthand.
After graduating from Harvard University in 1990, he tried a number of career paths, including sportscasting, product management, and entrepreneurship. He also worked at a retail golf store, coached high school soccer, and tried investment banking. Eventually he decided to go back to school to give an MBA a go and explore entrepreneurship. It was only after graduating from Harvard Business School did he land his breakout role at Amazon, just months before turning 30.
“I tried a lot of things, and I think that early on, it’s just as important to learn what you don’t want to do as what you want to do, because it actually helps you figure out what you want to do.”
Coins2Day reached out to Jassy for comment.
The value of failure—and asking questions
Exploring interests is one thing, but for Jassy, now 57, nothing may be more important for success than asking questions. Having a high quotient of “why”—or “WhyQ” is something he said helps careers thrive at Amazon.
“We ask why, and why not, constantly,” Jassy wrote in his most recent letter to shareholders. “It helps us deconstruct problems, get to root causes, understand blockers, and unlock doors that might have previously seemed impenetrable.”
For Gen Z in particular, being curious—and operating with the right mindset—can be a major stepping stone for careers, Jassy admitted.
“An embarrassing amount of how well you do, particularly in your twenties, has to do with attitude,” Jassy said in an interview with LinkedIn CEO Ryan Roslansky.
And while finding success ultimately also has an element of chance—and may involve multiple setbacks—taking it one day at a time might eventually land you a shot at the corner office.
“I feel like my journey or adventure was a lot of luck, and I think maybe one of the things I did best was not overthink it,” he added to David Novak.
CEOs who took the long way around to the top
While it may seem like the path to the top of the corporate ladder requires a hyper-focused career path, in reality, the journey can be long and squiggly—with Jassy being just one example.
After graduating as an undergraduate, Reed Hastings, the cofounder of Netflix, served in the Peace Corps as a high school math teacher in Eswatini, a small country in southern Africa. Only after his return did he go back to school and study computer science at Stanford University before helping start the tech company now worth over $500 billion.
Moreover, Bob Iger, the CEO of the Walt Disney Company, started his career predicting weather as an on-air meteorologist for a local television station in Ithaca, N.Y., before becoming one of the most notable media executives.
And even Jassy’s own mentor, Jeff Bezos, got his start with a quintessential teenage job: flipping burgers at McDonald’s.
“You can learn responsibility in any job, if you take it seriously,” Bezos said to Cody Teets, author of Golden Opportunity: Remarkable Careers That Began at McDonald’s. “You learn a lot as a teenager working at McDonald’s. It’s different from what you learn in school. Don’t underestimate the value of that!”
