“There's so many things that you can't control in your work life, but you can control your attitude.” Amazon CEO Andy Jassy’s best career advice

The Path is a video series where I chat with some of the most influential leaders in the world exploring the successes, missteps, and key pivotal moments that shaped their professional paths. It’s through these authentic stories that we can learn how to navigate our own career journeys.

My next guest is Amazon CEO Andy Jassy . 

Far from direct, Andy’s path to becoming Jeff Bezos’ hand-picked successor was a winding adventure. 

From youthful dreams of becoming a pro athlete, to flirting with the law, to dabbling in sportscasting and music management, with a business school stint in between, Andy's life before Amazon was a mix of exploration and learning.

In his youth, Andy loved playing sports, particularly soccer and tennis. He saw school as “just another game,” he said. “You had to study, you took a test, and you got a score, and you nominally won or lost. I never thought of myself really as a student of any sort, even though I did well in school.”

As a Harvard undergrad, Andy majored in government and considered going into law like his father, whom he continues to look up to. He got a summer job as a paralegal at a New York City law firm, which he said “was a great experience, but it also taught me that I didn't want to be a lawyer.”

Working on the business side of the school paper and helping launch a national college magazine called “Class Act” sparked Andy’s interest in media and gave him an early taste of entrepreneurship, which would come in handy later. 

A summer job at Fox TV New York further fueled that interest in media and inspired him to pursue sportscasting. He figured if he wasn’t good enough to be a professional athlete, he could at least talk about sports, which he still loves. He put together a reel and sent 80 copies out as graduation approached. Only hearing back from a few rural markets, Andy ended up working as a production assistant at ABC Sports during the week and NBC Sports for Sunday football. Ultimately, sportscasting wasn’t the right fit either, seeing a long road of paying dues before he would land anything substantial, Andy recalled, “I just didn't have the resolve and patience that some of my peers did in that time.”

The next turn on Andy’s path led him to a product management role at a direct marketing company called MBI. He stayed there for three years and learned as much as he could. Excited by the idea of entrepreneurship, he left MBI to launch two businesses. While they helped pay the bills, Andy quickly realized they didn't have much of a future and closed them down.

He tried his hand at a number of other jobs, including selling custom merchandise and investment banking, but he didn’t love those either. “I was just feeling lost, and I didn't know what I wanted to do. I just knew some of the things I didn't want to do.”

Andy decided going back to Harvard for his MBA “would be an interesting way to learn in some areas that I hadn't taken seriously or engaged in at all.”

Yet another field of interest emerged as he was finishing his degree. Still liking the idea of being an entrepreneur and now managing a band, Andy seriously considered starting some sort of music management and record label business. He was also talking to a few tech companies at that point, but Amazon wasn’t even on his radar. He was on Amazon’s radar, however, and they reached out to him about a job after getting a hold of his resume. “I didn't know that much about Amazon at the time,” Andy said, but after seeing it, “I loved it. I loved the people; I loved how smart they were and how motivated they were, and I thought I would take a shot.”

Even after landing at Amazon, Andy’s path wasn’t straightforward. Starting as a product manager, he bounced around the marketing department, got the opportunity to lead the company’s music venture, and returned to marketing to co-lead it. Soon after that he was offered the highly coveted and unusual role of Jeff Bezos’ “shadow,” which was “just an incredible experience,” for Andy. “I was in all his meetings, including his one on ones at the time. And we would spend time pretty much every week talking about the things that we heard that mattered. And then try to divide and conquer how to drive them.”

In 2003, Amazon entered the world of cloud computing with Andy leading the project. In 2016, he became CEO of the massively successful AWS, while still managing parts of Amazon including the internal and external payments business, the app store, and the gaming business.    

When Andy got the call from Jeff about becoming his successor, he hesitated. "When Jeff approached me about the job I'm in now, it was not a no-brainer just because I loved the AWS business." But after thinking about it and talking to his wife, he knew he was ready for the challenge.

Here are my takeaways:

Attitude is key: When it comes to Andy’s best career advice, he says, "There are so many things that you can't control in your work life, but you can control your attitude. I think people would be surprised how infrequently others have great attitudes. I believe it makes a big difference."

It’s ok if your “dream job” doesn’t work out: There’s also no rule saying you can only have one dream job. Andy had several. When one didn’t work out, his resilience and curiosity led him to try something else, all of which contributed to his knowledge and experience. As Andy pointed out: “Some of the most important time in my career was between that MBI experience and business school and was also some of my most unsuccessful time.” In the end, Andy did manage to find a way to achieve his earlier dreams of working in music, management and entrepreneurship within Amazon. 

Don’t worry about the destination: If you're concerned that your career path isn’t heading in a clear direction, just look at Andy’s. “Sometimes it's a straight line and there's certainly people who've had that. It was not my experience. But, you know, you'll wind your way around something that you're really good at. And along the way, you'll keep picking things up if you let yourself.”