Married business partners Imran Chaudhri and Bethany Bongiorno were Apple royalty: Chaudhri joined Apple when he was 21, around the time of Steve Jobs' return, and worked directly with Jobs until his death. Bongiorno project managed the most innovative Apple projects and teamed up with Chaudhri to usher in the main iOSs for the iPhone, Mac and other leading products. They fell in love and, together, left Apple at the end of 2016.
They now lead a stealth tech startup, Humane. But how do you know it's time to leave a secure position, especially at the most influential tech company in the world? It comes down to three ideas.
Recognize what you've already accomplished
No one can take away what you've done. A lot of time we fear big changes and gigantic risk, as if the risk of failure will wash away all you've done in your life. My mentor wasn't saying we weren't going to fail. Even if you do, it doesn't take away what you've done already. - Bongiorno
Perhaps the scariest part about leaving a esteemed position is thinking you leave all your accomplishments behind with the title. You have evolved, though, even in the most basic atmosphere.
With Apple, Bongiorno was reminded that she and Chaudhri wouldn't be starting from scratch. Keep in mind that Bongiorno led some of the most innovative groups at Apple and Chaudhri says he holds several thousand patents through his Apple work.
In other words, if they felt this way, then it's natural for all of us to feel this insecurity, too. A key move is to have people around you who remind you of your worth.
Tammy Perkins, whom left her prestigious positions at Amazon and Microsoft, put it like this: "Having a strong support system of friends, colleagues, and mentors can make a huge difference for people as they transition."
Know when you can't change the culture
Steve [Jobs]' motivations and intentions were very clear: Fighting for the customer, even if what was great for the customer may not have been best for our business model or company. After his leadership, trying to drive innovation, creativity and motivation while having to fight for the customers ourselves was like trying to turn a giant ship. - Bongiorno
Steve Jobs' departure had an indelible impact on Apple's culture, especially immediately after his death. I lived in San Francisco at the time and distinctly remember the entire Silicon Valley culture changing the very day of his passing.
Chaudhri was groomed by Jobs and Bongiorno led some of his most important teams. Jobs may have tried to pass on a legacy, but his living guidance was gone forever. In their words, the single-point leadership became more scattered across the company.
A literally death may not precipitate the end of your current work culture. The end may occur with a change in management, a shift in customers or a new economic cycle. "When values change in a company, you either have to get onboard or leave," Chaudhri says.
Have a bigger plan with or without the organization
We knew our future wasn't at Apple. We knew we had a loud enough voice, a strong enough perspective and collaboration between each other. We knew Apple was some place we came to develop as professionals, but that there was an afterlife beyond that. Knowing that is really important: Understanding the next stage, even if you may not have an exact answer. - Chaudhri
As I talk about in Bring Your Worth, the bigger the company, the harder it can be to remember that you are contributing to its success. Most people believe they are the single factor making the business a success or are an insignificant cog in the machine. Both ideas are false. Both ideas are equally dangerous.
Instead, look at your tenure as a mutual exchange: You create within this structure, and this structure gives you a foundation. It is a partnership. In Chaudhri and Bongiorno's case, they knew their partnership was limited. How? By having a vision.
Recently, I've been talking a lot about the Patagonia founder's 100-year vision for his company. But that's not just for organizations. What is the ultimate impact you want to make as an individual? If you know that, then you know when to adapt to an environment - and when to leave it.