Quitting your job and moving onto something new is always a nerve-racking process.
But just think about how people who’ve left the biggest companies out there must feel.
Business Insider has spoken to numerous alumni of some of the most talked about companies.
Many of them described leaving to tackle new ventures and chart their own course in the business world.
WayUp CEO and cofounder Liz Wessel got straight to the point in her interview with Google during her senior year in college.
She wasn’t planning on sticking around forever.
“I said, ‘I am really interested in taking this, but if I take it, I want to leave in two years and start a company. How do you guys feel about that?'” she previously told Business Insider.
Wessel knew from the get go that she wanted to found her own business early on in her career. The Google recruiters were extremely supportive of her plan. And sure enough, after two years at the tech giant, she left.
For Wessel, having a plan and finding an encouraging and educational environment like Google was a crucial step in her professional development.
“I was very adamant about starting a company while I was still young and could take big risks — not that you can’t when you’re older, but I just was really excited about the concept of it,” Wessel said.
Listen to the market
Joe Meyer was CEO of startup HopStop when Apple acquired the business for $1 billion in 2013, according to Fortune.
He stuck around at Apple for two years, before leaving to found careers site ExecThread.
In the end, he said it was hard to leave.
“Apple was treating me very well and they made it very difficult for me to leave,” he told Business Insider.
He said he has his positive experience at Apple to thank for some of the success of his new business, which now has around 20,000 users and has raised $6.5 million in funding.
Because he was in no hurry to leave, he worked on ExecThread as a side project until he was sure it was good enough to roll out.
“Apple really taught me to to do things well before you introduce them or market them,” he said. “I wanted to make sure there was really something here.”
Once his side hustle began receiving attention from other players in the recruiting industry, however, he knew it was time to leave.
“That was when I was like I need to focus on this full time,” he said.
Find something to run to
Chris Gomersall was Facebook and Instagram’s first creative strategist. He loved his job. Still, he left it in 2015 to start cloud-based marketing software company Atomized.
He had started Atomized as a side project, but said it had never felt like extra work.
“I think in general when you find a job you love, it just doesn’t feel like work,” he previously told Business Insider. “It never felt like anything more than doing what I love.”
Gomersall said that was how he knew it was time to move on and start something new. He recommends most people leave their job only when they’re certain a better, more fulfilling opportunity awaits them.
“It was really more of a calling,” he said. “I was running to something rather than away from something.”
Take baby steps
When it comes to seizing control of your career or leaving your job, there’s nothing wrong with taking a few baby steps before you make a huge decision. In many cases, it can prevent you from making a catastrophic career move.
Kathryn Minshew, CEO and cofounder of career site The Muse, worked at McKinsey and the Clinton Health Access Initiative before going off to launch her own business.
She previously told Business Insider it’s not a bad idea to start small, however. Running a side hustle or engaging in a hobby is a cautious and thoughtful way of figuring out whether your passion is worth pursuing full-time.
“Don’t be afraid to start small,” she says. “Find a nonprofit or a local organization where you could volunteer your skills on weekends or a couple of hours each week so you can start to build up some experience and begin to understand what the business of your passion looks like. Talk to people who have made that passion their full time job.”
Read more: The 21 most promising jobs of the future
Ask yourself questions
If you want to make a professional pivot, you’re going to need to be honest with yourself about what you really want.
Refdash CEO and cofounder Nikola Otasevic spent two years at Google. Before leaving, he said he had to answer a few questions. Namely, he thought about whether he truly wanted to start his own business, what drove him in his career, and what sort of environment he wanted to work in.
“If you are someone who gets a lot of ideas — like you’re showering in the morning and you just have an idea — in a startup, you can have that idea live and serving users by that afternoon,” Otasevic previously told Business Insider. “In bigger companies like Google or Facebook, you’ll probably need a month to roll that out. But everything you release in Google or Facebook will have millions of eyeballs on it.”
Pay attention to how you feel on Sundays
Former JPMorgan banker Sameer Syed said he always used to be bummed out by the end of the weekend.
“When I was in finance, every Sunday at night I would have the Sunday blues,” he previously told Business Insider. “It was like, ‘Oh God, I have work tomorrow. Oh God, I have to wake up early.’ I would dread Sunday nights.”
He ended up quitting investment banking for good in June 2012.
He joined a tech startup, and now works in strategic partnerships at Google and organizes quarterly round tables known as Wall Street to Silicon Alley to help financial professionals transition to jobs at tech startups.
“I wouldn’t say I’m always super excited to go to work, but it’s not something I think about,” he said. “I’m like, ‘OK, work tomorrow. Cool. That’s fine.’ It’s not a drag on me. I’m a little bit more excited.”
Go for the projects that excite you
Eric Lewis previously worked at Black & Decker, Amazon, and Google, before he quit to join Casper.
When he was offered the gig of VP of global operations, he jumped at it.
The reason? He was excited by the change of pace the mattress startup offered.
Lewis was drawn in by the company’s “rapid scaling” and the opportunity to work in a fast-paced startup environment, according to Business Insider’s Jillian D’Onfro.
“The opportunity to grow this business across the globe was the ‘pillows on the bed,’ as they say,” Lewis previously told Business Insider.
Listen to your gut
Win Smith said he knew in his gut when he needed to leave his role at Merrill Lynch. It was 2001 and Stanley O’Neal had just taken over as president, he previously told Business Insider.
“He made me an offer to stay as vice chairman but I was really concerned about his direction and I was really distressed that he didn’t seem to appreciate the culture or the history of the firm,” he told Business Insider.
As a result, Smith left the bank and went into private equity. Ultimately, he dedicated his career to running the Vermont ski resort, Sugarbush Resort. He said the choice has allowed him to experience the outdoors and pursue his passion full-time.
“If you can’t get excited when you wake up in the morning, if you’re not doing something you really love, then don’t do it,” he said. “I think at the end of the day too many people rationalize why they should stay, rather than launching out. When they launch out, they often find that they’re going to land on their feet.”
Don’t be afraid of the unknown
Jose Llorens worked at Google for three years before quitting to write his novel “Time on Earth.”
It was a big risk, but, in a contributed Business Insider post, Llorens wrote he knew the timing was right.
“I’ve had this story in my mind for the last five years,” he wrote.” The more I travelled and the more people I met, the more the narrative took shape in my mind, up the point that I had to take the time to spill it out on the pages.”
Ultimately, Llorens said it wasn’t enough to just have a job. He was looking for creative fulfillment. As a result, he said it’s important for people to take risks in order to beat our natural fear of the unknown.
“We want to be successful whilst having time to enjoy life at its fullest, and this is why we struggle so much when managing our most precious resource, time,” he said.