5 Risky Career Moves That Can Really Pay Off

Sometimes it’s the not-so-safe decisions that reap the greatest rewards.

5 Risky Career Moves That Can Really Pay Off
[Photo: TriStar/Getty Images]

You probably remember that defining scene in Jerry Maguire where Tom Cruise’s character distributes a company-wide memo about the faults of the sports management industry, leaves his company, and convinces another employee to join him. It’s one of those movie moments that inspires us to find our passion.


Of course, not every day at the office warrants such a dramatic change, but sometimes career risks can really pay off. Here, we share the stories of five people who took a chance and haven’t looked back, whether it was starting their own company or speaking up about a good idea:

[Related: 3 Techniques To Help You Take Better Risks]

1. Leaving A Secure Job To Follow Your Passion

I started out in a very safe and comfortable career [as] a nuclear medicine technologist. I had insurance and benefits, paid time off, sick leave, and maternity benefits. About three years into my career, I decided to quit and become a hairstylist.

Not only that, but after I finished beauty school I decided to open my own studio. I grew up in the hair industry because my mom is a stylist, but I didn’t really consider it a safe option because the pay isn’t great, and there’s usually little to no benefits package. [But] now, just two years in, I have a successful hair and makeup studio, I have been published in major magazines, and most of all, I am happy. Turns out there is great fortune in the hair industry if you are passionate and persevere through stereotypes and challenges.

—Shreeda Tailor, master stylist, J. Tailor Salon

[Related: 5 Ways Mentally Strong People Approach Taking Risks]


2. Pitching Your Boss On A Major Change

[My] company wasn’t always focused on modern and sustainable homes. Before I took over as CEO in 2011, we were focused on luxurious, Mediterranean homes. About five years ago, I realized how much Los Angeles was lacking in eco-friendly building, and decided to make it my mission to provide and educate people about the importance of building this way.

However, the CEO at the time did not believe that this was a viable option and did not want to change the direction and philosophy of the company. When I presented him with a new business plan, he rejected it. Seeing that I could not grow at the company, I left and moved to another company.

A year or so passed, and one day the CEO called me up. Prime Five Homes had put up the worst year since their incorporation. The CEO finally recognized that my ideas were the future of building.

—Mayer Dahan, CEO of Prime Five Homes

[Related: 7 Famous People Who Took Big Career Risks and Never Looked Back]

3. Starting A Time-Consuming Side Hustle

A year ago, I was making full-time income as a freelance proofreader. Lots of people had been asking me how I did what I did with only an iPad, how to market, and so on. So last November I decided to start a blog about freelance proofreading, called, on a total whim. I thought for sure it wouldn’t go anywhere.

But it did. It eventually turned into an online course in February, and since February, I’ve earned over $550,000 in revenue with the blog, 14 times what I made in a year as a proofreader. Now I’m a full-time blogger/entrepreneur, and I don’t have to to proofread anymore if I don’t want to.

—Caitlin Pyle,

4. Going With An Out-Of-The-Box Idea Over A Crowd-Pleaser

A month into my new PR job at a New York marketing firm, I was handed a major client, an operator of ski resorts throughout North America, with the goal of increasing awareness in the Big Apple. I wanted to make a good impression on my firm and on my new client. I needed a “big idea.” Yes, holding a media event around the building of a ski slope in the middle of Manhattan was the crazy, big idea I proposed.

Needless to say, despite an exhaustive effort, the ski slope idea never came to fruition—ultimately the client decided that the permit fees demanded by the city . . . were too outrageous. However, the impression I left on my boss and the client cemented my job security at the firm. First, it was a really big idea, super creative, and way out-of-the-box thinking. Second, I never gave up trying to show that it was a good one.

—Suzan French, president of FlackShack

5. Taking An Internship Over A Salaried Position

When I was 25, I worked at a small market research firm in a job that was going nowhere fast. While I made good enough money, it simply wasn’t the life I envisioned when I left college and embarked into the world. A few months [after my realization] . . . I packed up and moved to Barcelona to live out a dream I’d had since high school. As my time in Spain was winding down, I decided to follow one more dream I had. With the last of my funds, I packed up and moved to San Francisco to work in tech. I wanted to see if I had what it took to work alongside the industry’s best.

Unfortunately, I had neither the school nor career background to impress these companies, and I was forced to make a choice. I had two offers on the table: one was to work at a mid-level role at a struggling startup (one that paid well and had plenty of stock options), or accept an internship at Nokia at the ripe age of 27.

While I immediately leaned toward taking the role at the startup, I couldn’t shake the idea that I had come here to work at a company just like Nokia, and the choice became clear. A year later, Nokia was purchased by Microsoft, and I was considered an integral figure on a strong team—all the while, the startup had folded.

—Joseph Nagle, director of marketing, Evercharge

This article originally appeared on Levo and is reprinted with permission.