4 People Share Their Risky Career Moves That Paid Off

From putting a resume on a billboard to quitting high-paying jobs, these people found new careers by thinking way outside the box.

4 People Share Their Risky Career Moves That Paid Off
[Photo: Flickr user Lord Jim]

A year and a half ago, I took the biggest career leap of my life.


After years spent being a teacher who moonlit as a freelance writer, I felt compelled to leave the classroom and devote myself to writing full-time.

With an optimistic “It’ll all work out” attitude, I jumped off the cliff–and grew my wings on the way down.

It was anything but easy.


In fact, it was the toughest year of my life. But today, my schedule is full, my bank account is fed, and, oh yeah, I’m doing what I love.

The takeaway here is that landing your dream job takes guts. It requires risk and uncertainty–and pushes your faith and self-confidence to the max.

Just ask these four professionals, who stepped way beyond their comfort zones to snag better gigs. Their stories are sure to inspire … and maybe make you ponder if you’d ever be brave enough to do the same.


“I Got 150 Job Leads–Thanks to One Really Unorthodox Resume”

Phil Dubost, 31, a product manager in New York City

In 2013, I was pretty down in the dumps. The website I’d launched in 2011 wasn’t doing well, and I’d whittled my savings down to 10,000 euros.

I knew it was time to get a secure, full-time job, but I was picky. I wanted a well-paying product management gig in the U.S.–and those are competitive spots.


I was particularly interested in a position at Amazon, but I couldn’t even fathom how many résumés they must receive. I needed a way to get mine to the top of the pile.

That’s when I got a crazy idea.

The Career Leap of Faith Using editing software, I transformed an Amazon product page into my résumé–complete with my headshot, work experience, and top skills (shown above). Once I was happy with the results, I shot it off to Amazon and, sure enough, got a response.


Unfortunately, it was just to say that there were no openings available. But I wasn’t ready to give up hope, so I tweeted my résumé link to a popular tech blog.

From there, it went viral.

Within a week I had one million visitors to my website, and roughly 1,000 messages–about 150 of which were attractive job leads. I’d completely turned the tables: Instead of competing for a job, I had employers vying for my attention.


After filtering out the best positions, I had a handful of options to pursue. At that point it was up to me to sell my skills to land a gig–which is exactly what I did.

Two months later, I was officially offered a position as a technical product manager at a major beauty subscription box service in New York–making more money than I ever did in France.

I absolutely love my position and the opportunity to be creative. I guess you could say I’m thriving–all thanks to a clever twist I made to my résumé.


“I Gave Up A $500K Salary To Start A Blog”

Heidi Nazarudin, 34, a writer in Santa Monica, Calif.

After graduating at the top of my class from Mara University of Technology in Malaysia in 2003, my career took off.

I found success in the tech industry, handling big mergers and acquisitions–and, in just a few years’ time, worked my way up to CEO of a mobile tech company in Tokyo, earning about $500,000.


I had a pretty grand lifestyle–regularly going on shopping sprees and out to nice dinners–but I was bored. I had no passion for the tech industry.

What I did love was Tokyo’s colorful, in-your-face fashion scene. On the weekends I spent all of my time at Harajuku Park–the fashion capital for trendy Japanese youth–taking in the over-the-top designs.

Soon, my interest in fashion became an obsession, lighting a fire under me to pursue a career in it. I’d always enjoyed writing, and figured that’d be the best way to transition into the industry. So I enrolled in writing classes at night and on the weekends to sharpen my skills.


The Career Leap of Faith In 2007 I made my big move–resigning as CEO to ghostwrite fashion and beauty posts for a variety of blogs.

Drawing on my business chops, I boldly networked with big-brand marketing directors and pitched myself to new clients–determined to succeed.

The pay wasn’t great at first–I didn’t earn anything for the first three months–but I was able to stay afloat, thanks to my savings account.


After about a year of blogging, I moved to Los Angeles to supercharge my career, eventually starting my own blog, which speaks to ambitious working women. It’s all about incorporating style into your success strategy.

My business background was one of my biggest assets in getting my website off the ground, and I quickly found ways to monetize it by writing sponsored posts and working with advertisers. I also found a great way to generate additional income by hosting events–like special luncheons or runway shows–for big brands and department stores.

Eight years later, I’ve made a name for myself in the fashion industry, and am bringing in about $20,000 a month. While it’s not nearly as much as what I was making as a CEO, it’s still a great living.


In the end, my journey has taught me it’s possible to do what you love and still be a good businessperson. You just have to find the courage to take the risk.

“I Broadcast Myself On A Billboard”

Bennett Olson, 25, an AV systems technician in Minneapolis

Three years ago, as I was about to graduate from Liberty University in Virginia, I launched an aggressive job search.


I’d cast a pretty wide net applying for any gig that fit my business administration degree, but I wasn’t finding much success. So I started wracking my brain for a creative way to accelerate the process and nab a few interviews.

That’s when it dawned on me: What if I took out an ad on a local billboard? I’d never heard of it as a job-hunting technique, but something about it made sense.

The Career Leap of Faith My research revealed that for $350–a hefty sum for an unemployed 22-year-old–I could purchase a spot on a rotating electronic billboard for 24 hours. I deliberately chose one located in a high-traffic area in Minneapolis.

Part of me was worried it might seem unprofessional, but the potential payoff was worth the risk. So I bought it–a huge picture of my face with a line that read “Hire me!” above my website’s URL.

To hedge my bets I took a photo and posted it to Facebook, tagging some local media outlets. I never dreamed it would trigger a media storm.

Local news organizations interviewed me and featured the billboard, then my story spread to national media–I was a featured guest on a Fox Business show–and then it went international, from London to South Africa.

I got tons of responses–as well as an interview from a company specializing in 3-D laser scanning. They loved the ad, and just two weeks later, offered me $45,000 to be their sales and marketing coordinator. I happily accepted.

In the end, I didn’t end up staying at that position for long. Since my outside-the-box thinking had landed me the gig, I expected it to be more hands-on than simply making sales calls.

Today, I’m an AV systems tech for a large financial firm. Looking back, I may have jumped the gun by accepting the first job offer I received–but I have zero regrets. That sales job was an integral part of my journey because it helped me understand what I didn’t want.

I’m still a big believer in outside-the-box problem solving. If it doesn’t work out, at least you’ll learn something!

“I Traded A Cushy Corporate Gig For Non-Profit Work”

Anand Kesavan, 34, CFO of a charter school in Austin, Texas

In 2008, I was an investment banker earning a killer, several-hundred-grand salary. It was enough to pay for an amazing lifestyle and big-ticket extras–like a house for my parents.

I had it all … or so it appeared. The reality is that I was overworked, stressed, and 50 pounds overweight.

So I did something drastic: I took a leave of absence, sold all of my belongings and traveled the world for 18 months. My boss, who took the news as well as he could, told me I was crazy.

I set off with the goal of learning what would make me happy, while covering 28 countries.

I took up Thai kickboxing–and lost 40 pounds. I spent time in Guatemala at a community school, and then helped raise funds for another school in India.

The highlight was connecting with folks who valued commitment to community over an upper-class lifestyle. That’s what made me realize that money isn’t the true measure of success.

The Career Leap of Faith When I returned home I completed a two-year fellowship at Harvard geared toward policy and nonprofit work. After that, in 2011, I accepted a new position with my old employer–this time as an SVP, structuring investments for public projects and school buildings.

I enjoyed it, but not enough to ignore an offer that came my way the next year. It was a CFO job at a Texas charter school for kids in underserved populations. It felt like my chance to do good in the world.

Of course, that meant I’d have to move and accept a salary of roughly two-thirds less than what I was making.

Was I nervous to give up that security? You bet–but I knew I’d regret it if I didn’t go.

I’ve been in this position for a little over a year now, and I wouldn’t change a thing. I may not be able to afford the fancy vacations I could before, but I’m happy knowing that the work I do matters. That’s rich to me.

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