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‘The Best Leap I Ever Took’: 10 Career Risks That Paid Off


Due diligence is important, whether you’re taking a new job, making a career change, or starting a business. Sometimes, however, you have to jump and hope for the best. (Hopefully, you know, after some careful planning and building up a cushion of savings to soften your landing.) We asked Facebook users to tell us about the biggest risk they ever took … and how it made their careers.

leap of faith 

(Photo Credit: Joshua Earle/Unsplash)

1. Going back to school.

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Anne: I think mine was taking three years off “real work” to go to grad school for an MA and MFA in creative writing. It not only got me thinking about using my English degree in a non-scholarly way but it also positioned me physically to live off the east coast and live in Montana and Chicago. I’d never have moved to either place otherwise! I don’t know that I’d have risked that time off from a full-time salary if I hadn’t been in my early 20s, but I’m really glad I did it, now!

2. Chasing a job prospect that didn’t quite work out.

Colleen: Newlyweds … moved from Midwest to east coast with everything we owned and just a prospect for a freelance assisting gig … $2,000 and no place to live. He never hired my husband but that move led to everything that both of us have done freelancing for the last 16 years. Wouldn’t change a thing.

3. Following my heart, instead of the money.

Tom: I took a 50 percent pay cut from a Wall Street job I hated (and if I had stayed at it, I would have ended up earning much more) and took a job as employee #2 at start-up biotech company that all odds were against ever becoming anything. Eight years later, we took that company public, and with that on my resume, I now get to do EXACTLY what I want to be doing right now as an entrepreneur in the biotech industry.

4. Telling a little white lie.

Meghan: Answered an ad in The New York Times for a job at Columbia Business School. Paid to fly myself to the interview as I told them I was already in the process of moving. Got the job and was able to move to NYC with a paycheck and really good benefits.

5. Saying, “enough.”

Amanda: Mine was when I quit working early intervention to take a chance of becoming a writer. My heart hurt too much working with kids in therapeutic foster care. I took a leap, started pitching parent-oriented child development ideas, was very, very poor for many years and now have a thriving career.

6. Going home.

Pam: I left Massachusetts to move to Texas without a job lined up. Found a job at UT Austin within six months. Got closer to family, better job, and nobody laughs at me when I say “y’all” or “fixing to” or “pretty much.” And I can wear my western boots everywhere, even to weddings! In short, I can be ME again.

7. Moving to a place where I didn’t know anyone.

Jennifer: Went into big debt to go to grad school to get a unique major, and moved the family from a rural area to one of the fastest growing US cities, where we didn’t know a soul, to take a new job and launch a new career. Three years later, it’s safe to say the big risk has reaped big rewards.

8. Being loyal to myself, not the company.

Nancy: When I was starting out in the corporate world, I had a job as an administrative assistant. I quickly realized I was doing as much work as one of the account managers, if not doing HIS work. When I pointed this out to my boss, he agreed and said for my review, he would go to our director and ask for a promotion and raise. I waited two years. Every time I brought it up, he would placate me. Finally, I applied for the same job at our parent company, just one floor below us. I got it. When he found out, he lost it, but that was two years of salary I had lost out on, which is what I explained to him. I wanted to stay loyal to him, but it was in my best interest to move on. I did very well at the new company and it was a great decision.

9. Quitting the rat race.

Ferne: When I quit a very good job at an ad agency, left America and moved to London to go back to journalism as a freelancer. I’ve had some lean times since then and I’ve even been offered full-time jobs by clients but I would never give up my freedom to go back to an office job.

10. Becoming an intern … long after graduation.

Molly: Quit a full-time, well paid job with great benefits (but also terribly boring) for a summer internship at the age of 28. Eventually got hired by the magazine and have been an editor ever since! (Now also living the freelance life.)

Tell Us What You Think

Did your biggest risk pay off? We want to hear from you! Leave a comment or join the discussion on Twitter.

Jen Hubley Luckwaldt
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I started at the company I work for, 4 years ago as Senior Industrial Designer for their R&D Dept. Since then have started a new R&D Internal Solutions department and have saved the company $500K every year even if I leave they will continue to reap the rewards. I spoke to the CEO about 7 weeks back stating I was paid at less than 50% of average in our area and needed a large shift in title and salary. He… Read more »


Getting laid off from a big company. Best thing to happen to me. Would have stayed and grinded away. I stopped working downtown in a major city. Now open my own business outside of the big city and enjoying it. I would never go back to working for a big company, no matter the pay or benefits.


How about a job leap that doesn’t involve freelance writing?


I had a successful construction contracting business in the Pacific Northwest for 18 years that I started at age 25. I got married and had 3 kids , however there was not enough hours in the day to raise family and expand a business and the stress was unbeiveable. So I merged with another contractor in 2002 right before the big construction crash and 1 year later I walked away from it all. I took my talents and skills and… Read more »


It says risks that paid off in the title. Not every risk works out. If they did, they wouldn’t be called a risk. We all take risks in varying degrees. Some pay off in happiness, others in cold hard cash. As far as when you take risks, they can happen at any age. My father started his business at age 39 and had it for 40 years. I was 14 and probably more nervous about it than he was. So… Read more »


With due respect, most of the advices listed here are terrible. Sure, it can work once for someone in the right place at the right time, but by and large, these are just bad moves any way you cut it. A lot of people follow their hearts at age 18, party hard, get useless degrees and basically ruin their entire lives forever. Why do you think an average person – incapable of choosing for himself/herself and is typically fed bad… Read more »


My biggest gamble was moving from a large city Charlotte North Carolina where I live for 25 years and relocating to a small town Roanoke Virginia. I accepted a new job on a managerial level after spending years in a more technical frontline position. We knew no one in Roanoke. The gamble paid off even though my job lasted only one year because the company was bought out by a competitor. I was able to finish a masters degree in… Read more »

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