7 Financially Risky Careers That Actually Pay Off (Sometimes) 

With so many career options available, choosing the right path can be difficult. One intriguing option is a high-risk career that offers the potential of big financial rewards. The dream of being wealthy is alluring to most, but not everyone fits into the conventional mold. Some are willing to take risks in the hope that they pay off.

With so many career options available, choosing the right path can be difficult. One intriguing option is a high-risk career that offers the potential of big financial rewards. The dream of being wealthy is alluring to most, but not everyone fits into the conventional mold. Some are willing to take risks in the hope that they pay off.

Whether you’re the type who openly welcomes risk or just interested in the kinds of jobs that risky people embrace, the list of career paths below will be enlightening. These are seven financially risky careers that don’t offer any guarantees of success, but when they do pay off, the rewards can be immense.

Day Trading

When discussing high-risk career paths, day trading has to be mentioned. Doing well in this career often involves large sums of cash on the line. This job may be seen as a glamorous way to make big money quickly. While that may happen, more often than not it isn’t the case. It’s a serious job that requires nerves of steel. Your mind needs to stay focused, clear, and unafraid of risk. 

Day trading is complex and often difficult to understand. You need to be extremely aware of how the markets work, current market trends, and how to read signals and signs. But if you can do all that well, you can live very comfortably.

Professional Gambler

Have you ever watched a gambling tournament on TV and wondered how difficult it is to pursue a career as a professional gambler? Such gamblers belong in the financially risky career category because there is truly no guarantee they’ll succeed. The thing is, if you’re good and you start winning big tournaments, the payout can be massive. 

So, how do professional gamblers get started in their career? Chances are, they develop a career-long strategic mindset, with clear goals and an understanding of the steps needed to achieve them. This is in contrast to the primarily entertainment appeal of popular real money slots, which offer high volatility but no professional commitment. Professionals keep their eye on the prize and understand it will likely be a stressful and bumpy road.

Professional Athlete

Many kids take part in sports. More than just a great form of exercise, sports also build team-building skills and help with socialization. For many, that’s as far as it goes. Then there is the small group of people who aren’t just good at their chosen sport but excel. They may even become elite-level athletes, but does that mean they should go professional?

Professional athletes can make a lot of money not just during their career, but in the years to follow, thanks to sponsorships, endorsements, and relying on name awareness. All you need to do is refer to statistics from the U.S. Bureau of Labor Statistics to see that there are just under 15,000 sports competitors and athletes working in the country. Now compare those 15,000 professionals to the countless individuals participating in amateur sports. That is a very small percentage of people who make it. Not only do you need to be extremely talented to go professional, but you also need to dedicate your life to your sport. 

Freelance Artist

Being an artist is a gift. It’s something that many people aspire to but just don’t have the skills or vision. Still, some specifically pursue freelance artistry despite its challenges. Success is possible, but it may not be enough to sustain you, at least at first. It can take a long time to establish yourself as a serious artist, create interest in your work, and sell pieces. This is exactly why so many people pursue art as their side gig. It is risky and can be a slow climb to success.

Startup Founder and Entrepreneur

Entrepreneurship is one of the most impactful career paths out there but definitely belongs in the risky job realm. Entrepreneurs want to solve an issue or problem and often have innovative ways to do so. Even so, going from idea to a functioning and profitable business is a long road. According to recent data, up to 90% of startups ultimately fail. The first year is especially difficult for new businesses to get off the ground.

Regardless, for the 10% that do succeed, they can go on to great things. Some examples of startup success stories are Apple, Facebook, Square, Instagram, Airbnb, Uber, and Netflix.

Stunt Performer

This particular career path is incredibly niche—limited to those who have no fear, love adrenaline, and can routinely stare down physical injury and even the possibility of death. That’s right, we’re talking about stunt performers. There’s a reason this pool of professionals isn’t massive and why they are so widely respected. Despite their dedication, the risks are real—and tragically, some have lost their lives while performing or rehearsing. 

Social Media Influencer

Social media influencers are a career path that didn’t even exist 20 years ago. Today it has exploded, and many now believe they have what it takes to become successful. The problem with this career path is that the fan base can be fleeting and fickle. What’s trending today may fade in a matter of weeks, months, or years, so some influencers who hit it big years ago are now finding it difficult to stay relevant.

The sphere includes beauty and lifestyle influencers, TikTok creators, online gamers and streamers, and more. Some of those who’ve succeeded have amassed net worths in the hundreds of millions. But these are few and far between.

Is a Risky Job Right for You?

If any of these potential career paths speak to you, then you may be the ideal type for a risky job. It’s all about high risks for the chance of high financial rewards. While none of these careers offer guarantees, does any career truly guarantee success? There will always be some risk involved. Just how much you can tolerate is up to you.