Financial Education

Section Menu

Income Essentials

The Challenges of Choosing a Career

When I grow up, I want to be a ___________.”

Depending on who you are, filling in the blank above can be an exciting, troubling, or outright confusing task. If you happen to be a kindergartner, filling in the blank is awesome, because at that age, dinosaur and superhero are both perfectly viable career options. If you happen to be in high school, filling in the blank can be motivating because it takes all your talents and interests and captures them in a single goal that you can pursue through high school and past graduation day. If you happen to be an adult, filling in the blank can be a little bit terrifying because that could mean you’re now a grown-up (regardless of whether or not you feel like one) and here you are, still secretly looking for ideas.

Choosing a career path is a big deal. Even if you don’t consider yourself career-driven, your choice of vocation will inevitably influence your lifestyle. Income is only part of the equation—your career also has the ability to determine where you end up living, who you end up meeting, and the activities you end up having time for. So why is it so challenging to choose the right career? Read on.

Because careers can’t be prescribed

Did you ever have to take one of those career aptitude tests in school or online? Do you remember what your result was back then, and whether or not it holds true? Despite your Facebook feed’s desperate attempt to convince you otherwise, it takes more than an online personality test to figure out your ideal career. We often expect our perfect career to be prescriptive, as though there’s a single perfect job for each individual combination of skills (“Oh, so you’re a people person with great communication skills? You should be a sales manager!”). The truth is that the link between your abilities and the career that’s right for you is a lot more complex and nuanced. The same set of skills and interests (e.g., a steady hand and a love of art, science, and technology) can be a springboard for completely different career paths (e.g., a digital artist or a neurosurgeon). It’s also important to note that interests can be enjoyed and actively developed outside of your day job (so perhaps the person in our example becomes a wildly successful veterinarian who creates oil paintings on weekends). Career aptitude tests can help generate some job ideas, but don’t let a simple quiz have the final say. 

The takeaway: In order for you to be happy and successful, a career path doesn’t have to be a perfect translation of your unique signature of experience, skills, and interests. 

Because of career choice overload

It’s not often that we look back on medieval times with nostalgia and envy (they definitely had their share of bummers), but career choice was certainly a simpler process. Mainly because there were fewer career paths and, in many cases, the choice would be made for you! Today, there are hundreds of thousands of different occupations to choose from, and more are being created every day to keep up with new demands and technologies. There are many lucrative career fields today that did not even exist 15 years ago. How mind-boggling is it to think that you might be a good match for a job that hasn’t been invented yet? The sheer amount of career paths out there can cripple your decision-making process. And when you do finally make a decision, doubt starts to creep in. What if you had gone with that other option? In the context of choosing a career, the fear of missed opportunity can be overwhelming.

The takeaway: At the end of the day, we all want reassurance that we’ve made the best possible decision, but that requires a lot of comparison, analysis, and head space. Instead, define your goals and use them to guide your decision-making. Focus on meeting your career criteria without worrying about the possibility of there being something better. 

Because “occupationism” is everywhere

“Occupationism” is a relatively new term used to describe an age-old concept: discriminating against someone based on their career. Even if you don’t judge others based on their field of work, you may have caught glimpses of occupationism in conversations with friends or family who use job titles as shorthand for how successful or educated someone is (doctors and lawyers seem to be the go-to stereotype in these situations). Occupationism may have even affected your own career choices in the past if you’ve ever felt the need to choose a job based on its prestige, not on your genuine interest in it. On the surface, occupational prestige seems to be linked to money, success, and purpose—but when you really think about it, it is possible to achieve all three of those in any given field. 

The takeaway: Career stereotypes are pervasive, but that doesn’t mean you have to buy into them. Define your own success. 

Because it’s easier to be passive

Choosing a career is not something we see a lot of because most career choices are made “by default.” Think back on your choice of after-school activities, high school electives, and even your college major. Odds are that those choices resulted from a combination of pressure from your parents, influence from your friends, pursuits based on your interests at the time, and maybe a little bit of the occupational prestige mentioned above. It’s highly unlikely that you approached intramural volleyball from a perspective of how it would factor into your career path 10 years down the line.

All this isn’t to say that every single activity needs to come from the perspective of career building. It just illustrates how easy it is to coast on others’ expectations of us rather than actively making decisions ourselves. Acknowledge that carving out your career path is important, and that each decision deserves your thought and energy. 

The takeaway: Get to know yourself. You’ll find that it will help you make career decisions that are in your best interest. You might also find that you’ll be less likely to blindly follow the pack.


Finding your dream career is challenging on its own, and only made more difficult by others’ expectations and our own biases. Be mindful of your goals—any job that helps you achieve them is a benchmark for success. Remember that interests and skills change and develop over time, and therefore the need to make and reassess your career goals will continue through high school, college and beyond. Your career is important, and it deserves some serious reflection time.