3 Quirky Tactics for Choosing a Career Path

choosing a career path, sidewalk with share-the-path notice

“A helicopter pilot? That’s what it says?”

The high school career counselor stifled her smile. “Yep, that’s what it says.”

I looked down at the paper in my hand. I expected the test results to be silly, but not ridiculous. A helicopter pilot? I couldn’t even (and had little desire to) drive a stick. Moments before, when the career counselor handed me the test and asked me if I wanted to see what profession I’d be good at, I shrugged and said sure. I answered the test’s questions honestly, and tried not to roll my eyes when I encountered overly broad and generic questions like: Do you prefer to be alone, or with people? 

Below my too-cool-to-care facade, however, I was worried. I didn’t know what I wanted to do and I suspected that if I didn’t make the “right” career choice, then I would end up trapped in a profession that made me miserable. But how could I, aged 17, know what I wanted to do for the rest of my working life? I still had time to decide, didn’t I? I suspected that my peers had the same thoughts, but no one outwardly questioned the thinking behind the treadmill we were on — 12 years of generalized schooling, followed by college, followed by declaring a major right away, graduating on time, and embarking on a lifetime of 40+ hour work weeks. It was like adhering to a lifetime of swimming lessons, but no diving lessons, and then being expected to execute a perfect dive

Is Career Indecision a New Thing?

Meanwhile, the more I thought about what I wanted to be, the more it slipped through my fingers. Or, to be more accurate, I knew what I’d like to do, but an artist didn’t seem to me, or to my parents, like a viable career path (though my high school voted me most likely to become an artist). As I understood it from the adults in my life, you either chose a lucrative career at the outset or subsisted in near-poverty forever. So, I needed guidance toward a “real” career choice. It didn’t appear, however, that I would find said guidance at my high school.

In addition to feeling like I was lost in a minefield, I envied those who knew which career path was right for them, specifically their certainty and their assured steps forward. I also felt guilty for my indecisiveness. My maternal grandmother, who was born in 1915, had only two career options: nurse or teacher. She wanted to be a nurse, but her father and older sister didn’t approve, and so my grandma became a teacher. She said that she had a wonderful career, but to this day I wonder what she would have chosen if she’d had the options available to the current generation of young women.

Thinking back, I can picture my young high school self, backpack slung over one shoulder, as I walked into the career counselor’s office. Like most of my peers, I was an amusing combination of self-assured and naive. If I were that high school career counselor today, I would know the young adult before me would have two primary thoughts on her mind: Will I succeed? Can you help me? Yes and yes, and with my varied experiences in mind, I would begin my counseling with a nuanced approach.

The 3 Questions Career Counselors Should Ask

I would begin with a question that I now know is fundamental to making a career decision (whether it be your first, or your thirteenth): What personality type are you? Though who you are is ultimately undefinable, when contemplating a new career it is helpful to identify where you fall among others for traits such as openness, emotionality, and extraversion. Plus, the reward for any genuine attempt to answer this question is enhanced self-awareness. A caveat: if you take a personality test that is not the HEXACO Personality Inventory or the Big 5 Personality Traits (aka 5-Factor Model), don’t rely on the answers, says Angus Chen in “How Accurate Are Personality Tests? for Scientific American. In fact, you shouldn’t rely too heavily on any personality test, or think that you need a test to tell you who you are.

The test that I took as a graduating high school senior was similar to a personality test, but how my answers indicated that I should become a helicopter pilot is a mystery to me. Personality tests should be used as eye-openers, not as job-prescriptions. The tests should provide a starting point of self-awareness when considering career options, but the next step is up to you.

Question number two: How adept are you at reading others’ emotions? I’m talking about emotional intelligence, popularized by Daniel Goleman in 1996 with his book Emotional Intelligence: Why it Can Matter More Than IQ. To answer this question, I would recommend a fun activity: for one day, carry around a notebook and jot down what you perceive as the emotional state of everyone you directly encounter. Don’t include the person’s name, just the time of your interaction, and one or two descriptive words. Ideally, you should have around a dozen encounters by the end of the day. 

Find a quiet time at the end of the day to review your list. How many emotions did you identify? How varied were your conclusions? Why were some emotions unclear? After I completed this exercise, I felt more in tune and aware in every subsequent interaction with my co-workers. I enjoyed the effort so much that I repeated the exercise for a week. I was delighted by the richness and variety of my co-workers’ temperaments, and I was surprised by how much I didn’t notice before.  

Finally, the third question: Do you have a mentor, or a “frentor”? (A “frentor” is someone who is a peer at a similar experience level, but in a different job). If not, I would emphasize the need for one — someone who works in a similar field or position of interest. Ask if you can take them to coffee, and be upfront about your interest in gaining them as a knowledgeable coach for your career. Before your direct pitch, consider what value you can bring to them. Offer to enhance their day-to-day in some way. Make it clear that you do not expect them to open doors for you, but that you know you could benefit from their experience if they feel comfortable in sharing it with you. 

I would recommend reaching out to a number of contacts, and I would emphasize the importance of clarity on the details for each potential mentorship; the when, how, and for how long. Then, regarding an agreement, I would say, “Be reliable in your attentiveness. In short, show up and shut up. Don’t let your ambition block your receptiveness to learning from others.”

The Power of Grit and Hope 

When I left my high school career counselor’s office, I was more lost than before I stepped through the door, but I accepted my confusion as unavoidable and hoped for the best. Today, I know that career-confusion is avoidable. I wish that the career counselor had attempted to share with me something similar to the following outlook on careers, the one that I now live by: 

  • A career should enhance you, but not define you.
  • Hone your self-awareness, exercise your ability to perceive, and connect with others with the intent to learn, while providing value.
  • Be prepared to fail, and intend to learn from your mistakes

Finally, I wish the career counselor would’ve asked, “Why do you think that you can’t become a helicopter pilot?”

“If I could be anything,” I‘d say, “I would be an artist or a writer. But I don’t have a direct path to that right now.”

“Then as long as you don’t give up, you’ll get there,” she’d reply. “Your path may be a quirky one, but with grit and hope you’ll get there.”