This article is the second of a series about finding joy in work. If you missed the first installment, you can catch up here. In this piece, we will explore how to find work that truly aligns with your own personality.
I’ve had the fortune (or curse) of navigating five distinct careers – clinical medicine, management consulting, venture capital, medical affairs, and business development. Perhaps a sixth if you count being a CEO. While I try to leverage this diverse background in my current role, my career path could certainly have been simpler and more efficient. One key reason for this winding journey is that I didn’t fully understand myself—specifically, the kind of work that suits my personality and character. That’s what this article is about.
Let’s face it: as adults, our personalities are largely set. While we can adapt temporarily, we naturally gravitate back to what’s familiar or enjoyable. Instead of resisting this, I suggest embracing work that aligns with your personality. However, this isn’t as straightforward as it may seem. Who are we really, and what kind of work will we enjoy? I didn’t confront these questions until later in my career, and it would have been invaluable to do so much earlier.
To help, I propose a simple framework to map your character and identify work that suits you. This is a basic two-by-two matrix (forgive me, ex-consultant here) that maps affinity against ability. Affinity refers to what you enjoy doing, while ability is what you excel at. These are not always the same thing! Let me explain with some examples.
Many of you might remember William Hung from American Idol, who became famous after his unsuccessful audition singing “She Bangs” by Ricky Martin. William was endearing – he declared, “I want to make music my living” before his audition, only to have Simon Cowell promptly tell him, “You can’t sing, you can’t dance, so what do you want me to say?” William clearly loved singing (high affinity) but lacked the talent for it (low ability). His passion led to a brief cult following but, after the hype died down, he switched careers entirely, becoming a technical crime analyst for the LA County Sheriff’s Department.
Contrast that with my own experience in music. Like many Asian parents, mine heavily encouraged music, pushing me and my brother to practice rigorously. At my peak, I practiced four hours a day—two on cello and two on piano. This regimen made me start disliking music, turning it into a chore rather than a joy. At that point, I had high ability but low affinity. I eventually quit classical music and took up jazz piano, where my affinity soared. I could now play with friends, explore a new genre, and learn improvisation. As a result, I still play today.
OK, so we have this matrix where ability is on one axis, and affinity is on the other:
Now, how do you populate this matrix? Avoid listing hobbies (like singing Ricky Martin songs) or specific tasks (like writing LinkedIn articles). Instead, describe broader attributes of your character. Do you prefer leading groups or participating in them? Communicating in writing or speaking? Are you more of an individual contributor or a team player? Are you shy or outgoing? Detail-oriented or big-picture focused? Do you plan far ahead, or are you more spontaneous? Do you prefer immediate rewards, or can you wait patiently for outcomes?
Here’s an example from my life. During medical training, I was drawn to surgical specialties rather than medical ones. In hindsight, I now realize why – in surgery, you directly intervene and often provide a tangible fix, like repairing a hole or removing a lump. After finishing a procedure, I felt satisfied knowing I’d made an immediate, measurable, and direct impact. In contrast, medicine can be less defined, with outcomes often measured over months or years.
If I had better self-awareness earlier, I would have realized that I need to be in a role where I can see immediate results or at least have influence over decisions with direct impact. This insight would have steered me away from venture capital, which is inherently more removed from operations, or consulting, where implementation is largely done by the client not the consultant. Instead, I spent several years in those fields before finally realizing I belonged more in company operations. So, one of the top entries in my matrix under affinity reads, “make decisions where I can directly observe outcomes.”
Mapping out these attributes isn’t easy, and you might be blind to some aspects of yourself. You may not enjoy what you think you enjoy, or you might not be as skilled in an area as you believe. That’s why you need to test your assumptions with people who know you well—those who can tell you hard truths, like Simon Cowell did for William Hung. This is your trusted circle of friends, advisors, and family.
Once you’ve mapped out your character on this matrix, step back and ask yourself some honest questions about your career path and goals. Think boldly about where you want to be in 10 to 20 years. What kind of role and industry would suit you best? Are there attributes that are must-haves which would be difficult for you to attain? Are there aspects you fundamentally enjoy that are missing? Test these ideas with your trusted circle. Is your goal realistic? Brainstorm with them a feasible pathway to get there.
Stay tuned for the next article, where we’ll discuss the importance of understanding the big picture.