June 28, 2022

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Recently, I’ve been thinking about how character and capabilities shape our careers, and vice versa. There’s potentially much to explore here, so I’m breaking this missive into two-parts. Part 1 is about how our character and our capabilities interact to shape how we make decisions, and Part 2 (on or about 7/12) will be about how our career decisions can, in turn, shape our character.

So how do “character and capability” shape career decisions?

First, when I say capability, I mean someone’s skill or proficiency in doing something, and when I say character, I mean the distinctive nature of someone, their personality and values, their workstyle, their temperament, etc. In essence, who a person is and what a person can do.

[Note: the word character has a moral/ethical quality to it that I'm not exactly referring to here, though I do think there are moral/ethical questions that underpin career decisions (perhaps more on that next time).]

We may have natural talents and predilections that point us in a certain career direction, or we may let our personality and interests steer us and develop relevant capabilities along the way. Much career coaching takes this form - gain more clarity about who a person is, their abilities and their potential, then provide recommendations accordingly.

But interesting things that happen when character and capability develop at differing rates. Most notably, when capability development outpaces a person’s understanding of their character, their intelligence and determination will propel them down a career path to the point where they struggle to account for why they’re doing what they’re doing or whether they're doing The Right Thing. Sometimes this is called the capability trap - doing something because you’re good at it not necessarily because you enjoy it or it's a good fit.

A common example that I encounter is the liberal arts major who went to law school and then into law practice because they were smart and knew how to work hard. Then, 5 or 10 years down the line, they find themselves in a job they don’t particularly enjoy wondering what happened to the interests they had and the things they thought they’d do.

I think this happens because we’re not explicitly taught how to step back and think about what we want to do and why. We aren’t given that space, and once we start working we tend to be too busy to take/make that space.

As William Derescieweicz put it:

This only gets harder in adult life because the implications and consequences of making a different decision get amplified by other life commitments.

You’re working, working, working and, if you’re successful, you will likely find yourself in the position of having over-achieved and under-considered who you are in the absence of your work performance.

This creates all sorts of problems - mid-life crises, burnout, depressed/anxious parents, ungrounded leaders, etc. - because in the absence of examining more basic questions about who we are and why we do what we do, we (Americans at least) tend to default to a sort of capitalistic growth logic. Unless things are progressing upward - producing more, getting bigger - they are not successful or useful.

In careerland this means success is a bigger title and more income. For those in the capability trap, they will likely get the bigger title and more income because of their intelligence and determination, and they will be left wondering why things don’t seem to get easier, or why they are busier and no happier than before.

Even trickier, your capability - your ability to do something well - can start to shape your logic. If you are a very good attorney, but being a very good attorney makes you miserable, part of your decision making logic includes the fact that you’re a very good attorney, which makes it that much harder to make a decision to reconfigure your work and potentially become a novice again.

Is it worth being a very good [INSERT JOB] if it makes you miserable?

That is a question of values.

Here’s another way this plays out - I was recently talking to someone who has been very successful in her field. She is in a leadership role at a company that is being acquired and she stands to make a decent amount of money if the transaction goes through.

The problem is she’s miserable everyday at this job, it saps her energy, and makes her feel like a less patient and engaged leader and parent. She actively wants to leave. Fortunately, she was approached by a friend who wants to hire her into a role that will leverage her skills and experience at a smaller company that promises more equity over time. Making the decision now however, will require foregoing a possibly meaningful amount of money.

Her question: “Is it OK to leave money on the table?”

Depends on your values. Depends on how you understand yourself and why you do what you do. Depends on your financial and family situation. Etc, etc. In the capitalistic growth logic, the answer is likely no. Tough it out. Maximize your earning at all times.

My encouragement in these situations is to get outside input. Talk to a spouse, or a parent, or a teacher, or a therapist, or a coach to help you articulate the thoughts and feelings you're processing when making decisions like this.

Also, I would wager that when push comes to shove almost everybody knows the decision they should make (<- should alert). But that decision is almost always wrapped around complex feelings made more complex because they’re shaped by familial, societal, and economic pressures.

Independently considering the practicalities (e.g., what can I actually afford to do?), strategies (e.g., how will this decision set me up for what I want in the future?), and existential realities (e.g., is doing this job making me into the spouse or parent that I don’t want to be?) of a decision can also help you parse through some of your decision making logic and start evaluating what is most important.