Measuring virtue is difficult. For one, virtues have vague definitions or undefined. You don't know what you're measuring if you can't define it cleanly.

Thoughtfulness is a virtue. But what exactly is it?

We call people and acts thoughtful in several different contexts. There's the idea of a thoughtful act, such as giving a thoughtful gift. A thoughtful gift requires knowledge of the receiver and their tastes. There's also an idea of thoughtfulness as a trait that you'd seek in a collaborator or employee. If you say that someone is thoughtful during an interview debrief, it likely not because they brought a gift, but because of the quality of their answers and what it indicated about their decision making. In this context, you may also say that the candidate is considerate, but that would mean something different.

Thoughtfulness is distinct from other positive traits. Someone can be thoughtful without being courageous, compassionate, humble, or just. Is the thoughtful person nice? Not necessarily. Wise? Maybe not. Wisdom is greater attainment than thoughtfulness.

But what is thoughtfulness? One way to answer the question is to think about particular people that are thoughtful and ask what traits they have that make it seem that way. Another way is to consider what behaviors are associated with thoughtfulness. Finally, you can ask about what the results of the disposition are. You can also work from the other direction by bringing to mind people that aren't thoughtful, considering behaviors that reveal a lack of thoughtfulness, and listing the fruits thoughtlessness.

When I think of thoughtful people, they have traits like the following:

  • Clarity of thought.
  • Willingness to explore counter-examples.
  • Care, openness, and precision.
  • Aggressive pursuit of the truth.
  • Openness to ideas.
  • Detail-oriented personalities.
  • Diligence in gathering and weighing evidence.
  • Dispassionate communicators.
  • Patience with people and ideas.
  • Systematicity.
  • Curiosity.
  • Tact.
  • Prudence.
  • Independence.
  • Self-control.
  • Sustained Attention.
  • Honesty about what they understand.

These traits are evident in behaviors like:

  • Explaining thought clearly.
  • Publically considering evidence against their views.
  • Ensuring that others understand what they say.
  • Tactfully speaking up when they disagree - even in cases where doing so would be uncomfortable.
  • Asking "why" one more time than everyone else.
  • Spending time pouring through spreadsheets and papers to get to the bottom of something.
  • Remaining level headed even when discussing controversial or complicated matters.
  • Willingness to wait to get answers.
  • Having a plan, being prepared, not winging it.
  • Paying attention to others.
  • Using their own words for ideas, not copying others.
  • Asking questions when they don't understand something.
  • Receptiveness to feedback.

The results of thoughtfulness are intellectual and social. On the intellectual side, one is more likely to have a full picture of the relevant pros and cons of an issue or decision—thoughtfulness results in better decisions. On the social side, the thoughtful person has a strong sense of other people around them, who they are, and their value—thoughtfulness results in better relationships.

When I think of people who are not thoughtful, they have traits like the following:

  • Clumsiness.
  • Imprecision.
  • Lack of awareness.
  • Self-awareness.
  • Anxious.
  • Bias.
  • Lack of intellectual charity.
  • Impatience.
  • Conformism.
  • Excessive Combativeness.
  • Lack of interest in the truth.
  • Close mindedness.
  • Obliviousness.
  • Drunkenness.
  • Overconfidence.

Thoughtlessness results in behaviors like:

  • Untactfully or unnecessarily disagreeing with someone.
  • Missing details and asking about them later.
  • Hastily throwing a report together.
  • Not preparing for a presentation.
  • Becoming anxious when confused.
  • Saying things that don't make sense.
  • Communicating only 80% of what was intended.
  • Not being intellectually fair to the other side in an agreement, not being able to understand them.
  • Combative disagreement.
  • Believing something because everyone else in the group believes it.
  • Not considering an idea because the wrong people believe it.
  • Ignoring or forgetting the preferences of your friends.
  • Realizing what was said in a conversation months later.
  • Forgetting to wish someone happy birthday.

The road of thoughtfulness is narrow, while there are many ways to act thoughtlessly. The thoughtless have a shallow understanding, an incomplete view of the world, and other people surrounding them. The fruits of thoughtlessness are more flawed decisions and a tendency to misunderstand others. The thoughtless babble, they repeat and vary what others around them say without understanding. They may act with too much haste, overconfidence or

Each of us will exemplify thoughtfulness and thoughtlessness to some degree or other. Moreover, we may be thoughtful in one domain, but not another. It's easier to act thoughtfully towards our friends, harder to do so for others. Some people are a model of intellectual charity and dispassionate investigation when talking about scientific or philosophical issues, only to turn venomous when talking about politics or a work dispute.

It's not always vice to act in ways that are associated with thoughtlessness. Sometimes people have preferences that are worth ignoring. Or sometimes, they may not warrant our attention or consideration. Sometimes there won't be enough time for thought, and at other times, it's worth saying something that won't make any sense at all.

But in general, it's better to be more thoughtful than not.

Now that we've listed out related traits, behaviors, and fruits of the virtue, are we in a place to group them under a cleaner definition?

I think so; thoughtfulness is a matter of taking the relevant considerations into account.

There's an intellectual component to thoughtfulness and a social one - this was evident from the very beginning with the two cases. They come together in this definition. Thoughtful gifts are thoughtful in virtue of considering the other person, who they are and what they value. Intellectual thoughtfulness is a matter of carefully gathering, understanding, and weighing the relevant considerations.

Aristotle held that virtues fall in between the mean of two vices. As an example, courage falls in between cowardice and recklessness. Thoughtfulness falls in between the vices of thoughtless haste and overthinking. Impatience is a matter of not taking enough of the relevant considerations into account. Perhaps not gathering enough evidence before making a decision or failing to understand a vital part of the decision. Overthinking is a matter of spending too much time trying to gather, understand, and weight considerations. There are diminishing marginal returns on additional information at some point, and one must act - the person who overthinks an issue finds themselves paralyzed. Overtime, considerations become less relevant to the action.

With a cleaner account of virtue, it's easier to take a measure of oneself.