Achieving a goal only changes your life for the moment

- James Clear

We spend most of our time living with our habits and character. Echoing Heraclitus: "A man's character is his fate."

Habits and character are shaped by our values, yet it's difficult to pin down what precisely our values are. Determining what we value and what we ought to value is a messy and foggy affair. There aren't clear definitions for abstract notions like justice, courage, self-control, and wisdom. The definitions are more precise in the academic literature on character, but they're also different from each other. The motivation of this series is to make matters clearer for myself. Hopefully, others find it useful as well.

Today I'll focus on the idea of doing one's best.

It is better to look back on a day, year, or life, knowing that you did your best.

Doing your best is not trying your best. It's focused on doing.

If one concentrates too much on effort, then effort becomes the goal. One way we assess people is by how much cost they pay to achieve their goals. Hard work is admirable, but overemphasizing it is a mistake. In a culture that rewards public effort, there's a risk of forcing others to pay a cost to be recognized, essentially taxing everyone to play. We ultimately care about the work, not hard work.

Doing your best is less virtuous if what you were doing shouldn't be done at all. This is obvious when the activity isn't worthwhile or is actively vicious. Doing one's best involves doing what the best you would do. Yet some activities may be worthwhile, but not worth expending serious effort for. This is the lesson of "half-assing with everything you've got." The point is to achieve the goal with minimum effort. The relation between one's best and effort is incidental.

So doing one's best isn't about maximizing effort and isn't about pursuing just any goal. What is it?

Doing one's best is about directly pursuing worthwhile goals.

It's about caring enough about an activity, outcome, or state to pursue it with the required effort. I mean goals in a broad sense. They aren't merely something you check off once and forget. Being a compassionate person or parenting well can be a goal. Forming identities and excellence at never-ending activities can be goals.

Doing one's best becomes a virtue as it ingrained into us as disposition or habit. Ideally, it's a feature of a person. Not a one-off feature of single activities they decide to do.

So far, what I've said is difficult to operationalize. How do you track whether you are doing your best?

One option, is measuring input. Measuring how tired you every day doesn't work because we've broken the tie between your best and effort. Moreover, it's an empirical question whether maximizing inputs, maximizes outputs. At some point, one needs to sleep. You can improve this measurement by measuring quality inputs, such as measuring the amount of time spent doing deep work on a problem. That's an improvement, but likely not the best.

There are a few questions that you can ask yourself:

  • What would I do if I deeply and seriously cared about this?
  • What would more courageous, just, and energetic me do?

Imagine a better version of you dropped into your life. The version of your life that would joyously embrace each day, year. What would they do?

In many cases, it's not clear what the best version of you would do. Ok, what would they do to figure out what to do? What questions would they ask? Who would they talk to? Where would they look for answers?

Another question you can ask:

  • Am I directly pursuing my goal?

Directly pursuing your goal is a matter of doing what is required for the goal and nothing else. If you want to X, X. This seems obvious but is a frequent way people fail to do their best.

Indirectly pursuing a goal often indicates that it isn't a priority. An example of this is the idea of optionality in careers. A career gives you more optionality insofar as it doesn't lock you into a specific path and will unlock future opportunities. A career in consulting will give you more optionality than a PhD in literature. As a consultant, you'll have more jobs immediately available to yourself after a few years. Optionality can be very good, especially if you don't know what path you'd like. But if you think you know what path you'd like to take and you're taking an incidental route, that is a reason for pause.

Nick Winter has a line on this in the The Motivation Hacker:

Bad goals often take the form of intermediate steps. You might want to be rich. If so, then go do something that will make a lot of money—don't go to college, fight your way out of debt, work your way up, and then be rich.

Going to college is likely a fine step on the path to get rich. It depends and isn't straightforward. But the general principle is right.

Still another question you can ask:

  • Am I building the systems necessary for achieving my goal?

Doing one's best is a character trait, not a one-off end. I want to build the systems and behaviors that let me do my best in the long run.

It's often a matter of getting the basics right: Showing up on time, focusing, practicing, never giving in to adversity, seeking feedback, and having a theory of change.

And a final question:

  • Will I tolerate failure?

If you will, that's an indication that you aren't doing your best or don't want to. Which reminds me of the Rudyard Kipling line:

If you don't get what you want, it's a sign either that you did not seriously want it, or that you tried to bargain over the price

Doing one's best can be thought of as deriving from directly pursuing worthwhile goals. It's not an additional thing, above and beyond. It may be something to measure, to check in on every once and awhile. But the primary thing to keep one's eyes on is doing.

One way to put this: instead of asking, am I doing my best to be a good partner, coworker, citizen, focus on being a good partner, coworker, citizen.