Are you legitimately always trying to do your best,

No. I do my best when I feel like it or care about the task at hand. To me it means putting in earnest effort with the goal of achieving

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Which era of me are we taking as the baseline for performance?

I can understand the confusion. I treat “do your best” as an idiom rather than an imperative. I think it’s usually said in one of two contexts: (1) as a platitude similar to “good luck” or (2) as a response to the expectation of a subpar result. In the former, it could be a friend hyping me up before riding in a cycling race. The latter could be me telling my boss that we’re going to miss a deadline and they respond with that to tacitly tell me to finish it as soon as possible.

To your second question, it’s the latter. In my job, I work with a lot of print and I’m often juggling dozens of print assets at once. I’m always “doing my best” because my livelihood depends on it, but how much effort I put in to each project varies. If it’s a small project where we’re scraping pennies, I’m more inclined to let small imperfections slide. If it’s a major project, I’m nitpicking everything. Obviously, I want everything to be good, but I have to triage my efforts and I’m expected to do so.

To me, “doing my best” isn’t about perfection so much as maximizing results with as much effort as I have to give. If putting in x effort gets me 90% of the way to perfection, but 2x effort would get me to 95%, I’m inclined to stop at 90% unless perfection is needed or desired. How I quantify that percentage varies from task to task. If I’m painting a miniature, I may want to push for that 100% and truly do my best even though I’m going to be spending a lot of time on tiny details. If I’m vacuuming, maybe I don’t feel like moving all the furniture and something like 80% is my best. It’s all relative.

No matter what you do, you will always be “doing your best” because time is linear and you will always have done however well you did. If you could have done better you would have, because “your best” is dependant on you as you exist in the present (as both your physical/mental capability and your will to do something are determined by your material context at the time) and once something is in the past it cannot have been done any other way without changing the material conditions that shaped you back then, which you cannot do. Of course you can get better at doing the same sort of stuff by practicing it over and over, but you’ll still always be doing “your best” each individual time. Even if you deliberately half-ass something you “could” have done better, your choice to half-ass it was calculated based on your conditions at the time, and so you’d never have chosen to not half-ass it unless the conditions were different (which again you cannot change).

Personally I dont worry about it too much.

I’m a chronic perfectionist so doing my best usually means lying paralysed in executive dysfunction and crippling performance anxiety while I scream internally at myself for hours on end yet achieving nothing except compounding psychological torment.

Wait, this isn’t my therapist’s office 🫠

I don’t think “do your best” is synonymous with “try really hard” or “use as much energy as possible.” Rather, the energy at your disposal is another factor that determines what your best can realistically be. If you have to save energy for something else later in the day, that affects what your best is for this task.

In music and art, doing your best often requires you to relax rather than getting super tense and tryharding.

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seems stressful to attempt ‘your best’ at things, so often in the completion of a task you learn or find a better way so your ‘best’ now has a higher standard and then you should redo or continue instead of turning in a finished thing. ‘best that can be expected’ is a better calibration because you’d better believe the amount of care, time, and effort is contingent on who it’s for, and conditions.

Relevant communist song