Does "пожалуй" always convey a sense of reluctance?

Question

Ммм... пожалуй, я продолжу делать то, что хочу.

I wonder if "пожалуй" means more than just "perhaps" and conveys a sense of reluctance, as in:

I'm gonna keep doing what I love, I guess...

{or}: Well, I might as well keep doing what I love.

Answer 1

Пожалуй implies being presented with several options from which you choose.

I use пожалуй when i'm kind of hesitant and conflicted between a few choices but still do opt for one of them without being completely convinced it's the right or the preferable one.

It's translated as rather

-Ну так ты идёшь с нами или остаёшься? - So do you come along or stay here?
-Нет, я, пожалуй, останусь - No, I'll rather stay
OR
-Да, я, пожалуй, иду с вами - Yes, I'll rather go with you

To translate your example:

Ммм... пожалуй, я продолжу делать то, что хочу. - Erm... I will rather continue doing what I like

Semantically it's akin to скорее (also rather) and всё-таки (still), only that скорее and всё-таки make the fact of choosing much more obvious and would be used if there has been prior discussion or deliberation, known to the interlocutor, about what course of action to take.

-Ну так ты идёшь с нами или остаёшься? - So do you come along or stay here?
-Нет, я, всё-таки, остаюсь - No, still I'm staying
OR
-Да, я, всё-таки, иду с вами - Yes, I'm still coming with you

Answer 2

To my knowledge, it does not. In any dictionary it's defined more or less like:

Выражает допущение, возможность чего-либо (то же, что «наверное, вероятно, может быть»), а также некоторую предпочтительность какого-либо действия (то же, что «лучше»).

In sentences like: "Я, пожалуй, не пойду туда" there's no slightest hint on being reluctant - it's exactly the opposite, it's closed to definitely.

The other thing is that in phrases like: "Ну, я, пожалуй, пойду?" one want to show out of politeness his/her full determination to leave but not necessarily he or she wants to, so there's a tint of reluctance.

Answer 3

Пожалуй expresses equally probability and preference or is used to show a non-straightforward polite excuse.

Я, пожалуй, пойду, а то поздно уже. I'd rather go now because it's getting late.(polite excuse).

Я, пожалуй,попью чайку. I'd rather drink some tea.(preference )

Я, пожалуй, займусь этим проектом.I might as well pay attention to that project.(probability ).

There's no reluctance. Only intonation can show it.

Answer 4

It does not really include it by itself. But you can add reluctance with intonation. And in modern Russian it's often used in that context, but it's not up to word. Any of your usage examples are suitable. Russian is a very intonation-depending language, so that... depends.