Sometimes it just doesn't happen. The problem with setting goals is that it creates the preconditions for anger and disappointment. The universal trigger for anger is the blocking of goals, so by setting goals we inevitably have to accept there will be barriers and blocks between us and our goal. The problem comes when the pursuit of our goals starts to cause harm, to your self or others - but if you are anything like me, you sometimes can't differentiate between giving up and letting go, and my upbringing approximates giving up with being weak, not trying hard enough and generally failing. Which is not helpful. Giving up implies a dismissive acceptance that something is beyond our capability. Letting go implies choice, or even a wisdom that pursuing the goal is too harmful. On the one hand, it is easy to keep throwing good energy (either monetary, emotional, cognitive, all 3, etc) after bad. Like the gambler who wants to win back his losses, sometimes we start on a path with the best of intentions and then notice that - shit, this is not just hard, it is actually making me feel bad about myself. But without some objective perspective, how do you know if you are throwing good energy after bad - and should let it go - or we haven't tried enough, but are thinking about giving up. The negative connotations around "giving up" prevent us from letting go, lest it is seen as giving up. On the other hand, we are told that anything worth pursuing is bound to be hard and that we become stronger through overcoming adversity. Maybe just one more conversation, one more article, one more anything, will be what it takes to tip the balance from potential failure to possible success. So what is the answer? How do we know if we are giving up or if we should let go? It comes back to what was going on for you when you chose your goal. It's the difference, perhaps, between WANT and NEED. I only need x dollars per month to live, but I want 10 times that, because I want a nice house, nice car, nice holidays, fuck it I want a yacht! And the route that you choose to take in order to achieve that goal maybe the wrong one, and should therefore LET IT GO. You want a yacht but you don't need one, and certainly not at the expense of you enjoyment of life in the meantime. It could very well be the case that you, at this exact moment in time, lack the resources you need to bring enough $$$$ - either knowledge, skills, contacts, opportunities - in which case, LET IT GO. Letting it go is good because you recognize that right now, at this precise moment in your life, you see there is a gap between what you need to get that income stream and what you have at your disposal. Giving up on your goal could be because you recognize that things are different for you NOW from when you chose your goal. What ever resources you need still haven't arrived or been found, in which case GIVE UP. Change the goal. The Personal Development Police aren't going to abseil through your windows, stun grenade you and your family, and detain you for giving up on a goal that 2 years ago was desirable and now, not so much. In fact, were such an institution as the Personal Development Police to actually exist, they'd probably write you up a commendation for not sticking with a path that is doing nothing for you than bringing you anger and disappointment. So - getting towards an actual answer, when to give up and when to let go. If the goal is no longer valid or relevant to you then let it go. If the goal is still relevant, then ask yourself: do I have what I need to achieve it? If yes, keep going! If no, how much pain will it take to get those resources? If the pain outweighs the gain from achieving the goal, give up. If the goal holds sufficient allure to make the pain worthwhile - keep going! Get the resources you need, keep going, and focus on the joy you experience in making a valid goal a reality. You are a grown up and can do what you want.