accepting what i have vs. making plans for better future - good or bad?

Let me give a metaphor for this. Imagine you are standing at the foothill of a great mountain...

And you think, oh how nice would it be, to stand on top of this mountain. It would truly be a great sight, a majestic sight, a big achievement on my part - and what kinds of great friends would I make on the top! they would certainly be much more interesting people than ones I have down here. It would be so awesome to be up there! In comparison to that, how unfortunate I am to be down here! -- And so forth and so on, this is what goes through your mind.

Now, Buddhism does not say you should stay at the bottom all the time. But just thinking about the top is useless. Moreover, the craving for the top, and comparison with your position at the bottom - creates that painful feeling of wrongness, dukkha.

Instead, if you say: the top is up there. Let me look under my feet. Which little step can I make now? Let me forget about the top for now, let me forget about the levels, let me focus on the steps under my feet. I don't know exactly where I'm going - I've never been there. I don't know the exact path - and I can't spend my whole life planning it or I will never get anywhere. Instead, as long as I have the overall direction right, and start making the steps - I will get there sooner or later, guaranteed.

What do I need to do right here to get over there? Starting right now I must make every step as an investment. I must stop roaming randomly like others who don't have the same goal. Every step I take can get me either 1 inch in the right direction, 12 inches in the right direction, 1 inch in the wrong direction, or 12 inches in the wrong direction. So I must develop this habit of making a better step if possible every time. Start small: I have 10 dollars - no need to figure out the perfect way to spend them, just minimize waste. Minimize going in the wrong direction. Then with time it will come by itself, the knowledge of the best possible step.

Another way to approach this is by imitating the qualities of people who got to the top. How does the owner of the private business behave? Your manager at work asks you to do something - do you act like you are the real business owner? (This is called "taking the goal as the path". Some say this is the more advanced way, the faster way. The two schools keep arguing which way is better ;)

So in short, speculative thinking about the abstract goal is "bad" - it does not get you anywhere, it only generates suffering. Instead, by not going in the wrong direction today, by not going randomly here and there today, by minimizing the waste today, and by imitating the qualities of the people who did it, - we can create the path connecting this place under our feet with the high goal.

I hope this is not too abstract for you. By "going in the wrong direction" I meant spending money on things that will suck your money in the future. By "going in the right direction" I meant spending money on things that will bring you some money in the future. By "going randomly here and there" I meant spending money on other goals and random entertainment. By "minimizing waste" I meant every time you spend your money try to make a small improvement. By "imitating qualities of people who got there" I meant try to imagine how they think and do what they would do. Hope this helps.

And since we are on Buddhism Q&A site, by "wrong direction" I also meant unwholesome thinking, by "right direction" I meant wholesome thinking, by "minimize waste" I meant to watch for and control the hangups manifesting in daily life, and by "imitating" the accomplished people I meant trying to imagine how the Buddha would have reacted to the same life challenges.