Money is for enjoying, and for handing round
Because your Leo Sun works out of the 2nd house, wealth means little as a number and a great deal as an experience. A good meal shared, a gift that lands, an object made properly: that is what money is for. You need income that produces some visible pleasure rather than only a balance.
This makes you generous and occasionally poor at the same time, and the two are the same trait. Nothing here will turn you into a hoarder, so the useful adjustment is structural rather than a change of character.
One excellent thing rather than a full cupboard
Your instinct is toward quality that shows: the coat that lasts, the good tools, the thing that is obviously the real version. That is not vanity so much as a dislike of the second-rate, and it is generally a sound instinct. The failure mode is buying the standard before you have the income for it. Set the ceiling once a year rather than deciding item by item.
You reach for the bill without thinking
Paying for other people is one of your genuine pleasures, and you will do it when you cannot afford to rather than admit you cannot. The generosity is real; the concealment is the expensive part. Practise the plain sentence occasionally: not this month, let us do the cheap place. It costs you a moment of pride and saves a great deal of money.
Worth measured in what you can give
Your sense of your own value is bound to your capacity to be generous, which is why a lean stretch hits your confidence rather than only your budget. Notice the mechanism, because it means you will take badly paid visible work over well paid invisible work without quite knowing why. Neither choice is wrong, and it is better made consciously.
Keep something dull working in the background
The counterweight to a warm and slightly theatrical relationship with money is one boring automatic arrangement that you never look at and never touch. It is not a change of temperament, it is a floor under it. Set it up once at a level you will not notice, and let the rest of your income go on doing what it enjoys doing.
Automate the boring half
Willpower is not the tool here, since your spending is tied to pleasure and generosity rather than to carelessness. Structure is. Move the saving on the day the money arrives and make the account inconvenient to reach. Everything left is then genuinely yours to enjoy, which is the version that actually works for you.
Ask for the number out loud
Negotiating for yourself is harder here than it looks, because talking about your worth in monetary terms feels like reducing it. Prepare the sentence in advance and say it without decoration. You will find you are better at this than expected once the pride is on the side of asking rather than on the side of not needing to.
The one who pays for the celebration
Weddings, birthdays, the big meal, the flights for somebody who could not afford them: you end up funding the family occasions and you enjoy doing it. Keep enjoying it and put a figure on the year in advance, before the first invitation arrives. Generosity with a budget behind it is still generosity, and it lasts considerably longer than the other kind.
Hosting as a form of affection
Your friendships run through hospitality: you feed people, you organise the thing, you make the occasion better than it needed to be. That is how you say it. Let somebody host you occasionally, even badly, and resist improving the arrangements. A friendship where the giving only runs one way slowly turns into an audience, and an audience goes home.
Value that does not need a receipt
The long question is what you are worth when you are not able to give anything, which most people meet only in a difficult year. Answer it early, on paper: the qualities, the skills, the things people rely on you for that cost nothing. It reads as an exercise now and becomes the thing you need later.