One excellent thing rather than five adequate ones
Your luck speaks Leo and does its work in the 2nd house, so money is not a store but a statement: you would rather own one excellent thing than five that will do. Cheapness offends you more than expense does. What this needs is a definition of quality that does not require an audience.
Income tends to arrive generously and leave the same way, and you are considerably better at earning than at retaining. That is not carelessness so much as a genuine belief that money is for using, and the belief is not entirely wrong.
Your value is what you can hand over
Your sense of your own value is tied to being able to be generous, which is why a lean stretch is humiliating rather than merely inconvenient. That link is worth loosening. Find a way to be generous that costs nothing, and use it in the thin years, because the impulse is the point rather than the amount.
You will not appear cheap
Splitting a bill to the penny, haggling, declining because it is expensive: all of it feels beneath you, and it has cost you real money over the years. Nobody is watching as closely as you assume. Practise saying that something is outside your budget, plainly, since the sentence is far less damaging than the debt was.
Generosity that arrives before the arithmetic
The offer is made, the round is bought and the trip is funded before you have checked whether it is possible, because the impulse is faster than the calculation. Most of the time it works out. Keep a fixed amount available for exactly this, and let the impulse spend that rather than whatever happens to be there.
The good version, kept for years
When you do buy properly, you keep it: the coat, the instrument, the watch, the thing that was expensive once and has been in daily use ever since. That is a genuinely sound approach to owning things. Extend it deliberately, because the purchases you regret are almost all the adequate ones bought in a hurry.
You are the one who insists on paying
Among friends the bill tends to end up with you, partly from generosity and partly because being the one who pays is a position you enjoy occupying. Both halves are true and neither is shameful. Let somebody else host and pay this year without correcting them, since a friendship in which you are permanently the provider has an imbalance nobody has named.
You will not economise on rest
Where you spend properly is on comfort and recovery: the decent bed, the room with light in it, the holiday taken seriously. That instinct is sound and it is one of the reasons your stamina holds. Keep protecting the spend when money is short, because rest is the last thing you should be cutting and usually the first thing you offer up.
Earning is easier than keeping, by some distance
You can generally produce income when you need it, which is precisely why nothing accumulates: the confidence in your own earning power removes any urgency about reserves. Set the saving to happen automatically on the day money arrives, since a decision made later has to survive an optimism that has rarely lost an argument.
Paid properly, or not interested
Being underpaid affects you out of proportion to the money, because the figure reads as an estimate of your worth rather than as a budget. That reaction is information rather than vanity. Negotiate on the number early and openly, and be willing to leave over it, because resentment about pay reaches your work faster than it reaches your bank.
You want something to show for it
A life of quiet accumulation with nothing visible at the end of it does not appeal to you, and no amount of good advice has changed that. What you want is evidence: something built, something given, something bearing your name. Choose what the evidence is going to be, deliberately, before your spending chooses it for you.