Most people save; you back something
Most people put money aside against a bad year. You put it into whatever you have become convinced about. Pluto in Sagittarius in the 2nd house ties what you own to what you believe, so your finances rise and fall with your convictions rather than with your caution.
The Sagittarius colouring is inherited from the period rather than from you. Pluto crosses a sign over decades and everybody arriving in that window carries the same restlessness about meaning. The 2nd house is what your birth time added, and it is the individual half: the searching is aimed at possessions and self-worth, so the question of what is worth paying for is never merely a budgeting question.
The venture that took everything with it
At some point you committed resources to something you were certain about, and the certainty turned out to be the weakest part of the structure. What that taught you was not to stop believing, which is not available to you. It taught you the difference between a conviction and a plan, and the gap between them is where the money went.
Read as reckless, running on conviction
From outside, the pattern looks like poor discipline: the abrupt departure, the money spent on a course, the year taken off. From inside each decision was the only honest option available at the time. Both descriptions are accurate. Saying the reasoning out loud beforehand converts recklessness into a decision other people can plan around.
What the spending is chasing
Follow the money and it goes towards expansion: travel, study, an idea, a room full of books, anything that enlarges the account you have of the world. Very little goes on comfort. That is a real value system rather than an error, and it works far better once you can state it, because unstated it simply looks like leakage.
Fund the belief, not the whole of it
The workable version is a fixed proportion committed to conviction and a floor that nothing touches, decided when you are not in the grip of anything. You will resist the floor as a failure of nerve. It is the opposite: it is what allows you to back the next thing at all, rather than spending years recovering from this one.
Feast and famine, and both are survivable
Your income has already gone up and down more than most people would tolerate, and you have come through every trough, which is why the warnings do not frighten you. Fair enough. Put a number on the trough you could not survive, in writing, and treat that line as the only rule you keep. Everything above it stays yours to gamble.
What you are worth is not what you have
You have held this position sincerely for years and it is still worth testing, because it is easy to hold when the account is healthy. Notice how you speak about yourself during the thin periods. If the language changes, the belief was partly a luxury, and knowing that is more useful than defending it.
You went a different way with money
Whatever your family thought money was for, you decided otherwise, publicly enough that it has been discussed. That departure was genuine and it has a residue: a small readiness to be judged whenever your finances come up. Their opinion is decades old. Answer the version of them in your head once, in writing, and stop answering it at dinner.
Paid for what you are certain about
Teaching, publishing, advocacy, building something around a position you hold: your income is best where conviction is the product rather than a liability. Neutral work drains you and it also pays you less, because the persuasive part of you is not switched on. Choose the next role by what you would argue for unpaid.
Overshooting has a physical bill
The pattern is going too far because the cause was worth it, and the body settles the account afterwards, generally in the hips, the liver and an appetite that swings with the state of the project. Decide the limit at the start, while the enthusiasm is still theoretical. Inside the project you will not be able to see one.