One of my biggest mistakes . . .
Back in my "running a nonprofit arts organization" days, we would have years where we ended the year with a budget surplus.
These weren't huge surpluses, but they were significant amounts of money.
People wanted to reinvesting the surplus into next season's budget. They wanted the money to go toward increasing production values, paying people a bit more, that sort of thing.
The idea made a lot of sense, but a nagging question kept forming in my brain:
"Why don't we save some of the money?"
Instead of taking all the money and pouring it into next season, why not take some meaningful portion of it and stash it in the bank? We could have just put the cash into some boring, safe, investment and let it sit there as a "rainy day fund."
When I would mention the idea, in a manner which was (in hindsight) way too passive, I was reminded of all the pressing and urgent needs which the money had to be used for RIGHT NOW.
You can guess what happened next . . .
The surpluses immediately got sucked up into the black hole of "need". Basically every production run was do or die because we decided that having a better set (or whatever) now was more important than having some money in the bank for later.
Eventually the surpluses became deficits and it was (more or less) game over.
It's a tricky question: Where do you draw the line between producing the art and providing stability/security for the people who produce the art?
In hindsight, I can't help but feel like I failed in my responsibility as a leader. I allowed short term considerations to trump long term. I had a chance to give the organization a bit of a safety net and I didn't fight hard enough for it.
For me, it was a lesson learned.
For you, this may be a good time to consider how you would handle a similar situation.