Funds are dwindling to me

I have a problem with letting go of my cash. As of the first of this month, my checking account is going to be lower than it's ever been in a long time. And I'm not talking about the times in college when none of us had any money, I'm talking about now, as a supposedly successful employee. My accounts have dwindled down to almost nothing, and the irony is that I have nothing to show for it. The money goes out to dinners that I think I spent the money on, flights that I think I booked, and a photographer who I haven't ever met, but I hope is worth it.

In other words, I've lost control of my finances. I'm usually frugal and keep my wallet tight to my chest, but these days I'm told to "keep the money rolling". My new personal favorite is, "You can't take your money to the grave with you." Well I know that, and I wasn't planning on doing that. Rather, I horde my funds to make sure I have something in the bank to make that impulse buy and not feel bad about it. It's quite possibly a medieval thing to want to stash your cash underneath your bed, so to speak, but now, I'm just writing checks and paying bills online, trying to figure out what I feel comfortable paying for this month. It's ridiculous, and yet it's so accepted by others. If anything, it's expected of me.

Things are starting to get complicated.