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One of the biggest reasons you should put your finances on autopilot is for the sheer comfort of it.
Literally.
When your bills are getting paid automatically, your savings is being fed without you touching it, and your paycheck is going straight into your checking account, you don't have to worry about them. It's the biggest weight off of your shoulders.
You don't need to find the time to head to the ATM. You automatically pay yourself first. You don't have to worry about the post office losing your check in the mail.
The only bill I still pay by check is my credit card, and every other day I forget exactly when it's due and, therefore, when I need to send it in. It's weighing down on me.
So much about money management is mental. Am I saving enough? Should I save for the long run or the short run? Do I really need that thing I want?
The less you have to worry about, the better off you are. Don't let your finances overwhelm you.
Automate today and feel more comfortable.

[...] is easy, especially when you pay yourself first. With automatic transfers and recurring investments, you barely have to think about pocketing money for the [...]