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Step 1: Don’t hire McKinsey

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Set up autopay. I have text alerts for every transaction, which allows me to confirm charges as they’re made. I may scan my statement when it’s available, but it doesn’t take long because I’ve already reviewed each charge, but regardless, my payment is not held up by it.
Pro
I apologize for being harsh yesterday OP. I agree with the others who suggest autopay but I’d also suggest making a spreadsheet of the bill amounts and corresponding due dates so that you have a written reference of when everything is due and you can check them off each month once paid. Calendaring due dates with reminders is also a good suggestion in conjunction with autopay.
Pro
No offense, but this all sounds like you need to get yourself together a bit. It’s concerning for a lawyer to not be on top of their own deadlines - I’d hope this isn’t a reflection of how you handle your work and client deadlines.
A2 sounds like he/she is fun at parties.
Sounds like you need to take a vacation! Call your credit card company and ask them to waive the late fee, then call your dentist and make the payment. Take a deep breath. Everything will be okay.
Dealt with both. Definitely need a break.
Pro
Sorry about that OP.
Pro
I’ve definitely been there. It’s so easy do.
Pro
No. I hate auto payments. Just put into your calendar when stuff is due and pay it. Call them, explain, and see if they’ll waive the late fees. Though this never happened with my personal stuff, my company owns buildings and in our multifamily stuff we weren’t getting rents because of virus. Our lenders and building electric, water, etc., were good about payment arrangements and waiving late fees. We honestly waived late fees for our multifamily tenants who were struggling.
I don’t reconcile things but I do like to check before I pay and hence am hesitant about auto pay. I prefer calendaring the due date or a fixed date several days ahead of the due date to check and pay. I will try that first.
Maybe set up an automatic payment for the minimum amount as a fail safe in case you forget? Or I typically go in a couple of times a month and just pay whatever the balance is preemptively. I didn't know that credit cards cut you off for being two days late... I thought they just charged crazy interest on carry-over balances. Maybe look into new credit cards?
Pro
I’ve set up automatic payments on all of my bills for this exact reason!
I also dislike autopay and find the two times a month method works for me-I spend an hour on the last day and the fifteenth of each month to sit down and schedule payments for everything due in the next two weeks. Less hassle than remembering every deadline.
That’s great for you. I don’t always remember to check my statements regularly for the same reasons as OP, so I have found my happy medium to get bills paid
I also hate auto pay, but I am always worried I am going to forget, too. So I just set up auto pay for the minimum each month. I still go in each month and check everything and make a payment, but that way, even if I forget or am late, I’m still covered.
Auto payments, my friend...
I was going to check before I pay bills. But I guess I should set that up since I am the biggest offender here.
Like others who posted, I hate auto pay too. How I have resolved this is that I create a task to pay each bill that recurs every month. It is scheduled for 4 days before each bill is due. That way, if I'm not thinking about it, it pops up and tells me to do so. So for example, my CC bill is due on the 27th of each month - The task is set to pop up on the 23rd of each month as a reminder. Ditto with all of my bills. The other thing to do is to contact all of the companies that bill you and see if you can get the due dates all on the same day.
Rising Star
I second autopayments. I still regularly check the charges to make sure they are correct, so I’m not concerned I am being incorrectly charged. I don’t even have to think about my bills now. I don’t even know when they are due.
Can you line up your CC due date so it falls just before you get paid then you can pay it and all your other bills on pay day?
I can certainly pay on my pay day several days ahead of the credit card due date.
I was late on a cc payment by two days on a card I never use. No big deal in the end, doesn’t get reported until a month after. Dentist I doubt reported it. Don’t worry about it and just make sure to not let it happen again. It happens to all of us
Make it a point to pay off your credit card weekly. It will be easier to check your transactions and your credit score will improve as well