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Navigating the website to submit H.S.A. claims + uploading documentation. Had some surgeries this year so decided to pay with VISA for rewards. Not work it. Always using the H.S.A. debit card going forward.
My first career was a CPA specializing in tax, but I don’t even do my own taxes anymore. They are all but impossible to do without software. Fortunately, my daughter is a CPA.
Only doing taxes. Everything else is pretty much on autopilot or requires a few clicks on my iPad.
I don’t find any of it irksome. I actually like tracking my spending and seeing how it lines up or not with my budget. I guess I’m a nerd but I’ve only done this for the last few years and probably should have for the last 25 or so 🤣
A few come to mind:
1) Taxes – it used to be such a simple tax when all I had was one W2 and a Roth IRA contribution. Now I have an LLC, multiple W2s, 401k, 457, 403b, HSA .. I suppose those are good things to have though! I’m also concerned that I’ll miss something or get a dreaded IRS letter or audit.
2) Rollovers & account transfers – I think we all have accounts all over the place these days. Particularly young folks like me who job hop! Keeping track of all of those and trying to keep the fees low can be a headache. Then the process of moving them to one brokerage firm can be burdensome.
3) Health care bills – It seems to be a black box of what I’ll pay out of pocket for health care expenses. I get the service, then hope it works out without too much financial pain.
Organizing and paying bills. I’ve moved to mostly electronic, so its better. I think the keys pay them as soon as they arrive. You may waste a few cents on the float, but you won’t be late.
I have a system that I really like. It took me a bit of trial and error to get here but I’ve been using this system for at least 15 yrs.
My paychecks go into my checking account automatically. I have all of my bills set up to be paid on the same day I get paid regardless of due date. I split the bills’ total amounts evenly across my paychecks. In this way the impact on my account is even across the month, I don’t have to think about due dates, and I maintain a small credit balance by being a bit ahead of the bill.
I log in once in a while to make sure things look as they should.
Utility bills that fluctuate – I have on an equal payment plan so that I don’t have to pay attention to bills being different from one month to another. I just pay the same amount every month.
I don’t let any biller draft my accounts. By having auto payments from my bank account, I’m in complete control and can change, move, or cancel a payment any time up to the point that it goes out. My bank pays most things electronically. But if a biller doesn’t have that option, my bank cuts and mails a check on my behalf.
I also have money automatically go to savings and investment accounts the same way.
I don’t get any paper statements – so no mail to open and shred or file.
I like having bills automatically taken from my bank account or charged to a credit card (for rewards). Very few of our ongoing bills are sent to us.
R: I understand your perspective, but choose not to follow that approach. I don’t want ANYONE but me to have access to authorizing debits from my bank account. So, I spend a little extra time each month entering payments into the bill pay system. I schedule them to be paid 1 day before due so there are no chances for late payment fees and very little, if any, “float” such as Rick Connor mentions. There are a few monthly bills that I have charged to my credit card for the benefits perks, but I limit those to just a few. I would image that whatever system works for a person is “right”. Mine seems right for me.
Taxes. HATE’EM – it’s needlessly complex, it’s time consuming. For years my investments weren’t tax efficient, so paid way more than I should have. Tried hiring professional help – they made more mistakes than I did lol.
I’m penalized by paying 2x the ss just because I get paid as a 1099 worker vs an employee – one of the most puzzling and unjust tax laws. I get few deductions since I’m single and hate debt, so no juicy mortgage deductions. ARRGH! lol
I hate tracking my expenses but have been doing it weekly nonetheless since 2015. It’s annoying and time-consuming, but it helps me see if I’m on track to reach my saving goals, why I might be falling short, understand where I’m spending most, etc.
Tracking my expenses. For decades I’ve been looking for a better way. I feel like I’ve tried them all — Quicken, QuickBooks, Mint, and more — and I’ve yet to find one that doesn’t require hours of tedious maintenance.
But Adam, why do you track expenses? We need an article on this.
Hate paying bills and taxes. Our bills are almost entirely on auto-pilot. Taxes are done by an excellent accountant who’s also a great human being.
Doing my annual taxes tops the list. A close second is the precautionary tasks related to my identity theft. I need to periodically check my credit report and logon to financial accounts to spot any suspicious activities. I wish I could spend the time in better things.