In what’s become an ongoing saga with one of the only two guarantees in life; I’ve once again filled my taxes (the other guarantee being death). Every spring all Americans undergo this ritual and whether it’s with a CPA or with online software we all have to file our taxes by mid April (or get an extension) and then we’ll get a refund (yay) or we’ll owe money (boo). 

I had a whirlwind experience trying (and failing) to get a CPA in 2023 and I tried hard to get ahead of it this year. I interviewed a new CPA in the fall and then had almost everything to them by late February. Since this is my first time I actually did an in person meeting to review their work which went well! Overall I’ll owe a small amount so I’ll take that! People always say that getting a refund meant you gave the government a free loan but lol I don’t hate getting money back in my pocket. 

Here are a couple of my thoughts once again going through this process: 

Glad to see more free filing

A shockingly high number of Americans qualify for free tax filing each year. It always irked me a bit that you have to pay money to file your taxes with software like TurboTax or H&R Block. Of course you could always do it free with paper and mailing it in but that seemed way too complex to figure out – and I feel like I know a decent amount about how it all works!

A few years back I started seeing companies advertising the free option more – I think the government mandated that they do so. At first it was kind of confusing – classic companies playing games to get you to pay for something that could be free. But now this past year I’ve seen more ‘it’s truly free’ advertising. So if you qualify based on your income level don’t end up paying if you don’t have to! 

Taxes are a guessing game and you might know better

It continues to baffle me how complex our taxes are. You make money and you get all sorts of deductions. There are all sorts of rules and exceptions and ways to play with the numbers. As part of this it blows my mind that you fill out a form and put a number 0 to 5ish and then your employer pulls out money and then you reconcile it at year end. I genuinely struggle with the number of deductions to put and I know a lot of others do too! 

As such it’s a big guessing game. I feel like one year I’ll owe and I’ll adjust my deductions to be less so I’ll pay more then the next year I get a refund so I readjust and it feels like a moving target. 

I’ve tried to get better at reviewing my taxes from the prior year and trying to better withhold the appropriate amount of money. I’ll also review my withholdings quarterly and loosely know how much I should have withheld and adjust if needed. I did that this past year and there’s an option on your tax withholding form with your employer where you can do ‘extra withholding’ and I withheld an extra amount for a fee paychecks. 

I also sold some stock in 2023 which your brokerage firm (at least that I could find) won’t withhold taxes so I increased my paycheck withholdings to try to pay the tax I thought I’d owe. In 2024 I sold some more stock already and will make a special payment via the IRS website. I’m doing the best I can to try to end up with a very small refund!

Deductions all around

So. Many. Deductions. Which I guess isn’t a bad thing but part of me just wishes we would simplify things rather than continuing to complicate them. KiddoMoneyFinances continue to a) be expensive but b) come with some tax deductions in the form of daycare, 529 college fund contributions (on the state level) and in the standard deduction. There’s all sorts of small business deductions (ie this blog is a small business for me) and with real estate and other things we just didn’t qualify for but I’m glad we asked or had our CPA check for! 

Take your time and make sure you’re checking under all the rocks to ensure you’re getting all the deductions you can!

Experience working with a CPA

For the longest time, I’ve always done my own taxes. I feel like I knew enough to be dangerous and didn’t have any thing to financially complex in my life and I didn’t feel like I could figure out with H&R Block. It worked really good, and I was able to successfully navigating, found my own taxes for a number of years. However things started getting more complicated when our lives got more complex – particularly with becoming a landlord via a rental property and then with employee stock that I got to purchase at a discount. 

About 2 years ago I decided that I had enough complexity to where I was 75% sure I knew how to account for them in my taxes but not 100% and that 25% knowledge gap seemed worth paying for. As discussed I tried and failed to get a CPA but was successful this year in doing so. 

I’ll say that two things really helped make this an easy process. The first is starting early. As I mentioned, I got my stuff to my CPA in late February- so almost 2 months ahead of when it’s due. That gave him plenty of time to work through my taxes – and ask a few questions. The second thing is that I tried to be very organized- I organized everything in folders – one for income and one for deductions and I also created a one-pager summary document to orient my CPA to what he was looking at. This helped a lot and he commented on how organized I was! I figure he’s charging me for his time to if I can save him time by being organized why not! 

Since this was my first time working with him I opted to do an in person review which worked great! I had a few miscellaneous things to add and had the chance to clarify a few things too. I had a few questions on some strategies around retirement and donations and it was great to talk through in person!

So all told I think it’s been a great investment on me and Mrs Money’s part to hire a CPA! The total cost is just above $500, and I paid HR Block like $250 so it’s definitely pricier but for the peace of mind working with an expert I think it’s been worthwhile! 

Good luck to you filing your own taxes this year!