For the longest time I’ve always done my own taxes. I fancy myself somewhat financially savvy and had a good grasp on my finances. In the early years it was super easy – I had a regular paying job (W2 is a super common tax form) and some dividend income from my investments. Then as things got a bit more complicated I was still able to keep up; a house, kids, even a bit of crypto (face palm emogee). My tax software – I used H&R Block but I know that Turbo Tax is pretty comparable – kept us just fine and I felt good about it (well as good about taxes as one could feel).

Then things continued to get more complicated – a rental property, more ESPP (employee stock purchase program) and now in 2024 I’ll get getting into RSU (restricted stock units). I was getting to the point where I was pretty sure I was doing everything correctly but there was still a bit of uncertainty that I was dealing with. Also I was starting to look for a bit of advice here and there – when / how best / should I _________ fill in the blank with stock or real estate transaction. I’m learning there are all sorts of tips and tricks when it comes to taxes and as much as I hate the expression but I’ll use it here – you don’t know what you don’t know!

In early 2023 I started looking around for a CPA. I covered my saga in this article (LINKS) but TLDR I think I waited to late to get started with a CPA. One ended up ghosting me and the other didn’t get me my taxes until literally the day before tax day and some numbers seemed off to me so I went with my gut and just used H&R Block again.

I felt pretty defeated – I had tried to get a CPA – in fact 2 of them and neither worked out for me!

Better planning for 2023

I was reminded of the upcoming tax season by a friend recently over coffee (lol yes I love personal finance so much I discuss it in my free time with some friends) and decided to go ahead and get a head start on it for this year. In 2023 I think my mistake was waiting too long and by that time most CPAs were already a bit full with their clients.

I got a few recommendations and picked two that I wanted to chat with and ultimately decided to go with the slightly more affordable one. Both seemed super solid and qualified, understood my situation and seemed to be willing to give advice here and there throughout the year. I’m anticipating more complexity in 2024 and am grateful to have an expert able to help me out.

I went ahead and let my preferred one know that I’ll be using them and they agreed and said they could take me on! I’m excited and hopeful this year that I’ve gotten ahead of the situation and will have a smoother time filing my taxes in 2024!