That’s actually the main reason why I don’t hire a tax preparer – I’m already doing a TON of prep work so I might as well just enter it into TurboTax myself. I’ve learned a lot the past few years as I’ve ventured into side hustles, and I agree it’s crazy all the little things that can impact your taxes. You really don’t know about them until you have a reason to know about them.

Haha many of us have been there Syed, but I’m sorry to hear about your experience that first year! My wife was actually in tears the year we had to make a massive payment to the IRS! We were overly cautious the next year and got a similar sized return (instead of paying in – much preferred!).

Thanks! I’m glad you found it useful!

While I am definitely not a tax expert I have definitely become way more familiar with taxes and it’s amazing all the little nuances that people never think about.

Thanks for sharing!!!

That would be nice to hav ea bookkeeper! I have at least 8 hours – maybe 10 – of work to do to reconcile this year’s financials. It’s not fun but I’ve been through the process a few years now so I know what I’m getting myself into.

Great tip Kathryn! I agree it can be painful and confusing the first time you go through the process, but if you start regularly making side or extra income it becomes easier over time.

Since most of my income is from my day job, I didn’t think I really needed to pay quarterly taxes. But when I accounted for my freelance income on my year end tax return, I went from a nice refund to slightly in the red! I didn’t have to pay a penalty thankfully but it was an unwelcome surprise nonetheless .

Like you mentioned I increased the withholding at my regular job to make up for it since the vast majority of my income is from my day job. Won’t make that mistake again!