My Terrible Experience with Taxes My First Year of Self Employment (a story from Toni Witt)...
About two years ago, I dropped out of university, moved across the world, and became a freelance journalist. The hardest part? Taxes.
If you’re self-employed, you know what I mean.
Taxes always come at a time when there’s so much going on in life and the last thing you want to worry about is numbers, statements, and little rules that end up losing (or making) you thousands of hard-earned dollars.
I eventually found TurboTax self-filing. A CPA was just too expensive for me. And TurboTax did lead me through what I needed – and it didn’t take too long.
But I still felt blind. TurboTax was leading me, like a donkey, and I ceded control of the situation, which didn’t sit well.
I also realized that there were many things TurboTax didn’t help me with:
I should have been keeping track of my business expenses throughout the year and keeping receipts (there were a ton from the early months of the year that I didn’t remember if they were business or not)
I took a few deductions that were, at best, questionable. I had no idea if I would get audited. I heard horror stories from friends and lost sleep over that.
I missed a TON of writeoffs that I didn’t know about. I ended up overpaying by more than $1700.
And to top it off… I couldn’t actually pay that tax bill. I didn’t do a proper job at saving my paychecks, and had to ask my family for a small loan. Not a fun call to have…
That led to me taking a much deeper look at my finances and realizing how screwed up they were – and taking steps to make them better: looking at my top spending categories to reduce them, creating a HYSA savings account, keeping only what I needed in my checking.
Fast forward two years, the whole experience led me to starting Sweet – a one-stop-shop that helps self employed people track expenses, stay on top of their finances, find ALL possible writeoffs, file taxes, and more.
I really wish I had Sweet two years ago so I could focus on my freelance journalism work. If you find any of these things relatable, I’d be delighted to show you our platform 1:1 to see if it can help you.
What about you? I’m very curious to hear your self-employed tax stories, tips, and strategies.
#selfemployed #realtor #tax #entrepreneur