TaxPRolady

Client:   “How do I pay myself?” Me:   It’s simple—write yourself a check, make a transfer, or withdraw cash. It’s your business. Client:   “But my last tax preparer said I couldn’t pay myself from my own business. That it wasn’t allowed.” Me:  😲🙄🤦‍♀️ Let’s clear this up: If you’re a sole proprietor or a single-member LLC, you  can  absolutely pay yourself. That’s the whole point—you   are  the business. You’re not on payroll, so there’s no W-2 involved, but you’re entitled to take an “owner’s draw” as needed. If you’re working hard and bringing in income, there’s no reason that money should just sit in the business bank account untouched. Your business exists to serve you—not the other way around. 👉  And just to clarify: You do  not  have to issue yourself a 1099-NEC. You’re not a contractor to your own business—you’re the owner. However,  you do need to issue 1099-NECs to any independent contractor or non-employee service...

After a decade of preparing taxes commercially, I’ve finally compiled all my stories in one place. These are real experiences I’ve encountered over the past 10 years—shared with names and locations withheld to protect privacy. Each story is presented for educational purposes only , offering insight into the wild, unpredictable, and often eye-opening world of tax preparation. Whether you're a taxpayer, a business owner, or a fellow professional, I hope you find these lessons as enlightening—and sometimes entertaining—as I did living them. 1. “Lo Barato Sale Caro” — The $100 Tax Prep That Really Cost $775 This one is borrowed from a fellow tax pro, but I’ve seen it too many times myself. A client once told me he’d been paying only $100 cash for tax prep and always got direct deposit. I offered to review his prior return—confident, not cocky. And guess what? His “$100” return actually cost him $775! Here’s how: $675 was quietly taken out through a refund transfer product, and then the...