Managing Your Business
1099s Filings?
Hired Contractors? Remember — 1099s Are Due January 31st. 🙋♂️If your business paid $600 or more to any contractor, freelancer, or non-employee worker in 2025, you may be required to issue a Form 1099-NEC, and the deadline to send them is January 31. Here’s what business owners and solopreneurs should know: 1️⃣ Who needs a…
Read MoreTax Season Reminder To Fellow Practitioners
A Gentle and fun Reminder to Fellow Practitioners: Don’t Lose Your Zen This Tax Season 🧘 Tax season — January through April — has a way of turning even the calmest, most centered practitioners into tightly wound problem-solvers running on caffeine and deadlines. Tax season is intense.It is stressful.🙆♂️And yes — at times — it…
Read More5 Bookkeeping Habits That Make Tax Season Easier
👉5 Bookkeeping Habits That Make Tax Season Easier (and Less Stressful) Most small businesses and solopreneurs don’t struggle because the tax rules are impossible — They struggle because their financial records aren’t ready or accurate when it’s time to file. The truth is: better bookkeeping makes tax season smoother, faster, and more accurate. Here are…
Read MoreMissed Your 2025 Estimated Taxes?
Missed Your 2025 Estimated Taxes? Here’s What To Do Now. If you’re self-employed or earning side-business income, estimated taxes can feel like one more chore on a long list. And if you missed one or more quarterly payments last year, you’re not alone — and it’s not too late to get back on track. Your…
Read MoreMost Overlooked Tax Write-Offs
🙋♂️The Most Overlooked Tax Write-Offs for Solopreneurs & Side Businesses If you’re self-employed, a solopreneur, a freelancer, or earning side-business income, you might be leaving money on the table — not because the deductions aren’t allowed, but because they’re easy to overlook in the flow of daily business. Here are a few common, legitimate deductions…
Read More1099-Ks – What Changed?
1099-K: What’s Actually Happening for 2025 Tax Filings? There’s been a lot of concern about 1099-K reporting — especially for solopreneurs, freelancers, side-business owners, and anyone using online platforms like PayPal, Venmo, Cash App, Uber, Lyft, DoorDash, Etsy, eBay, or Airbnb. 👉Here’s what you need to know for the 2025 filing season (when you file…
Read MoreIf Only You Spoke With Your Accountant First
🙋♂️If Only You Spoke With Your Accountant First… Real situations I see too often — and how a short conversation could have saved money, stress, and missed opportunities. 👉After many years preparing taxes and advising families and solopreneurs, there’s a theme I can’t ignore: Most financial headaches could have been avoided with one planning conversation…
Read MoreWhat Clean Books Really Look Like
🙋♂️What Clean Books Really Look Like (At the Basic Level) “Clean books” don’t mean perfect spreadsheets or complicated reports. And… it shouldn’t mean undue stress, long hours away from running your solo business, or stolen family time. Clean books mean this:• Business and personal spending are clearly separated• Income is recorded consistently• Expenses are categorized…
Read MoreI’ll Fix It At Tax Time?
Why “I’ll Fix It at Tax Time” Rarely Works 🤔 “I’ll just fix it at tax time” is one of the most common things solopreneurs tell themselves. The problem?Tax time is about reporting, not rebuilding. When bookkeeping is left until tax time:• Important details get lost• Expenses are misclassified• Income timing gets messy• Assets and…
Read MoreThe #1 Bookkeeping Mistake Solopreneurs Make
The most common bookkeeping mistake I see isn’t complicated. 👉 It’s this: Waiting until tax time to deal with the bookkeeping. However, by the time tax season arrives:• Transactions are months old• Details are forgotten• Receipts are missing• Stress is already high What could have been a simple review and fix turns into a cleanup…
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