How to Make Your Accountant (Joshua T. Scott) Love You This Year
Tax season has arrived, and while no one wakes up excited to hunt for W-2s, there is a way to make the process smoother, faster, and far less painful—for you and your accountant.
Whether you’re working a traditional job, running a business, or enjoying retirement, the secret to stress-free tax prep is the same:
Give your accountant everything they need upfront.
Below is a simple, scenario-based guide to help you get organized and get Joshua T. Scott rolling without unnecessary back-and-forth emails.
First Things First (Everyone Needs These)
Before we break this out by life stage, everyone should be ready to share:
-
✅ Full legal name(s) (including spouse, if filing jointly)
-
✅ Social Security numbers (or ITINs)
-
✅ Current address & contact info
-
✅ Last year’s tax return (huge time saver)
-
✅ Any major life changes:
-
Marriage or divorce
-
New baby or dependents
-
Move to a new state
-
Job change
-
Started or closed a business
-
Think of this as the “opening handshake” of tax prep.
Scenario 1: Traditional Job + Side Hustle or Small Business
You’re not just a W-2 employee—you’ve also got something cooking on the side. Nice.
Here’s what Joshua needs to know:
From Your Job
-
📄 All W-2s (yes, all of them)
-
📄 Any bonuses, stock compensation, or unusual pay
-
🏥 Health insurance forms (1095-A/B/C if applicable)
-
💼 Retirement contributions (401(k), HSA, etc.)
From Your Business or Side Hustle
-
🧾 Income totals (1099-NECs, Stripe/PayPal reports, cash income)
-
🧾 Expense summary (or access to your bookkeeping)
-
🚗 Mileage or vehicle usage (business vs personal)
-
🏠 Home office details (square footage + total home size)
-
🧑💻 Business started this year? Say that early—it matters
📌 Pro tip: If your business is small, a simple spreadsheet is perfectly fine. Perfection is not required. Clarity is.
Scenario 2: Retirees (Congrats, By the Way)
Retirement doesn’t mean “no taxes”—but it does mean a different mix of paperwork.
Make sure Joshua has:
-
💰 Social Security income statements (SSA-1099)
-
🏦 Pension or annuity statements
-
📈 Investment income forms (1099-DIV, 1099-INT, 1099-B)
-
🏠 Property tax and mortgage interest statements
-
🩺 Medical expenses (especially if itemizing)
-
🎁 Charitable donations (cash and non-cash)
Also let him know:
-
If you sold property
-
If you made large gifts
-
If you withdrew from retirement accounts
These details can significantly affect your tax outcome.
Scenario 3: Full-Time Business Owners
If your business is your job, upfront communication is everything.
Joshua will want:
-
📊 Profit & loss statement
-
🧾 Balance sheet (if available)
-
🧾 Major purchases or asset acquisitions
-
💳 Owner draws or distributions
-
💼 Payroll reports (if you have employees)
-
🏛️ Estimated tax payments already made
-
📍 Multi-state activity? Very important to flag
Also helpful:
-
Any new loans
-
Any equity changes
-
Any accounting software access (QuickBooks, Wave, etc.)
📌 If something feels “complicated,” that’s exactly the thing to mention early.
One Last Thing: Communication Beats Perfection
You do not need to:
❌ Have everything perfectly categorized
❌ Understand tax law
❌ Guess what matters
You do need to:
✅ Be honest
✅ Be organized enough to explain what happened
✅ Ask questions when unsure
The more context Joshua T. Scott has at the start, the faster—and better—your return gets done.
Ready to Get Started?
If you’re unsure whether something is relevant, send it anyway.
If you think something might matter, mention it.
Tax prep is a team sport—and a little preparation goes a long way.
Here’s to a smooth, drama-free tax season 🍻