Your First Tax Season as a Business Owner: Free Email Course
Facing your first tax season as a business owner? This free 6-lesson email course walks you through records, income, deductions, self-employment tax and the Connecticut dates, one short lesson at a time. Checked November 3, 2026.
For general education only. Not tax, legal, insurance, or investment advice, and not a promise of any result. Tax rules and due dates change, so confirm with the IRS (irs.gov), the CT Department of Revenue Services (portal.ct.gov/DRS) or your town before you act, and ask your tax preparer about your own situation.
What you'll learn in your first business tax season
| Lesson | Topic | What it covers |
|---|---|---|
| 1 | Get your records in one place | Separate accounts, statements, a records folder, and the free organizer |
| 2 | What counts as business income | 1099-NEC ($2,000 for 2026 payments), 1099-K (over $20,000 and 200 transactions), income without a form |
| 3 | Expenses and deductions | Ordinary and necessary expenses, 2026 mileage rates, the home office simplified method, startup costs |
| 4 | Self-employment tax and quarterly estimates | 15.3% SE tax, the $1,000 estimate rule, federal and CT due dates |
| 5 | Connecticut dates and filings | LLC annual report, sales tax returns, personal property declaration, CT PET |
| 6 | Filing, extensions and next year | Due dates, extensions (time to file, not to pay), records to keep |
Who this tax season course is for
- You started a business, side business or freelance work in 2026, and this is your first tax season as a business owner.
- You're a sole proprietor, a single-member LLC, or not sure yet.
- You're in Connecticut, or you want the CT-specific dates. The federal lessons apply everywhere.
Want everything at once? Get the free First-Year Tax Organizer, try the What did I forget? CT tax checker, or browse tax deadlines.
Frequently asked questions
Is the first tax season email course free?
Yes. It's six free lessons by email. Some lessons mention optional paid kits, and you never have to buy anything.
How often will I get lessons?
One lesson every 2 days after you confirm your email, so the whole course takes about 10 days.
What should a new business owner do for their first tax season?
Gather your records and 1099s, total your income and expenses, check self-employment tax and estimated payments, and note the federal and Connecticut due dates. The course walks through each step.
Is this tax advice?
No. The lessons are general education with links to official IRS and CT DRS sources. Ask your tax preparer about your own situation.
Can I unsubscribe?
Yes, anytime, from the link at the bottom of any email.
Sources (Checked November 3, 2026)
For general education only. Not tax, legal, insurance, or investment advice, and not a promise of any result. Tax rules and due dates change, so confirm with the IRS (irs.gov), the CT Department of Revenue Services (portal.ct.gov/DRS) or your town before you act, and ask your tax preparer about your own situation.
Rather have help with your first business tax season? Tell us about your business.
Or call (475) 242-7941. Services are priced by quote.
Enhance Finance is a small-business finance practice serving Connecticut.