THE SUNLIGHT TAX BLOG:
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1099 Problems (and How to Avoid Them)
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In this episode of the Sunlight Tax Podcast, I explain what 1099 forms are, why accurate 1099 reporting matters, and how mistakes can impact your taxes if you’re self-employed. I break down common 1099 problems and how to avoid them. I also share what to do when a 1099 is wrong and how to make sure all your income is properly reported to the IRS. We also cover key 1099 deadlines and practical bookkeeping tips to help freelancers, contractors, and small business owners stay compliant and avoid costly surprises at tax time.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I explain what 1099 forms are, why accurate 1099 reporting matters, and how mistakes can impact your taxes if you’re self-employed. I break down common 1099 problems and how to avoid them. I also share what to do when a 1099 is wrong and how to make sure all your income is properly reported to the IRS. We also cover key 1099 deadlines and practical bookkeeping tips to help freelancers, contractors, and small business owners stay compliant and avoid costly surprises at tax time.
Also mentioned in today’s episode:
01:12 Understanding 1099s: An Introduction
03:21 The Importance of Accurate Reporting
06:25 Common 1099 Problems and Solutions
08:57 Tallying Your Income Effectively
12:03 Some Tips for 1099 Management
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Join my free class on 1/27 at noon EST: Make Taxes Easier and Stash an Extra $152k in Your Savings
Get my short course: All About 1099s
Check out my program, Money Bootcamp
Order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed
What’s New for Your Taxes This Year: Key Tax Changes You Need to Know
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In this episode of the Sunlight Tax Podcast, I break down the most important 2025 tax law changes in clear, jargon-free language. I explain the new Schedule 1-A and its temporary deductions, including no tax on tips, overtime, car loan interest, and enhanced senior deductions, plus what the latest tax bill really means for your wallet.
You’ll also learn about “Trump accounts” for children born 2025–2028, updated 1099 reporting rules, retirement catch-up contribution changes, and the higher standard deduction. This practical episode helps you understand key tax changes, which tax benefits apply to you, and how to avoid missing important deductions this tax season.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I break down the most important 2025 tax law changes in clear, jargon-free language. I explain the new Schedule 1-A and its temporary deductions, including no tax on tips, overtime, car loan interest, and enhanced senior deductions, plus what the latest tax bill really means for your wallet.
You’ll also learn about “Trump accounts” for children born 2025–2028, updated 1099 reporting rules, retirement catch-up contribution changes, and the higher standard deduction. This practical episode helps you understand key tax changes, which tax benefits apply to you, and how to avoid missing important deductions this tax season.
Also mentioned in today’s episode:
03:39 New Tax Forms and Deductions
06:44 Understanding the Schedule 1A
10:31 Trump Accounts: A New Initiative
13:14 Changes in 1099 Forms and Reporting
15:52 Updates on Standard Deductions and Child Tax Credit
18:47 Join my Upcoming Free Class
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Join my free class on 1/27: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed
It’s 1099 Time: Here’s Your Checklist for Stress-Free Filing
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In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.
I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.
I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.
Also mentioned in today’s episode:
01:00 Understanding 1099: The Basics
04:31 The Importance of 1099s
10:53 The kinds of 1099s you are going to be dealing with
18:20 Checklist for Issuing 1099s
25:45 Other Resources for filing 1099s
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Get my 1-hour course: All About 1099s
Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed
Healthcare Changes From the OBBBA: Expert Dr. Matthew Fiedler Explains
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In this episode of the Sunlight Tax Podcast, I talk with Dr. Matthew Fiedler about the new One Big Beautiful Bill Act—and what it could mean for your healthcare and taxes.
We break down how the government shutdown affects healthcare access, why there are major Medicaid cuts, and what trade-offs come with the new tax cuts. The conversation highlights the challenges faced by low and moderate-income individuals in accessing healthcare, especially in light of new administrative requirements and potential loss of coverage.
We also talk about what this means if you’re self-employed or run a small business. With shifting healthcare policies and tax laws, good bookkeeping and clear financial records matter more than ever.
Dr. Fiedler emphasizes the need for a more rational approach to healthcare financing and the importance of bookkeeping for self-employed individuals.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I talk with Dr. Matthew Fiedler about the new One Big Beautiful Bill Act, and what it could mean for your healthcare and taxes.
We break down how the government shutdown affects healthcare access, why there are major Medicaid cuts, and what trade-offs come with the new tax cuts. The conversation highlights the challenges faced by low and moderate-income individuals in accessing healthcare, especially in light of new administrative requirements and potential loss of coverage.
We also talk about what this means if you’re self-employed or run a small business. With shifting healthcare policies and tax laws, good bookkeeping and clear financial records matter more than ever.
Dr. Fiedler emphasizes the need for a more rational approach to healthcare financing and the importance of bookkeeping for self-employed individuals.
Also mentioned in this episode:
01:46 Understanding the One Big Beautiful Bill Act
03:07 Impact of Government Shutdown on Healthcare
08:05 Overview of Healthcare Provisions in the Bill
09:30 Trade-offs in Tax Cuts and Healthcare Funding
12:20 Medicaid Cuts and Work Requirements
16:00 Navigating Medicaid for the Recently Unemployed
20:16 Cost-Shifting from Federal to State Medicaid Programs
25:29 Consequences for Low and Moderate Income Individuals
28:18 Changes in Marketplace Coverage Requirements
30:38 Implications for Self-Employed Individuals
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
How OBBBA Changes Medicaid, Planned Parenthood, Health Subsidies and Access for Immigrants
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In this episode of The Sunlight Tax Podcast, I’m unpacking the One Big Beautiful Bill Act (OBBBA) and what its sweeping health care changes mean for real people and families. We’ll dig into how this new legislation affects Medicaid coverage, Planned Parenthood funding, and low-income immigrants, plus what’s changing for marketplace insurance subsidies and health savings accounts (HSAs).
I’ll also share key insights from an excellent healthinsurance.org article by Louise Norris, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” With her permission, I’ll be reading excerpts from that piece and you can find the full article linked in the show notes. It’s a must-read if you want a deeper understanding of how the One Big Beautiful Bill Act (OBBBA) could reshape American health care and insurance coverage in the years ahead.
Listen and Subscribe Here
In this episode of The Sunlight Tax Podcast, I’m unpacking the One Big Beautiful Bill Act (OBBBA) and what its sweeping health care changes mean for real people and families. We’ll dig into how this new legislation affects Medicaid coverage, Planned Parenthood funding, and low-income immigrants, plus what’s changing for marketplace insurance subsidies and health savings accounts (HSAs).
I’ll also share key insights from an excellent healthinsurance.org article by Louise Norris, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” With her permission, I’ll be reading excerpts from that piece and you can find the full article linked in the show notes. It’s a must-read if you want a deeper understanding of how the One Big Beautiful Bill Act (OBBBA) could reshape American health care and insurance coverage in the years ahead.
Also mentioned in this episode:
03:29 Health Care Provisions Overview
07:02 Medicaid Changes and Impacts
09:17 Planned Parenthood Funding
11:37 Subsidy Eligibility for Low-Income Immigrants
12:32 Impact of Subsidy Changes on Self-Employed
17:09 Health Savings Accounts and Marketplace Plans
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Credit:
Key insights in this episode come from an excellent article by Louise Norris for healthinsurance.org, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” Shared with permission.
Links:
Article by Louise Norris published in healthinsurance.org: One Big Beautiful Bill Act brings sweeping changes to health coverage by Louise Norris
Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
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