Self-Employed & 1099
When no one withholds taxes for you, falling behind is easy, and it often happens quietly across more than one year. Whether you have unfiled returns, a growing balance, or a notice about income the IRS already knows about, we help self-employed people get current and resolve it, without judgment.
Free 30-minute consultation · Confidential · No obligation
Why the Self-Employed Face the IRS
When you work for yourself, no employer sets aside taxes from your pay. The full responsibility, income tax plus self-employment tax for Social Security and Medicare, falls on you, and you are expected to pay it in quarterly estimates throughout the year. For anyone with irregular income or a busy season, those quarterly payments are easy to underpay or miss entirely.
The challenge is that the IRS often already has a record of your income. The 1099 forms that clients and platforms file mean the IRS can see what you were paid, even for years you did not file. That is why self-employed people frequently receive notices about underreported income, or discover that the IRS has estimated a balance for a year they never filed, usually a balance higher than what they actually owe.
Because it builds quietly, self-employment tax debt often spans several years by the time it gets attention. That can feel like a lot to face, but it is very fixable. Filing the missing years with the deductions you are entitled to often lowers the balance significantly, and from there the same resolution options apply. The first step is just getting an accurate picture of where you stand.
What We Handle
These are the issues we resolve most often for freelancers, contractors, and the self-employed.
A program to settle tax debt for less than the full amount owed, when eligible.
Learn more →How We Help
Getting current is usually the first move, and it is more manageable than it looks. Here is how we work.
Step 01
We start by mapping exactly where you stand: which years are filed and which are not, what income the IRS has on record from your 1099s, what you owe or are estimated to owe, and what records you have. For self-employed people, this picture is often less alarming than they feared.
Step 02
From there we build a written plan. That might mean negotiating an installment agreement, pursuing penalty relief, evaluating an Offer in Compromise, or requesting Currently Not Collectible status if paying would create genuine hardship. You see exactly what we recommend, and why, before anything moves forward.
Step 03
Once you approve the plan, we deal with the IRS directly. We file any outstanding returns, submit the necessary documentation, and handle the negotiation. You stop fielding the notices and calls, and we keep you informed at every step.
If you have lost track of where you stand with the IRS, a consultation is where it gets clear again.
Why Work With Us
Your case is handled by a licensed CPA, Enrolled Agent, or tax attorney with the authority to represent you directly before the IRS. No call-center reps, no commission-driven sales staff.
We quote the cost in writing before any engagement begins, in plain language, so you know exactly what you're committing to before you decide.
We tell you what actually applies to your situation, including when a dramatic settlement is not realistic. We would rather give you the honest picture than an overpromise.
Honest answers to the questions we hear most often from freelancers and the self-employed.
It may feel serious, but it is usually fixable. The IRS generally wants missing returns filed and the real balance established. Once the returns are filed, we can evaluate payment plans, penalty relief, hardship status, or other resolution options.
Often, yes. IRS wage and income transcripts can help reconstruct income reported on 1099s, and other available records may help support business expenses. The goal is to prepare accurate returns using the best records available.
It usually means the IRS received income documents, such as 1099s, that do not match what was reported on your return or that were not reported because a return was never filed. The notice needs to be reviewed carefully before you agree or dispute it.
Usually, yes. Self-employed taxpayers generally owe both income tax and self-employment tax, which covers Social Security and Medicare. That is one reason balances can grow faster than expected when estimated payments were missed.
Once the current issue is resolved, the goal is to stay compliant going forward. That may mean setting aside a percentage of income, making quarterly estimated payments, improving bookkeeping, or adjusting how you track business income and expenses.
We Also Help
Looking for a specific tax problem? See everything we resolve →
A 30-minute conversation can tell you which years to file, what you are likely to owe, and how to resolve it. No obligation, and no pressure to commit.
Prefer to talk first? Call 800-630-4374
Free · Confidential · 30 minutes · No obligation
