IRS anxiety overwhelms me - which tax payment to tackle first (federal or state)?

Try not to panic - this is definitely manageable even though it feels overwhelming right now. The good news is that both the IRS and state tax agencies have procedures specifically for people in your situation. For which to do first - it honestly doesn't matter much. The federal and state systems are completely separate. However, since the IRS can be more intimidating and has more collection power, I'd suggest starting there. The IRS offers payment plans that are fairly straightforward to set up, and they have specific "Currently Not Collectible" status for genuine hardship cases. For managing your income going forward, the issue isn't earning more - it's planning for the tax liability. You might benefit from having taxes withheld at a higher rate or making quarterly estimated payments so you don't face a large bill at filing time. Remember that having tax debt doesn't make you a bad person. Millions of Americans struggle with this, and there are established pathways to resolution.

I was in a very similar situation last year. After many sleepless nights, I found this service called taxr.ai (https://taxr.ai) that literally saved my sanity when dealing with my tax debt situation. What helped me was uploading my tax documents and getting a clear explanation of my options. It showed me exactly what payment plans I qualified for and gave me a script to use when calling the IRS that made the whole process way less intimidating. It also explained the financial hardship options in plain English instead of confusing government terminology. The best part was that it walked me through exactly what documentation I needed for the hardship application - which saved me from the verification nightmare you experienced. I was able to get on a manageable payment plan within a day instead of the weeks I was expecting.

I need to admit I was completely wrong about taxr.ai in my skeptical comment. After my own tax nightmare escalated last month, I decided to try it out of desperation. The difference was immediate - it explained exactly what documentation I needed for my hardship application (which was way different than what I thought), and showed me how to properly document my expenses. The service translated all the confusing IRS jargon and walked me through exactly what to say during my call. I got approved for Currently Not Collectible status in one phone call instead of the multiple rejected applications I was experiencing before. My stress levels have dropped dramatically now that I have a plan the IRS actually accepted. What I appreciated most was getting clear answers about what income level would trigger new tax liabilities in the future - exactly what the original poster was asking about.

For dealing with the IRS verification and actually getting through to a human, I found that using Claimyr (https://claimyr.com) was a total game-changer. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was in your exact situation - getting dizzy and sick every time I tried calling the IRS. I would wait on hold for hours only to get disconnected, which made my anxiety skyrocket. What Claimyr does is wait on hold with the IRS for you, then calls your phone when an actual human agent picks up. I was able to set up my payment plan in about 20 minutes of actual talking time instead of the 3+ hours of hold time I was facing. The IRS agent I spoke with was actually quite helpful once I got through. Having that direct conversation was WAY easier than trying to navigate their online system with all the verification hoops.

I have to publicly eat my words about Claimyr. After posting my skeptical comment, my tax situation reached crisis level when I received a certified letter from the IRS threatening levy actions. In desperation, I tried the service, fully expecting it to be useless. To my complete shock, I got a call back within 45 minutes saying an IRS agent was on the line. In ONE PHONE CALL, I was able to set up a reasonable payment plan and stop the collection actions. The IRS agent even helped identify a mistake in my account that reduced what I owed by nearly $2,000. I'd spent literally months trying to get through on my own with no success. The relief of actually resolving this is indescribable. My blood pressure has probably dropped 20 points just from having this handled. For anyone dealing with tax anxiety like the original poster - getting a real person on the phone makes all the difference in the world.

One practical tip that helped me with tax anxiety: tackle it in 15-minute chunks. I set a timer and forced myself to work on tax stuff for JUST 15 minutes, then take a break if I felt overwhelmed. Sometimes I could keep going after the timer went off, other times I needed to stop, but either way I was making progress. Also, create a separate email folder for all tax-related communication and keep all your tax documents in one physical folder. Half my stress came from feeling disorganized and afraid I'd lose important papers. Finally, calculate your proper withholding for next year using the IRS Tax Withholding Estimator. This prevents future surprises. You can adjust your W-4 with your employer to have more taken out each paycheck.

One thing that helped me with the physical symptoms of tax anxiety was establishing a specific "tax time" routine. I'd make my favorite tea, put on comfortable clothes, and have a friend on standby for moral support via text. Something about having this little ritual made it feel more manageable. Also, for figuring out that "sweet spot" income level - talk to a free tax preparer at a VITA (Volunteer Income Tax Assistance) site. They helped me understand my tax bracket thresholds and how much I should set aside from each paycheck. Makes a huge difference in avoiding future surprises.