Pay nothing until a live IRS agent is on the phone with you.
Can't reach IRS? Claimyr calls for you, so you don't have to wait on hold.
$0 upfront. We only hold your card.
No live agent, no charge.
$9.99 is charged only once a live IRS agent is on the phone with you.
Using Claimyr will:
- Connect you to a human agent at the IRS
- Skip the long phone menu
- Call the correct department
- Redial until on hold
- Forward a call to your phone with reduced hold time
- Give you free callbacks if the IRS drops your call
Ask the community...
- DO post questions about your issues.
- DO answer questions and support each other.
- DO post tips & tricks to help folks.
- DO NOT post call problems here - there is a support tab at the top for that :)
Join the conversation
Join the conversation
Has anyone compared Flyfin to TaxSlayer? I'm in the same boat with a day job and side gig, but I've always used TaxSlayer and wonder if it's worth switching.
I've used both! TaxSlayer is decent but Flyfin is better for side hustles specifically. TaxSlayer is more general purpose while Flyfin has more features targeted at self-employed people and finding those specific deductions. The AI actually learns your business type and suggests industry-specific write-offs.
I'm in a very similar situation - W-2 from my main job plus around $8,500 from freelance graphic design work last year. I ended up using TurboTax Self-Employed and it worked well, but I'm curious about Flyfin too after reading these responses. One thing I'd recommend regardless of which software you choose is to make sure you have good records of all your photography business expenses. Things like equipment depreciation, travel to shoots, editing software subscriptions, and even a portion of your phone bill if you use it for business can all be deductible. The better organized your records are, the more any of these tax programs can help you. Have you been tracking your business expenses throughout the year, or are you going to have to dig through bank statements? That might influence which platform would work best for you.
Join the conversation
My all-time favorite tax meme is the one where there's a person nervously looking at two buttons labeled: Button 1: "File taxes early and get refund ASAP" Button 2: "Procrastinate until April 14th because taxes are scary" And they're sweating trying to decide which to press 😂 Then there's a third hidden button labeled "File extension and deal with it in October" which is the one I actually press every year!
Filing an extension doesn't extend the time to pay though, right? Don't you still have to pay what you owe by April 15th?
The meme that perfectly captures my tax experience is the "Distracted Boyfriend" one where the guy (labeled "Me") is looking back at the girl walking by (labeled "Netflix") while his girlfriend (labeled "Tax Forms") looks annoyed. That's basically been my entire April! Another one that gets me every time is the Drake meme where he's rejecting "Organizing receipts throughout the year" but pointing approvingly at "Frantically searching through a shoebox of random papers on April 10th." Called out hard on that one 😅 But honestly, seeing all the helpful recommendations in this thread (like taxr.ai for document analysis and Claimyr for actually reaching the IRS) makes me realize maybe next year I can upgrade from memes about tax chaos to memes about being surprisingly organized!
Join the conversation
Something else to consider - if you're worried about your mom seeing deposits, maybe look into getting a prepaid card that you can use for receiving payments? That way the money doesn't hit your regular bank account that she might have access to. I do photography on the side and keep all those earnings separate from my main account. Services like Cash App, Venmo, and PayPal can all link to a separate card. Just remember they'll still report to the IRS if you go over $600 for the year.
That's smart! Do you know if those prepaid cards have any monthly fees? And would I need to show ID to get one? I'm trying to keep costs low since I'm not even sure how much I'll make from this yet.
Most prepaid cards do have some fees - usually a few dollars per month for maintenance, sometimes fees for loading money or withdrawing. I use the Bluebird card from Amex (through Walmart) which has almost no fees if you load it directly from your bank account. You will need to show ID for any legitimate prepaid card due to banking regulations. They all require identity verification to prevent money laundering. However, the card statement itself won't show what the money is for - just that funds were transferred from payment apps. If your mom doesn't have access to your payment apps, she wouldn't see the nature of the transactions.
Friendly reminder that if you do make decent money from this, you should consider making quarterly estimated tax payments! When I started my Etsy shop, I didn't know this and got hit with a penalty the first year. Self-employment income gets taxed at about 15.3% for the self-employment tax portion (Medicare/Social Security) on top of regular income tax. So definitely set aside more than you think you'll need.
Is there a minimum you need to earn before you have to make quarterly payments? I make like $200-300 a month from my side gig and have just been reporting it yearly.
Generally, you need to make quarterly payments if you expect to owe $1,000 or more in taxes when you file your return. For someone making $200-300 a month ($2,400-$3,600 annually), you'd probably want to start considering quarterly payments since the self-employment tax alone would be around $367-$551. The IRS safe harbor rule says you won't get penalized if you pay at least 90% of the current year's tax liability OR 100% of last year's tax liability (110% if your prior year AGI was over $150k). So if you're just starting out and didn't have self-employment income last year, you might be okay waiting until annual filing, but it's safer to make quarterly payments once you're consistently earning. You can make estimated payments online through the IRS Direct Pay system - it's pretty straightforward once you get the hang of it.
Join the conversation
The real benefit for the Cayman Islands isn't just registration fees - it's the entire ecosystem they've built. Banking in the Caymans is a massive industry. They have around $1.5 trillion in banking assets and $1.8 trillion in securities. Those institutions need actual offices, actual employees, and support services. Plus, their tourism industry is intertwined with their financial status. Wealthy individuals who establish financial relationships there often visit, purchase property, and spend money in the local economy. Many conferences and financial events are hosted there too. The Caymans could implement small taxes, but the competition between tax havens is fierce. If they added even a 5% corporate tax, businesses would flee to other jurisdictions like the British Virgin Islands, Bermuda, or newer players. It's essentially a prisoners' dilemma - they'd all benefit from coordinated tax increases, but whoever maintains lower rates wins the business.
This makes sense, but don't these places face international pressure to change their practices? I feel like I've heard about crackdowns on tax havens in recent years.
Yes, there's definitely been increasing international pressure, particularly from organizations like the OECD and larger nations concerned about tax base erosion. The Caymans and similar jurisdictions have made some concessions regarding financial transparency and information sharing. They've implemented various reporting requirements like the Common Reporting Standard (CRS) and Foreign Account Tax Compliance Act (FATCA) compliance. However, they carefully balance these concessions with maintaining their core competitive advantage. They comply with international standards just enough to avoid being blacklisted while preserving their attractiveness for legitimate tax planning. It's a delicate balancing act, but so far, places like the Caymans have managed to adapt while keeping their financial services industry thriving.
I researched this topic for a economics paper last year. One thing often overlooked is that the Cayman Islands collects significant indirect revenue through their work permit system. Foreign financial professionals working there pay hefty fees (sometimes $20k+ annually) for the right to work. Also, the Caymans have a 0% income tax for everyone - not just corporations or wealthy foreigners. This benefits local residents too, who enjoy no personal income tax. The government funds itself through import duties (which generate around 30% of government revenue), tourist taxes, and the various financial sector fees others have mentioned. Another factor: reputation matters. If they suddenly implemented taxes after decades of being a tax-free jurisdiction, it would seriously damage their credibility in the financial world. The damage to their reputation would likely far outweigh any short-term tax revenue gains.
This is super interesting! Do you know if other tax havens like Bermuda or the British Virgin Islands use the same model? Are there differences in their approaches?
Yes, there are definitely differences! Bermuda follows a similar zero-tax model but relies heavily on insurance company licensing fees - they're actually the world's second-largest reinsurance market after London. The BVI focuses more on company incorporation fees and has streamlined their process to be incredibly fast and cheap, making them popular for shell companies. Singapore and Hong Kong take different approaches - they have low but not zero corporate tax rates (around 17% and 16.5% respectively) but offer tons of exemptions and incentives. They've built themselves as actual business hubs with real operations, not just paper companies. What's fascinating is how each jurisdiction found their niche. The Caymans dominate hedge funds, Bermuda owns reinsurance, BVI does basic incorporations, and places like Malta specialize in gaming licenses. It's like they've divided up the offshore world by specialty rather than competing directly on identical services.
Luca Russo
does anyone know if you can switch from MFS to HOH mid-year if spouse abandons halfway through the year? my wife left in july and took the kids but they've been back with me since september. not sure if i qualify as HOH or still have to file MFS for 2024?
0 coins
Freya Andersen
•Your filing status is determined by your situation on December 31st of the tax year. So if your children lived with you for more than half the year in total (doesn't have to be consecutive months), and you paid more than half the costs of keeping up the home where you and your children lived, you might qualify for HOH. The key factors are: 1) Did your children live with you for more than half the year in total? 2) Did you pay more than half the household expenses for the home where you and the children lived? 3) Are you and your spouse living apart for the last 6 months of the year?
0 coins
Oliver Zimmermann
I went through a very similar situation in 2023 when my husband left us in March. The emotional stress is overwhelming, but you're definitely on the right track with Head of Household status. One additional point that really helped me - keep detailed records of ALL expenses you've paid since she left. Not just the obvious ones like mortgage and utilities, but also things like your son's daycare, medical expenses, school supplies, clothing, etc. The IRS requirement is that you paid "more than half" the cost of maintaining the home, and these child-related expenses count toward that calculation. Also, since you mentioned she completely ghosted you, make sure you claim your son as a dependent too. As the custodial parent who's been providing all support, you have that right even while still legally married. The good news is Head of Household will save you significant money compared to Married Filing Separately - both through better tax brackets and a higher standard deduction. In my case, it was about a $4,000 difference. Hang in there, and definitely keep all that documentation others have mentioned in case you ever need to prove the abandonment timeline.
0 coins