My Tax Fella

06/02/2026

𝙒𝙝𝙖𝙩 𝙝𝙖𝙥𝙥𝙚𝙣𝙨 𝙞𝙛 𝙮𝙤𝙪 𝙥𝙖𝙮 𝙦𝙪𝙖𝙧𝙩𝙚𝙧𝙡𝙮 𝙩𝙖𝙭𝙚𝙨 𝙡𝙖𝙩𝙚?

If you miss a quarterly estimated tax payment, the IRS treats it as an underpayment. Meaning you may owe an added charge for paying late, plus interest that keeps building until the amount is paid.

So no, one missed estimated payment doesn’t mean the IRS is going to send you a notice, but they do start to keep track.

Quarterly tax payments may apply when you have income that isn’t covered through regular withholding, such as self-employment income, investment income, rental income, retirement income, or passthrough income.

If you missed an estimated payment, don’t ignore it until it's time to file your taxes. Paying late before the tax deadline will still be better than waiting until you file.

06/01/2026

𝙃𝙤𝙬 𝙙𝙤 𝙮𝙤𝙪 𝙥𝙧𝙚𝙛𝙚𝙧 𝙩𝙤 𝙧𝙚𝙘𝙚𝙞𝙫𝙚 𝙛𝙚𝙚𝙙𝙗𝙖𝙘𝙠 𝙤𝙧 𝙧𝙚𝙘𝙤𝙜𝙣𝙞𝙩𝙞𝙤𝙣?

Some people appreciate a quick note. Others value a private conversation, a public shoutout, or clear next steps they can act on.

The same goes for recognition.

A simple “thank you” can mean a lot, but it means even more when it’s given in a way the other person actually receives well.

So here’s a good question to ask your team, your clients, or even yourself:

When someone wants to acknowledge your work, what feels most encouraging to you?

05/29/2026

𝙒𝙝𝙖𝙩 𝙖𝙧𝙚 𝙤𝙘𝙘𝙪𝙥𝙖𝙣𝙘𝙮 𝙩𝙖𝙭𝙚𝙨?

If you rent out your home, apartment, or spare room to guests, income taxes may not be the only tax issue on the table.

Occupancy taxes are taxes charged on the rental price paid by your guest. They’re sometimes called tourist tax, hotel tax, room tax, or lodging tax.

They’re different from income tax, which is based on your profit.

The confusing part is that occupancy tax rules can change depending on your city or county. And if the tax isn’t collected and sent in correctly, the penalties can be a real problem.

Have a short-term rental or thinking about starting one? Comment “RENTAL” to get help with the tax obligations.

05/28/2026

𝘾𝙖𝙣 𝙢𝙮 𝙨𝙩𝙪𝙙𝙚𝙣𝙩 𝙡𝙤𝙖𝙣𝙨 𝙗𝙚 𝙙𝙞𝙨𝙘𝙝𝙖𝙧𝙜𝙚𝙙 𝙞𝙣 𝙗𝙖𝙣𝙠𝙧𝙪𝙥𝙩𝙘𝙮?

Yes, student loans can be discharged in bankruptcy, but it’s not automatic like credit card debt.

You have to prove that repaying the loans would create an undue hardship for you and your family.

For federal loans, your financial records may be reviewed before you ever go to trial. If the Department of Justice agrees that your situation meets the hardship standard, they can agree to the discharge.

Before filing, gather your records and know what kind of loans you have:
• Federal loans
• Private loans
• A mix of both

If you want to talk further about how discharged student loans affect your tax situation, comment "HELP" below.

05/27/2026

Google's updates to its search bar are really interesting: https://www.techbrew.com/stories/google-it-while-you-still-can

And you might be tempted to ask all kinds of tax questions with the new features. And the thing is, the answer might sound definitive in the results but actually still be wrong for your situation.

Tax questions need details that AI agents don't think to ask for.

Maybe your income changed. Maybe you got an IRS notice. Maybe you’re asking about a deduction, but the real issue is how your business is set up.

Don't rely on quick answers from Gemini when it comes to your IRS obligations.

Ask a professional you can trust (we're right here).

05/26/2026

𝘿𝙤 𝙄 𝙝𝙖𝙫𝙚 𝙩𝙤 𝙥𝙖𝙮 𝙩𝙖𝙭𝙚𝙨 𝙞𝙛 𝙄 𝙧𝙚𝙣𝙩 𝙤𝙪𝙩 𝙢𝙮 𝙝𝙤𝙢𝙚 𝙤𝙧 𝙨𝙥𝙖𝙧𝙚 𝙧𝙤𝙤𝙢?

If you’re charging people to stay in your house, apartment, or even just a spare bedroom, that income may need to be reported on your tax return.

In the eyes of the IRS and state taxing authorities, you’re acting as a landlord once guests are paying to stay there.

But the tax treatment depends heavily on your personal use of the space.

Two questions to think about:
1. How many days did guests stay there?
2. How many days did you use the property yourself?

So if you’re renting out part or all of your home, don’t just look at how much money came in.

Your guest days and personal-use days matter too.

05/22/2026

"𝗛𝗼𝘄 𝗺𝘂𝗰𝗵 𝘄𝗶𝗹𝗹 𝗜𝗥𝗦 𝗽𝗲𝗻𝗮𝗹𝘁𝗶𝗲𝘀 𝗮𝗱𝗱 𝘁𝗼 𝗺𝘆 𝘁𝗮𝘅 𝗱𝗲𝗯𝘁?"

IRS penalties can grow quickly, but they aren’t always final. In some cases, you may qualify for penalty abatement, which could reduce or even remove certain penalties if you have a valid reason and present your case correctly.

Here are four common tax penalties taxpayers face:
1. Failure-to-file penalty: up to 5% of unpaid taxes per month, capped at 25%.
2. Failure-to-pay penalty: generally 0.5% per month on unpaid balances, capped at 25%.
3. Accuracy-related penalties: often 20% of the underpayment for negligence or errors.
4. Tax evasion: the most serious category, with major fines and possible jail time.

The IRS may consider penalty relief when there’s “reasonable cause,” like hospitalization, a death in the family, a fire that destroyed records, or an unexpected job loss.

The key is knowing how to document what happened and follow the IRS process.

Which is a process that we're experts at working through. Come talk to us, and we'll help you find out if penalty abatement could be an option for you.

05/21/2026

When you owe the IRS, even normal expenses can feel frustrating. Gas being one of the more consequential ones right now.

You still have places to be, but every fill-up takes money out of your already stretched budget.

Making each tank go farther won’t fix the tax problem. But it can give you a little more room while you work on the bigger issue.

A few small driving habits, as the article suggests, may stretch your tank a little further.

But if the bigger issue is tax debt for you, let’s talk about your options.

Toyota offers easy tips on how to get better gas mileage so you can drive more and fill up less. Learn simple tricks that will help you save.

05/20/2026

𝗖𝗮𝗻 𝗺𝘆 𝘀𝘁𝘂𝗱𝗲𝗻𝘁 𝗹𝗼𝗮𝗻𝘀 𝗯𝗲 𝗱𝗶𝘀𝗰𝗵𝗮𝗿𝗴𝗲𝗱 𝗶𝗻 𝗯𝗮𝗻𝗸𝗿𝘂𝗽𝘁𝗰𝘆?

Not automatically. You usually have to prove that repaying them would create an “undue hardship” for you and your dependents.

Most courts look at three things to determine undue hardship:
1. You can’t maintain a minimal standard of living if forced to repay.
2. Your hardship is likely to continue.
3. You’ve made good faith efforts to repay.

For federal loans, your financial records may be reviewed before trial, and the Department of Justice may agree to the discharge if you meet the hardship standard.

If student debt is making it harder to stay current with the IRS or other obligations, let’s talk through your options.

05/19/2026

What's the most unconventional thing you've heard of someone try to do to save money on their taxes?