Gregg Jaffe, Tax Accountant

06/03/2026

Getting paid without taxes being withheld?
Self-employed workers, freelancers, and many side hustlers may need to make quarterly estimated tax payments.
Missing those deadlines can lead to penalties later.
Read more:
https://www.greggjaffetax.com/post/quarterly-estimated-taxes-what-the-self-employed-need-to-know-before-june-15

If you are self-employed, a freelancer, or running a business where no one is withholding taxes from your income, the IRS expects you to pay as you go. That means quarterly estimated tax payments, and the second one for 2026 is due June 15.Most people who are new to self-employment are surprised by....

06/01/2026

Deadlines sneak up fast.
Missing one can mean penalties and added stress.
A clear calendar keeps everything on track.
Do you know your next tax deadline?
View calendar:
https://www.greggjaffetax.com/tools/tax-calendar

Stay on top of key tax deadlines with Gregg Jaffe’s Tax Calendar. Never miss a filing date or payment deadline with this essential tool.

05/29/2026

Helpful Tip Friday
Sold something online this year?
Payment apps and online marketplaces may send tax forms depending on how much you earn.
Even without a form, income may still need to be reported.
516-770-5305

05/27/2026

Not ready to file yet?
Filing an extension can help you avoid a late filing penalty.
It gives you time to file, but interest may still apply on unpaid taxes.
Read more:
https://www.greggjaffetax.com/post/filing-a-tax-extension-in-new-york-more-time-to-file-not-more-time-to-pay

An extension does not mean you are in trouble. It means you are not ready, and you know it. More than 19 million taxpayers file extensions every year, and the IRS treats them as routine. What trips people up is not the extension itself — it is misunderstanding what it covers and what it does not.T...

05/25/2026

Memorial Day is a time to pause and remember the men and women who gave their lives in service to our country.
Their sacrifice is the reason we can enjoy the freedoms we have.
Today, we remember, we honor, and we reflect.

05/22/2026

Helpful Tip Friday
Moved, changed jobs, got married, or had a child this year?
Life changes can affect your taxes more than people realize.
Keeping records up to date now can make next tax season much smoother.
516-770-5305

05/20/2026

Falling behind on taxes can feel overwhelming.
But ignoring it usually makes things worse over time.
Taking the first step to file again can relieve a lot of pressure.
Read more:
https://www.greggjaffetax.com/post/you-missed-a-year-or-a-few-here-is-how-to-get-back-on-track

Most people who have an unfiled return know they have one. They are not avoiding it because they do not care. They are avoiding it because they do not know where to start, and every month that passes makes starting feel harder.Whether you missed one year a while back or have not filed in several yea...

05/18/2026

Non-profits still have strict filing requirements.
Missing deadlines or forms can create serious issues.
Staying compliant keeps your organization focused on its mission.
Is your non-profit fully up to date on filings?
Learn more:
https://www.greggjaffetax.com/services/non-profit-tax-prep

Ensure compliance and maximize tax benefits with Gregg Jaffe’s expert non-profit tax preparation services. Specializing in Form 990 filing, charitable reporting, and tax-exempt status maintenance for organizations of all sizes.

05/15/2026

Started a side hustle this year?
Income from freelancing, online sales, consulting, or gig work may still need to be reported, even if taxes were not taken out.
Setting money aside throughout the year can help avoid surprises later.
516-770-5305

05/13/2026

Need more time to file your taxes?
An extension can give you breathing room to complete your return properly.
Just remember, any taxes owed are still due by the original deadline.
Read more:
https://www.greggjaffetax.com/post/filing-a-tax-extension-in-new-york-more-time-to-file-not-more-time-to-pay

An extension does not mean you are in trouble. It means you are not ready, and you know it. More than 19 million taxpayers file extensions every year, and the IRS treats them as routine. What trips people up is not the extension itself — it is misunderstanding what it covers and what it does not.T...