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The Great Tax Cliff: 3 Moves to Make in 2026 Before the Rules Change

by | Jan 20, 2026 | Tax & Accounting

Let’s be honest: nobody actually likes thinking about taxes in January, but this year is different. We are officially in the "final countdown" of the Tax Cuts and Jobs Act (TCJA). Most of the tax perks we’ve enjoyed since 2018 are scheduled to expire at the end of this year. If you wait until next April to look at your strategy, you’re basically leaving a "tip" for the IRS that you don't owe them. Here is a simple, human-language guide on how to prep this season and set yourself up for a win. 1. Play "Beat the Clock" with Tax Brackets Right now, tax rates are historically low. However, when the sun sets on current laws at the end of 2025, those rates are likely to jump back up. The Tip: If you have the option to take a bonus, sell a winning stock, or convert a Traditional IRA to a Roth IRA, doing it this year might be cheaper than doing it next year. The Logic: You’d rather pay 22% or 24% today than potentially 28% or 33% tomorrow. Think of it as buying your taxes "on sale" before the price goes up. 2. Rethink Your "Standard" Strategy Since 2018, almost everyone has taken the Standard Deduction because it was so high. But that’s about to shrink. The Tip: This is the year of "Bunching." If you usually give to charity or have major medical expenses, try to "bunch" them into this tax year. The Logic: Since the standard deduction is still high for your 2025 filing, you want to maximize every penny of it now. If you're close to the threshold where "itemizing" (listing your individual deductions) makes sense, do your big spending/giving before the rules tighten up. 3. Clean Up Your "Digital Paper Trail" The IRS has spent the last two years upgrading their tech. Their AI is now much better at spotting when your Venmo, PayPal, or Zelle transactions don't match your reported income. The Tip: Stop treating your business and personal accounts like a shared junk drawer. The Logic: If you have a side hustle, 2026 is the year to be meticulous. Download a simple scanning app and digitize every receipt the moment you get it. If the IRS flags a $600 transaction from a year ago, you don't want to be digging through a shoebox or scrolling through a thousand texts to prove it was a "reimbursement for dinner" and not "taxable income." The Bottom Line Tax season doesn't have to be a panic-driven sprint in April. It’s about making small, boring moves in January that save you big, exciting amounts of money later. Take an hour this weekend to look at your 2025 income projections. Are you ready for the rates to go up? If not, now is the time to pivot. Schedule your free tax consultation here

A Guide to Sunset Planning and Maximizing Your Deductions

Let’s be honest: nobody actually likes thinking about taxes in January, but this year is different. We are officially in the “final countdown” of the Tax Cuts and Jobs Act (TCJA). Most of the tax perks we’ve enjoyed since 2018 are scheduled to expire at the end of this year.

If you wait until next April to look at your strategy, you’re basically leaving a “tip” for the IRS that you don’t owe them. Here is a simple, human-language guide on how to prep this season and set yourself up for a win.

1. Play “Beat the Clock” with Tax Brackets

Right now, tax rates are historically low. However, when the sun sets on current laws at the end of 2025, those rates are likely to jump back up.

  • The Tip: If you have the option to take a bonus, sell a winning stock, or convert a Traditional IRA to a Roth IRA, doing it this year might be cheaper than doing it next year.
  • The Logic: You’d rather pay 22% or 24% today than potentially 28% or 33% tomorrow. Think of it as buying your taxes “on sale” before the price goes up.

2. Rethink Your “Standard” Strategy

Since 2018, almost everyone has taken the Standard Deduction because it was so high. But that’s about to shrink.

  • The Tip: This is the year of “Bunching.” If you usually give to charity or have major medical expenses, try to “bunch” them into this tax year.
  • The Logic: Since the standard deduction is still high for your 2025 filing, you want to maximize every penny of it now. If you’re close to the threshold where “itemizing” (listing your individual deductions) makes sense, do your big spending/giving before the rules tighten up.

3. Clean Up Your “Digital Paper Trail”

The IRS has spent the last two years upgrading its tech. Their AI is now much better at spotting when your Venmo, PayPal, or Zelle transactions don’t match your reported income.

  • The Tip: Stop treating your business and personal accounts like a shared junk drawer.
  • The Logic: If you have a side hustle, 2026 is the year to be meticulous. Download a simple scanning app and digitize every receipt the moment you get it. If the IRS flags a $600 transaction from a year ago, you don’t want to be digging through a shoebox or scrolling through a thousand texts to prove it was a “reimbursement for dinner” and not “taxable income.”

The Bottom Line

Tax season doesn’t have to be a panic-driven sprint in April. It’s about making small, boring moves in January that save you big, exciting amounts of money later.

Take an hour this weekend to look at your 2025 income projections. Are you ready for the rates to go up? If not, now is the time to pivot. Schedule your free tax consultation here 

I’ve put together the 2026 Tax Season’s’ Peace of Mind’ Checklist to help you. Download for free