Your 2025 Year-End Tax Planning Guider
As we approach the end of 2025, there’s still time to take action and make a real
difference in your tax outcome for the year.
With thoughtful planning and a few strategic steps, you can reduce your tax bill,
strengthen your retirement savings, and position your finances for a better 2026.
Below are some year-end moves to consider before December 31. Each one is
practical, IRS-approved, and designed to help you keep more of what you’ve earned.
1. Strengthen Your Business Deductions before
December 31
Prepay Expenses Under the IRS Safe Harbor
If you’re on the cash basis, you can prepay qualifying expenses up to 12 months in
advance and deduct them this year. That includes office rent, equipment leases, and
insurance premiums.
For example, if your monthly office rent is $3,000, prepaying $36,000 on December 31
to cover your 2026 rent gives you a $36,000 deduction in 2025—and it provides the
landlord with the income when he wants it, in 2026. Be sure to mail the funds on
December 31 so they arrive in January 2026, and keep documentation, such as the
USPS tracking number.
Hold Off on Year-End Billing
A simple yet effective move for cash-basis businesses: delay billing clients until January.
Since you don’t recognize income until payment is received, postponing invoices can
shift taxable income into 2026.
Purchase Needed Equipment
If you’ve been planning to buy office furniture, computers, or machinery, doing it now
can provide a full deduction through 100 percent bonus depreciation or Section 179
expensing—as long as you place the equipment in service before December 31.
Use Business Credit Cards Wisely
For Schedule C filers, the deduction occurs on the date of the charge, not when you pay
the bill. That means charges made in December are deductible this year. Corporations
can do the same when employees are using a corporate card.
Document and Claim Every Legitimate Deduction
Don’t avoid deductions because you think they might raise red flags. If they’re legitimate
and supported by records, you’re entitled to them. If deductions exceed your income,
that loss may create a net operating loss (NOL) that carries forward to offset future
profits.
Review Qualified Improvement Property
If you improved the interior of your business or one of your commercial rental properties
this year, those costs may qualify for immediate expensing rather than 39-year
depreciation. To take the deduction for 2025, you must place the improvement in service
by December 31.
2. Take Full Advantage of Retirement Savings
Opportunities
Retirement plans remain one of the most powerful tax-saving tools available to small-
business owners and self-employed professionals.
Establish or Fund a Retirement Plan Before Year-End
If you don’t yet have a retirement plan, setting one up before December 31 allows you
to make both employee and employer contributions for 2025.
For a solo business, a 401(k) plan (often referred to as an “individual 401(k)” or a “solo
401(k)”) is an ideal option. Your owner-employee contribution limits for 2025 are:
$23,500 if under age 50
$31,000 if age 50–59 or over 64
$34,750 if age 60–63
Your employer contributions to your retirement account (remember, you are both
employer and employee) can tally up to 25 percent of compensation, with a combined
maximum of $70,000–$81,250 depending on age.
Use Available Tax Credits
If you started a new plan this year or plan to, you may qualify for valuable credits:
1. A start-up credit of up to $15,000 for new plans
2. A contribution credit of up to $3,500 per employee for employer contributions
3. An automatic-enrollment credit of $500 per year for three years
These credits directly reduce taxes owed, not just taxable income.
Consider a Roth Conversion
If your income is lower this year or your investments have declined, converting a
traditional IRA or 401(k) to a Roth can be an attractive option. You’ll pay tax on the
converted amount now, but future qualified withdrawals are tax-free, and Roth IRAs
have no required minimum distributions during your lifetime.
3. Use Vehicle Deductions to Your Advantage
The One Big Beautiful Bill Act (OBBBA) expanded the deductions available for business
vehicles in 2025. Timing and vehicle type are critical.
Heavy SUVs, Pickups, and Vans
These vehicles with a gross vehicle weight rating (GVWR) over 6,000 pounds may
qualify for:
100 percent bonus depreciation
Section 179 expensing up to $31,300 for SUVs and $2.5 million for trucks and
vans
No luxury limits
Example. A $50,000 SUV used 90 percent for business produces a $45,000 deduction
this year.
Standard-Weight Vehicles
Cars (and lighter SUVs with GVWRs of 6,000 pounds or less) face luxury depreciation
caps—allowing only up to $20,200 in first-year deductions.
Act Before Year-End
To qualify, you must own the vehicle and place it in service by December 31—meaning
it’s ready and being used for business. Driving it even one business mile before
midnight proves eligibility.
Note. Electric-vehicle tax credits ended September 30, 2025.
4. Plan for Crypto Profits and Losses
Crypto investors had a strong 2025, and now is the time to manage taxes efficiently.
Harvest Gains or Losses
Tax-gain harvesting. Sell appreciated crypto now if you expect higher income
next year. Pay tax at today’s rate, and immediately repurchase to reset your
basis.
Tax-loss harvesting. Sell underperforming assets to offset other capital gains.
Excess losses can offset up to $3,000 of ordinary income, with the balance
carried forward.
No Wash-Sale Restrictions
Because the IRS treats crypto as property—not securities—you can sell to create
deductible losses and rebuy immediately without waiting 30 days.
Donate Appreciated Crypto
Donating directly to a qualified 501(c)(3) charity avoids capital gains and earns a
deduction for the fair market value. If the gift exceeds $5,000, obtain a qualified
appraisal and include Form 8283 with your return.
Gift Crypto to Family Members
You can give up to $19,000 per person in 2025 without any reporting requirement. The
recipient inherits your original cost basis and holding period.
Invest through Self-Directed Accounts
Consider a self-directed IRA or solo 401(k) that allows cryptocurrency investments.
You’ll enjoy the same tax-deferred or tax-free growth benefits available with traditional
investments.
5. Don’t Overlook Deductions Hidden in Your Current
Vehicles
Your existing vehicles can still produce valuable deductions before year-end.
Sell older business vehicles. You’ll capture deductible losses—especially for
those with declining business use.
Check vehicles purchased before 2018. If you traded cars under the old like-
kind exchange rules, you may have unclaimed losses built up over multiple
trades. Selling now could unlock a sizable deduction.
Convert a personal vehicle to business use. OBBBA allows up to 100 percent
bonus depreciation when you start using a personal vehicle for business. If you
operate as a corporation, the company must reimburse you for the deduction
before year-end.
6. Review Your Stock Portfolio for Tax Efficiency
Year-end is an ideal time to review and adjust your investments.
Offset Gains with Losses
Match short-term gains (taxed as high as 40.8%) with long-term losses.
Avoid Wash-Sale Traps
Selling and repurchasing the same stock within 30 days cancels your loss. Wait until
January to rebuy if you plan to claim the loss in 2025.
Share Wealth within the Family
Gifting appreciated stock to children or parents in lower tax brackets lets them sell at
0%–15% capital gains rates, freeing up after-tax cash for the family as a whole.
Donate Appreciated Stock to Charity
Instead of cash, donate appreciated shares. If you itemize your deductions, you’ll
receive a deduction for the fair market value and avoid paying capital gains on the
appreciation.
Sell Losers, Then Give Cash
If a stock has lost value, sell it to recognize the loss, then donate the cash proceeds.
This way, you claim both the loss and the charitable deduction.
7. Review Your Health Care Reimbursement Options
For small-business owners, properly structured medical plans can be powerful
deduction tools.
Reimburse Section 105 Expenses before December 31
If you have a Section 105 Health Reimbursement Arrangement (HRA) for your spouse-
employee, ensure that all reimbursements are completed before year-end so your
family’s medical expenses qualify for a 2025 deduction.
Consider a QSEHRA or an ICHRA
QSEHRA (Qualified Small Employer HRA): For businesses with fewer than 50
employees, reimburse up to $6,350 (individual) or $12,800 (family) tax-free.
ICHRA (Individual Coverage HRA): Works for employers of any size, and
reimburses employees for individual health insurance coverage.
S Corporation Owners
For you to qualify for the above-the-line deduction on your Form 1040, your S
corporation must pay or reimburse your health insurance premiums and include them
on your W-2.
Small-Employer Health Insurance Credit
If you cover at least half the cost of employee health insurance, you may qualify for a 50
percent tax credit for up to two consecutive years—another reason to review your
benefits before December 31.
8. Make Smart, Family-Focused Tax Moves
Put Your Children on Payroll
Paying your under-18 child reasonable wages for legitimate work can save thousands:
The wages are deductible for you.
Neither you nor your child owes payroll taxes.
The first $15,750 paid to the child is tax-free to the child due to the standard
deduction.
Your child can contribute up to $7,000 to a Roth IRA, building tax-free savings for
life.
Be sure to issue a W-2 (not a 1099) and keep clear records of work performed and
payment dates.
Consider Marriage or Divorce Timing
Your marital status on December 31 determines your filing status for the entire year.
Run both scenarios—married and single—to see which is most beneficial. Joint filing
usually lowers overall tax, but not always.
For divorces finalized after 2018, alimony is no longer deductible by the payer or taxable
to the recipient.
Mortgage and Relationship Planning
Two unmarried co-owners can each deduct interest on up to $1 million of mortgage debt
for older loans (or $750,000 for newer loans). Married couples are limited to a total of $1
million (or $750,000).
Use the 0 Percent Capital-Gains Bracket for Family Gifts
If you assist parents or relatives in lower tax brackets (say, with a joint income of under
$96,700), consider giving them appreciated stock instead of cash. They can sell the
stock tax-free, preserving more family wealth.
9. Make the Most of the Section 199A Deduction
The 20 percent deduction on qualified business income remains one of the most
valuable breaks for owners of pass-through entities such as sole proprietorships,
partnerships, and S corporations.
Eligibility Thresholds for 2025
$197,300 for single filers
$394,600 for joint filers
If your taxable income exceeds these levels, the deduction may phase out—especially
for specified service businesses such as law, health, or consulting.
Three Ways to Boost the Deduction before Year-End
1. Harvest capital losses. Lower taxable income by offsetting gains in your
investment portfolio.
2. Make charitable contributions. Prepay 2026 charitable gifts or donate
appreciated stock to increase itemized deductions and lower your taxable
income.
3. Buy business assets and place them in service. New equipment or property
expensed under Section 179 or bonus depreciation can bring taxable income
below the threshold and increase your deduction.
10. Review Your Year-End Tax Checklist
Here’s a quick review of some steps to take before December 31:
Prepay next year’s qualifying business expenses
Delay billing until January
Purchase and place in service needed equipment and vehicles
Establish or fund your retirement plan
Review current and older vehicles for possible loss deductions
Manage crypto and stock portfolios for gains and losses
Complete any health-insurance reimbursements or S corporation W-2
adjustments
Pay children for work performed in the family business
Confirm eligibility for the Section 199A deduction
Each of these moves can help reduce your 2025 tax liability and improve your long-term
financial position.
Disclosure: The information in this newsletter is not intended as tax, legal,
investment advice. You are encouraged to seek advice from your own independent
tax, legal and financial advisor. The content is derived from sources believed to be
accurate.
