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Should You Make A Roth Conversion Now Or Wait For January’s Tax Environment To Settle?

December 13, 2025 by Brandon Marcus Leave a Comment

Should You Make A Roth Conversion Now Or Wait For January’s Tax Environment To Settle?

Image Source: Shutterstock.com

Timing is everything when it comes to Roth conversions, and right now, the financial world feels like a rollercoaster with the lights off. Tax rules, market fluctuations, and political chatter are swirling together in a way that can make anyone’s head spin. Should you convert your traditional IRA to a Roth now to lock in current rates, or is it wiser to wait until January when the dust settles? The answer isn’t black and white—it’s more like a carefully layered financial lasagna, with different slices depending on your goals, risk tolerance, and tax strategy.

Understanding the nuances now can save you thousands later and help you sleep better at night knowing you made an informed move.

Why Roth Conversions Can Be A Smart Move

Roth conversions are appealing because they allow your money to grow tax-free from the moment it lands in your Roth account. Unlike traditional IRAs, where withdrawals are taxed as ordinary income, Roth IRAs let you plan for a future without surprises from Uncle Sam. Converting now could make sense if you expect your tax rate to rise in the coming years, because you’ll pay taxes at today’s rates instead of potentially higher ones later. It also gives younger investors or those with smaller conversions the ability to strategically manage their tax bill over several years. Finally, a Roth conversion can be a smart estate-planning tool, allowing you to pass on tax-free growth to heirs.

The Case For Waiting Until January

On the other hand, waiting until January has its perks, especially if your current tax situation is uncertain. Lawmakers often tweak tax rules at the start of a new year, and waiting could clarify what rates or deductions you’ll actually face. Market fluctuations can also play a role; a volatile market may make it more beneficial to delay a conversion until asset values stabilize. Additionally, spreading out conversions over multiple years can prevent bumping yourself into a higher tax bracket this year. Finally, delaying allows you to gather all necessary financial information and make a thoughtful, stress-free decision rather than rushing into it.

How Market Volatility Affects Roth Conversion Decisions

The stock market is unpredictable, and that unpredictability directly impacts the timing of a Roth conversion. Converting during a market dip can be advantageous because you’re paying taxes on a lower account value, leaving more room for future growth tax-free. Conversely, if the market surges right after your conversion, you might have paid taxes on less value than the Roth ultimately grows to—but the upside is that the growth is tax-free. Regular investors may prefer to wait until there’s some clarity in the market to avoid making a big conversion during a sharp swing. Ultimately, understanding your portfolio’s risk tolerance and expected returns is critical before pulling the trigger on a conversion.

Tax Brackets And Timing: A Delicate Balance

Tax brackets are a central piece of the Roth conversion puzzle. Paying taxes at a lower rate now could save you thousands compared to waiting for potentially higher rates next year. However, converting too much in one year can push you into a higher bracket, eroding the benefits. Strategic partial conversions over multiple years allow you to stay in a lower bracket while still benefiting from Roth growth. Calculating exactly how much to convert requires careful planning and an eye on your projected income for the current and upcoming years.

Personal Circumstances Matter More Than Headlines

It’s easy to get caught up in financial news and the latest chatter about tax reforms, but personal circumstances often matter more than national headlines. Your income, retirement timeline, and other deductions all play a role in determining whether converting now or waiting makes sense. Health considerations or plans to access funds in the near future can also impact your decision. If your job situation or financial needs are changing, flexibility becomes more important than theoretical tax gains. In short, your unique financial landscape should guide your timing more than external noise.

Should You Make A Roth Conversion Now Or Wait For January’s Tax Environment To Settle?

Image Source: Shutterstock.com

Partial Conversions Can Reduce Stress

If you’re unsure whether to convert all at once, partial conversions are an elegant compromise. They allow you to take advantage of current tax rates without the shock of a massive tax bill. Partial conversions also provide a buffer against market volatility by spreading the risk over time. This approach can keep you in lower tax brackets while steadily moving funds into a Roth account. Many financial planners recommend this method as a balanced strategy, especially when future tax policies remain uncertain.

Planning For The Long Term Matters Most

Roth conversions are ultimately a long-term strategy, and thinking beyond this year’s taxes can pay dividends. Tax-free growth over decades can outweigh the immediate sting of a conversion tax bill, especially if you anticipate higher spending or tax rates in retirement. Planning with a multi-year perspective allows you to optimize not just your taxes, but your overall retirement income strategy. It also gives you room to adjust if your personal circumstances or the economy shift. A thoughtful, long-term approach turns a short-term headache into a strategic advantage for your financial future.

Make An Informed Choice That Works For You

Deciding whether to convert now or wait for January isn’t about rushing to follow the latest headlines; it’s about understanding your personal finances and the interplay of tax laws, market conditions, and retirement goals. Roth conversions can be powerful tools, but timing them correctly requires planning, patience, and an eye on both immediate and future impacts. Whether you decide to act now or wait, the key is to make an informed, strategic choice that aligns with your financial reality.

Have you wrestled with the decision to convert or wait? Share your experiences, strategies, or thoughts in the comments section below.

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Brandon Marcus
Brandon Marcus

Brandon Marcus is a writer who has been sharing the written word since a very young age. His interests include sports, history, pop culture, and so much more. When he isn’t writing, he spends his time jogging, drinking coffee, or attempting to read a long book he may never complete.

Filed Under: Lifestyle Tagged With: 2026 tax law, 529-to-Roth rollover, business tax, financial changes, financial choices, financial moves, Roth, Roth 401k, Roth conversion, Roth conversions, Roth IRA, roth ira conversion, Roth IRA conversion ladder, Tax, tax brackets, taxes

Tax Tips for Tax Time

January 19, 2022 by Jacob Sensiba Leave a Comment

April is fast approaching and soon, everyone will have to visit their accountants and file their taxes. That said, we need to make sure we are filing taxes correctly. Keeping accurate and up-to-date records is important. Here are some tax tips and how to be well-prepared for tax time.

Contribute to retirement accounts

If you haven’t done so yet, or you’d like to contribute more, you have until tax filing day to do so. For a refresher, here are the contribution limits for some IRAs: IRA/Roth IRA – Max contribution is $6,000 ($7,000 if you’re over 50 or older).

If you have a SEP IRA and you get an extension, you have until October 17, 2022, to make your 2021 contribution.

This is more of a tip for the end of the year, but make sure you take your Required Minimum Distributions. For people that are either over 70 ½ or over 72, depending on when you turned those ages, you need to withdraw money from your IRA. If you don’t, you’ll pay a tax penalty of 50% of the amount you should have withdrawn. For example, if your required amount was $10,000. You’ll pay a $5,000 tax penalty if you didn’t take that distribution.

Make a last-minute estimated payment

If you didn’t pay enough or you didn’t make a payment to the IRS for 2021 taxes, you have until you file to make your payment.

According to the IRS rules, you must pay 100% of last year’s tax liability or 90% of this year’s or you will owe an underpayment penalty.

Get tax docs in order

Get all of your tax documents in order. For earnings for the year, you’ll need one to several forms, depending on what you do for a living and how your business is set up. W2s are pretty common. If you’re an independent contractor, you’ll need 1099. 

Itemize your deductions

Most people will take the standardized deduction, which is $12,550 for single filers and $25,100 for married couples filing jointly.

However, if you are self-employed or you have a lot of expenses that are tax-deductible, itemize your deductions. You could save a lot more money IF your total itemized deductions are larger than the standardized deduction.

Home office tax deduction

With the move to work from home still taking place, it might make sense to take advantage of the home office tax deduction. Here are some of the rules:

  • You must use the space exclusively for business
  • Expenses related to the space used for business are tax-deductible but need to be calculated according to the amount of square footage used for business
  • A lot of taxpayers stay away from this deduction, as they think it’s a red flag for an audit. If you’re legitimately using the space as you say and you aren’t fabricating numbers, then you have nothing to worry about

Last-minute tax tips for tax time

Triple-check your work if you prepared your own taxes and file on time. If you’re having someone prepare your taxes on your behalf, make your appointment ASAP because their calendars will fill up really fast.

Related reading:

Tax Tips for Small Business Owners

Are You Ready for Tax Time?

Why Financial Literacy is Important

Disclaimer:

**Securities offered through Securities America, Inc., Member FINRA/SIPC. Advisory services offered through Securities America Advisors, Inc. Securities America and its representatives do not provide tax or legal advice; therefore, it is important to coordinate with your tax or legal advisor regarding your specific situation. Please see the website for full disclosures: www.crgfinancialservices.com

Jacob Sensiba
Jacob Sensiba

Jacob Sensible is a financial advisor with decades of experience in the financial planning industry.  His journey into finance began out of necessity, stepping up to support his grandfather during a health crisis. This period not only grounded him in the essentials of stock analysis, investment strategies, and the critical roles of insurance and trusts in asset preservation but also instilled a comprehensive understanding of financial markets and wealth management.  Jacob can be reached at: jake.sensiba@mygfpartner.com.

mygfpartner.com/jacob-sensiba-wisconsin-financial-advisor/

Filed Under: money management, Personal Finance, Small business, Tax Planning, tax tips Tagged With: business tax, Income tax, Retirement, Tax, tax deductible, tax filing, tax planning, tax tips, taxes

Are Business Gifts Tax Deductible?

January 20, 2021 by Jacob Sensiba Leave a Comment

How do you strengthen relationships with customers and/or business partners? A tried and true way is using gifts. However, gifts cost money, so the next question is, are business gifts tax deductible?

The straight answer is yes, but it’s much more nuanced than that.

There are limitations

Business gifts are tax deductible, up to a certain dollar amount. You can deduct no more than $25 of the cost of the gift you give to each person through the course of the year.

Incidental costs such as engraving, packaging, and shipping are not included in the $25 limit as long as it doesn’t add substantial value to the gift.

Gifts that cost $4 or less are not included in the $25 limit IF the company name is permanently placed on the item and the gift is widely distributed.

Entertainment

Any item that can be considered a gift or entertainment is usually considered entertainment and is deducted at 50% of the value of the gift. For purchases that fall under both categories, use the “gift deduction” on lower-cost items and the “entertainment deduction” on items larger than $50.

Gifts to others

If you and your spouse give gifts to the same person, you’re treated as one taxpayer. The same rule applies to partnerships.

Gifting to a customer’s family counts as a gift to that customer, unless the customer’s family member(s) is a client as well.

The $25 limit only applies to gifts given to individuals. Gifts given to other companies, generally, don’t apply and are fully tax deductible.

Gifts to employees are taxable compensation.

Other relevant information

Keep adequate documentation that includes the purpose of the gift, what was spent, the date of purchase, and the business relationship.

Gifts given to a 501(c)3 non-profit are tax-deductible. Up to 25% of taxable income for a corporation.

A large majority of the information I have listed above came from the IRS publication about “Gift taxes”.

Related reading:

Some Often Overlooked Tax Deductions for Business Owners

 

**Securities offered through Securities America, Inc., Member FINRA/SIPC. Advisory services offered through Securities America Advisors, Inc. Securities America and its representatives do not provide tax or legal advice; therefore, it is important to coordinate with your tax or legal advisor regarding your specific situation. Please see the website for full disclosures: www.crgfinancialservices.com

Jacob Sensiba
Jacob Sensiba

Jacob Sensible is a financial advisor with decades of experience in the financial planning industry.  His journey into finance began out of necessity, stepping up to support his grandfather during a health crisis. This period not only grounded him in the essentials of stock analysis, investment strategies, and the critical roles of insurance and trusts in asset preservation but also instilled a comprehensive understanding of financial markets and wealth management.  Jacob can be reached at: jake.sensiba@mygfpartner.com.

mygfpartner.com/jacob-sensiba-wisconsin-financial-advisor/

Filed Under: business planning, Small business, Tax Planning, tax tips Tagged With: business tax, gift tax, Tax, tax deductible

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