Tax Strategies

Deductible Investment Interest

I'm using FreeTaxUSA, and I'm offered the Deductible Investment Interest. Setting aside (or not!) how this ever made it into the tax code, does anyone know how to take advantage of it with interest rates where they are today? Here's the description: > Deductible investment interest is interest paid on margin accounts or interest paid on loans used to buy or carry investments. For example, if you get a margin loan through your brokerage account and use it to buy more stocks, then the interest you...

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amberp

9 minutes ago 3 Share

Federal Tax Visualization

I came across this very neat online tool from [engaging-data dot com](https://engaging-data.com/tax-brackets/) to visualize Federal taxes owed. As you play with the inputs, you can very easily see the dramatic differences in tax between income from LTCG and qualified dividends (in blue) versus ordinary income and unqualified dividends (in green). In the snapshot below, a single filer in 2026 has income of $80K yet pays only $3,587 in Federal tax (in red)—a 4.5% effective tax rate.

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BostonFI

9 minutes ago 3 Share

Taxes in Year 1 of Retirement

I’m retiring from my W2 job in Q2 2027 and am reading up on estimated taxes to prepare. Am I correct that because I’ll have W-4 withholding in 2027 up until my retirement date, I’m exempt from needing to hit any of the usual quarterly estimated tax payment targets (25% of the year’s required payment by April 15, 50% by June 15, 75% by Sept 15, and 100% by Jan 15 of the following year)? I plan to do Roth conversions each year in retirement but wait until Q4 to do them so that I can adjust the siz...

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BostonFI

9 minutes ago 11 Share

My Tax Strategy

**Intro** I currently have a local government job where my salary is 82k and I max out 401k, 457b, HSA (with small employer contribution). Plus I contribute to a pension account I control instead of Social Security. I work some part time jobs also to make some extra money. I live in my SUV to keep my normal monthly expenses super low. All legal tax strategy… I keep the most of my money! The entire plan is to basically save 100% of my money from main job and live off of part time jobs. I want to...

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J.P. MoreGains

9 minutes ago 7 Share

Opening a Traditional IRA?

Hi FI friends, I am new to the community I have been tuning in for about a month or so now. I was considering opening a Traditional IRA to reap the tax deduction benefits. My employer doesn't offer a 401k, we only have profit sharing which I cannot contribute to. I currently have a Roth IRA and have been saving money for a few years now, I have about 15k saved in there. If I were to open a Traditional IRA, should I just contribute to that instead of my Roth from now on and convert later down the...

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Victor Zarour

9 minutes ago 11 Share

Too Much Roth? Wondering after listening to Ep 583

I have listened to a bunch of episodes now of the choose fi podcast. I have been bouncing around episodes and I just landed on the Incremental Gains and the detour episode (582 & 583). I love them as rapid (ish) fire points, but the Detour episode had me scratching my head to some extent. For Context: I am a firefighter and my wife has a more normal job. We are both 36 years old. I have been contributing to my 457 since I started my job ten years ago. These contributions have been all Roth, and...

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fishinphil57

1 day ago 19 Share

Tax Loss Harvesting with M1 Finance

After reading Brad's weekly update about tax loss harvesting I am considering taking advantage of the recent market downturn in my brokerage account. I hold my brokerage at M1 Finance, which uses "pies" to automate deposits and dividends etc. Currently, my pie is 100% VTI. I would like to sell some of my shares to lock in a loss to utilize for my 2026 taxes, but I am unsure how to do with with M1's platform. Does anyone have any insight into how to accomplish this? One potential solution would b...

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Patrick Gilbert

6 days ago 3 Share

529 unused funds and taxes for non qualified WD

I have 1 child who is no longer going to use the funds for college. I have transferred some of the account over to her ROTH and was going to take the rest and put in my individual account with Fidelity but would be paying taxes on $7,000 (and the 10% penalty). Wondering if there any work arounds or suggestions for this? Thanks.

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wendyneal1

1 week ago 7 Share

Spreadsheet from Cody & Sean's book?

Hi everyone! In their book "Tax Planning to and through Early Retirement," Cody Garrett & Sean Mullaney mention creating a spreadsheet in chapter 36 to track cap gains/losses for EOY tax planning, deciding whether to do a Roth conversion, etc. Has anyone already created a spreadsheet like this that they would be willing to share? They also mention current year tax planning software for this same purpose. Any recommendations? We are retiring in May and this part of retirement feels foggy to me- I...

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Charlotte

2 weeks ago 9 Share

How to minimize taxes and taxable income on RMD from inherited IRA?

My mother passed away and left me her IRA. Now I have to withdraw the account to zero in ten years, but I have two more years to pay off my federal student loans on an income-based repayment plan. How do I minimize my income to keep my monthly student loan payments from exploding while also trying to spend down the IRA?

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Anonymous

3 weeks ago 10 Share

𝘾𝙡𝙪𝙢𝙥𝙞𝙣𝙜: 𝘼𝘾𝘼 𝙄𝙣𝙨𝙪𝙧𝙖𝙣𝙘𝙚 𝙋𝙧𝙚𝙢𝙞𝙪𝙢𝙨

Some of you may be aware of a tax strategy known as 𝗖𝗹𝘂𝗺𝗽𝗶𝗻𝗴. Clumping is where you intentionally pay a bill in December that isn't technically due until January. The IRS allows clumping for an expense like interest payments or property taxes if you have already been billed and you choose to pay the bill before the due date. You cannot deduct expenses paid early that are not yet considered due. (Paying too early can result in you not being able to deduct that payment at all!) This definition can...

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Joel Corley

3 weeks ago 0 Share

Don't Forget to Claim State Tax Exemption for US Gov Securities

Filing your 2025 taxes? Don’t forget to claim the state tax exemption for interest and ordinary dividends earned from US government securities. Interest and ordinary dividends from US gov securities like treasuries and T-bills are taxable at the federal level but are exempt from state tax in most states. Many money market funds, ETFs and mutual funds derive some of their ordinary dividends from US gov securities. You’ll need to calculate the portion of your total ordinary dividends that came fro...

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BostonFI

3 weeks ago 1 Share

Tax on Tip Income

Hello, Is tip income that qualifies under the new tax bill considered above the line or below the line? ChatGPT, Copilot, and Gemini says it's above the line while Perplexity says it's below the line. I haven't found a clear answer going to the IRS. Thanks

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PizzaFiGuy

3 weeks ago 2 Share

Standard Deduction

Does standard deduction apply to dividends and interest?

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CreatingMarina

3 weeks ago 3 Share

Tax Loss Harvesting....

With current market volatility, I would like to capture losses with recent investments to offset my dividends/income. Where can I get more information on TLH (within Vanguard), documenting the losses for tax reporting purposes for the year, forms needed for 2026 tax prep to show losses for accountant and moving the losses forward should they exceed the $3,000 yearly limit? Thank you for any information I can get.

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Anonymous

3 weeks ago 9 Share

ADP Withdrawal 401 (k)

Hi everyone, long time lurker to the ChooseFI group and now I have my first personal question in regards to my finances. So last year I fully funded my 401 (k) for the first time and was really proud about that accomplishment. However, last week I noticed a large withdrawal from my 401 (k) - which is with Fidelity if that matters. I called right away in regards as to why that might be. I was told my corporate employer failed ADP testing and I would have to take forcible withdrawal from my 401 (k...

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Badger6117

3 weeks ago 5 Share

Full Traditional IRA Deduction vs. Low Effective-Tax Roth IRA

I feel pretty settled on my FI strategy overall, but one area I can’t quite reconcile is whether I should take the full Traditional IRA deduction (which I am eligible for) or instead accept a very low effective tax rate (~6%) and contribute to a Roth IRA. What feels paradoxical to me is that in order to qualify for the full Traditional IRA deduction, your AGI must already be relatively low — which often means you are paying low effective tax, a situation that (by non-FI conventional thought) usu...

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NickCincyFI

1 month ago 12 Share

S Corp

My husband and I both run our own small businesses (both single member LLCs) in two different industries farrier and personal trainer. Our CPA has recommended electing as a S Corp to help with self employment tax and that would should combine our businesses into one so we only need to file once instead of two separate filings. I'm curious if anyone has any experience or thoughts on this and then does that put both businesses at risk unnecessarily by combing them? I've also heard that I could sta...

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SpiceSorcerer

2 months ago 6 Share

Roth distribution and taxes

Hi ChooseFI community, I am struggling with a tax issue and thought I would see if anyone has additional thoughts. I will try to explain succinctly. In October of 2024 I received a notification from the IRS that I underreported on my 2022 taxes and owe taxes on a Roth IRA distribution ($35,000 I used towards a down payment on a home) and penalty and interest. I did miss reporting this on my taxes so made an honest mistake. However, I don't believe I owe the $15,000+ dollars the IRS claims I owe....

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abbrenner5

2 months ago 3 Share

457 rollover

Hello, I will be leaving a teaching career shortly after this semester. I have money in a 457 retirement account which I can use to draw on after I leave my employer. I am pretty sure I know the answer but want to be certain that I should leave the money in the 457 custodian rather than roll it over so I have the ability to withdraw earlier than 59 years old. Thanks

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Turizmo23

2 months ago 3 Share