Roth Conversions for a Smarter Retirement
Answering listener questions about how they can make smarter use of Roth accounts and tax-efficient retirement strategies and how they can think about reducing future RMDs. The post Roth Conversions f...
Retirement income can be subject to taxes depending on the specific type of retirement account or benefit you receive and your tax bracket. Here are a few examples of common types of retirement income and how they may be taxed:
1. Social Security benefits: Social Security benefits are generally taxable if you have other substantial income in addition to your benefits. The amount of tax you pay on your benefits depends on your taxable income and tax filing status.
2. Traditional Individual Retirement Account (IRA) and 401(k) withdrawals: Withdrawals from traditional IRAs and 401(k)s are generally taxed as ordinary income at your current tax rate.
3. Roth IRA withdrawals: Withdrawals from Roth IRAs are generally tax-free if you are over the age of 59 1/2 and you have held the account for at least five years.
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Answering listener questions about how they can make smarter use of Roth accounts and tax-efficient retirement strategies and how they can think about reducing future RMDs. The post Roth Conversions f...
Looking for a great retirement destination? Oregon has no sales tax, no state tax on your Social Security, highly rated health care and a temperate climate.
Robert Skinner II emphasizes high-conviction investing, tax efficiency and disciplined decision-making during volatile markets.
Instead of treating your Roth IRA as "the best account" for everything, consider keeping these seven assets in accounts with better tax benefits or flexibility.
Learn how CalSavers applies to California workers and employers, including automatic Roth IRA enrollment, payroll deductions, and benefits. The post How CalSavers Works: What California Workers and Em...
The contribution order for retirement accounts can affect how much your money compounds tax-free. Here’s how to prioritize for tax efficiency. The post The Retirement Account Contribution Order: Get M...
A listener asks about a spendthrift trust for his adult "airhead" granddaughter. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through thei...
What will you have: benefit cuts or tax hikes? Maybe a little of each. Here is what six potential solutions to the system’s bankruptcy would do to you.
What are Passive Income Generators (PIGs) and Passive Activity Losses (PALs), and how do they interact with each other on your tax bill? The post Using Passive Income Generators (PIGs) to Offset Passi...
Women should personalize their Social Security claiming strategy and run the numbers after considering life expectancy, tax situation and existing assets.
Choosing the best way to withdraw retirement funds depends on which paycheck system aligns with your lifestyle, tax plan and shifts in spending as you age.
Dream of a fabulous retirement? How to actually build a $10 million 401(k) from a top wealth manager all while saving taxes and building finanical freedom.
The Rule of 55 allows certain workers to take penalty-free withdrawals from a 401(k) or 403(b) if they leave their job in or after the year they turn 55. Income taxes still apply, and the funds must r...
Why is it so important that both partners in a relationship understand their tax situation, even if they’re not the ... Read more
Let's break down the disability insurance premium payment setups and show how each one could impact the tax status of disability checks. The post Are Disability Benefits Taxable? What Doctors Actually...
Older founders are three times more likely to succeed than 30-year-olds. Here's how to leverage your expertise while navigating the "Medicare gap" and self-employment taxes.
Last year’s tax bill created a new savings vehicle that starts as early as birth – the Trump account. While these accounts resemble IRAs in some ways, they offer distinct contribution rules, investmen...
From spousal and child benefits to taxes and timing, these 20 lesser-known Social Security rules can significantly impact your retirement income.
In this week's Ask the Editor Q&A, Joy Taylor answers questions on monthly Medicare premiums, IRAA and tax-deductible medical expenses.
Matt Wilson, Keen Wealth's Chief Investment Officer and President, recently hosted an excellent webinar on Tax Planning Through the Four Stages of Retirement. In addition to providing a thorough overv...
This retirement planning approach simplifies your decisions, improves your tax efficiency and provides you with peace of mind. This is how it works.
It’s natural to want to share your retirement nest egg with family. Learn how to give generously without putting your own financial security or tax bracket at risk.
My wife and I met with our CPA today to sign our 2025 tax forms. During our conversation, I asked him how much we could convert from my traditional IRA to my Roth IRA, without bumping us into a higher...
Or: Why you don't need to keep tax returns from your 20s and 30s.
A growing number of retirees have been paying federal tax on their benefits. A new $6,000 per person senior deduction reduce taxes for some seniors, but doesn’t change the way Social Security is taxed...
Being a top earner is relative: Why trading a high-tax zip code for a low-cost state is the ultimate retirement power move.
A resilient retirement plan is a flexible framework that addresses income, health care, taxes and investments. And that means you should review it regularly.
What are Trump Accounts? This guide explains new 530A child investment accounts, including eligibility, the $1,000 Treasury deposit and key tax rules.
Legacy planning integrates your values and stories with legal and tax strategies to ensure your influence benefits loved ones and good causes after you're gone.
For real retirement security, forget about chasing returns and focus instead on the things you can control: income, taxes, risk-taking and decision-making.
Happy 2026! Get the updated FAANG FIRE Cheat Sheet with new 401k limits ($24.5k), tax brackets, and triple paycheck dates.
We have some fun news to share at the end of this article, so keep reading to the end find out! Over the holiday break, I was helping a family member do some end-of-year tax planning (I know, we’re TH...
Retiring after age 65 changes the math and the priorities. You have fewer high-energy years, shorter tax planning windows, and RMDs much closer than most people realize. But you also often have higher...
2026 brings changes to your 401(k) cathc up contributions. Ignoring these changes could get you in trouble with the IRS or cause a suprise tax bill.
Wealthy retirees often overlook Social Security. But timed properly, it can drive tax efficiency, keep Medicare costs in check and strengthen your legacy.
Under new rules, you may lose an up-front deduction but gain tax-free income once you retire.
Saving a large percentage of your income, minimizing taxes and keeping spending in check can offer a more realistic path to retiring rich.
As 2025 draws to a close, take time to review your finances, maximize tax efficiency and align your goals for 2026 with the changing financial landscape.
A 23% benefit cut, retroactive payments, and new tax rules may impact when you should claim Social Security. These five factors can help you rethink your timing.
Medicare premiums and taxes can shrink Social Security benefits. Plan ahead to protect retirement income.
Roth conversions can save thousands in taxes, but they can also trigger Medicare IRMAA surcharges that quietly add up to more than $5,000 a year. Most retirees never see it coming, because the rules f...
Larry and Barbara Cook thought they were helping government agents. In the end, they found themselves victims of tax and Medicare gotchas, as well as the scammers.
In January, new Roth catch-up rules will prevent workers over 50 who earned more than $150,000 the prior year from making pre-tax catch-up contributions to their 401(k).
Jeremy Keil explores 7 money moves you can consider before the new year to lower your taxes and keep more of your money in retirement. Every December, people scramble to finish holiday shopping, trave...
Year‑end planning is critical for wealthy families, in order to preserve wealth, minimize taxes, and grow wealth. Review these key financial planning ideas before 2026.
With the tax-free money in a health savings account, a person can pay for eyeglasses or medical exams, as well as a $1,700 baby bassinet or a $300 online parenting workshop. Those same dollars can’t b...
Explore how Trump accounts compare to baby bonds, why tax policy favors wealthy families, and what economists propose to close the racial wealth gap.
As 2025 wraps up, now may be the perfect time to tighten up your finances and set yourself up for a stronger year ahead. These 12 year-end money moves may help you save more, lower your tax bill, and ...
What if you could employ gift giving strategies that benefit the receiver and also provide the giver significant strategic financial and tax planning advantages? The post The Unexpected Gifts of Givin...
About 10 years ago, I tried logging onto SSA.gov to check my Social Security benefits. You would think after decades of paying FICA taxes (6.2% for SS, 1.45% for Medicare), the government might make i...