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Learn how to keep more of your retirement income through tax planning in step 3 of the 5 step retirement plan.
When people think about retirement planning, they usually focus on two big questions: How much do I need to spend? and How much will I make in retirement? Those are important, but there’s a third question that often gets overlooked—and it could make or break your plan: How much of your money do you actually get to keep?
That’s what Step 3 of creating your retirement master plan is all about: keeping more of your hard-earned money through smart tax planning.
During your working years, your income is pretty straightforward. You earn a salary, and taxes get withheld from your paycheck. In retirement, things look very different. You now have more control than ever before over what your tax bill will look like. That’s because you can decide when and how to pull money from your accounts.
Two factors play the biggest role here:
Making smart decisions with timing and type could mean saving thousands of dollars in unnecessary taxes over the course of your retirement.
Here’s a simple example: if you withdraw money on December 31st versus January 1st, that income falls in two completely different tax years. Just a week’s difference could completely change your tax outcome.
But timing isn’t just about the calendar—it’s about your retirement phases:
Every one of these milestones creates “before and after” windows where your tax planning can make a huge impact. If you’re not planning around these, you might end up paying more than you need to.
Not all withdrawals are created equal:
The key is mixing and matching withdrawals across these account types in a way that minimizes taxes now and later.
If there’s one strategy that makes the biggest difference in retirement, it’s Roth conversions. Converting part of your traditional IRA into a Roth lets you pay taxes now (often at a lower rate) in exchange for withdrawals later.
But there are three big myths I hear all the time:
This is what I call the Golden Rule of Roth Conversions: choose the right year and the right amount. Get that right, and you could save tens of thousands of dollars. Get it wrong, and you might pay unnecessary taxes you can’t undo.
I worked with a couple who had room to do Roth conversions while staying in the 24% tax bracket. We created a plan to spread their conversions out over three years. But they decided to convert everything at once, thinking it wouldn’t matter.
Unfortunately, it did matter. Instead of keeping their conversions at the 24% tax bracket, much of their income spilled into the 32% and even 35% bracket. The result? I estimate they paid $23,000 more in taxes than they needed to.
That’s why timing and amount are so important. Tax planning in retirement isn’t a yes-or-no decision. It’s about making the right move at the right time.
At the end of the day, Step 3 of your Retirement Master Plan is all about keeping more of what you’ve worked so hard to save. Taxes are one of your biggest expenses in retirement, but with careful planning, you can reduce their impact and free up more money to spend, share, and enjoy.
If you’d like to dive deeper into this, check out my book Retire Today: Create Your Retirement Master Plan in 5 Simple Steps, or head over to JeremyKeil.com to learn more.
Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!
Subscribe to Retire Today to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337
Spotify Podcasts: https://bit.ly/RetireTodaySpotify
Additional Links:
Connect With Jeremy Keil:
Media Disclosures:
Disclosures
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
Additional Important Disclosures
By Jeremy Keil4.9
5656 ratings
Learn how to keep more of your retirement income through tax planning in step 3 of the 5 step retirement plan.
When people think about retirement planning, they usually focus on two big questions: How much do I need to spend? and How much will I make in retirement? Those are important, but there’s a third question that often gets overlooked—and it could make or break your plan: How much of your money do you actually get to keep?
That’s what Step 3 of creating your retirement master plan is all about: keeping more of your hard-earned money through smart tax planning.
During your working years, your income is pretty straightforward. You earn a salary, and taxes get withheld from your paycheck. In retirement, things look very different. You now have more control than ever before over what your tax bill will look like. That’s because you can decide when and how to pull money from your accounts.
Two factors play the biggest role here:
Making smart decisions with timing and type could mean saving thousands of dollars in unnecessary taxes over the course of your retirement.
Here’s a simple example: if you withdraw money on December 31st versus January 1st, that income falls in two completely different tax years. Just a week’s difference could completely change your tax outcome.
But timing isn’t just about the calendar—it’s about your retirement phases:
Every one of these milestones creates “before and after” windows where your tax planning can make a huge impact. If you’re not planning around these, you might end up paying more than you need to.
Not all withdrawals are created equal:
The key is mixing and matching withdrawals across these account types in a way that minimizes taxes now and later.
If there’s one strategy that makes the biggest difference in retirement, it’s Roth conversions. Converting part of your traditional IRA into a Roth lets you pay taxes now (often at a lower rate) in exchange for withdrawals later.
But there are three big myths I hear all the time:
This is what I call the Golden Rule of Roth Conversions: choose the right year and the right amount. Get that right, and you could save tens of thousands of dollars. Get it wrong, and you might pay unnecessary taxes you can’t undo.
I worked with a couple who had room to do Roth conversions while staying in the 24% tax bracket. We created a plan to spread their conversions out over three years. But they decided to convert everything at once, thinking it wouldn’t matter.
Unfortunately, it did matter. Instead of keeping their conversions at the 24% tax bracket, much of their income spilled into the 32% and even 35% bracket. The result? I estimate they paid $23,000 more in taxes than they needed to.
That’s why timing and amount are so important. Tax planning in retirement isn’t a yes-or-no decision. It’s about making the right move at the right time.
At the end of the day, Step 3 of your Retirement Master Plan is all about keeping more of what you’ve worked so hard to save. Taxes are one of your biggest expenses in retirement, but with careful planning, you can reduce their impact and free up more money to spend, share, and enjoy.
If you’d like to dive deeper into this, check out my book Retire Today: Create Your Retirement Master Plan in 5 Simple Steps, or head over to JeremyKeil.com to learn more.
Don’t forget to leave a rating for the “Retire Today” podcast if you’ve been enjoying these episodes!
Subscribe to Retire Today to get new episodes every Wednesday.
Apple Podcasts: https://podcasts.apple.com/us/podcast/retire-today/id1488769337
Spotify Podcasts: https://bit.ly/RetireTodaySpotify
Additional Links:
Connect With Jeremy Keil:
Media Disclosures:
Disclosures
This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.
The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past performance is no guarantee of future results.
Legal & Tax Disclosure
Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.
Advisor Disclosures
Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.
Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.
The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.
Additional Important Disclosures

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