The Roth IRA Conversion Ladder Dilemma - Route to Retire (2024)

The Roth IRA Conversion Ladder Dilemma - Route to Retire (1)

I’ve been a bit moody the past couple of weeks. I’ve been focusing a lot on trying to pinpoint our exact retirement date and I’ve been struggling. The problem all stems from the Roth IRA Conversion Ladder we plan to do.

First off, if you’re on the path to FIRE (Financial Independence/Retire Early) and you’re not familiar with how a Roth IRA Conversion Ladder works, this could be important to you.

It’s not the end-all-be-all solution, but the ladder is a method that many early retirees are able to use to make FIRE actually happen.

You see, normally you don’t have access to your traditional 401(k) and other retirement accounts until 59½. This is a problem for young whippersnappers trying to get out of the rat race once they have enough money to call it quits for good.

Yes, you can pull the money out of your retirement accounts before that age, but you’re going to be pummeled with a 10% penalty on top of the taxes. And in some cases, that 10% penalty might actually be an acceptable loss for your plan, but these circ*mstances aren’t very common.

So how the heck can we get to our money as an early retiree?

Enter the Roth IRA Conversion Ladder…

Roth IRA Conversion Ladder

The Roth IRA Conversion Ladder Dilemma - Route to Retire (2)

The Roth IRA Conversion Ladder is a method of getting your money out of your traditional accounts using a little bit of a workaround. This is completely legal to do, but the method involves a little planning.

Keep in mind, there are other ways to pull your money out of your retirement accounts at an earlier age, such as the Rule of 72(t), but we’ll save that for a different post. These other methods have some pros and cons, but they don’t fit as well into most scenarios.

The Roth IRA Conversion Ladder starts with you rolling over your 401(k) into a traditional IRA once you leave your job. So far, so good – no taxes or penalties to worry about.

Once that’s done, you move your money into a Roth IRA. Here’s where things get a little trickier though.

Moving your money into your Roth IRA is considered to be a conversion by the IRS and will trigger you to be taxed on it as income. This is why you shouldn’t move it all at once. The idea behind the conversion ladder is that you move it in smaller increments to keep the taxes low.

This money is considered extra income, so if you do this while still working, it will likely leave you with a nice bill at tax time. However, if you’re now done working, these smaller amounts should keep you in a lower tax bracket.

The idea is to convert an amount you need to cover your annual expenses… say $40k.And guess what? No 10% penalty for this conversion… woo-hoo! You’ll pay taxes on it, but as I write this in 2017, it’ll keep you in a15% bracket if you’re married. If you’re single, you might want to look at getting that number down to$37,950 to get you in the same bracket.

So you’re set, right? Now you can start pulling out that money and using it, right? Not so fast bucko!

The IRS doesn’t want to encourage people to do this, so that money is considered a conversion for the first five years. In other words, it needs to sit in your Roth IRA for five years before you can pull it out of there.

After that, it will now be recognized by the IRS as a contribution. And if you’re familiar with Roth IRA accounts, you already know you can pull out contributions from a Roth at any point in time with no penalty.

So, the ladder part of the Roth IRA Conversion Ladder comes from doing increments like this every year. Every year for the first five years, you’ll be converting money but not withdrawing anything.

In your sixth year though, you can now withdraw your first-year conversion amount. In your seventh year, you can pull on the second-year conversion amount. And so on.

Here’s a quick table to give you an idea of what this looks like. For this example, we’ll assume a withdrawal of $40k and then up that amount yearly to account for a 3% inflate rate…

YearAmount to ConvertAmount to Withdraw
2020$40,000.00$0.00
2021$41,200.00$0.00
2022$42,436.00$0.00
2023$43,709.08$0.00
2024$45,020.35$0.00
2025$46,370.96$40,000.00
2026$47,762.09$41,200.00
2027$49,194.95$42,436.00
2028$50,670.80$43,709.08
2029$52,190.93$45,020.35
2030$53,756.66$46,370.96

And the table could go on and on until you’re out of money in your IRA or until you reach 59½. At that age, you can skip the Roth IRA if desired and take your normal distributions (which will still be taxed).

Freebie! I created a spreadsheet to help you see the flow of how a Roth IRA Conversion Ladder works. I initially created it to help me visualize how the conversion would work for us. However, I think it would provide some good value to you as well. I’ll send you this and a number of other valuable resources I’ve been working on just for jumping on my mailing list…

My Dilemma

The Roth IRA Conversion Ladder Dilemma - Route to Retire (3)

So now that you know how the Roth IRA Conversion Ladder works, it’s time for me to get a little personal.

We’ve been building up our funds at a rapid pace lately. In fact, we now have enough money set aside to be considered financially independent if we take the plunge. This is assuming we move to Panama, which has a much lower cost of living.However, we have one teensy, weensy problem…

Our money isn’t allocated correctly in the right buckets for our situation. In other words, our taxable accounts are low – too low.

I’ve mentioned before that the 401(k) plan at my job offers a good match of 35 cents on the dollar invested with no max up to the federal limit. To put it another way, before I even make anything in the stock market, my dollar gets a 35% return.

I don’t have easy access to an investment that can give me that kind of return, so I max out my 401(k) plan every year.

Then there’s my HSA account– the ultimate retirement account. Tax-free contributions, tax-free growth, and tax-free distributions (when used for medical). Add in the ability to “beat the system”, along with my company’s contribution, and it’s hard not to max this one out as well!

Look, I make a decent living, but maxing out both these accounts is a fair amount of my salary. Somehow though (I feel like we save everything!), I’m maxing out my Roth IRA since that’s another tax-advantaged account.

After all is said and done, that leaves me with small potatoes to put into our savings. And what we save there, I tend to want to use as down payments on rental properties.

So here’s the problem…

We’ve built up enough to retire early. However, that 5-year waiting period for our Roth IRA Conversion Ladder to bake means we need to have enough up-front money to live on for that duration. And we don’t. Not even close.

I hate working right now, but I can’t figure out the smartest way to get out of this problem as quickly as possible.

With what we already have saved, I figure we need to come up with another $60-75k.

A Few Ideas

The Roth IRA Conversion Ladder Dilemma - Route to Retire (4)

Sell a rental property – I hate this idea, but we’re just brainstorming, folks – there are no wrong answers! If I sold either of my rental properties, I should have enough to cover that 5-year gap.

The biggest problem though is that we’d be selling off the golden goose. And if you recall, it’s all about the geese andnot the eggs! Once we would exhaust the proceeds from that sale, that would be it – gone forever! I enjoy owning the assets that keep giving us those golden eggs every month.

Take the hit – Another idea I don’t like. I could still do the rollover from my 401(k) after I leave. Then I could take the 10% penalty and start withdrawing money from the traditional IRA.

This is a horrible idea. That 10% would add up quickly and be a tremendous waste of money. And that’s the reason the IRS has it set up this way – they want to discourage people from going down this path.

Cut back on the savings – If I didn’t contribute to my 401(k) or HSA for a while, that would give me more money to sock away.

However, these are accounts that you should max out if possible because they help bring down your adjusted gross income. Not contributing would backfire as I would likely end up losing a portion of the money I saved to the taxman.

The Date

The Roth IRA Conversion Ladder Dilemma - Route to Retire (5)

Those ideas above suck and I don’t want to go down any of those paths, so I’ve decided that I’ll just suck it up and keep on working and saving. This isn’t set in stone, but I think that I can wrap things up at the end of 2019.

This will only work if we move to Panama, which is still the plan as of now. This is definitely a tricky one though since our daughter is currently in the 2nd grade.

Right now, she’s game for giving this a shot, but the longer we wait, the harder it’ll be. She’ll start making friends at school and won’t want to leave them.

If I wrap up working at the end of the year in 2019, I can start my Roth IRA Conversion Ladder in January 2020. We’ll stay where we’re at and let our daughter finish out the 4th grade in the spring.

After that…¡Adiós muchachos!

Relief

The Roth IRA Conversion Ladder Dilemma - Route to Retire (6)

Not having a finite plan mapped out was really weighing on my mind. I struggled to sleep for a number of nights and was a pain at both work and home to be around (sorry all!).

I’m excited to get something more concrete going. I’m not thrilled to have to put in more work time, but I still consider us to be blessed in our situation. Our hard work should pay off soon.

If you’re new to the FIRE path and plan on using the Roth IRA Conversion Ladder, don’t put yourself in the position I did. Focus on building up your taxable accounts as well so you don’t get stuck like I did!

Have you used or considered using Roth IRA Conversion Ladder as part of your path to early retirement?

Thanks for reading!!

— Jim

The Roth IRA Conversion Ladder Dilemma - Route to Retire (2024)

FAQs

What is the Roth conversion ladder for retirement? ›

A Roth IRA conversion ladder is a multiyear strategy that allows you to tap your retirement account without penalty before reaching age 59½. When you do a Roth IRA conversion, you must wait five years to withdraw the converted amount to avoid a 10% tax hit.

Do Roth conversions make sense for retirees? ›

In its simplest form, the decision in favor or against a Roth Conversion can be boiled down to one question: Are you paying a lower tax rate now than you will be in retirement? If yes, there's a good chance that conversions make sense. If not, a conversion likely does not make sense.

At what age should I stop doing Roth conversions? ›

However, there are no limits on conversions. A taxpayer with a pre-tax IRA can convert any amount of funds in a year to a Roth IRA. Roth IRAs also are exempt from required minimum distributions (RMDs). These mandatory withdrawals from retirement accounts begin at age 72 and can create a tax burden on affluent retirees.

Are Roth IRA conversions going away? ›

While it doesn't look like they'll be eliminated in 2024, the future of the Backdoor Roth IRA remains a target of proposed legislation. Some legislative efforts have already been taken to limit Roth IRAs or to change tax brackets and RMDs in the future.

What are the pitfalls of Roth conversions? ›

Since a Roth conversion increases taxable income in the conversion year, drawbacks can include a higher tax bracket, more taxes on Social Security benefits, higher Medicare premiums, and lower college financial aid.

What is the 5 year rule for Roth conversions? ›

This rule for Roth IRA distributions stipulates that five years must pass after the tax year of your first Roth IRA contribution before you can withdraw the earnings in the account tax-free. Keep in mind that the five-year clock begins ticking on Jan. 1 of the year you made your first contribution to the account.

At what age does a Roth IRA not make sense? ›

Even when you're close to retirement or already in retirement, opening this special retirement savings vehicle can still make sense under some circ*mstances. There is no age limit to open a Roth IRA, but there are income and contribution limits that investors should be aware of before funding one.

What is the sweet spot for a Roth conversion? ›

After you stop working, but before you start required withdrawals from retirement accounts, is “the sweet spot” for Roth conversions, according to JoAnn May, a Berwyn, Illinois-based certified financial planner at Forest Asset Management.

How to avoid taxes on Roth IRA conversion? ›

This is because a five-year waiting period is required if you are under age 59 1/2 before you can distribute the converted amount without owing the 10% additional tax. The longer the assets in the Roth IRA can be left untouched, the greater the benefit of tax-free earnings potentially accumulating.

What is the loophole for Roth conversion? ›

Although opening a "backdoor" Roth IRA may sound shady, don't let the name mislead you. It's a totally legal loophole. At its core, a backdoor Roth IRA is a simple conversion: You put money into a traditional IRA or 401(k), then convert it to a Roth IRA.

Can you take your RMD as a Roth conversion? ›

Can an RMD Be Converted to a Roth IRA? No, your RMD can't be converted to a Roth IRA. The IRS mandates that you first take the RMD for the year before you can perform a Roth conversion. The RMD amount is considered a taxable distribution and is not eligible for conversion.

Should I do a Roth conversion when the market is down? ›

Roth IRA Conversions When Stocks Are Down

You'll owe tax on any funds you convert, so a stock market downturn could make a conversion more appealing, as you'll pay tax on less money.

Is a Roth conversion ladder worth it? ›

The Roth conversion ladder is particularly advantageous in several scenarios: Lower Income Years: If you expect to have years of lower income—perhaps early in retirement or during a career break—these are ideal times for conversions since your tax rate may be lower than during your working years or later in retirement.

What is the hierarchy for Roth withdrawal? ›

The order of the distribution of assets is (1) IRA participant contributions, (2) taxable conversions, (3) non-taxable conversions, and (4) earnings. Roth ordering rules only apply when a withdrawal from an account is a non-qualified distribution.

How to execute a Roth conversion ladder? ›

How to set up your Roth Conversion Ladder
  1. Start by rolling over your 401k into a Traditional IRA. ...
  2. The next step is to transfer some funds from the traditional IRA account into a Roth IRA. ...
  3. Next comes patience. ...
  4. Finally, withdraw the money you converted like an old friend you haven't seen for five years.

What is the standard deduction for the Roth ladder? ›

$14,600 is your standard deduction, so you'll pay no tax on your 401(k) > Traditional IRA > Roth IRA conversion chunk. $47,025 is the upper limit for the 0% tax bracket for capital gains taxes on withdrawals of growth from a taxable account.

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