Should I do Roth conversions?

It makes sense to convert pre-tax assets to Roth when you can do so at a lower tax rate than you would be at when required to take distributions from those pre-tax accounts. If you don’t have a significant amount of money in pre-tax accounts, or if your income tax rate in retirement will be at an all-time low, then it may not make sense to convert assets to Roth.

For those who do have a significant amount in pre-tax accounts or have windows of opportunity before distributions start (periods of being in a lower income tax bracket than in retirement), Roth conversions can be a great way to pay less in taxes and can save you tens or even hundreds of thousands of dollars.

How do you know whether or not you should do Roth conversions? First, estimate your taxable income in retirement and your highest marginal tax rate. If you project yourself to be in the 10% or 12% bracket in retirement, there isn’t really any room to convert assets to Roth since there aren’t any lower tax brackets. If you project yourself to be in the 22% bracket, 24% bracket, or higher, are there any years you will be taxed at a lower rate when you have little or no taxable income? If so, those could be great years to convert assets to Roth.

There are a few periods in life where you may have a greater chance to do Roth conversions. Before you begin RMDs or start taking Social Security is one. Your taxable income is lower during this period so it could naturally be an opportunity to convert assets to Roth. If you are able to live on taxable accounts for a period of time, this could be another great opportunity to convert pre-tax assets to Roth. Your taxable income could be $0 if you are retired and living on money from a taxable brokerage account, which has already been taxed. This gives you the chance to convert a substantial amount of assets to Roth at a 10% or 12% federal income tax rate.

You may have an opportunity to turn lemons into lemonade if you were to lose your job. This obviously decreases your income depending on how long you are out of work, but could be a chance to convert pre-tax assets to Roth at a lower tax rate. It is not unusual for the stock market to be down at the same time many Americans are losing their jobs, and converting when the market is down is a great way to get a “discount” on your Roth conversion.

How to do Roth conversions

There are no income limits on Roth conversions (which is what enables the backdoor Roth strategy) and no limits to the amount you can convert each year. In fact, you could convert your entire 401(k) to Roth in a single year even if it was millions of dollars (the IRS would probably prefer it this way since you would pay substantially more in taxes). Converting pre-tax assets to Roth is only a good strategy when you do it the correct, optimal way. Recklessly converting to Roth could end up causing more harm than good.

So what is the “correct” or optimal way? It generally means filling up your lower tax rate buckets with conversions, like your 10% and 12% bucket, but it may not be beneficial to convert at rates of 22%, 24%, or higher, depending on your expected tax rates in retirement. Remember, converting is only worth considering when you can pay a lower tax rate now than you would in retirement.

How you pay the taxes on your Roth conversion can have a big positive or negative impact on your strategy. Whenever possible, you should pay the conversion taxes with outside money, not the money that came out of your pre-tax account. Paying taxes from the funds you are converting means less money going into your Roth account, which means less tax-free growth over time. It could still make sense to do Roth conversions if you don’t have any extra money to pay the taxes, but whenever possible, you should always pay the conversion taxes with outside funds.

There are a couple major mistakes people make when doing Roth conversions. The first is violating the five-year rule and subjecting themselves to unnecessary penalties or taxes. The rules are a bit different depending on your age. If you are younger than 59.5, you must hold the converted principal for five or more years or be subject to a 10% penalty. Any earnings are automatically subject to a 10% penalty and taxes if you withdraw before 59.5, so make sure not to touch those.

If you are older than 59.5, you can take principal or earnings out at any time with no penalty. However, you must wait five years from when you made your first Roth IRA contribution or conversion to withdraw earnings or those will be taxed.

The other big mistake often made when doing Roth conversions is not reconsidering asset allocation. The type of assets you invest in inside of a pre-tax account are substantially different from the optimal investments inside of a Roth account. Since Roth accounts grow tax-free and qualified distributions are entirely tax-free, you want assets that have the most potential for growth inside of your Roth accounts. This doesn’t mean you should change your overall allocation to be riskier, but you should consider shifting risk around to take more in your Roth account and less in other parts of your portfolio.

Converting pre-tax assets to Roth accounts can potentially save you six figures in taxes, but it is only beneficial if you do it the right way. If done incorrectly, Roth conversions could end up causing you to pay more in taxes. Make sure you are always converting at a lower tax rate than you expect to be at in retirement. Whenever possible, pay the conversion taxes with outside money so the full conversion amount goes in your Roth. Know the ins and outs of the five-year rule so you don’t pay any unnecessary penalties or taxes. Reassess your asset allocation after converting and make changes as necessary. If you can do all of that, you can save money on taxes and take larger distributions from tax-free accounts in retirement.

You only get one chance at a successful retirement. Besides the basics like saving more money, what can you do to ensure a successful retirement? What insights can we gain from those who are already retired to better plan our own retirements?

1. Retirement is better than working

The majority of retirees, 67%, are happier on a typical day in retirement than they were on a typical day while working. Of the 33% who are not happier in retirement, about half say they are lonely. It’s no secret that loneliness is a leading cause of unhappiness and depression in older Americans, and having a network of family and friends that you regularly see can help ward off loneliness in retirement. Consider living in a community where many of your neighbors are also retired. You don’t necessarily need to move to The Villages, but having close friends and neighbors who are also retired can prevent loneliness.

2. Take care of your health

Being in good health can make or break your retirement. Of retirees that reported being happier in retirement than they were while working, 49% of them said they planned ahead by prioritizing their health before retirement. 44% of retirees are concerned about their finances in retirement, while 34% say health issues are their biggest concern. Saving for retirement and taking care of your health must go hand-in-hand. If you don’t take care of your health, it doesn’t matter how much you have saved for retirement. Just like it is never too early to start saving, it is never too early to prioritize your health.

3. If there’s something you want to do in retirement, don’t wait to do it

There’s a big gap in what we imagine doing in retirement, before we retire, and what we actually end up doing in retirement. The top activities pre-retirees imagine for retirement are traveling (79%) and exercising (71%). That makes a lot of sense. Traveling extensively can be difficult to do while employed, and it’s a common dream to “travel the world” once you retire. And exercising to stay in good health is another great goal. However, the top activity for current retirees isn’t traveling or exercising but watching TV.

Don’t take anything for granted in retirement. If there’s something big you want to do or accomplish, make concrete plans now instead of potentially waiting until it’s too late.

4. You might worry less about money

Interestingly, many retirees report worrying less about money than those who aren’t yet retired. 34% of pre-retirees are worried they will outlive their money, while only 22% of retirees fear the same. 46% of retirees say they have fewer financial problems than they anticipated before retirement. This may sound strange, but it’s how it should be: worrying about money, and adequately planning, before retirement can make it much less of an issue in retirement. 78% of retirees say they have more than enough or just enough money to last them through retirement, while 19% say they have less than they need.

It should be encouraging that a large majority of retirees believe they have enough money to last them through retirement, and many worry about money less than they did before retirement. This doesn’t happen without planning ahead and saving what you know you need to save for retirement.

5. When you retire matters

The period of higher inflation we’ve experienced since 2020 will likely go down in history as not the best time to retire. In 2020, before inflation had really started impacting retirees, 17% said their spending was a little higher or much higher than they could afford. Last year, 31% of retirees said their spending was a little higher or much higher than they could afford. Periods of higher inflation often hits retirees the hardest since many are on fixed incomes, with pensions that may not adjust for inflation and Social Security, and the last few years have been no exception.

When planning for your own retirement, it’s a good practice to hope for the best but be prepared for the worst. What happens if inflation skyrockets when you retire? Or what happens if you retire at the beginning of a prolonged stock market decline? Make sure your retirement plan is ready for the worst-case scenario.

Retirement is an exciting period of life if you’ve prepared well. Listen to those who are retired now and prioritize your health, make plans to accomplish your goals, whether that’s traveling, spending more time with friends and family, or something else, and be prepared to worry less about money and be happier than you were while working.