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Four Essential Strategies for Building Roth Assets

Four Essential Strategies for Building Roth Assets

Four Essential Strategies for Building Roth Assets

Do you like tax-free money? Of course you do! Who doesn't? 

Unfortunately, there aren't many avenues for tax-free money. As I'm sure you've heard, the government likes you to pay taxes. Deferred retirement accounts, like Traditional IRAs and 401ks, save you on taxes now, but the bill comes due in retirement when you withdraw from the account. Taxable accounts can be managed in a tax-efficient manner, but you'll pay taxes on any bond interest, dividends, or realized capital gains. 

But how about Roth IRA accounts? Well, these are truly tax-free, and you should absolutely want more money in these accounts when the opportunity exists.(1)

So, let's talk about how to get more money into your Roth IRA and reduce your lifetime tax bill in the process. 

Note: Some of the strategies below can be quite complex from a tax perspective, and we suggest you seek the support of a qualified tax professional before making any major financial decisions. 

Roth IRA Strategy #1: Make Roth 401k Contributions 

Did you know that many employer-sponsored 401k's now offer the option of making Roth-style employee contributions? If you have this opportunity, instead of making a $6,000 annual contribution to your Roth IRA (or $7,000 for individuals age 50 and above), you can contribute up to $20,500 ($26,500 for individuals age 50 and above) in 2022. Any employer match on top of this will still be in tax-deferred accounts, but holy smokes, that's a big chunk of money to get into a Roth IRA.  Let's look at an example: 

Shae is 30 years old and chooses to max out her Roth 401k. She has followed this plan for 20 years and earns, on average, a 9% annualized return. At age 50, Shae has $1,145,571 in Roth assets in her 401k. Wow! 

Roth IRA Strategy #2: Backdoor Roth IRAs

Individuals with Modified Adjusted Gross Income over $144,000 and married couples filing jointly with Modified Adjusted Gross Income over $214,000 are unable to make Roth IRA contributions.
Enter the backdoor Roth IRA. The backdoor Roth IRA is a multi-step process allowing high earners to continue making Roth IRA contributions. Here's how you process the contribution: 

  1. Check to make sure you don't have a current balance in any existing Traditional IRA, SEP-IRA, or SIMPLE IRA accounts.

  2. Make a non-deductible Traditional IRA contribution.

  3. Convert the Traditional IRA to your Roth IRA on a timely basis.

  4. Now you have money in your Roth IRA and it is never taxed again.

Please note, if you have existing funds in a Traditional IRA account you may need to convert the account to a Roth IRA (and pay taxes on the conversion) or roll the account over to an existing 401k plan that accepts rollovers prior to implementing the backdoor Roth IRA strategy. You should consult with a tax or financial professional prior to enacting this process as the nuances can be quite complex. Additionally, there are tax forms to file annually when making backdoor Roth contributions. Once again, you should coordinate with your tax advisor on the specifics. 

Roth IRA Strategy #3: Roth Conversions

Roth conversions are a fantastic way to get more money into Roth IRA accounts. A Roth conversion essentially transfers money from a Traditional IRA to a Roth IRA account. You pay income tax on the conversion amount, but once the money hits the Roth account any future growth is entirely tax-free. In other words, you are realizing tax today for the opportunity to have tax-free money in the future. 

Roth conversions are best implemented in years with lower expected taxable income. For example, many retirees start Roth conversions in their early retirement years to reduce the tax impact of required minimum distributions in their 70's and 80's and increase tax diversification.

Roth conversions can be quite complex in their use cases and implementation. Still, the opportunity can be extremely advantageous for many individuals and families from a tax or estate planning perspective.

Roth IRA Strategy #4: Accumulating Assets within a Health Savings Account (HSA) 

Though technically not a 'Roth'- '-style account, HSAs offer an incredible opportunity to create tax-free future income. Individuals and families on a high-deductible health care plan can contribute to an HSA. Importantly, you do not have to use that money in the year of contribution. Instead, you can invest it for long-term growth. 

In other words, HSAs present the triple whammy of tax minimization: 

  1. Contributions reduce your taxable income.

  2. You can invest your HSA principal for long-term, tax-deferred growth.

  3. As long as you use the money for a qualified medical expense, withdrawals are tax-free.

Although not technically a 'Roth' style account, saving and investing in an HSA does create more tax diversification for your household balance sheet, which is an incredible advantage, especially in retirement! 
 

Interested in learning more about minimizing your lifetime tax rate or creating more tax-free Roth money? Schedule a Free Introductory Call with a member of our team below!

© 2025 Trailhead Planners

Trailhead Planners, LLC (“Trailhead”) is a registered investment advisor offering advisory services in the States of Oregon, Minnesota, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training.

The information on this site is not intended as tax, accounting, or legal advice, as an offer or solicitation of an offer to buy or sell, or as an endorsement of any company, security, fund, or other securities or non-securities offering. This information should not be relied upon as the sole factor in an investment making decision.

Past performance is no indication of future results. Investment in securities involves significant risk and has the potential for partial or complete loss of funds invested. It should not be assumed that any recommendations made will be profitable or equal any performance noted on this site.

The information on this site is provided “AS IS” and without warranties of any kind either express or implied. To the fullest extent permissible pursuant to applicable laws, Trailhead Planners, LLC, disclaims all warranties, express or implied, including, but not limited to, implied warranties of merchantability, non-infringement, and suitability for a particular purpose.

Trailhead does not warrant that the information on this site will be free from error. Your use of the information is at your sole risk. Under no circumstances shall Trailhead be liable for any direct, indirect, special, or consequential damages that result from the use of, or the inability to use, the information provided on this site, even if Trailhead or a Trailhead authorized representative has been advised of the possibility of such damages. Information contained on this site should not be considered a solicitation to buy, an offer to sell, or a recommendation of any security in any jurisdiction where such offer, solicitation, or recommendation would be unlawful or unauthorized.

© 2025 Trailhead Planners

Trailhead Planners, LLC (“Trailhead”) is a registered investment advisor offering advisory services in the States of Oregon, Minnesota, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training.

The information on this site is not intended as tax, accounting, or legal advice, as an offer or solicitation of an offer to buy or sell, or as an endorsement of any company, security, fund, or other securities or non-securities offering. This information should not be relied upon as the sole factor in an investment making decision.

Past performance is no indication of future results. Investment in securities involves significant risk and has the potential for partial or complete loss of funds invested. It should not be assumed that any recommendations made will be profitable or equal any performance noted on this site.

The information on this site is provided “AS IS” and without warranties of any kind either express or implied. To the fullest extent permissible pursuant to applicable laws, Trailhead Planners, LLC, disclaims all warranties, express or implied, including, but not limited to, implied warranties of merchantability, non-infringement, and suitability for a particular purpose.

Trailhead does not warrant that the information on this site will be free from error. Your use of the information is at your sole risk. Under no circumstances shall Trailhead be liable for any direct, indirect, special, or consequential damages that result from the use of, or the inability to use, the information provided on this site, even if Trailhead or a Trailhead authorized representative has been advised of the possibility of such damages. Information contained on this site should not be considered a solicitation to buy, an offer to sell, or a recommendation of any security in any jurisdiction where such offer, solicitation, or recommendation would be unlawful or unauthorized.

© 2025 Trailhead Planners

Trailhead Planners, LLC (“Trailhead”) is a registered investment advisor offering advisory services in the States of Oregon, Minnesota, and in other jurisdictions where exempted. Registration does not imply a certain level of skill or training.

The information on this site is not intended as tax, accounting, or legal advice, as an offer or solicitation of an offer to buy or sell, or as an endorsement of any company, security, fund, or other securities or non-securities offering. This information should not be relied upon as the sole factor in an investment making decision.

Past performance is no indication of future results. Investment in securities involves significant risk and has the potential for partial or complete loss of funds invested. It should not be assumed that any recommendations made will be profitable or equal any performance noted on this site.

The information on this site is provided “AS IS” and without warranties of any kind either express or implied. To the fullest extent permissible pursuant to applicable laws, Trailhead Planners, LLC, disclaims all warranties, express or implied, including, but not limited to, implied warranties of merchantability, non-infringement, and suitability for a particular purpose.

Trailhead does not warrant that the information on this site will be free from error. Your use of the information is at your sole risk. Under no circumstances shall Trailhead be liable for any direct, indirect, special, or consequential damages that result from the use of, or the inability to use, the information provided on this site, even if Trailhead or a Trailhead authorized representative has been advised of the possibility of such damages. Information contained on this site should not be considered a solicitation to buy, an offer to sell, or a recommendation of any security in any jurisdiction where such offer, solicitation, or recommendation would be unlawful or unauthorized.