One of the trickier decisions of saving for retirement is determining which accounts to prioritize with your savings.
Is it most important to max out a 401(k) before an IRA? At what point should you use a taxable account for retirement savings? How does debt play into these decisions?
This is one of those truly personal finance moments because everyone has different circumstances.
To simplify the many options for retirement investing along with multiple variables that go into the decision making process, here is the general order that I recommend saving for retirement.
1. Invest Enough in Your Company Retirement Plan to Earn a Match
It’s hard to find a guaranteed 100% return on your investment, but an employer match does just that. If your employer offers a match on some portion of your 401(k) contributions, invest at least that much. Otherwise, you leave free money on the table.
For example, if your employer has a 3% match and you make $100,000 a year, you’ll need to contribute at least $3,000 of your own money to your 401(k) to be entitled to your employer’s full matching contribution. Once you invest at least enough in your employer plan to receive the match, then move on to the next bucket.
If your employer doesn’t offer a match, skip this first item, and move to number 2.
2. Invest the Maximum Allowable Amount in a Health Savings Account (HSA)
A Health Savings Account (HSA) is a special account available to those participating in a High Deductible Insurance Plan that ca be used to pay for medical expenses and other qualifying health-related costs.
As a savings vehicle, the HSA offers a triple tax-advantage unmatched by any other type of retirement savings accounts by offering: (1) contributions that are 100 percent tax deductible, (2) interest and earnings are tax-deferred, and (3) withdrawals used to pay for qualified medical expenses are tax-free and penalty-free.
If you have enough cash flow to contribute the maximum allowable amount each year to your HSA and manage to pay for medical expenses out of pocket – a strategy I describe in greater detail here – you can leave those HAS contributions invested for years to enjoy unusual tax benefits and compound growth.
3. Invest in Roth IRA or Deductible Traditional IRA
Your ability to invest in a Roth IRA of deductible Traditional IRA depends on your income. If you’re eligible for a Roth IRA, then this is the next place to direct retirement savings. If you can’t invest in a Roth account, the next best option is to make contributions to a traditional IRA, so long as you are able to deduct the contributions from your income.
Both Roth and Traditional IRAs allow your money to grow tax-free, but the difference is the timing of tax payment.
A Roth IRA is funded with after-tax dollars, meaning your contributions don’t receive a tax deduction. But your withdrawals from a Roth IRA are tax free. A Traditional IRA, on the other hand, is funded with pre-tax dollars – you deduct the contribution from your income – and withdrawals are taxed as ordinary income.
If your income is too high to qualify for a Roth IRA or a deductible Traditional IRA, you can still contribute to a nondeductible IRA and enjoy tax-deferred growth, but that option is a little further down the list.
4. Invest the Maximum Allowable Amount in Your Company Retirement Plan
If you have a good 401(k) plan, then it might make sense to prioritize this account before the IRAs described above. It’s difficult for many individuals to tell if they have a good or bad plan, but there are several items you can objectively evaluate.
When you are ready to contribute to your company retirement plan, you may have the choice of utilizing a traditional 401(k) or a Roth 401(k).
If you expect to be in a higher tax bracket during retirement than you’re in today, the Roth 401(k) is the superior option. If you expect to be in a lower tax bracket during retirement than you are today, the Traditional 401(k) is the option for you.
If you aren’t comfortable projecting whether your taxes will be higher or lower at retirement, consider making contributions to both the Traditional and Roth options. This strategy is known as tax diversification.
5. Invest in Traditional Nondeductible IRA
Contributions to a nondeductible Traditional IRA do not receive a tax break and withdrawals are taxed as ordinary income during your retirement. You will, however, enjoy the benefit of tax-deferred compound growth.
For some investors, contributing to traditional nondeductible IRAs and converting the balances to a Roth IRA at a later date may prove advantageous, particularly if they expect to be in a higher tax bracket in retirement. This strategy is known as a backdoor Roth contribution.
Converting an IRA to a Roth IRA requires you to pay ordinary income taxes on any appreciation and earned income experienced in any of your IRA accounts, not just the account being converted. That means a Roth conversion decision requires an analysis of the tax cost, your life expectancy, and the desired beneficiary of the assets.
In my opinion, the tax benefits of Roth conversions are best for retired investors under the age of 72 with little to no ordinary income. If you’re working and have an existing IRA with considerable appreciation, this strategy is often not worth it.
6. Invest in a Taxable Account
If you’ve reached this point, congratulations! You’re doing a nice job of saving for your retirement.
While you’ve exhausted the best tax-advantaged options, you can always invest in a taxable account. The key here is to be aware of the tax efficiency of your investments.
Assuming you are utilizing the tax-advantaged retirement accounts above, there may also be opportunities to benefit from asset location strategies.
Next Steps
As you age and mature in life and your career, your investment priorities change, and your financial objectives shift. To help you reach your goals during life's journey, we've created an "investing by age" series to cover different investment strategies for each decade of your life. 
Disclosure:
This material has been prepared for informational purposes only and should not be used as investment, tax, legal or accounting advice. All investing involves risk. Past performance is no guarantee of future results. Diversification does not ensure a profit or guarantee against a loss. You should consult your own tax, legal and accounting advisors.
