What if taxes increase?

When I invest in a taxable account, I have to pay taxes on any ordinary and qualified dividends I receive over the course of an year. While I am a buy and hold investor, I also have the occasional capital gain or loss. Naturally, I expect to receive a net capital gain when companies get acquired or perhaps a smaller gain when they cut dividends.

Taxes reduce the amount I can re-invest back into my portfolio. I view these investment taxes as waste in the accumulation process.

I made the capital for my investments through labor. I pay taxes on the income I generate through employment, which further reduces the amounts I can invest every month.

As part of my investment plan, I try to prioritize investing through tax-deferred accounts first, before adding to taxable accounts.

I do this in order to minimize the tax bite on dividends and capital gains in the accumulation phase, which can amount to a substantial amount. I also do this in an effort to reduce the amount of taxes I pay upfront, and compound my dividend income and capital without tax waste for decades down the road.

When I reduce the amount of taxes I pay today, I have more money to invest. I achieve that due to the tax breaks I have up-front from some accounts such as regular 401 (k), H SA and SEP IRA. I also have more money to invest, since a larger portion of my investment income is now in tax-sheltered accounts. For regular IRA/401 (k) accounts tax may either be due at some point in 30 – 40 years. For others like my Roth IRA/Roth 401(k), I will never have to pay tax on the distributions.
You can read a brief overview of each account in this article. You may also find it helpful to read about ways to withdraw from retirement accounts prior to the age of 59 1/2.

I have discussed previously how utilizing tax-deferred accounts correctly can result in higher dividend incomes for the same levels of effort. This simple change can shorten your financial independence journey by shaving off years of extra effort toiling away at a thankless job for no other benefit than to pay more taxes. If you enjoy working, tax advantaged accounts help shelter a ton in taxes in the accumulation process, when you are in a higher tax bracket than when you retire.

I view investing through tax-deferred accounts as a natural hedge against rising rates on income.
When you are investing in a taxable account, you have to pay the going tax rate on dividends and capital gains. You will likely have to pay money every single year. Under the current administration it is possible to avoid paying taxes if you earn $100,000 in qualified dividend income and have no other income source. However, it would take you many years of paying a lot in taxes on income and investments before reaching this goal. Naturally, you will be having less dollars working for you, since you will be paying the tax man every year.

If you invest through a tax-deferred account, you get to defer paying taxes on dividends and capital gains. Roth IRA’s are funded with after-tax dollars, but you will not have to pay taxes on withdrawals. This means that you paid your Federal and State taxes first, and then used that after-tax money to start your Roth IRA. This concept is the same for Roth IRA, Roth 401 (K) accounts as well, even if their contribution limits vary. Typically, you can withdraw contributions after 5 years, but you can only withdraw gains penalty-free after the age of 59 ½. There are required minimum distributions for Roth 401 (k) accounts at the age of 72, but not for Roth IRA accounts. Withdrawals are not taxable. In order to avoid required minimum distributions on Roth 401 (k) accounts, an investor can simply rollover that Roth 401 (k) into a Roth IRA. There may be other considerations involved, like asset protection, so it may make sense to speak to a tax professional first.

Regular IRA’s are funded with before-tax dollars, meaning that you get to avoid paying a tax at the Federal and State level when you contribute to these accounts. The concept is the same for Regular/SEP IRA’s, Regular 401 (k)/457b/403(a) plans, even if the contribution limits for each account varies. As a result of this tax hack, you get more money to invest today, since you are reducing your taxable amount due to your retirement plan contribution. When you withdraw principal and earnings from the account, they are all taxable at your ordinary income tax rate. It is not a problem for most folks however, since people tend to be at higher tax brackets when they work, and in lower tax brackets when they retire.

Other benefits of before-tax accounts include reducing your taxable income, which may potentially qualify you for different credits or benefits such as ACA credits. If maxing out your 401 (k) put you in a lower taxable income, and you became eligible for the 2020 economic relief payments, that was an ROI that was unexpected, but still a plus for maxing out your retirement contributions.

The government does want you to start taking money out of these retirement accounts by the time you are 72, because they want you to start paying taxes and not just defer paying forever. There are ways to avoid taking distributions however. My popular one is that if you are still working at a company that you own no more than 5% in, your 401 (k) at this company does not need to start required minimum distributions. I am sure that there are other loopholes to defer distributions from an IRA or 401 (k), but you would likely have to hire an expensive CPA for it.

The nice thing about retirement accounts is that you get to defer or avoid paying taxes in the crucial accumulation phase. This may also simplify your life if you actively manage your investments too.
As I mentioned above, when people work, they are usually in a higher tax bracket than when they retire.

As a result, putting money in regular IRA/401 (k) accounts is better than using the Roth option, due to this tax arbitrage nature of things. The risk you face with regular accounts is that the tax rates will be much higher when you withdraw the money, even if you are in a lower tax bracket.

With Roth accounts, you are essentially locking in the money at your going tax rate. If you end up moving up in your career, you would likely be better off starting with a Roth and then evaluating if a Regular IRA is better for you. The risk you take with Roth IRA’s is that tax rates would go lower by the time you retire, which means that you would have ended up with less money than ideal.
I believe that contributing to Roth IRA’s or Roth 401 (k) is best if you are a in lower tax bracket today, and effectively want to lock that rate in. Another reason for contributing to a Roth over a Regular account is if you cannot contribute to a regular IRA.

I recently shared my ideas with investors, and received some interesting pushback. It looked like some investors prefer taxable accounts to retirement accounts, because they are afraid that tax rates in 20 – 30 – 40 years will be much higher than they are today.

Naturally, no one knows where tax rates will be in the next 30 – 40 years. However, we do know that in general, most folks will be in lower tax brackets in retirement, in comparison to the tax brackets they had when they were working. It is all a moving target of course, since the lowest tax rate in 40 years may turn out to be higher than the highest tax bracket we have today. It could also be that the highest tax rate in 40 years will be about the same as the lowest rate we have today.

I decided to run some scenario analyses, in order to compare and contrast different outcomes. You can download this spreadsheet that includes the calculations behind each scenario.

The first scenario looks at an investor who is in the 22% Federal Tax Bracket today, and is in the 5% State Tax Bracket. The tax on qualified dividends is 15%, and they also owe their friendly state another 5% on dividends. We are going to assume that this investor will generate a total return of 7%/year –5% for capital gains and 2% for dividends. Our investor will save $1,000 in 2020, and have the option of doing a regular taxable account or a regular IRA account. We would assume that our investor would be withdrawing ALL the money in 2060 at the prevailing tax rates. My assumptions are that Federal tax rates in 2060 will be at 40%, the state tax rates will be at 5%, and qualified dividends will be taxed at 15% at the Federal and 5% at the State Level. This is an unfair comparison to tax-deferred accounts, because it assumes that the tax rates on ordinary income double, while taxes on investment income stay flat. We are also deferring at a pretty reasonable tax rate today, but that rate is average. The numbers would look differently for a highly paid physician, lawyer or executive.
It looks like in 2060, the taxable account ends up being worth 12,891.05. After selling all stock, and paying taxes on gains (15% + 5% = 20%), we are left with 10,512.84.

The IRA account is worth 20,512.96 by 2060. If we withdraw the money at once, we pay 40% to the Federal Government and 5% to the state government, and we are left with 11,282.13. The Federal Tax rate would have had to increase to 43.50% for the after-tax return on traditional IRA to be on par with the taxable account.

The reason for the difference is because the taxable account pays taxes on dividends each year, which results in a net return of 6.60%/year, versus 7%/year for the tax-deferred account. This difference would have been more pronounced if dividend yields were higher than 2% too. In addition, by contributing to an IRA in the accumulation phase, we save $369.86 on taxes, which are then plowed back into that IRA.

I had to double check the amount saved on taxes and make sure it makes sense. If we have hit the limits on how much we can put in a tax-deductible IRA, the savings are simply the tax rate times the amount contributed. So the amount saved would be $270 invested in a taxable account.
Because the IRA limits are much higher than $1,000/year, we have at least $5,000 in extra room to contribute. And if you view the traditional 401 (k) as a form of traditional IRA, we have an additional $19,000 to contribute to.

When you receive a tax deduction to contribute to an IRA, and you have extra room left to contribute, you can compound those tax advantages in a way.

That’s because if we just contributed an extra $270 to the IRA from the savings on the $1,000 contribution, we would also generate tax savings on the $270. That’s 72.90 in savings on the $270 extra that we were able to contribute to the IRA, because of tax savings in the first place.
That 72.90 in additional tax savings open up room for 19.68 in additional tax savings… And so on, until we are left with a total savings of $369.86 merely because we contributed to an IRA that is tax-deductible.

Either way, the upfront tax savings, and the deferral of investment gains for 40 years definitely help the traditional IRA investor over the taxable one.

If we had simply placed the money in a Roth IRA however, we would have not generated any upfront tax savings. However, we would have compounded the money at 7% per year, and we would have $14,974.46. Since there are no taxes on withdrawals, we have 14,974.46 to withdraw.

It looks like under this scenario, the Roth IRA beats the traditional IRA and the taxable account on an after-tax return basis. On a gross return basis in 2060, the IRA beats the Roth and taxable accounts.
The increase in taxes definitely makes the traditional IRA a worse option than the Roth in this scenario.

If you could pay less than 27% in taxes on the Traditional IRA distributions, you would have done better than the Roth. That would require forecasting future tax rates, but also knowing the intricacies of the tax code. If it comes down to moving from a state with income tax to a state with no income tax, this may be worth it. Again, a good CPA may be able to find a way to help you keep a larger portion of your wealth. And they may be able to help in planning along the way.

In a real-time scenario however it may be possible to withdraw money strategically, by increasing distributions before taxes rise and reducing them when they are higher. But tackling every individual scenario is beyond the scope of this blog post. You should feel inspired or bored out of your mind so that you think about your tax planning situation, and perhaps even hire a friendly CPA/tax accountant to help you plan ahead and devise a plan to minimize taxes and maximize wealth.

If you could pay less than 27% in taxes on the Traditional IRA distributions, you would have done better than the Roth. That would require forecasting future tax rates, but also knowing the intricacies of the tax code. If it comes down to moving from a state with income tax to a state with no income tax, this may be worth it. Again, a good CPA may be able to find a way to help you keep a larger portion of your wealth from the hands of the tax man.

The second scenario will look at the same inputs as the first one. The difference will be that taxes on dividends will rise to 20% at the Federal Level in 2021 but stay at 5% at the State Level. Taxes on Federal Level will be at 40% and at State Level 5% in 2060. The return assumptions are the same.
It looks like in 2060, the taxable account ends up being worth $12,416.07. After selling all stock, and paying taxes on gains (15% + 5% = 20%), we are left with 9,562.06. We end up compounding money at 6.50%/year, due to higher taxes on dividend income in the accumulation phase.

The IRA account is worth 20,512.96 by 2060. If we withdraw the money at once, we pay 40% to the Federal Government and 5% to the state government, and we are left with 11,282.13. The Federal Tax rate would have had to increase to 48.50% for the after-tax return on traditional IRA to be on par with the taxable account.

The Roth IRA ends up with $14,974.46 to withdraw tax free. It is a clear winner, unless you managed to find a way to obtain the distributions from a Traditional IRA while paying less in taxes. If you could pay less than 27% in taxes on the Traditional IRA distributions, you would have done better than the Roth. That would require forecasting future tax rates, but also knowing the intricacies of the tax code. If it comes down to moving from a state with income tax to a state with no income tax, this may be worth it. Again, a good CPA may be able to find a way to help you keep a larger portion of your wealth.

The third scenario looks at a situation where tax rates are unchanged for 40 years. This means that we get to withdraw the money at the same rates used when we put money in.

It looks like in 2060, the taxable account ends up being worth 12,891.05. After selling all stock, and paying taxes on gains ( 15% + 5% = 20%), we are left with 10,512.84.

The IRA account is worth 20,512.96 by 2060. If we withdraw the money at once, we pay 22% to the Federal Government and 5% to the state government, and we are left with 14,974.46. The after-tax return on the traditional IRA matches that of the Roth IRA in this example.

The fourth scenario looks at a situation where tax rates are lower in 40 years. The rates at which we would be contributing stay the same ( 22% Federal, 5% state, 15% dividends), but the rates at which we withdraw money will be reduced ( 12% Federal, 0% state, 0% dividends).

At this level, the rates of return for taxable and Roth and Regular IRA are at 7%/year. We end up at the same level of worth for the taxable and Roth IRA’s - $14,974.46.

For the Traditional IRA, we end up with 20,512.96 pre-tax. After we withdraw the funds, and pay the 12% tax rate, we are left with $18,051.40.

After reading through these examples, it may seem to you that I am a little biased towards the traditional IRA/ 401 (k). It is likely the case, or perhaps it is wishful thinking on my part that building a higher net worth in a traditional IRA is better from a pure numbers perspective, because it gives you a higher base to work with. It is easier in relative terms to have $1 million in an IRA, and have to worry about paying $200K - $400k in taxes on it, than to have $600K in a taxable account. You will likely find a solution on how to minimize the tax bite on the traditional, and find ways to tap the money in a tax-efficient way too.

In my personal situation, my assets are diversified across traditional 401K and IRA and Roth IRA /Roth 401 (k) accounts. I also have a taxable account. Since there are limitation on how much I can contribute, I maximize everything I am eligible for today. I see various scenarios playing out, so I will do differently under each. My withdrawals will be optimized to the situation at the time of withdrawals.

I try to maximize the traditional 401 (k) and IRA’s first, because I believe that I will be in a lower tax bracket than today when I withdraw these funds. This may be because my income is lower, because taxes are lower or because I may have also moved to a state that doesn’t tax income. Or perhaps a combination of all of the above. I would put H S A in this category as well. I am not going to calculate the effect of using H S A versus other accounts, because it affects social security contributions and income. I am not an actuary so I won’t go there today. You have already been bored sufficiently on this tax tirade.

I then try to max out any Roth amounts. If there is anything left over, I place it in a taxable account.
I would prefer tax-deferred compounding to compounding in taxable accounts.

My goal is to keep building, because I enjoy building my portfolios. I will probably defer withdrawing funds for as long as possible and just live off any active income I generate in the process (and trying to save and invest any remaining amounts too).

Right now, I won’t have to withdraw until the age of 72. I will consider converting regular 401 (k) dollars into Roth 401 (k) or Roth IRA if I ever find myself in the lowest tax brackets along the way.

As you can see, there are various scenarios when it comes to tax-deferred accounts. And we are assuming a typical 40 year career. Imagine how much more complicated the situation gets if we were looking for an early retirement, where we have to withdraw money in our 30s or 40s.

I actually discussed that in a way in a previous post. But the short summary is that you can withdraw Roth IRA/Roth 401 (k) contributions after 5 years. You can withdraw earnings after the age of 59 ½ without penalty.

For Regular IRA/401 (k) plans, the withdrawal options are very different. If you convert a 401 (k) into a Roth, you will pay taxes on the proceeds, but then you can withdraw that money in 5 years tax free. This makes sense if your rate in retirement is lower than the rate at which you were accumulating capital. You also have the 72 t option, which is the Substantially Equal Periodic Payments option, which allows you to withdraw money from retirement accounts according to a longevity formula. You have to do it every year. Finally, for 401 (k) accounts, you can start withdrawals from the 401 (k) account at the company you worked at, if you leave at or after the age of 55.

Today, we looked at a few different scenarios for contributing money to taxable and tax-deferred accounts. We also looked at how those scenarios play out when we change our assumptions just a little bit. I encourage you all to play around with the spreadsheet assumptions, and test various outcomes. I would also encourage all of you to think more about tax planning.

We also revisited various retirement account types in brief, and also discussed ways to withdraw from them early.

We should remember that life is not linear, and we will have occasional bumps on the road. These may be blessings in disguise. For example, a person who is laid off a couple of years before they plan to retire may be able to convert old IRA's into Roth by paying a minimum amount in taxes. Alternatively, a younger person may also be able to Rothify their 401 (k) accounts if they take an year off for graduate school for example, after a few years of working.

There are avarious possiblities and outcomes to think through. This is why I believe that it is important as investors to think through various scenarios, and learn at least a basic understanding of the tax code. That may pay real dividends down the road.

That being said, if you are afraid of taxes rising in the future, hedging that bet by maxing out retirement accounts may be a good start. Investing in a taxable account is an inefficient way to build wealth, particularly in the accumulation phase for dividend investors.

Thank you for reading!

Relevant Articles:

- Taxable versus Tax-Deferred Accounts for Dividend Investing
- How to buy dividend paying stocks at a 25% discount
- How early retirees can withdraw money from tax-deferred accounts such as 401 (k), IRA & HSA
- How to Grow Dividend Income Much Faster With Tax Advantaged Accounts