Archives for June 2024

Get new articles by email:

Oblivious Investor offers a free newsletter providing tips on low-maintenance investing, tax planning, and retirement planning.

Join over 24,000 email subscribers:

Articles are published every Monday. You can unsubscribe at any time.

Investing Blog Roundup: Solo 401(k) and the “Age 55 Rule”

A question that comes up from time to time regarding solo 401(k) plans is whether self-employed people with such a plan could ever take advantage of the “age 55 rule.” The tricky point is that you have to “separate from service” in order to take advantage of that rule. And, if you have separated from service (i.e., you’re no longer doing the self-employed work in question), would you still count as an “employer” in order to maintain the plan, or does the plan have to be rolled into an IRA?

Sean Mullaney recently did a deep dive into that topic, and I find his reasoning convincing:

Other Recommended Reading

Thanks for reading!

Why Are ETFs (Sometimes) More Tax-Efficient Than Mutual Funds?

A reader writes in, asking:

“Could you provide an explanation of why ETFs are often said to be more tax efficient than mutual funds or index funds? I’ve read about it before but have never been able to follow.”

I’m happy to discuss this, but in order to understand the idea, we have to cover some background information first. Specifically, we have to discuss:

  • One basic concept about the tax treatment of funds, and
  • How shares of an ETF are created.

What Happens When a Fund Sells Something?

Whenever a fund (whether an ETF or traditional mutual fund) sells one of its holdings from the portfolio, if that holding is sold at a gain, shareholders of the fund have to pay tax on their share of that gain (if they hold the fund in a taxable brokerage account, that is).

How ETF Shares Are Created

When an investor buys shares of a traditional mutual fund, the transaction is a transaction between the investor and the mutual fund itself. The investor gives cash to the fund, and the fund creates new shares of the fund, which are given to the investor.

In contrast, when you or I buy shares of an ETF, we’re buying already-existing shares from some other shareholder who already owned those shares. So how do ETF shares get created in the first place?

The answer has to do with entities known as “authorized participants.” Authorized participants are generally super big financial entities (e.g., banks).

When a company that runs an ETF wants to create shares, it essentially does a swap with an authorized participant. It creates new shares of the ETF, and it gives those shares of the ETF to the authorized participant, in exchange for cash or a “basket” of securities (e.g., the 500 stocks in the S&P 500, if it’s an ETF that tracks the S&P 500). These swaps are usually done in very large dollar amounts (e.g., 50,000 shares of the ETF in exchange for the appropriate amount of other securities).

The ETF Tax Advantages

When an investor in a traditional mutual fund wants to sell his/her shares for cash, the transaction is again a transaction with the mutual fund itself. The fund needs to have cash on hand, so that it can pay that cash out to the shareholder redeeming the shares. And sometimes (depending on how many shares are being redeemed on any given day) raising that cash requires selling stuff. And as we discussed earlier, when a fund sells anything at a gain, shareholders in that fund have to pay tax on their share of that gain. In other words, when one shareholder sells his shares of the mutual fund, if the fund has to sell stuff at a gain in order to pay off that shareholder, that creates a tax cost that will be ultimately be paid by the remaining investors in the fund.

In contrast, if you or I want to sell shares of an ETF, that’s a transaction that happens on the secondary market. We aren’t transacting with the fund itself at all. We’re just selling our shares to somebody else who wants to buy them. And that means that the ETF doesn’t have to do anything — doesn’t have to sell anything, and no tax costs are incurred by remaining shareholders in the fund.

In addition, when an authorized participant wants to redeem shares of the ETF, the ETF basically does the share creation process (i.e., the swap described above), just in the opposite direction. This is known as a share redemption. In an ETF redemption, the ETF gives shares of investments to an authorized participant, and the authorized participant gives ETF shares back to the fund. And because this is an “in-kind” transaction, it’s not considered a taxable event. So the ETF is able to hand off those underlying investment shares without technically having sold them — no tax cost.

This is made even more tax-efficient by the fact that, when the ETF swaps out shares of any given company, it will naturally choose to give away the shares that have the lowest cost basis (i.e., keep the ones that have the highest cost basis, in case they have to be sold — thereby allowing any gains that have to be realized to be smaller gains).

So, in short, ETFs are often more tax-efficient than traditional mutual funds because they have a way of satisfying redemptions without having to actually sell anything and because they have a way of strategically unloading their shares of investments with the lowest cost basis (without generating a capital gain in the process).

Two Important Caveats

While the ETF structure does give it some tax advantages over a traditional mutual fund, there are two important caveats to keep in mind.

First caveat: the underlying portfolio and investment strategy of the fund still matters. It matters a lot. For instance:

  1. A fund (whether it’s an ETF or mutual fund) that follows a “total stock market” strategy is going to be much more tax-efficient than an actively managed stock fund that does a lot of buying and selling. Because, as discussed above, selling stuff at a gain results in tax costs to shareholders. So, higher portfolio turnover generally means worse tax-efficiency, and lower portfolio turnover generally means better tax-efficiency — regardless of whether the fund is an ETF or traditional mutual fund.
  2. A fund that pays a lot of fully-taxable ordinary income (e.g., a high-yield corporate bond fund) is simply not going to be very tax-efficient — and that’s true regardless of whether the fund is an ETF or traditional mutual fund.

Second caveat: this whole discussion largely does not apply to Vanguard ETFs as compared to Vanguard index funds. That’s because for many Vanguard funds, the ETF and index fund are literally the same fund. They’re just different share classes. So the share redemption process that ETFs can use (i.e., swapping out shares of holdings with low cost basis, to authorized participants) benefits the Vanguard index funds as well (as long as the index fund in question also has an ETF share class). In addition, the Vanguard patent on this “ETFs as a separate share class of an existing fund” idea recently expired (in May 2023). So it would not be at all surprising if other fund companies eventually implemented the same concept. (And many companies are already actively in the process of doing so.)

Investing Blog Roundup: IRS Direct File to Be Made Permanent, Expanded

At the end of April, the IRS announced that their pilot program Direct File went very well by any measure. Now, they’ve announced that the program will be made permanent, and access will be expanded both in terms of available states and tax situations covered.

Without exaggeration, I think this is the best development we’ve seen in the tax world during my entire time in the industry.

Other Recommended Reading

Thanks for reading!

What Roth Conversions Are Likely (And Unlikely) To Achieve

The topic that I help clients with most often is retirement tax planning. And my approach to that work includes modeling different tax strategies in financial planning software.

When I do that, what I find is that a plan for tax-efficient spending (i.e., which dollars to spend each year in retirement) often has a significant impact on retirement safety. For example, it often has the result of:

  • Reducing the projected probability of portfolio depletion by several percentage points (e.g., from 20% to 14%), while also
  • Pushing back the date at which those depletion scenarios do occur (e.g., so that in the “unlucky” scenarios, the household now runs out of savings in their mid 90s instead of late 80s).

But once you have a tax-efficient spending plan in place, a Roth conversion plan does not usually result in any meaningful improvement to retirement safety. That is, conversions don’t typically improve either of those metrics above by a meaningful amount.

And that has been my experience with a broad range of clients — ranging from super financially secure to more borderline, with varying ages upon retirement, and with a wide variety of portfolio sizes and compositions. And that has been the case using a broad variety of assumptions (e.g. varying assumed lifespans, average investment returns, etc.).

Roth conversions simply do not tend to increase retirement safety.

Why?

This is a simplification, but I often think of Roth conversions as a tool for solving/alleviating two “problems.” (For more on these topics, please see this article: The 4 Effects of Roth Conversions.)

  1. Required minimum distributions (RMDs) from tax-deferred accounts (both during your lifetime and after your death).
  2. The ongoing tax drag that occurs in taxable accounts (i.e., by letting you use taxable dollars to pay the tax on a conversion — thereby effectively using your less-tax-efficient taxable dollars to buy very tax-efficient Roth space).

But neither RMDs nor tax drag in taxable accounts is on the list of “stuff that’s likely to cause portfolio depletion in retirement.”

RMDs simply do not cause people to go broke. (In fact, RMDs are often recommended as a strategy for spending from a portfolio.)

And in unlucky retirement scenarios (e.g., poor investment returns early in retirement or a major spending shock early in retirement), the problem of tax drag in the taxable account typically solves itself, because the taxable account usually gets spent down pretty quickly in those scenarios anyway.

So Why Bother with Roth Conversions?

Given the above, you might ask why a person would bother with Roth conversions. The answer is that, in cases in which Roth conversions are suitable (which, for many but not all households, is in the years after retiring but before collecting Social Security and before RMDs kick in), they provide a significant increase in the the after-tax bequest that is likely to be left to heirs. (Again, please see this article for a discussion of the mechanics.)

In other words, a well-crafted Roth conversion plan typically:

  1. Does not make the unlucky outcomes significantly better or worse and
  2. Makes the lucky outcomes significantly better.

When I say “a well-crafted Roth conversion plan,” what I mean is a plan that carefully considers whether conversions should be done each year, and if so, to what threshold. Roth conversions are not suitable for everybody. For instance, households with large charitable intent are much less likely to benefit from conversions, because they can use qualified charitable distributions to satisfy RMDs and because the after-death tax rate on their tax-deferred accounts will be 0% to the extent the balances are left to charity.

Retiring Soon? Pick Up a Copy of My Book:

Can I Retire Cover

Can I Retire? Managing a Retirement Portfolio Explained in 100 Pages or Less

Topics Covered in the Book:
  • How to calculate how much you’ll need saved before you can retire,
  • How to minimize the risk of outliving your money,
  • How to choose which accounts (Roth vs. traditional IRA vs. taxable) to withdraw from each year,
  • Click here to see the full list.

A Testimonial from a Reader on Amazon:

"Hands down the best overview of what it takes to truly retire that I've ever read. In jargon free English, this gem of a book nails the key issues."
Disclaimer: By using this site, you explicitly agree to its Terms of Use and agree not to hold Simple Subjects, LLC or any of its members liable in any way for damages arising from decisions you make based on the information made available on this site. The information on this site is for informational and entertainment purposes only and does not constitute financial advice.

Copyright 2026 Simple Subjects, LLC - All rights reserved. To be clear: This means that, aside from small quotations, the material on this site may not be republished elsewhere without my express permission. Terms of Use and Privacy Policy

My Social Security calculator: Open Social Security