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A Basic Financial Planning Checklist

A realization that has only very slowly occurred to me, over 15 years in the world of financial planning, is that the most common financial planning mistake that I see people make is not so much a particular bad decision, but rather completely ignoring certain parts of financial planning.

In many cases, that shows up in the form of focusing too much on the investing part of the picture, while having some other critical financial planning need that is going unaddressed.

And that’s not terribly surprising. Investing involves thinking about upside — how your assets will grow (and how they could grow, if you make a high-risk bet and get lucky). That can be fun.

In contrast, many critical financial planning tasks involve thinking about downside. (What if you become disabled or die earlier than anticipated?) That’s less fun.

In addition, a lot of critical financial planning tasks look suspiciously like work.

What follows is just a brief checklist of financial planning topics, all of which should probably be addressed before spending much time thinking about exactly what is the correct allocation to international bonds or whether index funds are preferable to ETFs.

Insurance planning:

  • Do you have health insurance? (And if it’s open enrollment season, have you checked to see whether there’s a different plan that might be a better fit for your household?)
  • If anybody is financially dependent upon you, do you have sufficient life insurance? (Alternatively, have you canceled any coverage that is no longer necessary?)
  • If you are still working, do you have sufficient disability insurance? (And does the policy check all the necessary boxes? For instance, is it “own occupation” if such is important in your case?)
  • Do you have sufficient homeowners/renters insurance?
  • Do you have sufficient liability coverage on your auto policy?
  • Do you have an umbrella policy?

Cash flow planning:

  • Do you know how much you spend each month (or over the course of a year)?
  • Do you have a sufficient emergency fund? (Of note: a retirement portfolio can often serve as an emergency fund, once it is of sufficient size.)
  • Are you saving enough each month to meet your goals? (Or if retired, are you confident that the amount you are spending per year is sustainable?)

Estate planning:

  • Have you checked the beneficiaries (including contingent beneficiaries) of your retirement accounts and life insurance policies recently?
  • Do you have a will in place?
  • Do you have a durable power of attorney for finances?
  • Do you have a healthcare power of attorney?
  • When was the last time the above documents were updated?
  • Have you considered whether a trust of any sort would help you to achieve any postmortem goals for your assets?

Tax planning:

  • Are you confident that you are contributing to (or withdrawing from) the right types of accounts each year? (For example, should you be making Roth contributions instead of tax-deferred contributions?)
  • Have you considered whether Roth conversions would be useful now or in the near-term future? (Most often, this is helpful during years of retirement prior to RMDs and prior to Social Security.)
  • Do you know whether you are in or near the phaseout ranges (or other thresholds) for any tax credits or other significant tax provisions?

Basic investment planning:

  • Is your portfolio reasonably diversified, as opposed to having a large portion allocated to one stock (e.g., an employer or former employer)?
  • Is the basic allocation (i.e., the stock/fixed-income allocation) roughly appropriate for your risk tolerance?
  • Are you using funds with reasonably low expense ratios?

Basic retirement planning:

  • Do you have a plan for when you intend to retire? (And have you thought through the potential ramifications of being forced into retirement somewhat earlier than the intended date, due to illness, job loss, etc.?)
  • If nearing age 62 (or 60 if you’re a widow/widower), do you have a plan for when you will claim Social Security benefits?

In my opinion, most people should just be using a very simple portfolio (e.g., a basic three-fund portfolio or even a simple all-in-one fund if the portfolio is entirely in retirement accounts) until they’ve taken care of the above items. Using a basic portfolio frees up time and mental energy to focus on other things that matter quite a bit more.

And even for people who have taken care of these other financial planning to-do items, there’s still no need to spend time thinking about particularly advanced asset allocation questions. In nearly all cases, it’s perfectly fine to stick with the three-fund portfolio (or, again, a low-cost all-in-one fund if your portfolio does not include taxable accounts).

To be clear, the above list is not absolutely-super-duper-all-inclusive. For some people there will be additional points in one category or another that should be addressed. Also, the order of priority will vary from one person to another. For example, if you’re unmarried and have no kids, estate planning would be a lower priority than it would be for somebody with children. And estate planning would be an especially high priority for a married couple who each have children from a prior marriage.

Will a Total Bond Fund Keep Up With Inflation?

In reply to the previous article about fixed-income options in a low-yield environment, a reader wrote in with the following question:

“Would Vanguard’s Total Bond Market fund (or the equivalent) be expected to match inflation over time?”

For a bond (or bond fund), the best estimate for its expected return is its yield. Right now, the SEC yield for Vanguard Total Bond Market Index Fund is 1.19% You can find this on either the “Overview” or “Price & Performance” tab on the fund’s page on the Vanguard site.

But there are two important points of note here.

First point of note: that’s the expected return over the fund’s average duration. We can click over to the “Portfolio & Management” tab to find the fund’s average duration: 6.5 years. So what we’re seeing here is that the fund’s expected return over the next 6.5 years is 1.19%.

For periods shorter or longer than 6.5 years, there’s a greater degree of uncertainty about what the actual return will be.

For shorter periods, 1.19% is still probably the best expected return estimate, but the actual return is going to be primarily affected by price movements (i.e., whether the bonds’ prices move up or down as a result of interest rate changes). See any of the following articles for a discussion of how bond prices respond to changes in interest rates:

For longer periods, 1.19% is (again) likely the best guess, but we (again) have a lower degree of certainty. In this case, a major cause of the uncertainty is that, as we look at longer and longer periods, we simply don’t know what bonds are going to be in the fund’s portfolio. For example, imagine that we were concerned with the expected return over the next 20 years. Given the fund’s average effective maturity of 8.5 years, most of the bonds currently held by the fund will have matured before the 20-year period is even halfway over. In other words, the return earned by the fund over the next 20 years will be hugely affected by the yields on bonds that it hasn’t even bought yet — and which haven’t even been issued yet. And since those bonds don’t even exist yet, we have absolutely no way to know what their yields will be.

Second point of note: because this is a nominal bond fund, the 1.19% figure is a nominal yield (i.e., before inflation) and therefore a nominal expected return.

A good way to get a rough estimate of the market’s expectation for inflation over a given period is to find the difference in yields between TIPS and nominal Treasury bond for the period in question. For example, since our expected return is for a 6.5-year period, we could look at the yields for 7-year TIPS and 7-year Treasuries. Right now, the yield on 7-year TIPS is -1.10%, and the yield on 7-year Treasuries is 0.55%. That’s a difference of 1.65%, which tells us that the market is expecting inflation of roughly 1.65% over the next seven years.

So, in summary, with an expected nominal return of 1.19% over the next 6.5 years and expected inflation of roughly 1.65% over the next 7 years, we can say that the expected return for Vanguard Total Bond Market Index Fund is about 0.46% below inflation over the next 6.5 years.

But that’s just an expected return. The actual nominal return could be meaningfully different from the 1.19% figure. Or inflation could be meaningfully different from the 1.65% figure. And as discussed above, for periods shorter or longer than 6.5 years, there’s an even greater degree of uncertainty.

How Does the Fed “Prop Up” the Stock Market? (Interest Rates and Stock Prices)

A reader writes in, asking:

“I’ve read over and over this year that the Fed is ‘propping up’ the stock market by keeping interest rates low. How does that work?”

Broadly, there are two ways in which low interest rates help to keep stock prices high.

Firstly, to the extent that corporations are borrowers, keeping interest rates low reduces their costs and therefore directly improves their profitability, which of course helps keep their share prices higher. In the case of a struggling corporation, having access to low-cost capital can even make the difference between declaring bankruptcy or not. And of course avoiding bankruptcy proceedings is good for shareholders.

The second effect has to do with the way stocks are priced. (I think it’s actually easier to understand this effect from the perspective of increases in interest rates. So we’ll start with that.)

Stocks are quite a bit riskier than Treasury bonds. So why do you own stocks at all, rather than just buying Treasury bonds with all of your savings? Presumably, you own stocks because you hope to earn additional returns beyond what Treasury bonds earn. That additional return that you hope to earn is known as a risk premium (i.e., additional return to compensate you for the additional risk).

The price of a stock reflects the (market’s consensus as to the) present value of the future cash flows from the stock. And the discount rate used in that present value calculation is usually something along the lines of “whatever we could earn from bonds, plus a risk premium.”

So when interest rates go up, the necessary discount rate goes up. A higher discount rate means a lower present value, which means stock prices go down.

Or you can think of it this way: imagine that TIPS yields suddenly went way up to 3%, rather than the roughly -1% range where they are right now. Maybe you had been estimating that stocks would earn a 4% real return going forward. Before, that was a 5% risk premium. But with TIPS yielding 3%, a 4% real return would only be a 1% risk premium. Maybe you decide that a 1% expected risk premium isn’t high enough to justify the additional risk from owning stocks, so you sell your stocks to buy TIPS.

Collectively, lots of people would be selling stocks to buy bonds in such a scenario. So the price of stocks would fall. When the price falls, the expected return going forward goes up (because a new buyer is paying a lower price for a given amount of dividends/earnings). And the price would continue to fall (i.e., people would keep selling stocks) until the price was low enough that the expected return was high enough to earn whatever the market collectively decided was a sufficient risk premium over bonds.

So that’s what happens when interest rates go up: it has a downward effect on stock prices.

When governments or central banks make efforts to keep interest rates low, the opposite occurs: it exerts an upward pressure on stock prices. That is, low interest rates make the alternatives to stocks not look very appealing — and that helps keep stock prices high.

To be clear though, while low interest rates have an upward effect on stock prices (i.e., they make stock prices higher than they would otherwise be, all else being equal), they do not prevent stock prices from falling. When events occur that worsen the outlook for corporate profitability, stock prices will still fall.

Why is the Market Doing Well Lately?

A reader writes in, asking:

“We’ve basically had a full blown bull market since the bottom in March. VTI has a positive 34% return in just two months. How does that make any sense at all? Unemployment is higher than any time since the Great Depression. The death toll continues to climb, and everybody still says that a vaccine is a year away at least. What gives? It seems like the market has become completely disconnected from reality.”

The first thing to understand is that there’s a big difference between “the stock market” and “the economy.” And this distinction is not a new COVID-19-related phenomenon.

The value of the stock market at any given time is essentially the market’s consensus as to the present value of the expected future earnings of publicly traded companies. That is, the stock market is concerned with the profitability of publicly traded companies. Nothing more or less than that.

So unemployment only affects the stock market to the extent that it affects expectations of profitability. If unemployment goes up by, for example, 10%, that doesn’t mean profits will go down by 10%. The change in expected profits could be greater or smaller than the change in unemployment. Relevant factors there would include:

The second critical point to understand is that that the stock market’s valuation is based on an “expected” (i.e., probability-weighted) value of earnings.

The easiest way to understand this concept is to imagine a company that is undergoing a massive lawsuit. If the suit fails in court, the company would be worth $100 billion. But if the suit succeeds, the company will be bankrupt. Given those facts, what is the company worth right now? That depends on the likelihood of the suit succeeding. If the suit has a 30% probability of success, the company should be worth $70 billion right now (that is, 70% chance that it ends up being worth $100 billion, 30% chance it’s worth zero). If the suit has a 50% probability of success, then the company should be worth $50 billion right now.

As the apparent probability of success of the lawsuit changes, the firm’s value will change.

In the middle of March, extremely catastrophic COVID-19 scenarios (e.g., millions of deaths in the U.S.) were being discussed as real possibilities. We really didn’t know what to expect, and the range of potential outcomes was very wide.

Now, those very worst-case scenarios appear quite a bit less likely. Even if the most likely outcome is approximately the same as it was two months ago (i.e., still not good at all), the probability-weighted outcome can be quite a bit better, because the very worst outcomes have become (apparently) less likely.

But of course that means that the market could still fall again in the near future. If something happens to make the really bad outcomes appear more likely — or if something happens that makes the most likely outcome appear somewhat worse — or if something happens to make the best-case scenario outcomes no longer as good — then the market would probably fall again.

Why It’s Hard to Pick Stocks

A friend (who works in a field as far removed from finance as a field can be) recently asked me why I do not invest in individual stocks. Rather than trying my normal direct explanation, I replied with the following analogy. It’s not perfect, but I think it got the point across. Hopefully you’ll find it entertaining or useful.

Imagine that a friend asks you to go with him to an antique show/fair that’s going to be in town this weekend. It’s a decent-sized one. There’s going to be several thousand items for sale.

You’re not particularly interested in acquiring anything for your own use. But you decide to go along, hoping that you can find a “deal” — something that’s significantly underpriced, which you can sell on eBay for considerably more than you’ve paid for it.

What’s going to affect your likelihood of finding such a deal?

Here are a few factors that I can think of:

  • How early you arrive.
  • How many other shoppers there are.
  • How well informed the other shoppers are.
  • Whether you have any relevant expertise (e.g., if you have an encyclopedic knowledge of rare coins, that could be helpful).

You arrive at the market as soon as it opens, Saturday morning.

But you promptly learn that your friend misread the advertisement. The show opened yesterday. Thousands of shoppers — including many experienced antique bargain hunters — have already been through, picking over all the items.

In fact you learn from another shopper that many of the vendors themselves shopped around at other booths, buying items they thought were underpriced, and then putting them back up for sale at their own booths, at higher prices that they considered more appropriate.

How optimistic are you at this point that you’re likely to find a bargain worth buying?

Not very, probably.

That’s the stock market. Except in the case of the stock market, the market has already been open for many years. There are literally millions of other shoppers. Thousands of professional bargain hunters, shopping every day. And there’s a good chance that you have no particularly relevant expertise.

Dividend Reinvestment FAQs

I thought I’d do something different with today’s article. Below are a few questions — from different readers — about various aspects of reinvesting dividends. None of them required a long enough answer to constitute its own article, but the topics in question are likely to be of interest to other readers.

“I’ve read that from 1960 until now, 82% of the stock market’s overall return is from reinvesting dividends. But I’ve also seen that dividends are usually only 2-3% in a given year, whereas the market’s overall return might be something closer to 8%. I guess what I’m asking is why are dividends so much more important than the increasing price, even though they are a small part of the return?”

It’s not that the dividends are more important than the price appreciation. It’s simply that they are a significant part of the return, and leaving off a significant part of the return dramatically reduces the overall accumulation over an extended period. (This is the same reason that mutual fund expense ratios are super important.)

The longer the period in question, the more pronounced this effect. For example, a $1 initial investment that grows at 8% per year for 75 years will come out to about $321. Reduce the return to 7% instead, and the final result is just $160. In other words, reducing the return by one eighth cut the final value by half. If you instead reduce the return from 8% to 6%, you end up with just $79 — a one-quarter reduction in return reduced the final value by more than three quarters.

That’s why when you read about statistics regarding the importance of dividends over several decades, you see very pronounced effects. Any change to the rate of return will have a magnified impact on the ending value. The effect is smaller if we look at periods that are shorter but still significant over a person’s lifetime (e.g., 20 years).

To reiterate, dividends are important, because they are a significant part of the overall return. But the idea that they are far more important than the price appreciation is simply a misunderstanding of the math involved.

“Why does the price of a mutual fund fall when it pays a dividend?”

In short, the price falls because the fund has less assets, which means it’s less valuable. (The same thing happens with individual stocks, by the way.)

For example, imagine that a fund has a net asset value (NAV) of $25 per share on a given day, made up of $24 worth of various stocks holdings and $1 of cash. Then the fund declares a $1 cash dividend.

Anybody who buys the fund before the ex-dividend date will essentially be getting $24 worth of stocks and $1 of cash. Anybody who buys after the ex-dividend date will be getting just the $24 worth of stocks. Point being: the price should fall by $1 on the ex-dividend date. (Of course in the real world it’s messier than that, because the prices of the various underlying stocks would also be moving around from one day to the next.)

To be clear, the fact that the price falls on the ex-dividend date doesn’t mean that you lose something when your fund declares a dividend. The price falls, but you now have an equivalent amount of cash in your brokerage account. (Or, if you reinvest the dividend, you’re in exactly the same place as before, tax considerations notwithstanding.)

“Should I set my mutual fund to automatically reinvest dividends?”


Having dividends automatically reinvested means that your money begins to earn a return sooner, which is a good thing.

But, if the account in question is a taxable account, it also means that there’s more tracking to be done, because you’ll have a greater number of dates and prices at which you purchased shares. But if you aren’t tracking your cost basis yourself anyway (e.g., you’re using the “average cost” method, and you are relying on your brokerage firm to calculate such for you), then the additional complexity doesn’t much matter. (To be clear though, I would encourage you to keep your own cost basis records, rather than completely relying on another party.)

You should also be aware that automatic reinvesting of dividends could result in a wash sale if you sell the investment in question at what would otherwise be a loss. Generally, this would not be a major reason not to reinvest dividends, as the effect would usually be small. But it’s something to be aware of so that you can report your taxes appropriately.

“How do I calculate the gain or loss on a sale of a mutual fund when I have had dividends and capital gains reinvested? Last year I invested $40,000 in a mutual fund, and it was worth about $40,500 at the end of the year. My dividends and taxable gains for that year, all of which were reinvested, were about $1,700 according to my online statements. Let’s say my fund’s value is $40,500 when I sell it this year. What would be my gain or loss?”

Because you have the account set to reinvest dividends and capital gains, you actually purchased $1,700 worth of shares over the course of last year. So your total basis at the end of the year was $41,700.

So if at the beginning of this year (i.e., before any new money gets invested or distributions get reinvested) you had sold all of the shares for a total of $40,500, then you would have a capital loss of $1,200 (i.e., $40,500 realized on the sale, minus $41,700 cost basis).

If further dividends/capital gains had been reinvested this year before the sale, those would be added to your cost basis as well.

Whether or not you could actually claim this loss would depend on whether or not it’s a wash sale — which it could be, if you own other shares of this same investment (or something else that is “substantially identical”) in another account.

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