This is a blog comment I wrote to a reader question sent to Alicia Adamczyk on Lifehacker’s Two Cents blog, titled “How Freelancers Can Save for Retirement Beyond an IRA.” The question is from a freelancer in animation or a related entertainment profession. This person is unable or can’t figure out how to contribute more to his or her 401(k), is contributing the maximum to an IRA, and has a “sizable” emergency fund but worries about income stability.

I would prioritize investigating and gaining online access to your current 401(k) to see what it’s being invested in, what the management fees are, and whether you can change to a low-fee index fund of the whole U.S. stock market or S&P 500.

You are already ahead of the curve to be contributing $5,500 per year to an IRA and by having an emergency fund. The two main reasons to start investing for retirement early are (a) compounding returns and (b) tax avoidance. You can’t go back years in the future to make an IRA contribution for the 2018 tax year, for example, nor can you make up for compounding returns.

With a time horizon of many decades, equities (stocks) are the best investment. You can divide your monies between index funds of the U.S. stock market and the international stock market (i.e., all other countries except the US) for further diversification. Investing in any particular stocks or market sectors is a bad idea.

As mentioned, an SEP IRA for self-employment income is an option. Another would be to get a second job just to contribute more to a 401(k) plan (the annual limit for employee contributions is $18,500, presently). For instance, Starbucks allows employees to contribute up to 75% of their paycheck to a traditional or Roth 401(k) plan, and matches the first 5% contributed.

As mentioned, a taxable brokerage account is also recommended. It can be invested in the same broad index funds at the same low management fees, and most of your gains and losses are “unrealized” until you start cashing out later in life. While the quarterly dividends you will receive are taxable, many of these will “qualified” dividends that are taxed at a lower rate, or not at all, depending on your income.

Although the traditional advice is to have an emergency fund of six months living expenses, as a freelancer your income is less stable so you may want to increase this to 12 months. The emergency fund should be liquid and non-volatile, meaning it should NOT invested in equities. As of May 2018, there are many savings accounts through reputable online banks (e.g., Ally Bank, Discover Bank) that pay 1.50% APY or slightly more, and your deposits are FDIC insured up to $250,000.

One reason to keep your emergency fund in a savings account, rather than plowing it into equities, is that stock market crashes often occur at the same time as tough job markets. You don’t want to be in a position where you must sell your stocks during a recession just to pay your bills.

New: I made a narrated video explaining the questions and answers.

This is a financial literacy quiz written by Richard Thripp in April 2018 and published on Tippyfi in May 2018. It covers interest rates, compounding, numeracy skills, stock investing, tax issues, healthcare, and retirement. After submitting, you will see how many points you scored, the answers you chose (marked with a red X if incorrect) and the correct answers (marked with a green checkmark) for all questions, and explanations for all questions.

1. Suppose you deposit $1,000.00 in a savings account that earns interest, amounting to a 1.00% annual percentage yield (APY). This means that after each year passes, the account balance will be 101% of what it was a year before. After two years, what will your account balance be?


2. Suppose that when a person earns money, they pay 10% of their earnings as a tithe to their church. Pretend that other expenses and taxes (e.g., income, payroll, and sales taxes) are zero. For this person to be able to afford to purchase a $100.00 item, how much money must they earn?


3. If five (5) people all have the winning number in a lottery and the prize is $2,000,000.00 (two million dollars), how much will each of them get? Assume the prize is split evenly, taxes are zero, and that there is no penalty for a lump-sum payout. (Question adapted from the 2004 Health and Retirement Study)


4. Suppose that a credit card charges a 24% annual percentage rate (APR) on purchases, compounded daily from the date of purchase (365 days per year). This means that each day, the amount owed is 100.06575% of what was owed the previous day. One year after a purchase is made, how much of the original amount will be owed? Assume no payments are made toward this purchase and no penalties are assessed.


5. If inflation increases prices by 2.00% per year for a given item that costs $100.00 now, how much will this item cost in 10 years?


6. You are shopping at a clothing store in a clearance section where all items are 50% off the marked prices. Items marked with a yellow tag receive an additional 30% off. Which method of computing the discounted price would result in a lower price for the customer?


7. Over a 30-year timeframe starting now, which of these is most likely to be the most profitable investment?


8. Avoiding income taxes is a reason to contribute to an individual retirement arrangement (IRA).


9. Monies contributed to individual retirement arrangements (IRAs), 401(k) accounts, and 403(b) accounts can be invested in certificates of deposits (CDs), money market accounts, and fixed-income assets (bonds), but cannot be invested in equities (stocks).


10. In a 10-year period, which of the following earnings scenarios will result in an unmarried individual paying less money in U.S. federal income taxes?


11. Given the performance of U.S. equities (stocks) in the past, if one invests in an index mutual fund of the whole U.S. stock market, the probability of making money in any particular one-year period is approximately what?


12. Given the performance of U.S. equities (stocks) in the past, if one invests in an index mutual fund of the whole U.S. stock market, as the number of years one stays invested increases (e.g., 10, 20, 30, 40 years, etc.), the probability of making money gets closer and closer to 100%.


13. If one has plenty of money saved, it is generally a good idea to purchase insurance that protects against minor expenses.


14. In most U.S. states, giving a person durable power of attorney means they can make medical decisions for you if you are incapacitated, even if their decisions are contrary to your family’s wishes.


15. Generally, designating someone as a payable-on-death beneficiary of a bank or investment account supersedes or bypasses beneficiaries named in a will.


16. A downside of health insurance is that hospitals typically negotiate higher rates with insurance companies than what they would bill an individual who did not have health insurance.


17. A disadvantage of accumulating an emergency fund is that you may become ineligible for means-tested benefits such as Supplemental Security Income (SSI).


18. Overall, the distributions of income and wealth in the United States have both been becoming more equitable since the 1970s.


19. On a dollar-for-dollar basis and without considering taxes, funds acquired through hard work and funds acquired via a windfall (e.g., winning the lottery) are of equal value.


20. Which of the following has a positive impact on your credit scores?


Investing in the stock market is fundamentally risky. Although in 2018, capitalization-weighted stock market index funds with small expense ratios are finally approaching ubiquity, the risk of an investment in the whole U.S. stock market losing nominal dollars in any one particular calendar year is nonetheless about 25% (this is similar for the S&P 500, which by market cap is almost 90% of the U.S. stock market). Of course, the risk of losing nominal dollars in a bank account, certificate of deposit (CD), or Treasury bill in any one particular year is 0%. For a capitalization-weighted bond market index fund, the risk is greater than 0% but much less than 25%.

Based on this volatility, standard, “time-tested” investment advice is to reduce one’s proportional exposure to stocks as one ages. Considering stocks and bonds, the two major classes of investments, authors and financial advisors often advise portfolio allocations looking something like this based on a person’s age:

Typical Asset Allocations Pie Chart

This is the “glide path” by which one reduces exposure to risk as he or she ages, accumulates wealth, and eventually stops working. The theory is that in youth and middle age, you can fall back on your earnings and many remaining decades of life. Although you will make money in about 75% of one-year periods in U.S. stocks, you will make money in 100% of 30-year periods. That is to say, over longer time horizons, U.S. stocks always outperform bank accounts, CDs, T-bills, and bonds. Because people who are still working can live off their earned income, in theory there should be no reason to withdraw money from your investments in capitalization-weighted stock market index funds until you retire. This would include stock investments in your individual retirement arrangements (IRAs), 401(k) or equivalent accounts, health savings accounts (HSAs), and taxable brokerage accounts.

A Litany of Problematic Assumptions

Percentage-based portfolio allocation recommendations are fundamentally stupid. In theory, they suggest that your investments should be of the same proportions whether you have $1,000 or $1,000,000,000. There is no accounting for human behavioral foibles nor your portfolio size, earnings, living expenses, future living expenses, retirement target date, or legacy.

Human Behavioral Foibles

Although a younger person should be more tolerant of risk, it is actually more likely that they will sell their investments out of fear when the U.S. stock market drops. While a good financial advisor might talk them out of such foolishness, it is necessary for a young person to fully comprehend the nature of the stock market. Otherwise, they are likely to sell at the worst possible time (i.e., the next recession) and never buy back in due to psychological trauma.

Sequence Risk

Sequence risk is the primary, existential threat to a retiree’s portfolio. If the next Great Recession occurs right at the start of your retirement, you could wind up destitute if you follow Dave Ramsey’s clownish advice that you can count on 12% annualized market returns and an 8% annual withdrawal rate in retirement (both of Dave’s suggestions are manifestly, positively, 100% wrong). If the market tanks by 50% and you then withdraw 8% of the pre-crash value, you are down not 58% from your initial portfolio size, but 66%. With 34% of your initial investment remaining, you would now need your portfolio to triple just to get back to the starting point. In a nutshell, this is sequence-of-returns risk.

Because no one can time the market with consistency and accuracy, competent financial advisors suggest a 4% annual withdrawal rate. Although this sounds overly conservative, the conservatism is necessary to account for the possibility of a market downturn early in retirement. In the majority of scenarios, a retiree should die with more money than they started retirement with, because there is no way to time the market. Consequently, it is impossible to plan things out so one runs out of money just as they kick the bucket.


Percentage-based portfolio allocations suggest moving increasing proportions of your money into low-risk, low-yield investments as you age. Although financial advisors actually consider (or, should consider) your personal situation, it is nonetheless pervasive that blanket percentage-based “rules of thumb” be proffered based on one’s age, such as “invest your age in bonds.” These recommendations are often misguided and, frankly, preposterous. They unnecessarily assure diminished returns in middle and old age.

Not Accounting for Portfolio Size and Living Expenses

The size of your portfolio and your living expenses are actually critical factors in the proportion of your portfolio that you invest in stocks. If, in retirement, your living expenses are more than covered by Social Security and a pension, you might continue to invest 100% or most of your portfolio in stocks, because even if the market tanks, you don’t need to withdraw any money. After human behavioral foibles, the second biggest risk of investing in stocks is that you might have to take your money out during a recession. If the timing of deposits and withdrawals is stochastic (i.e., random, with no consideration of market value), then the duration of investment is the determinant factor in returns, with respect to the U.S. stock market or global stock market.

Of course, among American investors (and others), the timing of deposits and withdrawals is not stochastic. People tend to withdraw money during a recession, often because of psychology, poor planning, and job loss. People put more money in at the market’s peak, rather than as the money becomes available to them.

Say that your living expenses are $40,000 per year and your portfolio is worth $2,000,000. Then, 4% of $2 million is $80,000, which is double your living expenses. If you are Age 65 and having most of this $2 million in bonds, you will miss out on tremendous returns in old age, which might extend into your 90s. On the other hand, you could have 80% of the $2 million in stocks and, even in the worst scenario, not need to liquidate stocks for 10 years by withdrawing the proportion of your portfolio ($400,000) invested in bonds. (When stocks go down, bonds do not tend to similarly decline.) Living expenses also trend lower in a recession, and you may have other income from Social Security, et cetera.

On the other hand, if you have the same retirement portfolio but need $200,000 per year to live, neither a conservative nor aggressive allocation will suffice, because your expenses are simply too high (or, alternately, your portfolio size is too small).

Future Living Expenses

Your future living expenses are also something to consider. They could go up or down in retirement. A common observation is that living expenses tend to go down after Age 80 or so (although, of course, medical expenses can go way up). If your living expenses are going to decline drastically, such as due to downsizing your home and no longer having to pay for children’s college expenses, your portfolio can be more aggressive (a larger proportion in stocks) because you will not need to withdraw as much.

Retirement Target Date

Becoming financially independent and retiring early (FIRE) is popular among a small section of Americans who read Mr. Money Mustache and other authors. The 4% rule is not about winding up with $0 after 30 years—it is aimed at indefinite sustainability. This is why FIRE hopefuls are so concerned with cutting expenses. Cutting $1,000 out of your annual expenses means you are financially independent (i.e., your portfolio can indefinitely sustain itself) with $25,000 less. If your annual expenses are $40,000, you can usually be financially independent with $1 million, but if you can cut your expenses to $20,000, you only need $500,000. The bulk of your portfolio should be invested in stocks, and you should be prepared to spend less or earn more (a “soft retirement”) if the market declines early in your retirement (sequence risk). On the other hand, if the market increases, this will not be necessary.

Percentage-based portfolio recommendations fail to consider any of these factors.


Fundamentally, this is the same problem that Harvard University’s endowment and the Nobel Foundation face. The manner in which both of these learned institutions handle their portfolio is spectacularly terrible. They insist on employing highly paid fund managers in the fruitless and detrimental pursuit of picking stocks and timing the market, rather than passively investing in the whole market. Then, we have the Nobel Foundation going on the record in 2012 saying they expect low equities returns in the future, which of course was followed by tremendous returns, showing that market predictions are often wrong. Although a passive index-investor had tremendous returns since 2012, it is likely that Harvard, the Nobel Foundation, and others had lower returns due to their active investing practices.

It is misguided to tell someone to invest a certain proportion of their portfolio in stocks without specifying that this money should be in an S&P 500 or broader, low-fee index fund. Certainly, many endowment managers invest a large proportion in stocks, yet their returns are muted due to trying to pick stocks and sectors, and not investing for the long haul. This is called the investor gap. When a foundation’s investment time horizon is basically eternity, it is inexcusable for their assets to be so spectacularly mismanaged.

Sadly, misinformation on the Internet is widespread. Many thousands of websites suggest that active management, picking market sectors, and timing the markets are worthwhile, simply because stockbrokers profit from charging load fees, transaction fees, and management fees. These practices are diametrically opposed to leaving a financial legacy to heirs or charity. Like many other issues, they are not addressed in mainstream portfolio advice.

Although most people will agree they should learn more about it, most people aren’t interested or motivated to learn about personal finance and apply the knowledge to their lives. There is obviously an overwhelming amount of information available online, yet seeking it out is a problem for many. At the same time, there are large communities of what we might call enthusiasts or “hyper-financially educated people,” such as Mr. Money Mustache.

The problem is: How do we bridge the gap between the financially illiterate and the financially hyper-literate?

The majority of people reading this website or others on personal finance probably have caught the financial “fever,” so to speak. However, to bridge the gap for the uninitiated, some strategies might be:

1. Being educated by a family member, mentor, or friend
2. Engaging in “information-seeking behavior,” which involves asking questions, searching online, and finding consensus from multiple sources
3. Reaching a tipping point where you are “fed up” with your financial life and actively seeking a change
4. Personal finance is eclectic and pervasive—it touches all areas of life. Therefore, many other skills are important to being financially successful, such as being organized, a good negotiator, and possessing both written and quantitative literacy.

Strategies of prime importance are to seek information, seek second opinions, and give oneself time to think when it comes to financial decisions. Personal finance is not “common sense.” For example, American credit scores work in a manner that is convoluted and arcane to most Americans. If you haven’t actually sought out information on this, you might think paying your utility bills on time helps your credit score (it doesn’t), or that spending a lot on your credit cards builds your credit (it doesn’t—owing more than $0.00 on your statement each month and then making a payment does).

Many Americans don’t investigate or put up a fight when getting a raw deal when it comes to their finances. For example, hospitals might over-bill you for services not received, or fail to process your insurance correctly, resulting in a higher bill at chargemaster pricing that ends up going to collections and damaging your credit. Although you can intercede by contacting the medical billing company to correct your insurance information, by negotiating a lower bill, or later on, by disputing the derogatory marks on your Equifax, TransUnion, and Experian credit reports if they are erroneous, many people simply don’t look into this.

Although knowledge is power, inquisitiveness is a prerequisite.

Many people focus their energies on working harder rather than smarter. If the options for using your time are (a) pick up over-time shifts at work or (b) call your credit card and auto loan issuers and get your interest rates reduced from 20% to 15% with a few simple phone calls, clearly Option B is the better use of your time. Yet, doing more of the same is the easier, more comfortable option.

The returns on becoming financially educated and putting this knowledge into action are huge. It is perplexing to me that so many people find it boring and unmotivating. For instance, many Americans are working extra hours to bring in more money, while failing to claim their tax refunds, and, in aggregate, leaving billions of dollars on the table.

It is completely senseless to work more hours to make $15 per hour when doing some financial reading might be worth $500 per hour, in the long run. If this insight alone is not enough to incite Americans to want to learn about personal finance, then the cause might be hopeless, and the efforts of financial educators might be better focused on taking those who are already financially literate to the next level.

Even up to the tax filing deadline for the prior year, it is still possible to make contributions to individual retirement arrangement (IRAs) and health savings accounts (HSAs) for that year. For 2017, this means you have until April 17, 2018 to contribute.

On the other hand, 401(k) and 403(b) accounts must be made through employer payroll deductions, so you cannot go back and contribute for the prior year to receive the tax advantages. You can go through your employer’s HR or payroll department to start making contributions on your next paycheck, however.

If you have received a windfall (e.g., a tax refund!) or just learned about retirement accounts, you can make retirement contributions for the prior year in January–April of the next year. Typically, you would want to max our your IRA first and then your HSA.

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