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  • Writer's pictureMark Fonville, CFP®

How to Invest in Retirement: A Comprehensive Guide

Updated: Nov 2, 2023

How to invest in retirement: A Comprehensive Guide

When you think about how to invest in retirement, what comes to mind?

Chances are, it’s something related to how to invest so you don’t run out of money. If so, you're not the only one who feels this way.

In a 2020 investor survey by Dimensional Fund Advisors, 11,236 investors were asked to state their greatest fear about personal finances.

On average, 49% of investors said that not having enough money to live comfortably in retirement was their number one financial concern!

Greatest fear about personal finances for retirees.

Unfortunately, many people don’t know how to invest in retirement even though they may have significant investable assets.

Before we dive into how to invest, it’s essential to identify the obstacles you face.

Here are three significant obstacles we often encounter when helping clients plan for retirement:

  • Investor behavior gap – Poor investment behavior causes many investors and professional money managers to underperform market returns.

  • Sequence of return risk – Even more important than the returns you receive, the order in which you recieve those returns can mean the difference between maintaining financial security in retirement and running out of money.

  • Income taxes – High taxes and inefficient tax management can destroy your hard earned savings.

Let’s take a look at each obstacle to help you understand what’s at stake before you learn how to invest in retirement.

Investor Behavior Gap in Retirement

Dalbar, a leading financial research firm, released its latest report on investor behavior back in 2019 and the findings, though not surprising, do not bode well for future retirees.

The study showed that the average investor underperformed the market—by a considerable amount.

For example, in 2018, the S&P 500 lost -4.38% vs. the average stock market investor’s return of -9.42% for the year. This means that investors unperformed the market by 5.04%!

The 2019 study results weren’t an anomaly, unfortunately.

If you want to know how to invest in retirement, it’s important to know that the odds of achieving good long term performance are stacked against you.

There are a variety of reasons for investor performance lag, but poor investor behavior tops the list.

The study found that investors hung onto their stock and bond positions for just under four years before selling them for another investment. This frequent trading, or what we call turnover, can ruin the potential for long-term growth.

So much for long-term investing!

Additionally, many investors in retirement gave into “panic selling,” pulling money out of an investment at the worst possible time because market commentators stoked their fears.

Lack of diversification also contributed to poor returns.

It’s not just individual investors who underperformed the market—even professional money managers fail to meet their benchmarks despite charging high fees for their services.

Each year, the S&P Dow Jones Indices release an annual report card showing how various funds and fund managers performed against their respective index.

In 2020, 47% of small company value fund managers underperformed their benchmark, as did 63% of large company stock mutual funds.

According to Dimensional Fund Advisors, over the last 10 years, only 21% of equity mutual funds across all investment categories underperformed their index benchmark!

But, investment performance isn’t the only obstacle when it comes to knowing how to invest in retirement.

Sequence of Return Risk

Investors face an entirely different set of challenges when it’s time to turn their growth portfolio into an income portfolio in retirement.

Few investors have ever heard the term “sequence-of-returns risk,” or simply “sequence risk,” but it can have a significant impact on your ability to take sustainable income withdrawals from your retirement portfolio.

Imagine two couples, the Washingtons and Lincolns, as outlined in the chart below.

Both have identical account balances of $2 million at age 60, both wish to withdrawal $50,000 per year from their portfolio, and both receive an average return of 4.28% per year starting at age 60.

However, let’s assume that each couple receives their returns in the opposite sequence of the other as shown below in our sequence of return chart.

How to invest in retirement - 4

Example 1: The Washington Family

Mr. and Mrs. Washington begin retirement during a bear market, defined as a period when the stock market declines more than 20%.

At the time of their first income withdrawal of $50,000, the portfolio is actually generating negative returns. As a result, they have to spend over 7% of the portfolio value in year one just to meet their income needs in retirement.

Unfortunately, poor returns continue and don’t rebound until halfway through their retirement.

The result: The Washingtons run out of money by the time they turn 81!

Example 2: The Lincoln Family

The Lincoln family, on the other hand, entered retirement in an upward trending bull market. When they take their first withdrawal of $50,000 in retirement, it represents less than 2% of the portfolio value.

The Lincolns continue to have high returns in the early years and don’t face severe downturns in the market until later in retirement.

The result: The Lincolns end up with $3.8 million by the time they are 88 years old and never run out of money in retirement.

But remember, their average return was the exact same as the Washington family.

How to invest in retirement - 5

The financial consequences of retiring in a bear market are twofold:

  1. Due to market declines in the early years, the Washingtons have far less money in their portfolio in the early years.

  2. The Washingtons must withdrawal a bigger percentage of their portfolio just to meet their fixed expenses in retirement.

That’s sequence risk in a nutshell, and it’s an issue everyone must consider when planning how to invest in retirement at age 55, 60, 65, or older.

The good news is that sequence of return risk can be mitigated with the right portfolio strategy.

Tax Implications of Investing in Retirement

Many investors either don’t understand or fail to consider the tax implications of their investment choices when it comes to investing in retirement.

For example, a study by Vitali Kalesnik and Trevor Schuesler entitled: “Is Your Alpha Enough to Cover Its Taxes? A Quarter-Century Retrospective.” The authors conclude that the average actively managed mutual fund in their study lost 2.4% of their return per year to taxes!

Another study by Vanguard revealed that investors can potentially improve their after-tax investment returns by up to 0.75% per year by implementing just one tax strategy, called asset location.

Ignoring taxes when investing in retirement has many implications, including:

  • Taxes can reduce the income and earnings available for reinvestment. This hurts your ability to compound your investment portfolio at a faster rate over time.

  • Taxes can reduce the amount of money you have available to fund your goals in retirement.

  • Unnecessary realization of capital gains. High capital gains can boost you into a higher tax bracket in retirement unnecessarily.

Any investor who wants to know how to invest in retirement must understand the tax implications of their investment decisions. Otherwise, you risk paying Uncle Sam more and having less money to fund your retirement goals.

While learning how to invest in retirement may feel like rocket science for some – fortunately, it isn’t impossible with the right advice.

Here’s how to invest in retirement condensed into 7 steps:

1. Identify Your Risk Tolerance

How much risk is too much? That’s a significant question you need to ask when it comes to knowing how to invest in retirement.

Since 1973, the S&P 500 has posted an average annualized return of over 11%.

But, stocks have historically experienced massive declines of 50% or more in periods of economic uncertainty.

To help assess how much volatility you can tolerate with your investments, we recommend that you take a risk assessment quiz.

For example, here is an example of a risk tolerance quiz we created for use with our own clients. The results are generated from a series of questions designed to better understand investor preferences and tendencies when it comes to earning money and losing money.

A proper risk assessment will help you determine your willingness to lose some or all of an investment in exchange for higher potential returns.

We've found that individuals generally differ in the amount of risk they feel comfortable taking. You may embrace uncertainty, while others may tend to avoid it at all cost.

If you’d like help understanding your own risk tolerance, just contact us.

While not guaranteed, for long-term investors who are well-diversified, corrections and downturns shouldn’t be cause for panic because the market has historically always rebounded over time.

Case in point: The S&P 500 lost 37% in the financial crisis of 2008; today, it is up tremendously from its low point in March 2009. Long-term investors can weather market storms.

2. Choose Your Investment Approach

Knowing how to invest in retirement requires an investment strategy that is verifiable and defendable. It's also important to understand your retirement investment options.

Having an investment philosophy will help guide your decisions during turbulent markets. As a result, you may become a more disciplined investor.

At the least, we recommend that you ask yourself several questions to help guide your investment thinking in retirement:

  • Does your investment approach stand up to academic scrutiny?

  • Does your investment approach work in U.S. and Non U.S. markets?

  • Does the cost of implementing your approach outweigh the benefits?

  • Has your approach been tested across hundreds of time frames?

Formulating your investment approach can be a challenge. To help, here is a short video explaining our investment principles at Covenant Wealth Advisors.

While there are literally thousands of different investment strategies to choose, most of them can be divided into two approaches:

  • Active investment management

  • Passive investment management

So, what’s the difference?

Active Investment Management in Retirement

Active money managers try to outperform the market by buying what they believe to be “good" investments and avoiding the “bad” ones. This is done by attempting to forecast the direction of stock or bond markets or by timing the market. "Market timing" is the concept of trying to get in and out of the market at the “right” time.

Examples of active investment managers:

  • Franklin Templeton Investments

  • Pimco

  • American Funds

  • T. Rowe Price

  • Dodge and Cox

Passive Investment Management

Passive investment managers don’t try to beat the market.

Instead, their goal is to capture the market’s returns. Instead of attempting to outperform the market, they focus on letting markets work for them.

They seek to increase diversification and focus on keeping costs low to achieve higher potential returns. Passive managers can also be more tax-efficient than their active counterparts.

Examples of passive investment managers:

  • Dimensional Fund Advisors

  • Vanguard

  • Blackrock

While the idea of active investment management can be appealing, stock-picking is a bit of a gamble; even the most experienced investors underperform the market long-term and can end up increasing risk at the same time.

So, should you choose active investment management or passive investment management?

To answer this question, you can start by looking at the evidence. As it turns out, passive investment managers have historically provided far better results.

As illustrated in the chart below, you’ll notice that only 21% of actively managed U.S stock mutual funds outperformed their index benchmark from 2010-2019.

While a few active managers were successful, the odds don’t look favorable for active management.

Mutual fund survivorship 2019
Source: Dimensional

Index mutual funds and exchange-traded funds can be a better choice for most investors.

These types of investments are passively managed, which keeps fees low, especially compared to actively managed mutual funds.

Exchange-traded funds (ETFs) are another excellent low-cost option for retirement investing. ETFs can also track an indexing or passively managed approach, but they trade like stocks on the exchange.

You can track a variety of asset classes including stocks, bonds, and commodities with both index funds and ETFs to keep your portfolio in balance and your expenses low.

The point is that investing in passively managed index funds or ETFs may improve your probability of success in retirement.

3. Choose Where to Put Your Retirement Money

Now that you understand your tolerance for risk and have an investment philosophy to guide you, you'll need to design your asset allocation plan.

Your asset allocation in retirement is simply the right mix of stocks and bonds for you and your family.

Remember, it’s crucial to take into account all of your savings and investment accounts when thinking about the allocation that is right for you, and not just your "retirement" accounts.

Many investors end up making a big mistake by keeping too much money in cash. While this can feel safe in the short-term, too much cash can slow down the growth of your total savings. Lower returns may result in running out of money in retirement.

Let’s break down asset allocation in retirement a bit further.

How should you divide your retirement savings between stocks and bonds?

Generally speaking, how much you invest in stocks and bonds should be dependent on two questions:

  • How much return do you need to fund your retirement goals?

  • How much could your investment portfolio value fall before you decide to sell and go to cash?

In the chart below, we outline seven hypothetical portfolios with differing percentages of stocks and bonds.

How to invest in retirement - 7

Which portfolio in the chart above would make you most comfortable?

Notice that average historical returns increase as the percentage of stocks increases within the portfolio. While higher returns can be favorable, you’ll also notice that portfolios with a higher percentage of stock also experience steeper declines when stock markets drop.

The right portfolio mix of stocks and bonds will depend on your own ability to tolerate market declines and your need to take risk in the first place.

Your risk assessment should help guide your thinking.

Some people have a meltdown when an investment loses 5%; others are comfortable with a 20% or 30% temporary decline.

Once you’ve established the right mix of stocks and bonds, you’re ready to select the appropriate asset classes for your retirement portfolio.

Asset classes are simply a distinct group of stocks or bonds that have similar characteristics.

For example, U.S. Large Caps are companies based in the United States that represent the largest companies available for investment.

U.S vs International Stocks

Diversifying your retirement portfolio across both international and U.S. stocks may help manage the ups and downs of your portfolio value over time.

As the leader of the free world, America is a great country to live in, but over the past several decades, the United States has never been the #1 best performing stock market in the world.

In the chart below, we rank the performance of stock markets in 46 countries across the world over the past 10 years through 2017.

Ten years ago, almost no one would have predicted that emerging countries like Thailand, the Philippines, and Denmark would do so well. Fifteen to twenty years from now, poorly performing countries of the past may very well be the best-performing countries going forward.

How to invest in retirement visual of stock market returns around the world through 2017.

Many investors fear diversifying overseas because we tend to distrust investments that aren't geographically close. This behavioral phenomenon is called "home bias."

However, you may be surprised by the number of household brands and companies that are located outside of the United States.

The truth is, nobody knows the future. Not even Jim Cramer of CNBC!

Investing is really about ownership in the future revenue of a company.

No matter what country's stock market you invest in, there will always be entrepreneurs with great ideas working hard to build a company that can implement those ideas.

By diversifying your investment portfolio across many countries, you may better position yourself to capture the potential returns when and where they occur.

Proper diversification is a key element of knowing how to invest in retirement.

Keep in mind that international stocks can be riskier than U.S. stocks, due to currency and political risks, among others.

This is why it is so important to carefully decide how to diversify your portfolio between U.S. and international companies.

A great financial advisor should be able to help.

Small and Value Companies Vs. Large and Growth Companies

In retirement, every penny of added return can matter.

But, it can be challenging to increase expected returns by forecasting or trying to predict the stock market.

Moreover, nobody wants to take a risk that you’re not rewarded for over time.

So, how can you invest in retirement to increase expected returns in your retirement portfolio?

All investing involves taking on some risk. After all, risk and return are related when it comes to investing. In a well-diversified portfolio, the more risk you take on in your portfolio, the higher your expected return potential. The opposite is also true. When you reduce risk in your portfolio, your expected returns are lower.

Academic research has shown that stocks from different kinds of companies have different expected returns.

For example, in the chart below, you’ll see that small company and value company stocks have higher expected returns — and greater risks — than growth company and large company stocks.

How to invest in retirement - 8

As an investor, you should consider how much of these risks you are willing to take.

Value stocks are usually associated with corporations that have experienced slower earnings growth or sales or have recently experienced business difficulties, causing their stock prices to fall. Value stocks have higher expected returns due to this uncertainty.

Small companies are defined as those with a market capitalization of $300 million to $2 billion. Small company stocks may be subject to a higher degree of market risk than the securities of larger companies because they may have fewer sources of revenue and are less liquid.

Academic research has shown that tilting the stock portion of investment portfolios toward value and small companies may increase your expected return.

This strategy, known as factor investing, has been shown to reduce the risk of running out of money in retirement.

Fixed-Income Investments in Retirement

Don’t forget to add fixed-income elements to your portfolio.

In retirement, it's paramount to offset stock risk with the safety and liquidity of bond investments. Doing so may reduce the sequence of return risk and provide a reliable source for income during market downturns.

Fixed income in your portfolio can resemble shock absorbers on a car. While the return from fixed income may not be exciting, you’ll be glad you had the added cushion when, not if, the next stock market collapse occurs.

But, not all fixed income investments are the same.

While all investments entail risk, some of the safest investments for retirement can include:

  • Short-term government bonds or bond funds

  • Short-term and high-quality corporate bonds

  • FDIC insured CDs and savings accounts

Investing in a broadly diversified bucket of safe investments for retirement may reduce your risk exposure when you need it most.

4. Design Your Tax Plan In Retirement

While stock markets can’t be controlled, taxes are something you can control. Every sound investment plan needs to incorporate a tax plan, too.

Proper tax planning can give you more control over your tax bracket in retirement.

Optimizing your investments from a tax standpoint can also help reduce your taxable income and increase your after-tax returns. That can translate into more money in retirement.

There are three primary “tax buckets” when it comes to your savings and investments. Each bucket has different tax treatments.

How to invest in retirement - 9
Taxation of income withdrawals by investment vehicle

Taxed Forever Bucket (or tax-deferred)

The "taxed forever bucket" includes investment vehicles that are funded with pre-tax dollars.

The money grows tax-deferred and is fully taxed upon receipt of the income. This means that you will be required to pay federal and state income taxes on this income at the highest marginal tax rate for which you qualify, once withdrawals begin.

What’s included in the taxed forever bucket?

  • Up to 85% of your social security income

  • Pensions

  • 401 (k)

  • 403b (k)

  • Traditional or rollover IRA


The taxed forever bucket may lower the taxes you pay on the front end. However, the IRS wants to get paid, which is why you’ll pay taxes upon withdrawal.

Unfortunately, many investors end up with most of their money in the taxed forever bucket. This is a mistake that can be avoided.

Never Taxed Bucket (or tax-free)

The never taxed bucket includes investment vehicles that are funded with after-tax dollars, grow tax-free, and provide tax-free income in retirement.

Because your guaranteed income sources (Social Security and pensions, for example) are taxable, you should aim to build your never taxed bucket to help reduce the taxation of your income in retirement.

What’s included in the never taxed bucket?

  • Roth IRA

  • Health Savings Account (HSA)

  • Municipal Bond Interest

Investment earnings and withdrawals from a Roth IRA are tax-exempt, but your contributions are not tax-deductible.

If you believe your federal and state tax rate will be the same or higher in retirement, you may consider maximizing contributions to your Roth IRA before you retire.

Withdrawals from a health savings account, or HSA, are also tax exempt. Individuals can contribute up to $3,600 a year, or $7,200 a year for families in 2021, to an HSA to cover health care expenses.

There’s no minimum mandatory distribution for HSA funds, and you can leave them in your account indefinitely.

Tax-Advantaged Bucket (or taxable)

Don’t overlook the tax advantages of an individual brokerage account When investing in retirement.

Although interest, dividend, and capital gains income distributed to your account are taxed during the year in which they’re realized, there are still some essential tax strategies to reduce tax and maximize the assets you transition to heirs in the future.

Here are several planning strategies and tax benefits to the tax-advantaged bucket, which includes individual brokerage and revocable trust accounts:

  • No required minimum distributions. There are no required minimum withdrawals, so you don’t have to withdrawal the money unless you want to.

  • Step-up in cost basis. You get a step-up in cost basis upon your death. This means your heirs will continue to love you forever because they likely won’t owe taxes on their inheritance.

  • Tax-efficient investments. You can invest in tax-efficient index funds or exchange-traded funds (ETFs) to help reduce taxable distributions on your earnings.

  • Liquidity for large purchases. The tax-advantaged bucket is a great source to help fund large purchases without increasing your taxable income.

  • Tax-loss harvesting. You can use losses in your brokerage account to offset capital gains. If you have a poorly performing stock or fund in your account, you can sell it and use the loss to reduce any capital gains tax liability you might incur.

Tax Strategies for Income in Retirement

To maximize your tax-free income in retirement, consider strategies to convert assets from your “Taxed Forever” bucket to your “Never Taxed” or “Tax-Advantaged” bucket.

If you need help with these strategies, just contact us.

Just remember, how you diversify across these tax buckets can impact how you invest for retirement.

5. Rebalance Your Portfolio

Have you ever heard of the investing idea of “buy low, sell high”? While great in concept, few investors actually know when markets are high or when they are low.

That’s where portfolio rebalancing can help.

It’s important to rebalance your portfolio at least once a year to keep your portfolio in proportion to your ideal percentage of stocks and bonds.

If left untouched, your portfolio can become more aggressive over time. Rebalancing can also help ensure that your portfolio remains aligned with your risk tolerance.

Example 1: Portfolio Rebalancing

Let’s assume that a proper portfolio for you is 50% stocks and 50% bonds. If left untouched, your investments may shift to 75% stocks and 25% bonds due to stocks growing faster than bonds over time.

A proper rebalancing strategy may sell off your excess stock holdings and replenish your bond investments to bring your portfolio back to the correct proportions.

While not guaranteed, portfolio rebalancing has historically been shown to manage risk in retirement better. Improved risk management may positively impact the ability to create sustainable income in retirement.

6. Manage Your Emotions

The most successful retirement investors don’t even attempt to time the market. For most people, it’s merely a waste of time and money that doesn’t do a thing to increase returns.

Investing can be an emotional roller coaster. Our brains are hard-wired to make irrational decisions about money at precisely the wrong time.

How to invest in retirement visual of the cycle of market emotions when investing in retirement.

Even the most astute investors can “buy high” and “sell low" instead of "buying low" and "selling high." Stock markets are predisposed to sharp and erratic movements, which can influence investors to sell at the wrong time.

For example, during a bull market, investors often rush into the market because they feel “elated” and buy at the peak.

Ultimately, this kind of emotional, short-term behavior can have detrimental consequences, including dramatic portfolio underperformance.

7. Establish Your Income Plan

Have you ever heard of the 4% rule in retirement?

It’s a well-known study on retirement income distribution strategies published in a 1998 paper entitled: Retirement Savings: Choosing a Withdrawal Rate that is Sustainable.

In short, the study concluded that a portfolio with at least 50% in stocks could sustain a 4% income distribution for 30 years, accounting for inflation.

For example, if you have $1 million, the 4% rule says that you can take $40,000 as income in year one and increase that amount by the rate of inflation every year.

Unfortunately, the study did not account for investment expenses and our current low yield environment. Experts now say that even lower withdrawal rates may be more prudent.

Once you determine how much money you’ll need from your portfolio monthly, now you’ll need to assess your income strategy.

Total return vs. Yield for Income

There are two primary approaches to generating income for retirement: Yield and Total Return.

The “Yield” school prioritizes income-generating investments over portfolio growth and requires a sizable amount of capital to be successful.

With a Yield portfolio, you’re sacrificing overall returns in favor of guaranteed income from instruments such as bonds and Treasuries. The problems with a yield approach to income are:

  • No adjustment for inflation.

  • May increase your risk by focusing on higher risk investments.

  • May increase your taxation.

The Total Return approach is more balanced, focusing on asset growth and fixed income investing.

With Total Return investing, you develop a diversified portfolio of growth and value stocks, you can draw down during retirement—all while hedging your risk with “safer” fixed income-generating assets that protect your principal.

The Total Return approach has several advantages over the Yield approach, chief among them that your money continues to grow even in retirement, extending the life of your savings. The Total Return approach can also give you more control over taxation and risk.

That’s important because life spans are increasing at a dramatic pace, adding about three years per generation. A man who is 65 years old today can expect to live to age 83, while a 65-year-old woman today has a life expectancy of 87.

While no investment approach is perfect, the Total Return approach is better suited for longevity—your investments have a higher potential for growth even as you draw them down for income during retirement.

Determine the right income withdrawal strategy in retirement

know how to invest in retirement isn’t just about growth of your assets. The order in which you withdraw your income in retirement matters just as much.

Traditional thinking says to withdraw retirement income first from taxable accounts, then tax-deferred accounts, and finally tax-free accounts such as Roth IRAs or HSAs.

However, we find in practice that traditional thinking is often wrong when it comes to knowing how to invest in retirement.

Sometimes it can be better to draw your income equally from all of your accounts, while other times it actually makes sense to draw from your tax-deferred accounts first.

Our independent custodian, Fidelity, provides a helpful overview of tax savvy withdrawal strategies here.

In short, be sure to consider the appropriate withdrawal strategy for you. If you’re unsure, contact a fee-only financial advisor who can help.


You've worked hard for your money. That‘s why it’s so important to know how to invest in retirement.

But, when you retire, you need to change how you think about investing in retirement to preserve your wealth long-term.

Understanding this research-based and tested framework for how to invest in retirement may seem straightforward, but implementing and fine-tuning your plan can be hard.

You know what you want to do but aren’t quite sure about the steps to get there.

A fee-only, Certified Financial Planner professional may be your best defense against potentially catastrophic mistakes in your retirement plan.

Whether you need advice on comprehensive financial planning, investment management, retirement income projections —or all three—professional advice from someone who understands your needs and shares your values is a great first step.

Periodic check-ups will keep you on track so you can be confident in your retirement plan.

So, if you’re still having trouble figuring out how to invest for retirement or you simply just don’t have the time or confidence, contact us.

If you liked this post, please share it with your friends and on social media.

Mark and Katherine Fonville

Mark Fonville, CFP®

Mark has over 18 years of experience helping individuals and families invest and plan for retirement. He is a CERTIFIED FINANCIAL PLANNER™ and President of Covenant Wealth Advisors.


Disclosures: Covenant Wealth Advisors is a registered investment advisor with offices in Richmond and Williamsburg, VA. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital.

The views and opinions expressed in this content are as of the date of the posting, are subject to change based on market and other conditions. This content contains certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected.

Please note that nothing in this content should be construed as an offer to sell or the solicitation of an offer to purchase an interest in any security or separate account. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax or legal advice. If you would like accounting, tax or legal advice, you should consult with your own accountants, or attorneys regarding your individual circumstances and needs. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place.

Registration of an investment advisor does not imply a certain level of skill or training.


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