Starting your investment journey can be daunting. Believe me, I know the feeling. When I began investing years ago the vastness of knowledge, terminology, and options left me paralyzed. Should I buy unique stocks? What is the difference between a Roth IRA and a traditional IRA? How much money do I need to start investing?
Here's the truth: investing doesn't have to be complicated, and you don't need to be wealthy to begin. In fact, the sooner you start, the better off you'll be, thanks to the magic of compound growth. This guide will walk you through everything you need to know to begin investing confidently in the United States, from the absolute basics to building a solid investment strategy.
Let's start with a reality check. By leaving all your money in a savings account, you're decreasing your purchasing power. The average savings account in the U.S. pays approximately 0.5% interest a year. While inflation typically falls between 2% and 3% a year. So, you are decreasing the value of your money each year.
For example, after one year your $10,000 in a savings account costing 0.5% will only have a principal value of $10,050. But if inflation is 3%, you'd need $10,300 to buy the same things you could purchase with $10,000 today. You're falling behind by $250 in purchasing power.
Now imagine that same $10,000 invested in a diversified portfolio earning the stock market's historical average return of roughly 10% annually. After one year, you'd have approximately $11,000. After ten years, assuming the same average return, you'd have about $25,937. That's the power of putting your money to work instead of letting it sit idle.
The key insight here isn't that investing guarantees wealth—markets fluctuate, and there are risks involved. Rather, it's that not investing almost guarantees that inflation will erode your purchasing power over time.
Before you invest your first dollar, you need to ensure your financial house is in order. Think of investing as the roof (or top) of your financial structure. You need solid walls and a strong foundation first.
Emergency Fund First
An emergency fund should absolutely be your first priority. There is no bargaining here. Life will throw you curveballs: like job loss, medical emergencies, heavy car repair, or large home maintenance. If you don't have an emergency fund, you'll be forced to sell your investments at the worst time possible, or assume high-interest debt.
Aim for three to six months' worth of living expenses in a high-yield savings account. If that seems daunting, start with $1,000 and build from there. Yes, this money won't grow much, but that's not the point. This money is insurance, not an investment.
High-Interest Debt is Your Enemy
If you're carrying credit card debt charging 18-25% interest annually, paying that off should take priority over investing. No investment strategy can compare to those interest rates. For every dollar you pay down your high-interest debt, you have effectively guaranteed yourself a return equal to that interest rate!
While you should not feel like you have to pay off all your debts before beginning to invest. It is possible to have low-interest debt (federal student loans usually are at 3-6% interest, while mortgages are sometimes around 6-8% currently) and still invest, with the potential of finding more in the market than you will be paying in interest on your debt.
If your employer offers a 401(k) match, contribute enough to get the full match immediately. This is free money—typically a 50-100% instant return on your contribution. Even if you have other debt, at minimum contribute enough to capture the full match.
Understanding Different Types of Investment Accounts
Not all investment accounts are created equal, especially when it comes to taxes. Understanding the differences can save you thousands of dollars over your investing lifetime.
These are your standard investment accounts with no special tax treatment. You can contribute as much as you want, whenever you want, and withdraw money anytime without penalties. However, you'll pay taxes on dividends and capital gains.
The advantage? Complete flexibility. Need money for a house down payment in five years? A taxable account gives you access without restrictions. The trade-off is less tax efficiency than retirement accounts.
Traditional 401(k) and IRA
These accounts offer upfront tax deductions. Money you contribute reduces your current taxable income, but you'll pay taxes when you withdraw in retirement. For 2024, you can contribute up to $23,000 to a 401(k) (plus an additional $7,500 if you're 50 or older) and $7,000 to an IRA ($8,000 if 50 or older).
Traditional accounts make sense if you expect to be in a lower tax bracket in retirement or if you want to reduce your current tax bill.
Roth 401(k) and Roth IRA
With Roth accounts, you pay taxes upfront but enjoy tax-free growth and withdrawals in retirement. You can't deduct contributions from your current taxes, but qualified withdrawals (including all growth) are completely tax-free after age 59½.
Roth accounts are particularly powerful for younger investors who expect to be in higher tax brackets later in life. There are income limits for Roth IRA contributions, but not for Roth 401(k)s.
Health Savings Accounts (HSAs)
If you have access to an HSA through a high-deductible health plan, consider it the ultimate investment account. HSAs offer triple tax benefits: deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. After the age of 65, you can use your HSA money for anything (paying taxes like a traditional IRA).
Many people keep their HSA money in cash, which is a mistake. Instead, invest your HSA cash for long-term growth and if you can, try to pay for your medical expenses out of pocket.
Now let's consider the actual investments you can select. You can think of these investments as tools in your investment toolkit. Each serves a purpose.
Individual Stocks
Purchasing individual stocks is essentially a purchase of ownership in specific companies. When you purchase stock in Apple, you own a very small piece of Apple. If Apple has a strong quarter, the price of Apple's stock goes up. If Apple has a rough quarter, its stock price goes down.
Individual stocks can provide incredible returns! (For example, Amazon returned over 2,000% since 2009.) However you can also lose a sizeable amount of money in this investment category very quickly. Remember Enron, Lehman Brothers, or more recently, some meme stocks that crashed after their initial surge?
The challenge with individual stocks is that success requires extensive research, emotional discipline, and often some luck. You're betting on specific companies rather than the broader economy.
Exchange-Traded Funds (ETFs)
ETFs are like baskets holding many different stocks or bonds. When you purchase shares in an ETF, you own a small portion of every single item in the basket. For instance, the SPDR S&P 500 ETF (SPY) includes all 500 of the companies in the S&P 500 index.
ETFs provide immediate and low-cost diversification. Unlike buying and researching dozens of individual stocks, you can, via a single purchase, own shares in hundreds or thousands of companies. Most ETFs charge expenses ratios of .03% to .20% annually, significantly less than a typical actively managed mutual fund.
Mutual funds are similar to ETFs. Like ETFs, mutual funds pool money from investors in order to buy a diversified portfolio of stocks, bonds, or another types of assets. Unlike the ETFs discussed above, mutual funds tend to charge higher fees, and they can usually only be bought or sold once at the end of each trading day at the close price.
Some mutual funds are actively managed by professional fund managers who try to outperform their benchmark by picking winning investments. Other funds are index funds that track market benchmarks like the S&P 500.
Index Funds: The Investor's Best Friend
Index funds deserve special mention. In many cases, index funds are the best option for new investors. Index funds are essentially purchasing every stock contained in a specific market index. Most fund companies have their own version of an index fund. The reason for the simplicity of index funds is they only buy and sell the stocks in their index.
You aren't trying to beat the market – you are simply getting the market returns with very little cost. A great example of this would be the Vanguard Total Stock Market Index fund; with an expense ratio of 0.03%, this fund gives you ownership in almost every publicly traded U.S. company.
Data is very compelling regarding index funds as an investing strategy. On average, over 20-year time horizons, about 80-90% of actively managed funds will not beat their benchmark index before fees and taxes.
Target-date funds are intended for hands-off investors. The investor chooses an investment option based on their expected retirement date, for instance, Target Date 2060 if the investor wants to retire around 2060. The target-date fund will automatically rebalance the investors portfolio forma time-weighted average target-date for retirement although they offer less flexibility by design.
For younger investors, their initial portfolio investment might consist of about 90% stocks and 10% bonds. By the time the investor is near retirement, the random blend of stocks and bonds may be close to 40% stocks and 60% bonds. Target-date funds are not perfectly balanced but present a solid "set it and forget it" investment for investors who want to identify a target-date for their expected date of retirement and don't want to actively manage its portfolio weighting.
Bonds and Fixed Income
Bonds are basically IOU's. When you buy a bond, you lend a government or corporation money and receive interest payments in exchange for your loan. Bonds are less risky than stocks for the most part, but also less return.
U.S. Treasury bonds are viewed as one of the safest investments in the world, since they are backed by the U.S. government's ability to tax and print money and flow-free for no expenses. On the other hand, the greater yield of corporate bonds comes at the risk of the corporate business defaults on the loan.
Most young investors make bonds a very small percentage of their portfolio since they can weather the volatility over the long period of time in which equities may be less stable. Nonetheless, bonds can generally provide stability and income as you get closer to retirement.
Now we get to the big question - how do we put together all the information we have into a legitimate plan in the form of a strategy? The answer depends on your goals, timeline, and risk tolerance.
Determine Your Risk Tolerance
Risk tolerance isn't just about how much volatility you can theoretically handle—it's about how you'll actually behave when markets get scary. During the 2008 financial crisis, the S&P 500 fell about 37%. During the early COVID-19 pandemic in March 2020, markets fell about 34% in just a month.
If you would panic and sell everything during a major market decline, you need a more conservative allocation. There's no point in having an "optimal" portfolio if you can't stick with it during tough times.
Generally, younger investors can tolerate more risk because they have decades for their portfolios to recover from market downturns. As you approach retirement, gradually reducing risk makes sense since you'll have less time to recover from major losses.
Asset Allocation: The Most Important Decision
Asset allocation—how you divide your money between different types of investments—is the single most important factor determining your investment returns. In terms of stock versus funds, that's less important than your overall allocation.
For a young, new investor a reasonable first allocation could look like this:
The general strategy, is to gradually transition from stocks to bonds as you age. A common rule of thumb is to hold your age in bonds (meaning if you are 30 years old, you can hold 30% in bonds). But, in recent times, with our longer life expectancies and historically low interest rates, many investing professionals are arguing to hold more bonds.
Diversification: Don't Put All Your Eggs in One Basket
Diversifying still lowers the overall risk without necessarily lowering the return. Instead of just buying a U.S. large-company stock, you will be able to more effectively utilize your capital by buying from a diversity of stocks / bonds:
The goal is not to avoid all losses - because diversification simply does not work that way. Rather, it's to ensure that no single investment or market sector can devastate your entire portfolio.
Should you invest all your money at once or spread purchases over time? Mathematically, lump sum investing typically produces better results since markets generally trend upward over time. The sooner you invest, the sooner your money starts growing.
Nonetheless, dollar-cost averaging—the process of investing an identical amount regularly while ignoring market conditions—may be easier on the psyche. It's also a way to reduce the likelihood you'll invest everything, and then, the market declines significantly.
For most people, they dollar-cost average unintentionally through the continued contributions to their retirement accounts with every paycheck. If you happen to come into a lump sum, such as an inheritance or bonus, and you think you can withstand the potential short-term volatility, you can invest that cash in one single shot.
Do you want to get started? Follow this step-by-step action plan:
Pick a Broker
You will need a brokerage account to buy and sell investments and, luckily for us, competition has driven fees to almost zero. Most of the major brokers (Fidelity, Schwab, Vanguard etc.) offer stock and ETF trades without commission fees.
Make sure to consider:
For first time investors, Fidelity, Schwab, and Vanguard are all good options that are low-fee, and have many available investment options.
Start Simple
Your first investment doesn't need to be complicated. Consider starting with:
You can always add complexity later as you gain experience and knowledge.
Automate Everything
The best investment strategy is one you'll actually follow consistently. Set up automatic transfers from your checking account to your investment accounts. Automate your 401(k) contributions. Make investing as effortless as breathing.
Automation also removes emotion from the equation. You'll invest the same amount whether markets are soaring or crashing, which typically leads to better long-term results.
Keep Learning, But Don't Overthink
Continue educating yourself about investing, but beware of analysis paralysis. Reading about investing and following market news can be helpful, but don't let perfect become the enemy of good. A simple, low-cost, diversified portfolio that you stick with will beat a complex strategy you abandon during tough times.
Learning from others' mistakes is cheaper than making them yourself. Here are the biggest pitfalls new investors face:
Trying to Time the Market
Market timing—attempting to buy low and sell high—is incredibly difficult, even for professionals. Study after study shows that investors who try to time markets typically underperform those who stay invested. The market's biggest gains often come during volatile periods when timing seems most logical. Missing just the 10 best days in the market over 20-year periods can cut your returns roughly in half.
Chasing Performance
Last year's winning investment often becomes this year's loser. Investors frequently buy funds or stocks after they've had great runs, then sell after poor performance—buying high and selling low.
Instead of chasing hot investments, stick to your long-term strategy. Rebalance periodically to maintain your target allocation, which forces you to sell high-performing assets and buy underperforming ones.
Paying Too Much in Fees
Investment fees might seem small, but they compound over time just like returns. A 1% annual fee might not sound like much, but over 30 years, it can cost you hundreds of thousands of dollars in lost growth.
Focus on low-cost index funds and ETFs. Expense ratios under 0.20% are reasonable; under 0.10% is excellent. Avoid funds with sales loads (upfront fees) entirely.
Letting Emotions Drive Decisions
Fear and greed are investors' worst enemies. During bull markets, greed makes people take excessive risks. During bear markets, fear causes panic selling. The most successful investors are often the most boring ones. They stick to their strategy regardless of market conditions.
If you find yourself making investment decisions based on daily market movements or financial news headlines, step back and refocus on your long-term goals.
Not Taking Advantage of Tax-Advantaged Accounts
Many people invest in taxable accounts while ignoring 401(k)s and IRAs. This is backwards. Max out tax-advantaged accounts first—you're essentially getting a guaranteed return equal to your tax savings.
The tax benefits of retirement accounts can compound over decades. For example, if you are in the 22% tax bracket and put $6,000 in a traditional IRA, it saves you $1,320 in current taxes while you create retirement wealth.
The Psychology of Money: What They Don't Teach You
The mental game of investing is just as important (if not more so) to consider before you employ some advanced strategy. I've seen hundreds of people over time ruin perfectly sound investment plans because of failing to understand the mental challenges of daily fluctuations in prices, or simply giving the psychology of investing a passing thought.
The stock market is more than numbers on a ticker tape: it's a long-term, collective view of millions of people combining their emotions, fears, and hopes. If you really want to help yourself invest intelligently, this realization will help you infinitely more than knowing the last five years' worth of financial ratios or economic indicators.
When your portfolio drops 20% in a few weeks, your brain doesn't distinguish between losing money in the market and facing a physical threat. The same fight-or-flight response kicks in. Your heart rate increases, your palms get sweaty, and every instinct screams "DO SOMETHING!"
This reaction served our ancestors well when facing saber-toothed tigers, but it's terrible for investment decisions. The investors who consistently build wealth are those who've learned to recognize these emotional responses and develop systems to counteract them.
I remember my first major market downturn. It was 2018, and the S&P 500 fell about 19% between September and December. Despite knowing intellectually that market corrections are normal, watching my portfolio lose thousands of dollars daily was gut-wrenching. I caught myself checking my accounts multiple times per day, each time feeling worse.
The lesson? Your emotional response to losses will be stronger than you expect, regardless of how much you've read about market volatility. Plan for this reality, not the idealized version where you remain perfectly rational.
The most successful investors develop specific habits and systems to manage their emotional responses. Here are strategies that actually work in practice:
The 48-Hour Rule: Never make investment decisions within 48 hours of major market movements. When markets crash or soar, write down your immediate reaction and what you want to do. Then wait two days before acting. You'll be amazed how often your initial impulse was wrong.
Reframe Volatility as Opportunity: Instead of seeing market drops as losses, train yourself to view them as sales on quality investments. It should be clear by now that Warren Buffet is famous for saying that he is "fearful when others are greedy and greedy when others are fearful." This is not only wordplay, but can be used as a reframing technique.
The Annual Review Method: Check the performance of your portfolio once, each year, on your birthday, or on New Year's Day. Checking your performance daily or even weekly, will create too much emotional noise in your decision making process. An annual review provides adequate data to provide a meaningful adjustment, without getting distracted and caught up in the short-term swings of the market.
Automate to Remove Temptation: Set up automatic investments and then make it deliberately difficult to access your accounts. Some investors even give their login information to a trusted family member and ask them to change the passwords during volatile periods.
Intelligence and investment success aren't strongly correlated. I've seen PhD economists panic-sell during market downturns and high school dropouts build impressive portfolios through patient, consistent investing.
The reason is that intelligence can actually work against you in investing. Smart people often:
Meanwhile, successful investors tend to share certain behavioral traits: patience, consistency, humility, and the ability to stick with boring strategies for decades.
Your investment environment has a significant effect on your investment behavior, often, in a meaningful way, without you even realizing it. If your coworkers are discussing hot stock tips or their amazing gains in cryptocurrency, you will feel a pull, if not pressure, to pursue equivalent returns. If your family has the mindset that investing is gambling, you may unconsciously sabotage your own success.
Be aware of the financial discussions that surround you. Are these conversations healthy or harmful to your long-term investment goals? You may want to seek a community of like-minded investors who are committed to slow, deliberate and long-term wealth accumulation versus the fad of get-rich-quick.
Social media provides another challenge related to investing. You can be bombarded by Twitter posts and Reddit threads of major market euphoria or panic. When there are exciting bull markets, you will see multiple tweets of screenshots demonstrating significant gains and maybe feel inadequate to your steady 7% return. During bear markets, you'll encounter predictions of financial apocalypse that make selling everything seem prudent.
The solution isn't to avoid all investment-related content, but to be highly selective about your sources. Follow investors who've succeeded over decades, not those chasing the latest trends.
Once you have learned the basics and have been investing on a regular basis, you will want to consider you might some other advanced options:
Tax-Loss Harvesting: The Details Matter
In taxable accounts, you can sell any losing investments for tax purposes to offset any gains you might have with winning investments, thus reducing your tax burden. Tax loss harvesting works best with broad market index funds than it does with individual stocks.
But here's what most guides don't tell you: tax-loss harvesting is more nuanced than it appears. The wash sale rule prevents you from buying the same or "substantially identical" security within 30 days of selling it for a loss. This means you can't sell an S&P 500 index fund and immediately buy another S&P 500 index fund to harvest the loss.
The workaround involves using similar but not identical investments. For example, you might sell a total stock market index fund and buy an S&P 500 index fund, or vice versa. These funds are similar enough to maintain your desired exposure but different enough to avoid wash sale rules.
However, don't let the tax tail wag the investment dog. I've seen investors make poor investment decisions in pursuit of tax benefits. The goal is to minimize taxes while maintaining a sound investment strategy, not to minimize taxes at any cost.
If you are likely to be in a higher bracket when you retire, you might consider a transition of traditional IRA money into Roth IRAs in years when your income is down. You will pay the tax now, but then enjoy tax-free growth going forward.
Most of the time Roth conversions are best done during a down time in the market. You are taking advantage of a dip in your traditional IRA balance because of market losses. This is beneficial because you will be able to convert more shares for the same tax bill. As the market recovers, the shares you converted are now growing tax-free in your Roth account.
Understand using this example: You have $100,000 in index funds in a traditional IRA. The market crashes, and you traditional IRA balance is now $70,000, a 30% downturn. You convert $20,000 of shares (at a depressed price) you will pay taxes based on $20,000 of income. And, if you returns to their pre-crash prices, you effectively converted $28,571 of income and only paid taxes based on $20,000.
Be careful, tax planning and tax criteria are very complicated related to opportunity taxes and benefits. There are real benefits, but the important part is to properly execute.
Some investors base their portfolios to be somewhat 'tilted', toward certain factors, such as value stocks, small-cap stocks, or profitable companies backed by research that indicate they might outperform in the long run.
However, these strategies require patience since factor premiums can disappear for years at a time. The academic research supporting factor investing is compelling, but the real-world implementation challenges are significant. Value stocks, for instance, have underperformed growth stocks for over a decade. Small-cap stocks have had extended periods of underperformance relative to large-caps.
Factor investing works over very long time horizons—we're talking decades, not years. If you can't stick with a value-tilted portfolio while watching growth stocks soar for 10+ years, factor investing isn't for you. The psychological challenge often outweighs the potential benefits.
A more practical approach might be to make small tilts toward factors you believe in while maintaining a core holding of broad market index funds. For example, you might allocate 70% to total market funds and 30% to value funds, rather than going all-in on factor strategies.
While U.S. stocks have performed well recently, international diversification can reduce portfolio volatility and capture growth in global markets. Consider allocating 20-40% of your stock portfolio to international funds.
But international investing isn't just about buying foreign stocks. Currency fluctuations add another layer of complexity. When the dollar strengthens against foreign currencies, your international investments may underperform even if the underlying companies do well. Conversely, a weakening dollar can boost international returns regardless of company performance.
Emerging markets deserve special treatment. Countries like India, Brazil, and many other developing economies in South East Asia have incredible growth potential albeit with greater political, economic and currency risk. The younger you are, and the higher your coded risk tolerance, the easier it is to reasonably allocate a small (5-10% of your total portfolio) amount to emerging markets.
Developed international markets - Europe, Japan, Australia, etc - also offer diversification benefits, and with less risk than emerging markets. However, many developed markets are also dealing with demographic headwinds (an aging population with low birth rates) that could potentially moderated their growth potential overtime.
The practical alternative do this: start small with a very broad international index fund that includes developed and emerging markets; and once you feel familiar and comfortable you can allocate small (and larger) portfolio allocations to emerging markets focused on particular regions or countries.
It is helpful to contextualize your investment strategy based on your own individual investment objective and timing:
Since retirement savings are a long-term investment, you should be comfortable taking on more risk in this time frame.
Concentrate on growth assets in stock-heavy portfolios. Add to tax-advantaged accounts to maximize the benefit then use taxable accounts, if you run out of contribution room.
The numbers here matter more than you might think. Let's say you're 25 years old and want to retire at 65 with $1 million. If you can achieve a 7% average annual return, you need to save about $381 per month. Wait until you're 35 to start, and that number jumps to $820 per month. The ten-year delay more than doubles your required monthly contribution.
But here's something most retirement calculators don't account for: sequence of returns risk. It's not just the average return that matters, but when those returns occur. Poor returns early in retirement can devastate your portfolio even if the long-term average looks good.
This is why the traditional advice to shift from stocks to bonds as you age makes sense, but the specific timing and extent of that shift deserves more thought. Some financial advisors now recommend a "bond tent" approach: gradually increasing bond allocation as you approach retirement, then potentially decreasing it again in early retirement as your time horizon extends.
As someone saving for a house down payment, the timeline is not necessarily short. You may still want to be a bit more conservative. A balanced portfolio with 50-60% stocks and 40-50% bonds may be appropriate, or you may want high-yield savings accounts if your timeline is very short.
The goal of a house down payment presents uniquely challenging issues that most investment guidance does not cover. Compared to retirement, the timeline in which you can execute a house purchase can be immediately influenced by your market timing, life events, or opportunities to purchase that cannot be postponed.
I can attest to this personally while searching for a house back in 2019, when I invested my down payment savings in a relatively conservative portfolio. I thought I was being smart by earning a little return while saving, and during the time I was able to save before finding a home, we became very experience with price increases in every market we searched in. Then I found the perfect house—but it was during a market downturn, and my portfolio was down 15%. I had to choose between selling at a loss or missing the house.
The safer approach for house down payments is to use a high-yield savings account or short-term CDs once you're within two years of purchasing. Yes, you'll miss some potential returns, but you'll have certainty that your money will be there when you need it.
Consider a hybrid approach: if you're saving $2,000 monthly for a house down payment and you're three years out, maybe put $1,000 in high-yield savings and $1,000 in a conservative investment portfolio. As you get closer to purchase time, gradually shift everything to guaranteed accounts.
529 education savings plans allow for tax-advantaged education savings, starting both aggressive when young then becoming more and more conservative when approaching college.
The world of 529 plans has changed dramatically. With so many more options for investment through the plans, it is no surprise that they can be used for K-12 tuition (in amounts up to $10,000 per year) and even payments for student loan expenses. But the rules can feel tricky, and overfunding the plan can be an economic mess for you if your child decides not to attend college or receives substantial scholarships.
One of the most common mistakes is sometimes being too conservative early. If your "youngster" is 5 years old, you have 13 years until college---plenty of time for the stock market to increase in value. In many 529 plans, there are age-based portfolios where the plan automatically adjusts the allocation to ensure proper alignment as the child nears college age, so you do not have to guess.
Here is your reality check on college costs: they will likely remain out of control for the foreseeable future because they have outpaced inflation for the last several decades; just don't assume they always will. For example, factors such as increased online education, community college transfer programs, and increased competition for price can bring about moderation. And please, quit panic-saving for college based on simply current cost projections.
Keep your emergency savings in high-yield savings accounts or money market funds. Never invest emergency money in stock as there is a chance that the stock market might be down when you need it.
How do you determine the total for your fund? It is not as simple as "3-6 months of expenses." Your specific situation matters tremendously. A government employee with strong job security might need less than a commission-based salesperson whose income fluctuates wildly.
Consider your insurance coverage too. If you have good health insurance, disability insurance, and homeowner's/renter's insurance, you need less cash for emergencies. If you're self-employed with minimal insurance coverage, you need more.
Also think about accessible credit. If you have a large unused credit limit on low-interest cards or a home equity line of credit, you might need less cash emergency fund. The key is ensuring you can access money quickly during actual emergencies without being forced to sell investments at bad times.
Every investing guide makes the process sound clean and rational, but real life is messier. I want to share some of the challenges you will encounter, challenges that no other guides mention.
You will have a great set up with an automatic investment plan in place, and then your life will take a few unexpected swings at you with some surprise expenses. These expenses will force you to stop out of or reduce your contributions. This is not a failure—this is simply part of life, and you can work through it.
The key is to get back on plan as soon as possible, not quit the plan altogether. For example, one year I had some big expenses for my car for major repairs, my basement flooded, and I incurred some costs for medical expenses....all of which happened over the course of six months. My careful investment plan went out the window temporarily.
Instead of viewing this as a complete failure, I reduced my contributions to the minimum needed to capture my employer match and resumed full contributions once I rebuilt my emergency fund. The most successful investors aren't those who never deviate from their plans, but those who return to their plans quickly after life interrupts.
Your investment success doesn't exist in isolation. If you're married, your spouse's feelings regarding money and risk will alter your strategy. Likewise, if you have any parents who will need your financial help or grown children asking for money, this should inform your planning.
I've seen marriages ruined by disagreements about how much risk to take with the investments. One spouse wants to invest aggressively for growth while the other spouse prefers the stability of buying CDs. Most of the time this will end up being a compromise and plenty of discussion about what risks and fears each party has, as well as their goals.
If you are in a position where you are the first one to create significant wealth in your family due to investing, there may be pressure to provide some of this wealth to relatives. This is not a bad thing, but once again, it should be planned instead of dealt with as an ongoing catastrophe.
As you navigate your financial journey - you will always be exposed (via social media or conversations with friends) to people who are seemingly doing better than you financially. Your coworker mentions their Tesla stock gains. Your neighbor talks about their real estate investments. Your college friend posts about their startup exit.
These comparisons are mostly meaningless because you never see the complete picture. The Tesla stock winner might have a portfolio full of other losing positions. The real estate investor might be highly leveraged and stressed about payments. The startup founder might have sacrificed years of steady income for that one big payday.
Focus on your own progress toward your own goals. If you're consistently saving and investing according to your plan, you're succeeding regardless of what others appear to be doing.
The rise of commission-free trading apps has made investing more accessible, but it's also created new behavioral challenges. The convenience of being able to buy and sell stocks instantly from your phone can lead to excessive trading.
These apps often turn investing into a video game by offering confetti animations for trades, frequent push notifications about stock movements and social elements that encourage trading. Also keep in mind that with every trade you make, there's an opportunity for you to make a mistake. The best traders are the ones who trade the least.
If you find yourself checking investment apps multiple times per day or making frequent trades, consider deleting the apps from your phone and accessing your accounts only from a computer. The extra friction can help prevent impulsive decisions.
Perhaps the most important lesson in investing is this: time in the market beats timing the market. The sooner you start and the longer you stay invested, the better your chances of building wealth.
Markets crash, recessions come and go, political turmoil occurs, and crises occur that we can't even fathom today. Generally, the investors that are disciplined, stay calm, remain consistent in their decisions, and continue to invest capital regularly usually win.
Successful long-term investing requires developing a personal philosophy that you can stick with through various market conditions. This philosophy should be based on your values, goals, and temperament rather than the latest market trends or expert predictions.
My personal investment philosophy centers on a few core beliefs: markets tend to rise over long periods, costs matter enormously, diversification reduces risk without necessarily reducing returns, and behavioral factors matter more than analytical factors for most investors.
Your philosophy may highlight different aspects - you may highlight simplicity first, domestic investments versus global, or avoiding companies that do not align with your values. The exact details of the content matter less than simply having a framework around which you make decisions.
Write down your investment philosophy and go back to it when you are uncertain. When the markets are extreme and you feel the temptation to change course drastically, ask yourself if those changes are consistent with your core beliefs around investing.
Even with my emphasis on simple, DIY investing examples, there are times when I think it makes sense to get professional help. A fee-only financial advisor can add value through advanced financial planning, collaborating on tax-smart decisions, visualizing a full estate plan, and potentially serving as behavioral coaching in turbulent times in the market.
The important part is to realize what you are paying for and if it is worth the cost. Financial advisors who charge 1% annually to put your money in index funds aren't providing enough value to justify their fees. Advisors who help you optimize your entire financial picture, plan for complex tax situations, and keep you disciplined during market volatility can be worth their cost.
Interview potential advisors carefully. Ask about their investment philosophy, fee structure, credentials, and how they work with clients during market downturns. A knowledgeable advisor will be clear about how they will communicate their process and be able to explain how they can provide value beyond just choosing investments.
There is no need to remind anyone how the COVID-19 pandemic showed how unexpected events can impact both markets and your finances. While no one can predict the next crisis, you can still develop a financial plan that can soften the blow of unexpected events.
A financial plan that addresses the unexpected includes ensuring you have enough cash saved for an emergency, do not take on too much unnecessary leverage, diversify your investments, diversify your income when you can, and have enough insurance. It also means developing the emotional resilience to stick with your long-term plan during short-term chaos.
The investors who thrived during and after the 2020 market crash weren't necessarily the smartest or most sophisticated—they were the ones who maintained their discipline, avoided panic selling, and in some cases increased their investments when prices were low.
Just remember, investing is a marathon; not a sprint! You are not trying to get rich quickly; you are working to build your wealth slowly over several decades. All the dollars you invest today are dollars working for you in the future.
The most powerful piece of long term investing is likely not any strategy or security selection, but the compound effect of your consistent disciplined actions over many years. Small differences in your actions can lead noticeably different outcomes over the decades walking the same path.
Consider the difference of earning 6% versus 8% a year over 30 years. A $10,000 investment at 6% and 8% earns about $57,400 and $100,600, respectively. A difference in annual returns of 2% leads to a difference of 75% in final wealth.
So, that is why being focused on low fees, tax aware and behavioral consistent, is way more important to your overall wealth than stock picking winners and timing the market. Over long time periods; boring, methodical investment approaches win out. Most successful investors are not the smartest or the most sophisticated, they are just disciplined investors who start early, invest regularly, keep costs down, and remain invested in all market conditions.
Your investing journey begins with just one step, by opening that first account and making that first investment! Don't wait for the perfect moment or the perfect strategy. Start where you are, with what you have, and improve along the way.
The best time to start investing was 20 years ago. The second best time is today.
Please keep in mind this is educational materials and not personalized financial advice. You may wish to consult a qualified financial advisor about your specific circumstances. Actual performance in the past is not a guarantee of future performance. All investments have actual potential to lost more than the original amount invested.