You're not behind forever. You can learn this.

• You put in a set amount on a regular schedule (say, every paycheck), no matter what the market is doing.
• When prices are lower, that amount buys more shares. When prices are higher, it buys fewer.
• It takes the "is now a good time?" guessing out of investing and builds a steady habit. Paycheck contributions to a workplace plan already work this way.
• It doesn't guarantee a profit or prevent losses in a falling market. Whether to invest a lump sum all at once or spread it out depends on your situation.

• The year in the name (for example, a "2055" fund) is roughly the year someone expects to retire.
• One fund holds a mix of stocks, bonds, and cash, and the mix shifts automatically toward bonds and cash as that year gets closer (called the "glide path").
• They're a common default choice in workplace plans, and they rebalance for you.
• Two funds with the same year can hold different mixes and charge different fees. They aren't guaranteed and can lose money, even near or after the target year. The fund's fact sheet shows its mix and expense ratio.

Good question to ask your plan: "What's the stock/bond mix and expense ratio of our target-date fund?"

• Asset allocation is how your money is split among stocks, bonds, and cash.
• Stocks have historically grown more over long periods but swing more. Bonds and cash usually swing less and grow less. Your mix shapes both the growth and the bumps.
• Markets push your mix off target over time. After a strong year for stocks, you may hold more stocks than you planned.
• Rebalancing moves it back, for example once a year or when it drifts too far. Many plans offer automatic rebalancing. Selling in a taxable account can trigger taxes; inside a 401(k) or IRA it generally doesn't.

• Money you contribute from your paycheck is always 100% yours.
• Employer money, like a match, may follow a vesting schedule: all at once after a set time ("cliff") or a bit more each year ("graded").
• If you leave before you're fully vested, you may lose the unvested part of the employer money.
• Your plan's Summary Plan Description or account website shows your vesting schedule and vested balance.

Good question to ask HR: "What's my vesting schedule, and how much of my match is vested today?"

• When you leave a job, common options are: leave the money in the old plan (if allowed), move it to your new employer's plan, roll it into an IRA, or cash out (usually taxes, and possibly penalties).
• A direct rollover (plan to plan, or plan to IRA) avoids taxes being withheld. If a check is paid to you, the IRS generally gives you 60 days to deposit it, and taxes are withheld from plan payouts, so you'd need other money to roll over the full amount.
• Compare fees, investment choices, and protections before moving anything. Roth money generally goes to a Roth account.
• Lost track of an old account? Check old W-2s and statements, call a past employer's HR, or search the U.S. Department of Labor's Retirement Savings Lost and Found.

Good question to ask your old plan: "What fees do I pay here, and how do I request a direct rollover?"

• Some plans can automatically raise your contribution rate by a small step each year (for example, 1% of pay) until it hits a cap.
• Increases often happen once a year, so they can line up with a raise and you may barely notice.
• It turns "I'll save more later" into something that happens without willpower.
• You can usually change or turn it off in your plan's settings. Not every plan offers it.

Good question to ask HR: "Does our plan offer automatic contribution increases?"

• A health savings account comes with certain high-deductible health plans. It has a triple tax benefit: money goes in pre-tax or tax-deductible, it can grow without being taxed, and it comes out tax-free for qualified medical expenses.
• Unused money rolls over every year and stays yours if you change jobs. Many HSAs hold cash unless you choose investments.
• Some people pay medical bills out of pocket now and leave the HSA invested for later.
• Non-medical withdrawals are taxed as income and generally hit with an additional 20% tax; after 65, the additional tax no longer applies. 2026 limits: $4,400 self-only, $8,750 family, plus $1,000 at 55+. State tax rules can differ.

Good question to ask HR: "Is our health plan HSA-eligible, and can I invest my HSA balance?"

• Dividends automatically buy more of the same investment, often in fractional shares.
• That feeds compounding over time.
• In a regular taxable account, reinvested dividends are generally still taxable; inside a 401(k) or IRA they aren't taxed when paid.

Read the full DRIP lesson and hypothetical example

• At 50 or older, the IRS generally lets you contribute extra on top of the normal yearly limit.
• 2026, 401(k)/403(b)/most 457 plans/TSP: $24,500 normal limit, plus $8,000 catch-up at 50+ (or $11,250 at ages 60 to 63).
• 2026, IRAs: $7,500, plus $1,100 at 50+. HSAs allow an extra $1,000 at 55+.
• Your plan has to allow catch-ups, and a rule for higher earners can require 401(k) catch-ups to go in as Roth (after-tax). It's a real lever for late starters.

Good question to ask HR: "Does our plan allow catch-up contributions, and can they go in as Roth?"

• Each retirement account (and many insurance policies) has its own beneficiary form naming who receives it if you die.
• That form generally decides who gets the account, even if your will says something different. An outdated form can send money to someone you didn't intend.
• Name a primary and a backup (contingent) beneficiary, and review them after marriage, divorce, a birth, or a death.
• Some plans require a spouse's consent to name someone else. An estate attorney can help with trusts or minors.

• Social Security pays a monthly benefit based on your lifetime earnings record.
• You can start as early as 62, but the check is permanently smaller: about 30% less if your full retirement age is 67.
• Full retirement age is 67 if you were born in 1960 or later. Waiting past it raises your check 8% a year (for anyone born 1943 or later) until age 70.
• You can see your own estimate with a free my Social Security account at ssa.gov. The best claiming age depends on health, work, marriage, and other income.

• Tax-deferred money can't stay untaxed forever. Under current IRS rules, you generally must start taking a minimum amount out each year starting with the year you reach age 73.
• It applies to traditional IRAs, SEP and SIMPLE IRAs, and workplace plans. Roth IRAs don't require withdrawals while the original owner is alive.
• The amount is based on your balance at the end of the prior year and an IRS life-expectancy table. Withdrawals are generally taxed as income.
• Still working? Many workplace plans let you delay RMDs from that plan until you retire (not if you own 5% or more of the business). Missing an RMD can mean an extra tax, and inherited accounts have their own rules. The starting age has changed before, so check IRS.gov for your birth year.

Advanced topic: worth a quick check with a pro.

• From historical U.S. research (William Bengen, 1994): take out about 4% of your savings in the first year of retirement, then adjust that dollar amount for inflation each year. Historically, that lasted about 30 years.
• Simple arithmetic example: 4% of a hypothetical $500,000 is $20,000 in the first year.
• Limits: it's based on past U.S. markets, assumes about a 30-year retirement and a fixed spending pattern, and ignores taxes, fees, and your investment mix.
• It's a rule of thumb, not a guarantee or a plan. Many professionals adjust it, for example spending a bit less after bad market years. It doesn't include Social Security or pensions.

Advanced topic: worth a quick check with a pro.