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Key Takeaways
- Employers can contribute to employee HSAs and FSAs, which help pay for qualified medical expenses tax-free.
- Enroll in a 401(k) to capture employer matching or use an ESPP for discounted company stock.
- Check for valuable workplace perks like tuition assistance, commuter benefits, and wellness reimbursements.
- Tax credits directly reduce what you owe at tax time—more impactful than deductions.
- Earn rewards on everyday spending with a credit card, but always pay your balance in full.
The Powerball jackpot for Sept. 6, 2025, has ballooned to a staggering $1.8 billion, luring millions to dream of instant riches. But with odds of just 1 in 292 million, a smarter bet for obtaining “free money” is leveraging your employer benefits, making the most of credit card rewards, and claiming available tax credits. Taking advantage of these options can give you more money back without having to rely on luck.
Max Out Your Health Savings Account (HSA)
If you have a high-deductible health insurance plan, you can pair it with a health savings account (HSA), which uses pre-tax dollars through payroll deductions, lowering your tax liability.
Your money grows tax-free, and you can make tax-free withdrawals for qualified medical expenses like medical equipment, copays, and eligible services. The maximum amount you can contribute is set by the Internal Revenue Service (IRS) and adjusted annually for inflation.
Some of the benefits of holding an HSA include:
- Your employer can also contribute to your HSA.
- You can invest money in your HSA in assets like stocks, bonds, and more, the same way you would with a retirement account.
- Investing annually in an HSA allows you to take advantage of compound growth.
- Any unused money can be rolled over to the next year.
- If you change jobs or health plans, you can take your HSA with you to your new employer.
HSAs can be a valuable retirement planning tool, so tap into the account only when necessary.
Use Flexible Spending Accounts (FSAs) Before They Expire
A flexible spending account (FSA) is an employer-sponsored benefit that lets you save pre-tax dollars from your paycheck for qualified healthcare and dependent care expenses. These include out-of-pocket costs like deductibles, copays, coinsurance, and certain drugs. Your employer may also contribute to your plan.
Since an FSA uses pre-tax dollars, it lowers your taxable income. The money you put into your FSA is not subject to income taxes. You can make tax-free withdrawals from your FSA as long as they are for qualified medical expenses as outlined by the IRS.
There are certain rules you need to know about FSAs:
- You can’t use an FSA with a marketplace health insurance plan. You can use an HSA with a marketplace plan, though.
- The IRS sets and adjusts FSA limits annually for inflation. Some employers can set lower limits for their own plans. Married couples can contribute to their own plans to meet a combined household limit.
In most cases, you must use the money in your FSA within one year. Any leftover cash cannot be rolled over into the following year. If your employer allows it, you may have a grace period of up to 2½ additional months or a rollover of $660 into the next year for any leftover money. This is voluntary, and companies aren’t required to provide either option.
Don’t Miss Your 401(k) Match
A 401(k) lets you save pre-tax money from your paycheck using payroll deductions. Like an FSA, this lowers your taxable income and your tax bill. The IRS limits how much you can save each year, adjusting annually for inflation. If you’re 50 and older, you’re allowed a catch-up contribution, giving you additional money in your nest egg.
Many companies provide an employer match, where the company contributes a percentage to their employees’ retirement plans. For instance, some companies offer a 100% match on the first 3% of your salary. So, if you earn $50,000, your employer will contribute $1,500 to your 401(k).
Consider any employer match when you decide how much to contribute. According to Fidelity, aim for at least 15%. So, if your employer contributes 3%, you should contribute at least 12%. Using the example above, your 12% annual contribution would net $6,000 on a $50,000 salary, giving you a total of $7,500 with your employer match.
Fast Fact
According to Empower, 29% of savers aren’t taking advantage of their company’s 401(k) matching contributions.
Evaluate Your Employee Stock Purchase Plan (ESPP)
Don’t turn down an employee stock purchase plan (ESPP) if your employer offers one. This lets you buy your company’s stock at a discount. Here’s how it works:
- Determine how much you’d like deducted from your pay between the offer and purchase dates.
- The company deducts after-tax dollars from your paycheck through payroll deductions.
- The stock is bought on the purchase date, usually at a discount of between 5% to 15% of the market price, depending on the type of plan. Plans can be qualified (more tax-favorable) or non-qualified.
Some companies require you to work for at least one year to qualify, and the IRS caps the annual contribution limit to $25,000 based on the stock’s fair market value (FMV).
Plans often come with what’s called a lookback feature. They compare the price of the stock on the offer and the purchase dates, giving you the better deal between the two.
Ensure that you diversify your holdings and you aren’t putting all your eggs in one basket. And make sure you review the holding periods and tax treatments of ESPPs before you dispose of any stock to avoid any income tax shock:
- You must hold stock in an ESPP for at least one year after the purchase date and for at least two years after the offer date. If you don’t, the discounted portion may be subject to ordinary income tax.
- Capital gains taxes apply to any profits. Short-term gains are applied to stock held for less than 12 months as ordinary income, while long-term capital gains are realized on stock held for more than one year at a rate of 0%, 15%, or 20%.
Check for Hidden Workplace Perks
Employers often offer “free money” perks as incentives for their employees. Look for the following:
- Educational benefits: Some companies offer tuition reimbursement, scholarships, and stipends. You can use these to fund and further your professional development.
- Commuter benefits: Your company may grant you money to cover the cost of public transport, parking, or rideshare services.
- Health and wellness benefits: Use these to cover things like meal allowances and gym memberships.
You may need to enroll and reapply for these benefits each year. Benefits like these can save you a lot of money and cut down your cost of living.
Claim the Tax Credits You’re Eligible for
Tax credits can be a boon at the end of the tax year and often are more valuable than tax deductions because they directly reduce how much tax you owe. Some of the most common (and most overlooked) tax credits are:
- Earned Income Tax Credit (EITC): You can reduce your tax liability and potentially increase your tax refund if you have a low or moderate income.
- Saver’s Credit: This non-refundable tax credit helps you save for retirement as long as you meet certain age, income, and retirement account requirements.
- Child Tax Credit: You can reduce your federal tax liability if you have one or more qualifying children by claiming this credit. You can claim the credit even if you don’t owe any taxes.
- Child and Dependent Care Credit: You can claim a tax credit if you paid for the care of a qualifying child or other individual so you or your spouse could work.
- Home energy tax credits: You can claim tax credits for certain qualifying home improvements you make.
- Educational tax credits: You can reduce the amount of tax you owe by claiming an educational credit, such as the American Opportunity Tax Credit (AOTC) and the Lifetime Learning Credit (LLC), as long as you qualify.
Keep in mind that this isn’t an exhaustive list, and your eligibility may depend on your income level and tax filing status.
Make the Most of Rewards Credit Cards
A rewards credit card provides certain perks whenever you make purchases. Many cards offer you a percentage of your spending as cash back. For instance, some cards offer a flat percentage on all purchases, while others divide cash back through tiered categories, such as 3% on groceries, 2% on dining, and 1% on all other purchases.
If you’re a new cardholder, you may qualify for a sign-up bonus if you meet the introductory offer. Card issuers often offer generous bonus rewards if you spend a certain amount within a specific period on the card.
Cash back cards make sense only if you pay your balance in full. If you don’t, the interest charged to the card negates any cash back you earn. Keep in mind that some card issuers may cap how much you can earn, especially on tiered or special categories.
The Bottom Line
Using workplace benefits, tax credits, and cash back credit cards can help put more money back into your pocket. Many of the options listed above, such as health accounts, retirement and stock accounts, workplace perks, tax credits, and cash rewards credit cards, can easily give you free cash as long as you meet the eligibility requirements and know how to use them.

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