You’re far less important to your employer than you think—but far more important to your family than you could ever possibly imagine.
Greg Spears was HumbleDollar's deputy editor. Earlier in his career, he worked as a reporter for the Knight Ridder Washington Bureau and Kiplinger’s Personal Finance magazine. After leaving journalism, Greg spent 23 years as a senior editor at Vanguard Group on the 401(k) side, where he implored people to save more. He currently teaches behavioral economics at St. Joseph’s University in Philadelphia as an adjunct professor. The subject helps shed light on why so many Americans save less than they might. Greg is also a Certified Financial Planner certificate holder. Check out his earlier articles.
Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.NO. 39: WE SHOULD worry less about dying early in retirement—and more about living longer than we ever imagined. Faced with that risk, we might delay Social Security and buy lifetime income annuities.
RISK-FREE RATE. This is the return you can earn with little or no risk of loss. If you buy anything riskier, the expected return needs to be higher to compensate for the chance you’ll lose money. Experts point to Treasury bonds as the ultra-safe option. But if you have debt, arguably your risk-free rate is the interest cost you could avoid by paying down that debt.
BUNCH CHARITABLE contributions. The 2017 tax law’s higher standard deduction, coupled with the $10,000 cap on deducting state and local taxes, means you may get no tax benefit from charitable gifts. One possibility: Bunch, say, three years of contributions into a single tax year. You might even set up a donor advised fund and spoon out gifts from there.
COST-BENEFIT analysis. Before committing to a goal or a purchase, we should ponder alternative uses for our time and money. As we weigh our various options, it’s often easy to visualize the benefits. But what about the costs? Those will likely be paid by our future self, who might have to deal with, say, the resulting credit card bill or the ongoing hassles involved.
NO. 39: WE SHOULD worry less about dying early in retirement—and more about living longer than we ever imagined. Faced with that risk, we might delay Social Security and buy lifetime income annuities.
IT’S BEEN MORE THAN three years since my wife and I paid off the last of our consumer debt. Since then, we’ve enjoyed the benefits of a debt-free life: less stress, no interest payments and a lower cost of living.
While these reasons alone make a strong case for paying off credit card balances, car loans and other consumer debt, the true cost of borrowing goes beyond the obvious. Here are five drawbacks that I wish I’d considered before taking on debt:
1.
WHAT IF I SAID YOU could borrow to buy a home and have no mortgage payment? Would you think I was nuts?
Trust me, I’m not. If you’re age 62 or older, it’s possible to finance a home purchase and have no ongoing mortgage payments. How? By taking advantage of a home equity conversion mortgage, or HECM. The federally insured HECM is the most popular reverse mortgage in America today.
Now, I know what you’re thinking.
THE GREAT RECESSION highlighted the frightening amount of debt—especially mortgage debt—that had been taken on by many American families.
A decade later, the picture is far brighter, with one exception: student loans. Since 2008’s third quarter, education debt has ballooned 144%, according to data just released by the Federal Reserve Bank of New York. But the total of all other debt—mortgages, car loans and credit card balances—is up less than 1% over the same period.
I HAD A NEW HOME built in 2017. I financed it with a 30-year mortgage at a 3.875% interest rate.
Early last year, when interest rates dropped due to the pandemic, I suggested that readers refinance. I took my own advice, replacing my 30-year loan with a 15-year mortgage at 2.99%. The cost of refinancing seemed well worth the reduction in my loan interest rate.
Two months ago, I saw that mortgage rates had continued to decline,
SOARING STUDENT DEBT is putting the kibosh on another major financial goal: buying a home. According to a study by researchers at the Federal Reserve Bank of Cleveland, 40% of those age 18 to 30 have student debt, up from 27% in 2005. For these borrowers, the debt burden is staggering, with student loan payments estimated to devour more than 20% of their income in 2015.
With so much of their income devoted to servicing student loans,
American credit card debt just broke the trillion dollar level. Taking on debt, “ bad” debt, credit cards , auto loans and similar, is a like attending a raucous party , taking in too much alcohol , etc.
The aftermath , paying off high interest loans, is like the worst hangover, ever. It can take decades to recover from it.
Often, too much alcohol can kill you, quickly or long term, * alas , debt can kill you,
Social Security – Why I Chose FRA
Langston Holland | Dec 20, 2025
Humble Christmas and Holiday Message
DAN SMITH | Dec 20, 2025
The Benefits of 401(k)
Greg Spears | Dec 19, 2025
- Tax saving is habit-forming. Section 401(k) was originally introduced to help Eastman Kodak employees save their big, year-end bonuses before paying federal income taxes. Even today, most workers save their pay into the 401(k) before taxes are paid. Yes, they will owe taxes on withdrawals, and, yes, after-tax Roth contributions make sense for all kinds of reasons.
Once you’ve filed a tax return sheltering a big hunk of income within a 401(k), however, it’s hard to imagine backtracking. I came to depend on the 401(k) as a big tax shelter every April 15, along with millions of other workers. Eventually, I maxed out my plan savings and, later on, so did my wife.- The employer match is a big gain. Under a typical formula, workers save 6% of their pay to collect their employer’s 3% match. Now, 3% doesn’t sound like a lot. If you hang around long enough to vest, however, it’s a 50% gain on your contributions. Where else can I earn that much risk-free return? Not down at the bank.
- The early withdrawal penalty encourages the long view. If I withdrew money from my 401(k) before age 59½ (or 55 under certain circumstances), Vanguard would have withheld 20% in federal income taxes plus a 10% penalty. On a $10,000 withdrawal, that would have felt like throwing $3,000 out the window.
The phone representatives at Vanguard go over these numbers in excruciating detail on a recorded line before asking, “Do you still wish to continue?” For anyone not in dire need of money, that cold shower tends to keep 401(k) balances intact. Because returns compound, being a long-term investor has great value.- Low fees, high services. When a truck driver invests in the 401(k), he’s treated like a big shot. That’s because most large employers—where most 401(k) savers work—have billion-dollar balances in their 401(k) plans. They use that size to bargain for lower-cost institutional funds and the latest services.
Employers put out requests for proposals all the time. Investment companies scrap for the business, cutting investment fees and adding benefits like automatic enrollment, target-date index funds, and free investment checkups. Workers are better invested, at lower cost, than ever before.- The magic of the market. Stock prices in the United States have a 200-year history of rising. Not every year, but two out of three, on average. Seeing the magic of stock returns over the long run has made millions of working Americans committed long-term investors.
Little wonder. The idea of making money without setting an alarm, or joining another Zoom meeting from home, has greater appeal the longer you work.Can we be completely safe?
Ben Rodriguez | Dec 17, 2025
The Festive Sweater and the Dilemma
Mark Crothers | Dec 19, 2025
Boring……
Bill W. | Dec 20, 2025
Six Ways to Grow Income
Greg Spears | Dec 18, 2025
Personal Finance Reading List
Adam M. Grossman | Dec 20, 2025
Business and Side Hustle Tax Tips
Bogdan Sheremeta | Dec 20, 2025
- $23,500 to a pre-tax account as an employee
- $25,000 as an employer (up to 25% of your W-2 compensation)
In total, you can contribute $48,500 to your Solo 401(k).However, if your Solo 401(k) plan allows, you may also take advantage of a strategy called the “Mega Backdoor Roth,” also known as the after-tax account. Going back to our example, the maximum 401(k) contribution (employee + employer + after-tax) allowed under the rules is $70,000. Since we already contributed $48,500, we still have $21,500 of room left (the maximum limit you can contribute to such a plan is $70,000, or $77,500 if age 50+, up to your compensation). You can contribute to an after-tax account and roll it over into a Roth 401(k) or Roth IRA. This strategy is extremely useful for someone with a high-earning W-2 and a side hustle. For example, if someone has $500K per year in W-2 income, already maxed out the employee side ($23,500) at their main job with no match, and has a $100K (net self-employment earnings) consulting gig on Schedule C, they can effectively contribute:- $20,000 to an employer pre-tax account
- $26,500 to an after-tax account, for a total of $70,000 in retirement contributions.
Having the right entity If you are self-employed, you have to pay self-employment taxes (7.65% as the employee and 7.65% as the employer, for a total of 15.3%) if you are a sole proprietor. However, you could elect your business to be taxed as an S corporation, which could potentially help you save money on self-employment taxes. You would have to pay yourself a reasonable salary and can take the rest of your income as a distribution. As a rule of thumb, an S corporation could help you save once you make $100,000 net from your self-employment activity. But it comes with extra steps, such as:- Filing Form 1120-S
- Filing a W-2 and paying yourself a salary
- Paying FUTA/SUTA taxes
- State tax compliance and potential additional fees
So, it’s important to analyze the cost of the additional compliance fees to determine whether it’s worth it for your specific scenario. Shifting income/expenses Something that not a lot of people think about is how you can be strategic about the timing of your expenses and income. Most self-employed business owners are on a cash basis. This means that they pay taxes on the cash that is constructively received, not when it is earned and services are provided. This provides an opportunity to shift income depending on when you invoice and receive the money. For example, say you are going to retire next year and your income will drop. In that case, it could make sense to bill a customer (for services provided) next year (the year of retirement) rather than in the current year. Similarly, if you are experiencing incredible growth where you will make, say, $200K this year but are expecting $300K next year, it may make sense to postpone some of your expenses to the next year. For example, instead of upgrading your computer in 2025 and using bonus depreciation to write off 100% of the cost, you could buy it in 2026 instead and save money. So it all depends on your current income and your projected income next year. If income will be higher next year, try to postpone expenses to next year. If income will be higher next year, try to realize as much income as you can this year. Hiring your child Hiring your child could be a legitimate tax and wealth-building strategy for business owners, but it must be done correctly. And it’s one of those strategies that is often abused or incorrectly set up. Here are some tips:- The work must be legitimate. Your business must have age appropriate, reasonable tasks your child can actually perform (e.g. admin work)
- Pay reasonable wages. Pay what you would pay an unrelated worker for the same job. Document how you determined the wage.
- Track everything. Hours worked, duties performed, and proof of work.
- Have your child complete and sign time logs.
- Run payroll and file forms. Issue a W-2, file required payroll reports (941, 940, state filings), and tax return
- Actually pay your child
- Follow child labor laws. Comply with federal, state, and local rules (e.g. work permit for minors).
The tax savings would depend on your circumstances (e.g. are you in a 37% tax bracket?) Just have to make sure you do it legitimately and document (!). Have you used any of these strategies? Let me know in the comments!Modest Leverage for Young Investors
Mark Gardner | Dec 18, 2025
Under the Tree-a Christmas story
R Quinn | Dec 19, 2025
Interest Rates Battle
Adam M. Grossman | Dec 13, 2025