Business

A Terrible Life Insurance Mistake That Cost Me A Fortune

In late 2022, my wife and I were finally able to lock in matching 20-year term life insurance policies at an affordable rate through Policygenius. For five years prior, I had been concerned that I wouldn’t be able to get approved at a reasonable price—all because of a mistake I made by visiting an overzealous sleep center.

Back in 2016, I was tired of paying $1,800 a month for a health insurance plan with UnitedHealthcare and never using it. I hadn’t seen a doctor in years, so when a new sleep center opened up nearby, I figured I might as well get checked for snoring and put my insurance to use.

Of course, one check turned into a full battery of tests, costing my insurance company about $3,800. At first, I felt good—I was finally getting something for all those insurance premiums! But little did I know, that visit would come back to haunt me. The unfortunate consequence of going to the doctor was being flagged with a “sleep-related” issue, such as sleep apnea, which made it much harder to qualify for affordable life insurance later.

When I tried to renew my 10-year term life policy through USAA in 2017 at age 40, they quoted me $450/month—up from the original $40/month. A ridiculous 11X higher! No thanks. I’ll look elsewhere.

Table of Contents

My First Two Life Insurance Mistakes

My first real life insurance mistake was going to a doctor before renewing my policy. Had I kept a clean medical record—aside from routine physicals—my new policy would have cost closer to $120/month now that I was 10 years older. Always lock down an affordable life insurance policy before seeing the doctor for anything out of the usual.

But frankly, the first mistake was only getting a 10-year term policy at age 36. I should have gone for a 30-year term at around age 30. After 30, life tends to get much more complicated with housing and family.

Just a year later, I took out another $1+ million mortgage to buy a fixer-upper. Three years later, my son was born. When you have children and debt, life insurance becomes a priority. A 30-year policy back then would’ve cost me about $30/month—an absolute bargain in hindsight.

At least I managed to course-correct by securing a new 20-year, $750,000 term policy through Policygenius for $110/month in 2023. They matched us with SBLI, a carrier willing to underwrite both me and my wife, even with my prior sleep center visit.

But then I made another mistake—by far the worst one yet. It sickens me to write this, but as always on Financial Samurai, I share both the wins and the painful losses to try and help as many people as possible.

The Worst Life Insurance Mistake Possible

My wife recently asked me to send her our rental insurance policy from USAA because Wells Fargo, which holds our remaining rental property mortgage, needed proof of coverage.

When I logged into my USAA dashboard, something odd caught my eye:

“Level Term Series V Policy – $1,000,000 for 10 years.”

It looked like my old term life policy, so I clicked in. And then—WHAM.

The number that jumped out? $885.79/month.

What the hell? What was this doing here? Was this an advertisement or what?

Nobody in their right mind would pay nearly $900 a month for just a $1 million term policy—unless they were terminally ill and had no other options. I certainly wouldn’t.

USAA is the worst. Charged me $885.79/month in life insurance premiums for a $1 million term policy without my consent. This is an auto-debit.

But dread began creeping in. What if I had been paying this all along?

I quickly logged into my Citi bank account, where USAA autopays are debited, to investigate.

Unnoticed Payment For Two Years

Here’s what I discovered when I logged into my bank and searched for USAA. And let me tell you, it wasn’t good.

A Terrible Life Insurance Mistake That Cost Me $20,000

To my horror, I had been paying over $800/month to USAA for at least 18 months straight. That’s as far back as my bank’s custom search would let me go.

My stomach sank. How could I be so careless?

Back in late 2022, I thought I told USAA I wasn’t willing to renew my 10-year term life policy when they quoted me ~$450/month—a drastic jump from my original $40/month rate.

So why, without my consent, why did they charge me even more?

Since my original 10-year term policy with USAA expired in January 2023, I’ve paid over $20,000 in premiums to USAA despite thinking my policy had ended!

My whole point of getting a new 20-year, $750,000 term-life insurance policy through PolicyGenius in 2022 was so that I wouldn’t have to pay the new $450/month rate USAA quoted me back in 2017. Oh my.

How Could I Have Missed Overpaying for So Long?

I’ve asked myself this question more than a dozen times. Here are five reasons:

Bundled coverage: USAA handles multiple insurance lines for me—rental properties, auto, umbrella, valuable personal property—so when an $800+ charge hit, I didn’t think much of it.
Inconsistent billing cycles with auto-debiting: USAA bills me monthly, semi-annually, and annually across different policies. Whenever I saw a large charge, I assumed it was for a quarterly umbrella renewal or something similar.
Bad timing: Sometimes I didn’t see the charge at all. If I didn’t log into my bank that week, the transaction got buried by the time I checked.
Blind trust: I trusted USAA to do the right thing. It never crossed my mind that they’d continue my 10-year term life policy and charge me 18X more per month than I’d been paying. I’ve been a loyal customer for 23 years.
Cash flow cushion: I’m fortunate to have strong savings habits and solid cash flow. The $740–$885 monthly charge for over two years didn’t impact my spending behavior. I save first, spend later—but the downside is being less watchful with expenses.

Despite all this, I take responsibility. No one forced me to set up auto-debit. I should’ve been more diligent about reviewing my finances regularly.

Don’t Expect Your Insurance Carrier to Voluntarily Save You Money

Since 2020, I’ve had multiple conversations with my insurance provider about property, auto, and life coverage. Not once did a representative flag my life insurance policy or ask, “Whoa—are you sure you want to pay over $700 a month for this? Let’s see if there’s a more affordable option that fits your situation.”

Instead, I received periodic nudges—emails and calls—urging me to increase my property insurance coverage. That meant coordinating with a property assessor, letting them in, and ultimately paying more when the policy renewed.

Don’t be lulled into thinking your insurance company is actively looking out for your best financial interests. Their job is to protect you from risk, yes, but they’re also a business. Once you set up auto-debit, they can quietly raise premiums, and you might not even notice. At the end of the day, they have a fiduciary duty—not to you—but to their shareholders.

Is It Legal for Life Insurance to Automatically Renew Like This?

Some of you might have empathy and wonder if jacking up a customer’s life insurance rate by 18 times or more is legal. Sadly, the answer seems to be yes.

If your original policy has a “guaranteed renewal” clause, and you don’t explicitly cancel, the insurance company can continue the coverage as an annually renewable term (ART) policy.

This means:

You keep your coverage without new underwriting
But the premium skyrockets every year as you age

Most people don’t realize this clause even exists. It’s often buried deep in the fine print. Therefore, another step for all of us is to thoroughly read the contract and ask questions about things you don’t understand. Don’t just trust your insurance carrier to do the right thing.

So technically, USAA didn’t break the law—but they sure didn’t do me any favors. The representative told me they have clients who pay these huge premiums because they simply can’t get coverage elsewhere.

Many policyholders fall into this trap. They assume the policy just ends—or that premiums stay flat. Insurers bank on that assumption to make maximum profits.

What I Did to Try And Get A Refund

Not one to lie down and get trampled on back and forth by a 7-ton elephant, I decided to contest the charges. I thought I clearly told USAA in 2017-2019 I would not renew the policy at their quoted rate of $450/month. So I most certainly wouldn’t have agreed to $720/month in January 2023 and the most recent $886/month charges.

Here’s what I did

1. Called USAA Immediately

Explained:

I was not clearly notified of the shift from level term to annual renewable term (ART)
I explicitly declined their renewal offer i
I only just discovered the $885.79/month charges
I’m requesting a retroactive cancellation and full refund of premiums charged since the term expired

I used firm but respectful language, such as:

“I would never have agreed to continue coverage at this rate. I feel misled and would like a refund for all premiums charged after my level term expired.”

2. Escalate if Necessary Or Desired

If USAA doesn’t do something, I may file complaints with:

My state’s insurance commissioner
The Better Business Bureau (BBB)
The Consumer Financial Protection Bureau (CFPB)

These agencies track complaints and put pressure on companies to resolve issues.

My Life Insurance Premium Refund Request

I understand I received coverage during the time I was paying premiums. Had I purchased a new 20-year term policy starting at age 45, I would’ve expected to pay around $150/month, or $1,800/year. I also recognize that if I had died during this period, USAA likely would have paid out the $1 million death benefit to my wife. Thankfully, I’m still alive—so here we are.

That said, I’m not asking for a full refund of the $20,000+ I paid. Instead, I believe a $16,000 refund is a fair compromise ($20,000 I paid minus the $4,000 I would have been willing to pay for two plus years).

No healthy 45-year-old male in 2023 would knowingly agree to pay $886/month for a $1 million term life policy. That’s not just overpriced—it’s highway robbery. I feel like USAA mugged me for my wallet and then slashed my tires on the way out.

How USAA Initially Responded

When I first called USAA to explain what had happened, the life insurance representative I spoke with was dismissive. She said there would be no refund and that the best she could do was cancel the policy. She claimed USAA had sent a notification about the renewal—one I never saw—and added that some members continue paying the exorbitant rate for whatever reason, which in her view justified the lack of follow-up.

After the call, I sat in silence for about 20 minutes, feeling defeated. Then I decided to call back—this time to request proof of where the notification had been sent. Because really, is a notification valid if the client never sees it or confirms their intent? I don’t think so. A default setting that quietly charges a customer 18X more without explicit confirmation feels predatory.

The second representative I reached was much more empathetic. She said she wouldn’t have paid that premium either. She explained that the notification had been sent to my online message center. Sure enough, when I scrolled back to November 2022, I finally found it.

Maybe an email alert had been sent to let me know there was a new message in my inbox—but if so, I missed it. Thankfully, this rep took my concerns seriously. She said she’d escalate the issue to her manager and the “Member Advocacy Team.” Hallelujah.

She assured me the advocacy team would do a thorough review, including listening to our recorded calls and examining the full account history.

The Feedback From USAA After Their Investigation

The representative from the Member Advocacy Team came back with an offer: a credit of two months’ premiums totaling $1,771.58. It was a good first step, but still felt far short. I had hoped for a more reasonable compromise—something closer to a $16,000 credit.

Then the tone shifted. She noted that after reviewing call logs dating back to 2022, she didn’t hear me explicitly say I didn’t want to renew the policy. Instead, she claimed I was simply inquiring about my options. To me, that should’ve strengthened my case—why would I be asking about options if I intended to keep paying an exorbitant premium? But she disagreed.

So I encouraged her to dig deeper into their call logs, further back in time, to see if there was any record of me clearly expressing my unwillingness to pay a fortune for life insurance. She agreed and asked me to email any supporting information I could find in the meantime.

Evidence I Wasn’t Willing To Pay the Higher Premium

I searched my archives and found two articles I had written that clearly documented my struggle to find an affordable life insurance policy before my 10-year term was set to lapse. I sent both to USAA, complete with publication dates, to reinforce my position.

“Convert Term Life Into Permanent Life Insurance To Keep Your Rate Class” – Published June 5, 2020
This post outlines how, after my son was born in 2017, I contacted USAA to explore extending my policy. After undergoing a medical exam, I was shocked to find my premium jump from $40/month to $450/month due to sleep apnea. I declined the offer, stating it was far too expensive, and made it clear I would search for a more affordable option.
“How I Finally Got An Affordable Life Insurance Policy With No Medical Exam” – Published December 21, 2021
This article details how, after years of searching, I finally secured a 20-year, $750,000 term policy through SBLI for $110/month. I noted that I was willing to carry both policies temporarily—doubling coverage for a year—while preparing to transition off the USAA plan.

These publicly documented posts show my intent and efforts to avoid high-cost life insurance by USAA and prove I never agreed to such a steep renewal. I could only hope they help USAA reevaluate their position.

Hard to Trust USAA With Our Insurance Needs Anymore

Unfortunately, USAA came back from further investigation and said the $1,771.58 credit was the best they could do. They were shutting the case. Ugh.

What’s most disappointing is that, after 23 years as a loyal USAA member, I truly believed the company would do right by me. I’ve consistently paid my premiums on time and have been a responsible, engaged customer.

Most people don’t fully understand the intricate details of life insurance policies, renewals, and their fine print. I did my best to stay informed, yet I still feel like I was misled and ultimately taken advantage of. Communication is not effective if the other side doesn’t receive or acknowledge.

Without a more equitable resolution, it’s hard for me to continue placing my trust in USAA.

The One Silver Lining From This Careless Debacle

If there’s any silver lining, it’s this: by sharing my story, I hope to prevent at least one person from falling into the same trap. Don’t assume your term life insurance policy ends when the term is up—it often doesn’t. Unless you actively cancel it, it may auto-renew, and the premiums can skyrocket.

All this time, I thought I was being a responsible father and husband—saving money and protecting my family in case I were to pass. In reality, I was a careless fool who failed to double-check his expenses.

As a result, I actually put my family in a more compromised position due to our reduced monthly cash flow. I had bought a house in October 2023, which drained my liquidity and increased my stress for at least six months.

The first year after a home purchase is the most financially vulnerable time and I sure could have used that extra ~$800/month in health insurance premiums I didn’t realize I was paying.

Tips to Save Money on Life Insurance Premiums

Be loud and clear about your intentions on recorded calls—don’t assume anything will be understood or noted unless you say it explicitly.
Review your expenses monthly. Don’t let auto-debits go unchecked. If something looks off, cancel or investigate immediately.
Lock in a 30-year term life policy around age 30 while you’re still young and likely healthier for the best rate. Your life will most likely get more complicated and expensive.
Avoid unnecessary doctor visits right before applying for life insurance—they might uncover minor issues that raise your premium.
Don’t expect your insurance carrier to proactively save you money. Their goal is to maximize profits, not look out for you.
If you’ve had health issues, go on a health kick for at least six months—then reapply to try qualifying for a better rate.
No matter how badly you fail, keep fighting to protect your family’s financial security. No one else will do it for you.

Going forward, I’m returning to my “broke mindset”—keeping my checking account lean, like a college student on minimum wage. Having extra cash flow felt nice, but for me, it bred complacency and laziness. That ends now.

As punishment for my carelessness, I’m committing to a strict no-spend challenge until I make up for the $14,228.42 in excessive life insurance premiums I paid ($20,000 total minus the $1,771.58 refund and the $4,000 I would’ve paid for 26 months of coverage). Alternatively, I’ll side hustle or make new investments to recoup the $14,228.42 in overcharges.

I’ve already spent hours fighting my case and writing this post, and I hope it helps you make better life insurance decisions. Now it’s time to move forward in the way only I know how.

Readers, have you ever gone through something similar with a life insurance policy—or any other product or service? Have you ever discovered you were paying for something you didn’t realize, thanks to auto-debiting or just plain oversight? If so, please share your story so I don’t feel like the only one who got duped by carelessness. Misery loves company—and maybe we can all learn a little from each other’s mistakes.

Life Insurance Policy Recommendation

If you have debt and dependents, getting life insurance is one of the most responsible financial moves you can make. I recommend checking out Policygenius, an insurance marketplace I’ve trusted for over 10 years. Simply enter your coverage needs, and Policygenius will match you with top-rated carriers offering competitive rates.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

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Business

The Cost of Supercommuting: Way More Than Just Gas Money

A typical supercommuter spends 60–90 minutes or more one way commuting to work or school. As the cost of living continues to outpace wage growth, supercommuting is growing in popularity. According to a recent U.S. Census Bureau report, an estimated 5 million people are now supercommuters—up from roughly 3.42 million in 2012.

I hate long commutes. Taking the bus or driving to work was one of my top three annoyances while I was employed.

When I retired in 2012, one of the greatest joys was never having to commute again. Getting back that time, energy, and mental clarity was a truly lifestyle-enhancing benefit of retirement. Then, when the pandemic hit in 2020, millions around the world got to experience that same freedom. Is there any wonder why it’s been so hard to convince workers to go back to the office?

In this post, I want to highlight the hidden toll of supercommuting to work or school. Sure, you’ll spend more on gas if you drive. But that’s just the beginning. So before you buy a more affordable home in exchange for a longer commute, be forewarned: the trade-offs may not be worth it.

Table of Contents

My Experience With Supercommuting

After deciding not to pony up a small fortune for a vacation rental in Honolulu, I opted for my family of four to stay with my parents for up to five weeks. They have three free bedrooms in their five-bedroom house, and it’s a home I’ve returned to for 39 years. It feels comfortable to me, but not to all.

Some of you thought this was a good way to save money. Others—mostly women—said it was cruel to subject my wife to such confinement for so long. I get it. Staying with your in-laws for more than a few days is a lot to ask, especially without en suite bathrooms or separate kitchens and entrances. And not everybody likes to be in Hawaii during the summer heat.

Still, the cheapest suitable three-bedroom rental I could find cost $16,000 after taxes and fees. A nothing fancy four-bedroom rental, without a pool, which we liked, was $24,000. After owning real estate since 2003, I just can’t bring myself to spend that much on a temporary stay that builds no equity.

To find a compromise, we stayed at my aunt and uncle’s place on the North Shore—up to 1.5 hours away—after 13 days with my parents, to give both my wife and mom a break for nine days. It gave me a break too as I could return to living without worry of doing things in a way that would displease my mom, e.g. cut fruit on the right side of the sink instead of the left.

The kids were happy wherever they were, so everyone won, well, except for me who had to drive ~2.5 more hours a day for five days.

The False Start

We picked up our kids at 4:55 p.m. Friday from summer school at Punahou to head to Laie for the weekend. All was well—until six minutes in, our five-year-old daughter announced she had to pee. I turned around and went back to school so she wouldn’t have to hold it.

Had we been commuting from my parents’ house, just eight minutes away, I would’ve just kept driving. That’s one unexpected cost of supercommuting—having to manage bodily functions mid-ride. Most adults can uncomfortably hold it for an hour or two. But kids? Not so much.

We finally arrived in Laie an hour and 25 minutes later. The kids napped for 35 minutes, so the trip felt like a breeze to them. Although I was tired, I was also excited to enjoy the freedom of having our own space again.

Supercommuting from Laie to Punahou School in Honolulu takes about 1 hour and 15 minutes each way — Supercommuting from Laie to Punahou School and back

The Monday Morning Supercommute

After a fun weekend filled with Pokémon Go Fest, Giovanni’s garlic shrimp, and beach walks, reality returned Monday morning.

I passed out by 10 p.m. Sunday after putting the kids down by 9:20. I woke up at 2:45 a.m. to get a head start on publishing a new post, responding to comments, and going for a morning walk on the beach.

The kids woke up at 6:30 a.m., and we left by 6:55 to make it to school by 8. Back in Honolulu, we usually leave at 7:40, so the earlier start was a shock for my wife and daughter, who aren’t morning people.

Right away, I could tell the drive would take longer than expected. We were stuck behind a gasoline tanker on a single-lane road for about 15 miles, averaging just 32 mph instead of the usual 40–45.

About 45 minutes in, I got a text from my wife thanking me for the ride and the peace and quiet. At a stop light, I couldn’t help replying with a GPS screenshot to show where we were—7 minutes behind schedule. Usually, the GPS arrival time was conservative and easy to beat.

But then I made a mistake. I resumed driving while glancing at the screenshot I had sent her instead of the live Apple Maps. That brain fart cost us another 11 minutes. Instead of arriving at 8:05 a.m., we got to school at 8:16. Ugh—I hate being late.

Supercommuting and showing a screenshot of my arrival time — The screenshot I sent and followed my mistake

A Place To Hang Out Made Supercommuting More Manageable

At first, I thought I’d just hang out at the beach or mall all day before picking the kids up at 4:55 p.m. My wife also wanted me to pick up some groceries. No problem. There was no way I was going to drive 1.15 hours back to Laie after drop off and then do it again in the afternoon. I figured I’d nap in the car under a banyan tree if I had to.

Then I remembered my parents’ house was only 8 minutes farther. I could write, rest, and manage the renovation of an in-law unit I was working on. Having a home base made the day much more manageable. If I had to also work a full-time job during that commute, I would’ve been completely wiped.

In fact, after dropping off the kids, I spent the day in the city writing a post, recording a solo podcast episode, talking to my parents, grabbing lunch, and squeezing in a quick 15-minute nap.

Then I dealt with the handyman, swung by Whole Foods for groceries, and picked up the kids at 4:55 p.m. The day flew by—and by the end of it, the thought of driving 1 hour and 15 minutes back to Laie was the last thing I wanted to do.

The Next Day of Supercommuting (Good Then Bad)

By the second day of supercommuting, I felt more confident. I knew the route better and had learned from my mistakes. I got the kids to school 10 minutes early and shaved 20 minutes off the drive. It felt like a small win. But of course, good things never last.

When I arrived at my parents’ house—another 10 minutes from school—the plumbers had already shown up early. Then, 30 minutes later, the handyman arrived. In total, I spent nine hours managing five different workers trying to fix up our long-neglected in-law unit. I hate remodeling and swore to never do so again. But here I was, like a masochist, doing it again while I was supposed to be on vacation. If I didn’t lead the charge, nobody would, as the place has been neglected for over five years.

To make the most of the downtime, I brought my laptop outside and worked on a new post. But with the sun blazing and temps hitting 85 degrees, I was drained by mid-afternoon.

By 4:40 p.m., all I wanted to do was lie down in an air-conditioned room and take a nap. But no such luxury. I had to hop back in the car, drive 10 minutes through rush hour to pick up the kids, then endure another 1 hour and 10 minutes back to Laie.

My zest for life? Gone. After 10 minutes of small talk with the kids about their day, I turned on some music and just listened like a zombie. I didn’t have the energy to keep the conversation going.

By the time we got home, I was toast—just a tired, slightly grumpy dad who wanted nothing more than to kick back and crack open a cold beer.

Positive Thoughts To Gut On Through

Even though I was commuting about 2.5 hours extra a day, I told myself it was worth it—for my wife’s sanity, my mom’s peace, and even my kids’ resilience. Maybe the longer commute would build their endurance and teach them the value of waking up early.

Perhaps most importantly, my wife appreciated the effort I put in to make her happy. Judging by her FaceTime calls from the beach, she definitely seemed more relaxed and content! With appreciation, I’m happy to keep on supercommuting.

As a father, you do what you can to provide. A little extra effort plus some problem-solving goes a long way to making a suboptimal situation better. Got to think positive!

Besides, knowing the supercommuting stint was temporary made it tolerable. My kids had Friday off for the 4th of July, so I only had to supercommute for four days—a total of ~11 hours of additional driving.

The Hidden Costs of Supercommuting

At first glance, supercommuting might seem like a reasonable trade-off. Save 20–60% on housing and spend an extra two hours and thirty minutes commuting a day? Maybe not so bad, especially if the median home price is above $1 million.

But in addition to hundreds more in gas and transit costs each month, here are other downsides:

Increased risk of injury or death – More time on the road means more exposure to accidents, especially when driving with kids. I literally saw a car on a residential street near my parent’s house flip upside-down because it got t-boned at an intersection. One of the cars didn’t stop at the stop sign.
Higher stress and cortisol levels – Bad drivers, traffic jams, and road rage add up, draining your emotional reserves for the day and evening. You might end up developing chronic pain, raise your stress levels, and ultimately, shorten your lifespan as a result.
Wear and tear on your vehicle – More miles mean more maintenance, especially if your car isn’t ultra-reliable. For example, changing four tires on my Range Rover sport costs $1,650, and they only last about 16,000 – 18,000 miles.
Greater chance of getting tickets – From parking mistakes to speeding tickets, increased driving time raises your chances of infractions. In turn, your car insurance premiums could go up.
Reduced happiness and harmony with your significant other – Long commutes drain your energy and patience, which means by the time you get home, you might be more irritable, checked out, or just plain exhausted. Small disagreements can flare up more easily when one or both of you are running on fumes. Over time, the emotional toll of being physically distant and mentally unavailable adds up.

If You Are Going To Regularly Supercommute

If you plan to supercommute regularly, two things are imperative: a safe, reliable car and life insurance.

My wife and I have matching 20-year term life insurance policies, which have provided tremendous peace of mind. I recommend locking in an affordable policy through Policygenius to cover your debts and protect your children until they become adults.

Here in Honolulu, however, we don’t have what I’d consider a safe-enough car for long-term supercommuting. We’re using my dad’s 1997 Toyota Avalon. While it’s a nostalgic beast, it has poor acceleration for evasive driving, a wobbly axle, shaky brakes above 45 mph, no side curtain or rear airbags, no blind spot detectors, no sensors, and no rear camera. I’m not even sure the front airbags work—my guess is they haven’t been replaced since he bought the car.

As a result, I drive slowly and try to stay extra alert. The one saving grace is that the speed limits between the North Shore and Honolulu are relatively low—35 mph on the single-lane “highway” and 50 mph on the main freeways. So it’s not like mainland highways where people routinely push 70–85 mph.

If we return to this same living and commuting arrangement again, I plan to rent a new car. It’ll not only be safer, but it’ll also free up my dad to run errands during the week with his own 28-year-old car. A win-win.

Final Thoughts on Supercommuting

Supercommuting might seem like a smart financial move, especially when housing near work is unaffordable. But before you commit, look beyond the savings. Living in a smaller house or apartment to save time commuting is my preference .

Every hour on the road is an hour not spent with your loved ones. Every stressful drive takes a toll on your mood, focus, and health. And every unexpected delay chips away at your patience—especially when you’re juggling the demands of family life and work.

For me, those long drives were about more than transportation. They were about making a tough situation work, even if only temporarily.

If you’re going to supercommute, have a plan. Know your timeline. Understand your reasons. And make sure the trade-off is truly worth it. Because in the end, a cheaper home isn’t worth it if it leaves you drained and hating life.

The Value of a Well-Located Home

Personally, a comparable home would need to be at least 75% cheaper to justify adding two extra hours of commuting each day. And even then, I’m not sure the trade-off would be worth the toll on my time, energy, and well-being. The time I get to spend with my kids after school is simply too precious to sacrifice.

If you live within 15 minutes of both your work and your children’s school, consider yourself fortunate. While remote work surged during the pandemic, in-person collaboration has made a strong comeback. As a result, well-located homes in job-centric cities—especially where supply is constrained—may outperform in the future.

When my children’s school moved in 2024, our drop-off time shrank from 15 minutes to just 8. That may not sound like much, but it’s been a noticeable quality-of-life upgrade. Now, if I need to swing by school to drop off lunch or attend an event, it’s a quick and easy trip.

Of course, if I had to commute downtown daily, the drive would stretch to around 25 minutes, or 25 minutes by MUNI, including walking to the station—just beyond my ideal maximum for a work commute. Fortunately, we don’t have to go into an office anymore. And for that, I’m especially grateful.

Readers, are any of you supercommuters? If so, how do you make the long transportation time more bearable? Are there any unexpected benefits to supercommuting beyond saving on housing costs or being closer to family or a better school? I’d love to hear your strategies and insights.

Pick up a copy of my USA TODAY national bestseller, Millionaire Milestones: Simple Steps to Seven Figures. I’ve distilled over 30 years of financial experience to help you build more wealth than 94% of the population—and break free sooner.

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Business

Barbara Corcoran Retains Staff With Wild Perks, No Turnover

1752003513 Barbara Corcoran GettyImages 2207922626

Barbara Corcoran, the 76-year-old founder of the real estate firm The Corcoran Group, claims to have created a work environment where there was “no turnover.”

In an Instagram post shared with her 1.2 million followers on Monday, Corcoran outlined the “crazy things” she would do to keep her staff happy. For example, Corcoran would bus hundreds of agents to the country for midweek picnics, each with its own memorable feature, like a 60-foot-tall hot air balloon or a 5,000-pound elephant offering safari rides.

She would also provide babysitters for employees who wanted to bring their kids to work and offered plenty of office perks, like yoga classes, free lunches, and massages.

Corcoran recognized top performers by giving gold ribbons to anyone who closed a million-dollar sale, and gave one of her top brokers a Bentley with the license plate “SOLD1” to highlight her stellar performance in front of the whole company.

She additionally claims to have thrown “the wildest parties in town” for her employees, complete with their own “wacky” themes — and dressing up was mandatory.

The end result of these initiatives? People were “lining up” for jobs at The Corcoran Group, and Corcoran didn’t have to advertise new job openings. There was also zero turnover; employees chose to stay.

“People are most creative when they’re having fun, and we had more of that than anyone else,” Corcoran wrote in the post. “I stopped advertising to hire because people were lining up to work at The Corcoran Group! Fun builds loyalty, and we had no turnover.”

Corcoran founded The Corcoran Group in 1973 with just $1,000 and seven agents. By the time she sold the brokerage firm for close to $70 million in 2001, the team had grown to encompass 700 employees.

Corcoran also noted in an Instagram video in March that she is “the best boss” she has ever met because she follows a simple principle: She works for whoever works for her. In other words, she works for her employees, and her perspective is always tied to what she can do for them.

“I shower my people with anything they need selflessly,” Corcoran said in the video, adding later that, “I don’t think anyone could be a better boss than me.”

Corcoran is now an original cast member of “Shark Tank.” She has appeared on the show for 16 seasons and made more than 650 deals. She makes about $4.5 million a year from her investments, including profits from deals from the show.

Barbara Corcoran, the 76-year-old founder of the real estate firm The Corcoran Group, claims to have created a work environment where there was “no turnover.”

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How to Turn Summer Travel into More Business and Less Taxes

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Opinions expressed by Entrepreneur contributors are their own.

According to a recent Bankrate survey, fewer than half of Americans plan to travel this summer. Among those staying home, most cite cost as the main reason.

That’s a missed opportunity.

Travel isn’t just a luxury — it’s a strategic tool. For entrepreneurs, stepping outside the day-to-day grind creates space to think creatively, meet new people and gain the fresh perspective that fuels innovation. One good conversation or idea sparked on the road could become your next big business move.

Here’s the best part: if you’re strategic, you can align your travel with your business goals — and potentially write off a portion of the cost. The IRS allows business owners to deduct legitimate business-related travel expenses. With the right planning, your summer getaway can double as a business trip that moves your company forward.

Table of Contents

Travel with purpose

Making the primary purpose of your trip business-related doesn’t mean you have to spend your days in meetings. For travel within the U.S., the IRS allows deductions as long as more than half of a standard workday (four or more hours) is spent on qualified business activities.

That could include meeting with clients, scouting investment properties, researching a new market, or connecting with potential partners. The key is intention and documentation.

If you’re in the 32% tax bracket, treating your travel as a legitimate business expense can result in a 32% “discount” via tax savings. That’s not a loophole—it’s a smart use of existing tax code designed to support business growth.

Take one of my clients, for example. He built a vacation around scouting real estate deals in New Mexico, a place he already loved visiting. The trip saved him around $3,000 in taxes—and even better, it led to a property deal that eventually earned him over $1 million in profit.

What qualifies as deductible business travel?

The IRS has clear rules on what counts as a deductible business expense. Common eligible expenses include:

Airfare, train fare, or mileage to and from your destination
Hotel or lodging costs
Ground transportation (Uber, taxis, car rentals, airport transfers)
Baggage fees
Laundry or dry cleaning during the trip
50% of non-entertainment meal costs

To qualify, expenses must meet four basic criteria:

Business purpose: There must be a clear business reason for the trip.
Ordinary and necessary: It should be a typical and reasonable expense in your line of work.
Directly related to business: The activity must advance or support your business.
Properly documented: Keep records—receipts, dates, contacts, meeting notes, and outcomes.

If your spouse or children are active in the business and perform meaningful work during the trip, their expenses may also be deductible. For example, if your spouse is a co-owner or your children help with content creation, marketing or research, their travel may be part of your business plan — if documented correctly.

Work with a trusted advisor

Blending business and personal expenses adds complexity to your tax situation. A tax advisor who specializes in entrepreneurs can help ensure your strategy is sound and legally compliant. The goal isn’t just to deduct travel. It’s to structure your business in a way that supports growth and lowers your tax liability year-round.

Final thoughts

Before you book your next trip, ask: How could this support my business?

Maybe it’s an investment scouting trip. Maybe it’s reconnecting with a client in a new market. Maybe it’s simply taking space to think clearly and plan your next move.

When you approach travel with intention, the possibilities multiply. That break you’ve been craving could be the catalyst for your next revenue stream or expansion play—and with a smart tax strategy, the IRS could help fund it.

If you love where you’re traveling, why not plant business roots there? You’ll have a reason to return—on another deductible trip—with even more upside next time.

Because when travel helps you grow your business and lower your tax bill, the real question isn’t whether you can afford to travel—
It’s whether you can afford not to.

According to a recent Bankrate survey, fewer than half of Americans plan to travel this summer. Among those staying home, most cite cost as the main reason.

That’s a missed opportunity.

The rest of this article is locked.

Join Entrepreneur+ today for access.