An Awkward Money Situation Reveals An Uncomfortable Truth

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Money is great, but it can also create awkwardness among friends, colleagues, or even strangers. In this post, I want to share an awkward money situation that dragged on for months.

In the end, the money situation was resolved. However, it made me realize that we personal finance enthusiasts are an unusual bunch. It also made me realize the risks of voicing your beliefs if you desire a better life.

The Unfortunate Incident

Several months ago, I took my son to school as I normally do every weekday. I parked on the left-hand side of the curb, got him out, and we were about to head off when I heard a loud thud.

Despite over 80 feet of space in front of my car, a driver had somehow clipped my right tire as she was pulling in. I told my son to wait as I went to inspect the tire, which unfortunately had a large gash in the sidewall. If left unfixed, the tire could blowout and result in a catastrophe.

My immediate thought was relief since the driver could have bashed into my car’s body. This had happened before in Lake Tahoe when a laundry truck under valet’s care hit my car overnight. The damage was about $13,000, and the car took two and a half months to fix.

The driver who clipped my tire was apologetic. I told her I would have to change both front tires for safety reasons, which would cost about $900. The tire folks always recommend changing all four tires to have matching treads whenever one is in need of change for a 4-wheel-drive vehicle, but I felt that was overkill since my rear tires were only a couple of years old.

After some consideration, I asked her if she’d be willing to just pay to replace the one gashed tire instead. My two front tires had about 15,000 miles on them, so they weren’t new, but they also weren’t old, with at least two years of usage left. Therefore, I decided I would just pay for the other matching one.

She agreed, no problem, but was clearly frazzled by what she had done.

The Creation Of Awkwardness

After changing both tires for a total of $873.80, I sent her the receipt and asked her to pay $436.90. She could either leave a check at the front desk of the school under my name or mail it to me. She agreed to leave the check at the front desk. Easy peasy.

A week went by, and there was no check at the front desk. Maybe she had forgotten? We saw each other at drop-off the next week, and I thought nothing of it. Then I saw her a couple more times over the next two weeks at drop-off, and still, there was no check. How strange.

If I owe someone money or tell them I will pay them, I do so ASAP. I cannot focus on anything else until the money is paid.

A couple more weeks went by, and I actually forgot about getting the check from her. It was only after seeing her again at drop-off that I remembered.

She told me, “Sorry, I’m going to write you the check. I’ve just been busy.” It was awkward, but I told her not to worry about it. If it was more convenient, she could just mail me the check. She said OK.

Two and a Half Months Go By and Still No Money

Two and a half months went by since I changed my tires, and still no check at the front desk or in the mail. At this point, it was getting comical since we had run into each other at least six times.

Not sure what to do and not wanting to make things more awkward, I asked my wife for advice during our picnic. She suggested, “Just send her my Venmo account. This way, she’ll have no more excuses not to pay.” She was shocked the driver still hadn’t paid.

Ah hah! Why didn’t I think of that? Well, it’s because I still don’t have a Venmo account. Further, my Paypal account is a business account.

I texted the driver, “Howdy X, you can send the $436.90 to my wife’s Venmo account if you have one too. Let me know. Thanks!”

She responded quickly, “Perfect, that would be easier. So sorry for the delay! We had some budgeting items to work around. Now is OK. I just sent payment to your wife.”

Felt Bad Asking Her to Pay

The reason why I didn’t ask the her to pay for two new front tires, let alone four, was because I felt bad. Dealing with car issues is such a hassle that I wanted to minimize her troubles. She was already embarrassed to have hit my car.

It was incomprehensible to me that she clipped my right front tire when pulling in, given there was so much space ahead. So I figured perhaps something was off that morning. Maybe she got in a fight with her husband or her kids slept in or were being difficult. We’ve all been there.

I’ve also never seen her partner drop off the kids, so I felt a kinship since I do 99.9% of all drop-offs and pickups. It’s no fun rushing to school or driving in rush-hour traffic. Commuting was a top-three pain point when I was working. By discussing how the accident could have been much worse and having her just pay for one tire seemed like a fair and easy resolution.

As someone fascinated with money psychology, I was also curious to see how long it would take her to pay. I didn’t want to push her because that would create more awkwardness. However, I was also impressed by how willing she was to endure our awkward encounters multiple times for the sake of delaying payment.

Different Financial Priorities and Financial Health

When she texted back, “We had some budgeting items to work around,” I was surprised and also felt bad again. However, if I owe money, that debt rises to the top of my budgeting/spending list. Nothing matters until that debt is paid. This prioritization is why I would never not pay my rent or mortgage. I signed a contract, so I must honor it.

I was also surprised because I’ve often heard surveys report things like, “Most Americans can’t come up with a $1,000 emergency.” I’ve always viewed these surveys with suspicion, given that having at least six months of living expenses liquid is a fundamental principle of personal finance.

Finally, given this is an independent school with expensive tuition, I didn’t think paying $436.90 would be that big of a deal, especially if you caused the damage. However, I realize not every family who sends their kids to an independent school has lots of money.

I would have waited until the end of the school year to follow up, or a total of four and a half months since she agreed to pay. If she didn’t and disappeared, I would just chalk it up to bad luck.

We Are Aberrations When It Comes to Money

Alas, the more I interact with society again, the more I realize most people are not personal finance enthusiasts. If you’re reading Financial Samurai, you are probably an aberration when it comes to thinking about money too.

We talk about aggressively saving and investing money to achieve financial freedom all the time! But that is because perhaps many of us simply don’t like our jobs enough to do them long term. Hooray FIRE! Whereas most people don’t mind what they do, hence, don’t save as much to break free sooner.

I haven’t had a day job since 2012, so I haven’t been regularly interacting with other adults my age in a work setting. Sure, I hang out with other adults when playing tennis or pickleball, but we only touch upon money and business once in a while. Instead, we are mainly focused on leisurely topics.

I used to live in an online bubble where I could write freely without having to interact with people I didn’t like. However, that changed when our children attended school.

Be Careful Sharing Your Money Views In Person

Hence, one lesson I’ve learned from this awkward money situation is to be careful about making assumptions about how other people view money. Chances are high they have completely different money philosophies and habits than you. As a result, it’s best to show some flexibility and grace.

Most importantly, be careful about sharing your money views in person or publicly. They might come across as “out of touch” or “elitist” if you believe people should:

For A Better Life, Keep Quiet

The more your beliefs contradict the majority, the more you may encounter opposition and hate. Therefore, to garner more love and peace in your life, it’s advisable to align yourself more closely with the prevailing norms and practices. The chant “We are the 99%” immediately came to mind.

As a minority living in America since 1991, I’m intimately aware of the hate that can come your way if you look differently. I’m also aware of how it’s easier to get ahead if you are part of the majority because people naturally tend to befriend and take care of those who resemble them.

You can’t help the way you look. But if you also think differently, you could easily be ostracized by the majority. This can happen both online and offline, to the detriment of your financial and mental well-being. Hence, it’s probably best to keep your unique opinions to yourself.

Think About Your Children

It may be too late for you and me, but it’s not too late for our children. Teach them this important lesson of assimilation while privately pursuing their dreams.

This uncomfortable truth may sound sad—like how schools indoctrinate our children and stamp out all their creativity by the time they graduate from college. Then it’s off to make as much money as possible in a soul-sucking job.

However, if you are not yet financially independent, you can’t afford to stray too far outside the lines. If you do, your life will become much more difficult as you get passed over for promotion, fail to get support for your creative endeavors, and face other challenges.

Once you have “f you money,” then you can more freely speak your mind. But before then, assimilate with the masses. Be patient. Your time to unleash the Kraken will eventually come!

Reader Questions About Awkward Money Situations

What awkward money situations have you encountered? How did you deal with or resolve them? Besides lending and borrowing money, what other financial situations can create tension and awkwardness?

Would you have waited two and a half months to get paid, despite running into the person multiple times? If not, how long would you have waited before sending a follow-up text?

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