As a young twenty-something, well-meaning family and mentors offered me the same cliché career advice that everyone gets in their youth.
Don’t choose a career based on money potential. Do something you enjoy.
Like most folks that age, I dutifully nodded in agreement and then disregarded the advice.
Twenty-five years later, after bouts of burnout and disillusion, I finally recognized the tired old wisdom of my youth was more than just refrigerator magnet philosophy.
Why did it take so long to figure out?
My story played out much like everyone else's. Mounds of advice for decades from trusted figures failed to convince me. I needed proof that money couldn’t buy happiness — the one maxim you can only learn through experience.
For most other life-lessons, you don’t need to suffer the negative consequences before heeding its message. The sharing of wisdom can spark insight, enabling more informed decisions and the avoidance of tragic mistakes.
These four lessons would have been most useful if someone had knocked sense into me thirty years ago. Instead, I learned the hard way — via painful experience.
1. Clinging to dead relationships.
Whether it’s boredom, the fear of being alone, or the unwillingness to let go, we will always regret hanging onto relationships that no longer make us happy.
You see it in friends all the time, but it’s difficult to recognize when you’re the one spouting that nonsense excuse. But I’ve invested so much time into it already. I can’t throw it away.
When we reason like that, we exhibit what’s known as the sunk cost fallacy. In the financial world, it influences us to throw more money at losing investments because we refuse to recognize the loss.
The same dynamic plays out in relationships. We invest more time with partners we no longer love because we’re unwilling to acknowledge the time and effort already lost — costs we can never recover.
Eventually, we realize the futility of the situation and part ways. But because of our stubbornness to hang on, we waste far more time than if we had just ended the relationship when its demise had become evident.
When you find yourself in this situation, remind yourself of the sunk cost fallacy. Lost time can never be recovered. It helps to change perspective and think about prospective cost — a future cost you can avoid by taking action. By ending dead relationships without delay, you’ll avoid wasting months or years ahead of you.
2. Violating your principles “just this once.”
Years ago, I worked as a car salesman. One afternoon, a young pregnant woman walked in the door with a baby and her mom in tow, near salivating over the lineup of new cars.
For the next hour, I gave her the full sales treatment, to which she said, “Okay. How do I buy it?”
I could smell an easy sale. Not even a single objection. That seldom happened. Dollar signs flashed in front of me until she handed me her credit application. That’s when my oh shit moment manifested.
Next to the question about her monthly income, she indicated $1,500 a month, barely above the poverty line. I mentioned it would be difficult to get her loan approved, but she said her mom (who spoke no English) would cosign.
I took the papers to my manager, who took one look at the young woman and used a sales ploy designed to exploit unsophisticated buyers. I brought the offer to my customer — no price, just a choice between loan terms, each option equally obscene.
My customer pointed to one.
“Are you sure?” I asked, hoping she’d object.
At this point, I could tell her she could negotiate and risk getting fired, or I could take the offer to my manager and make a bundle of money. I chose the latter and took home a sizable bonus that night. The deal terms were so outrageous the finance company balked. A senior manager had to throw in some bullshit dealer add-ons to make the numbers look right.
That night, I went home and puked after suffering through hours of stomach pains. The next day, I called in and quit.
I still regret my actions even though seventeen years have passed. Violating your principles will haunt you forever. It’s a lesson you should heed without experiencing it yourself.
3. Letting a bully attack you without defending yourself.
In one of my first jobs after college, I worked the front desk at a famous hotel in New York City. The entitled clientele who brandished their hefty expense accounts enjoyed ridiculing, insulting, and abusing the staff. This was the 90s, so we just had to smile and take it. The customer was always right, and back then, they meant it.
On a busy night, the line in front of my station stretched about twenty deep. A guy in a fancy suit tried to cut the queue a few times, claiming his importance entitled him to preferential treatment. I politely asked him to wait his turn. When he finally reached the desk, he looked me in the eye and said, “You’re an asshole. Do you know that?”
I said nothing, too shocked to respond.
He continued. “I asked you a question. Do you know you’re an asshole?”
I responded with something like, how can I help you.
Twenty-five years later, it still riles me that I allowed this guy to abuse me without standing up for myself.
On the flip side, the experience bothered me so much; it transformed me. From that day forward, I asserted myself whenever someone tried to bully or insult me.
Don’t make the same mistake I did. Stand up for yourself. You don’t want that residual memory lingering around your conscience.
4. Passing up love because of status.
Kim and I were seniors in college when we met. When I first got to know her, I immediately became infatuated. One problem haunted me. She ran with a group of people my friends thought were losers. It shouldn’t have bothered me, but it did.
Kim and I would be living about fifteen minutes from each other after graduation, so we could keep up our relationship, assuming it survived the last six months of school. Still, I couldn’t get past my idiot roommate who warned me about dating down. For months, I played coy until she put me on the spot.
We were alone at a bar, touchy-feely like two people who wanted to take the next step but were too hesitant to make a move.
When the bartender sounded “last call,” she squeezed my shoulders, breathed deeply, and invited me to a graduation dinner with some of her friends.
I was in love with her, or so I thought, but I declined her invitation, almost reflexively. She frowned and then put on a fake smile. I regretted my answer, thought of changing my mind but never did.
Months later, we had finished college and had started new jobs. Free of past constraints, I finally asked her on a real date. She declined. Our friendship fizzled soon after.
It’s so challenging to find someone who clicks with you. Focus on what really matters, and don’t worry about what other people think.
For some of life’s wisdom, you must experience the pain before heeding the lesson. That’s not the case for most of the challenges we face in life. With a bit of knowledge, you can avoid many common mistakes that lead to regrets later in life.