Menu
Before reading, watch the video below. It covers several decisions that can create years of regret—and includes additional tips and examples that are not discussed in this article.
https://youtu.be/bG3ThZUZxdk
Most bad decisions don't feel bad when we make them. That's part of what makes them dangerous.
They often feel justified, necessary, satisfying, or even courageous. You send the email because the other person deserves it. You stay in the relationship because you've already invested three years. You fight because backing down feels weak. You postpone a difficult decision because there will always be tomorrow.
The consequences frequently arrive much later, when the anger is gone, the relationship is over, the opportunity has passed, or the internet has preserved something you desperately wish it had forgotten.
As a lawyer, I have seen how seemingly small decisions can follow people for years. A text message becomes an exhibit. A social-media post becomes the centerpiece of a disciplinary proceeding. A lie that seemed insignificant becomes more damaging than the conduct it was intended to conceal.
But this isn't simply about avoiding legal trouble. It's about making decisions today that your future self won't have to spend years trying to undo.
Here are ten of them.
You write the perfect email. Every sentence lands. You finally tell the other person exactly what you think of them.
Then you hit send.
The satisfaction lasts five minutes. The message may last forever.
Anger creates an illusion of urgency. It tells us that something must be said right now, even though waiting until tomorrow would often completely change what we say—or convince us not to say it at all.
This matters particularly with texts, emails, and social media because electronic communications can become permanent evidence of a temporary emotion.
Before sending something when you're angry, ask yourself:
Would I be comfortable having this read aloud in a courtroom, disciplinary hearing, job interview, or meeting with my employer?
If the answer is no, don't send it.
You've spent four years in the relationship. Ten years building the career. Thousands of dollars on the business. Months fighting the dispute.
Walking away now feels like admitting that all of it was wasted.
So you invest more.
This is the sunk-cost fallacy: allowing what you've already invested to dictate what you should do next.
But yesterday's investment does not make tomorrow's investment worthwhile.
Ask a different question:
Knowing everything I know today, if I were starting from zero, would I choose this again?
If the answer is no, the amount you've already invested may be a reason to reconsider—not a reason to continue.
Sometimes quitting is not failure. Sometimes refusing to quit is.
One of the most expensive habits you can develop is the need to prove that you're right.
Not every insult requires a response. Not every unfair accusation deserves a battle. Not every disagreement needs a winner.
I see this frequently in legal and disciplinary disputes. Someone becomes so determined to expose another person's wrongdoing that the original objective gets lost.
The question stops being, “How do I get the best outcome?”
It becomes, “How do I prove that they were wrong?”
Those are very different objectives.
Before escalating a conflict, ask yourself:
What exactly do I gain if I win?
If the answer is merely satisfaction, think carefully about what that satisfaction may cost.
Many terrible decisions solve an immediate problem.
Lying avoids an uncomfortable conversation. Cheating avoids a bad grade. An impulsive post releases anger. Ignoring a letter postpones anxiety. Spending money you don't have provides something you want today.
The immediate benefit is real. That's precisely why these choices are tempting.
One way to resist them is to mentally move yourself forward five years.
Imagine sitting across from the person you will be five years from today and explaining the decision you're about to make.
Then ask:
Would that person thank me for doing this?
People make serious mistakes.
Students get suspended. Professionals lose jobs. Relationships collapse. Businesses fail. People say things they desperately wish they could take back.
The original mistake can be damaging. But another mistake sometimes follows: deciding that what happened permanently defines who you are.
It doesn't have to.
A much better response is to acknowledge what happened, take responsibility where appropriate, repair what you can, learn from it, and begin accumulating evidence that the mistake was an event rather than a character trait.
Five years is an extraordinarily long time when you use it well.
The email you don't answer.
The bill you don't open.
The academic warning you dismiss.
The uncomfortable conversation you keep postponing.
The letter that has been sitting unopened on your desk for two weeks.
Many crises begin as manageable problems.
Avoidance is seductive because doing nothing eliminates discomfort today. Unfortunately, it often purchases much greater discomfort tomorrow.
There is a useful rule here:
When something makes you anxious enough that you don't want to look at it, that's often exactly when you should.
We live in an economy that rewards attention.
Provocation gets clicks. Outrage gets shares. Extreme statements attract audiences. Social media encourages people to publish thoughts that previous generations would have expressed privately and forgotten.
But attention and reputation are not the same thing.
Employers, universities, professional licensing boards, clients, colleagues, and future business partners may encounter something you posted years earlier.
And context disappears much faster than screenshots do.
Before publishing something provocative, ask yourself whether you're comfortable allowing a stranger five years from now to use that statement to decide what kind of person you are.
A friendship ends. A romantic relationship collapses. A colleague betrays you. Someone humiliates you.
At that moment, retaliation can feel irresistible.
But consider something that anger makes very difficult to appreciate:
Someone who occupies enormous emotional space in your life today may be almost irrelevant to you five years from now.
The consequences of what you do because of that person may not be.
A criminal charge, disciplinary record, lawsuit, destroyed professional relationship, or damaging online post can remain long after the person who provoked it has disappeared from your life.
Never give a temporary person permanent influence over your future.
Not every regrettable decision involves something you did.
Some involve what you didn't do.
People postpone starting businesses, applying for jobs, changing careers, writing books, traveling, returning to school, pursuing relationships, or acting on ideas because they're waiting to feel ready.
The problem is that confidence frequently comes after action, not before it.
You learn by beginning. You become comfortable by being uncomfortable. You develop confidence by surviving uncertainty.
Five years from now, you may regret trying something and failing.
But there's another kind of regret:
Never finding out what would have happened if you had tried.
This may be the quietest regret of all.
People choose careers because their parents approve. They pursue titles because colleagues admire them. They buy things because successful people are supposedly expected to own them. They remain on paths they dislike because changing direction would require explaining themselves.
The approval feels good.
But eventually, you have to live the life those decisions created.
A useful question is:
If nobody else ever knew about this decision, would I still make it?
If the answer changes when nobody is watching, pay attention to that.
Good judgment doesn't mean never making mistakes. Nobody achieves that.
It means learning to create enough distance between an emotion and a decision to see beyond the next five minutes, five hours, or five days.
When you're facing a consequential choice, ask yourself two questions:
How will I feel about this tonight?
Then:
How will I feel about this five years from now?
Those answers can be remarkably different.
And remember that the video at the beginning of this article includes additional decisions, examples, and practical tips beyond the ten discussed here.
If you've already made one of these mistakes, there is little value in spending the next five years punishing yourself for something you cannot change.
What matters now is the next decision.
Take responsibility where appropriate. Stop making the problem worse. Get good advice when the stakes are high. Repair what can be repaired. Learn what the experience is trying to teach you. Then move forward.
You cannot renegotiate a decision you made five years ago.
But the person you will be five years from now is being shaped by the decisions you're making today.
Choose accordingly.
Adam Lamparello is an attorney and the founder of Lamparello Law, Education, and Advocacy. This article is for general informational purposes and does not constitute legal advice.
© 2026 Adam Lamparello, Esq.
| View Our Disclaimer | Privacy Policy
Law Firm Website Design by The Modern Firm