Manual Just the Right Amount of Regret

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And the only thing people regret is that they didn't live boldly enough, that “I've got a bad case of the am guilts - you know, when you lie in bed awake and replay all those things you didn't do right? Pittacus Lore, I Am Number Four.
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Chester See - A Life Of Regrets Lyrics

It's tough. There are always worries. I'll make it up with the family this weekend. Days turn to months and then years and then decades. Believe it or not, a lot of our biggest regrets in life have to do with things that happened to us in grade 4 or some other early age.

We were too scared. And by the way most of us have also met up with a bully in our work life. Maybe he was our boss.

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We remember that one time we wish we'd told him off - even if it cost us our job. We usually take some small solace in hearing that that bully later on made some unfortunate career stumble. There's usually one childhood or high school friend who we were best buddies with. Then, one of us moved away. We might have stayed in touch at first but then got busy.


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Sometimes, we thought to pick up the phone, but maybe we don't have their number or email any more. We always wonder what it would be like to sit down with them again for a coffee. We sleep with it next to us. We know constantly checking email and Twitter in the evenings and on weekends takes us away from quality time with family and friends. Romance is a big area of regret for most of us. Maybe we dumped someone that we wish we hadn't. Most play a never-ending game of "what might have been" for the rest of their lives.

It is tough to simply be happy with the love that you've found and takes away from the special moments you have today, if you're constantly thinking back to what you once had -- which actually might not have been half as good as we think it was. Most of us place way too much importance on what other people around us think about us.

How will they judge us? In the moment, we think their opinions are crucial to our future success and happiness. On our death beds, none of that matters. Related to the previous point, a big regret for most of us is questioning why we had such little confidence in ourselves. Why did we allow the concerns of others to weigh so heavy on us instead of trusting our own beliefs? Maybe we didn't think we were worth having what we wanted.

Maybe we just thought poorly of ourselves. Later on, we wish we could have been more self-confident. Related to that lack of confidence, a lot of us get sucked into living the life that we think a good son or daughter should live. Whether because we're explicitly told or just because we unconsciously adopt it, we make key life choices - about where to go to school, what to study, and where to work -- because we think it's what will make our parents happy. Our happiness is derived through their happiness - or so we think.

A panic can start to set in. Whose life am I living any way? Maybe we didn't apply for that job we always wanted to because of a child, or because our spouse didn't want to move cities. It might not have been the perfect job for us, but we always regret not trying out for it. Do you think Katie Couric regrets giving the nightly news gig a shot? No way. Seems strange to say, but most of us don't know how to have fun.

We're way too serious. We don't find the humor in life. We don't joke around.

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We don't think we're funny. So, we go through life very serious. We miss out on half or maybe all the fun in life that way. Do something a little silly today. Do a little dance. You'll probably smile, on the inside if not the outside. Now keep doing that, day after day.


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Most folks stay close to home. Yet, big trips with friends and family - to Disney World, to Paris, or even to the lake - are the stuff that memories are made of later in life. We're all thrown in to some new unfamiliar situation together. We've got to figure it out as a group - and it's fun, even when it rains. We really remember trips. Back to romance now. If you ask these folks, they'll tell you that it was for the best. And, of course, there are some marriages that shouldn't go on and where divorce is the best for all parties involved. However, if you talk to many people privately, they'll tell you they regret their marriage breaking up.

It's never just one thing that ends a marriage - even if that one thing is infidelity.

The 25 Biggest Regrets In Life. What Are Yours?

The regrets most of us have is that we didn't correct some or most of those "little things" along the way. We can't control our spouse but we can control our actions and we know - deep down - we could have done more.

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Kids love their parents, but they love doing stuff with their parents even more. And it doesn't have to be a vacation at the Four Seasons. It could be raking leaves, learning how to throw a football, or cleaning up a play room together. I know family members that haven't talked to a brother or sister for 30 years.

One's in bad health and will probably die soon. But neither he nor the other brother will make an effort. They've both written each other off. And there's blame on both sides - although I take one's side more. But these were two guys that were inseparable as kids. Now, neither one will make a move to improve things because they think they've tried and the other one is too stubborn. They think they've done all they can and washed their hands of the relationship.

When You Want to Live Without Regrets

A lot of times, we override that voice. We do a matrix before taking that job and figure out a way to prove to ourselves that, analytically, this makes sense. We can forgive ourselves that we didn't screw up enough courage to ask that boy or girl out on a date or to the prom. But that doesn't mean that we still won't think about it decades later. Sometimes people regret seeing someone famous or well-known in real life and not going up to them and telling them how much they inspired them in our lives.