People have a difficult time letting go of the past because they are held back by unfinished business. They may regret choices they have made or feel guilty about past actions. As long as guilt and regret are not resolved, it is difficult to move forward.

The Regret Epidemic
Regret is an emotion that feels similar to depression or sadness. It also feels like guilt, but it isn’t the same thing. Sometimes a wave of regret seems to come out of nowhere. You might become aware of it when you lose something or someone, or when you meet someone from your past. It is a common feeling in our culture for several reasons.
1. We have too many choices.Since we have so many options, there are many more opportunities to regret the paths we didn’t take.
Example: When Linda was a senior at a major university, she interviewed with over 30 companies on campus. She was offered jobs in five different cities and had a difficult time choosing. In the end, she moved to Los Angeles and began an executive training program in a large company. A few years later, she began to wonder whether she had made the wrong choice. She thought she might have been better off in Kansas City, which had been her second choice. The regret leaves her feeling stuck and dissatisfied.
2. Endless possibilities.Another factor causing many of us to feel regret is that in the North American culture, there is a belief that life has no limits. Our culture has an insatiable appetite for new experiences, adventure, and newness. When faced with the reality that certain things will not work out or change, we find it hard to accept.
Example: Karen has turned 45. She has never married and has no children. She has always believed that “There is always tomorrow” and “I have plenty of time to make my mark.” But now, realizing that she may never be a mother and probably won’t be the CEO of her company, she is feeling like life has passed her by.
3. No rules.Along with all of these options, our lives have become confusing because there are few guidelines for what choices we should make.
Example: Most women who have children struggle with the choices of what role employment should play in their lives, and many women feel like they made the wrong choice. Options include staying home with the children, working full-time at a demanding profession, or choosing a less demanding or part-time job.
Example: Many people feel compelled to continue on the ladder of success as long as they are being rewarded for it. When work becomes demanding and is no longer fun, it is hard to turn down promotions and pay increases in favour of less demanding, more satisfying work. People feel locked in to their career tracks and don’t know how to get off the treadmill.
4. We value self-sufficiency.Our culture has always valued independence. Somehow, we all get the message that it is better if we achieve our goals on our own, without the help of anyone else. The problem is that when we cannot accept support from others, we become isolated. Living a completely self-sufficient life violates the basic human need for affiliation.
Example: Matt’s mother, Sarah, is 75. She is a widow and lives alone in an apartment in New York City. Matt left New York after finishing college and now lives in Florida. Sarah’s friends are gradually moving to Florida, too. Matt has urged Sarah to move to a nearby condominium, and has even taken her to see a few of them. She resists, saying that she doesn’t want to be a burden.
Meanwhile, Sarah is becoming increasingly isolated and depressed. She sits in her New York apartment and remembers the sunny condo she saw in Miami a few years back. She is filled with regret but won’t change her mind. She feels like she has no choice but to remain independent and self-sufficient.
5. Instant gratification.Many people escape the pressures of daily life through drugs and alcohol. There are messages everywhere suggesting that we use alcohol and drugs to relax, escape, have fun, and be sexy. When this becomes a lifestyle, it often results in consequences that one can only regret: drunk driving, accidents, death and injury, relationship problems, poor attendance at work, or being fired.
6. Constant comparisons.When we compare our lives with others, it’s easy to feel regret. Most of us expect ourselves to have it all together. We learn to act as if we are in control and compare ourselves with our friends, coworkers, neighbours, and the characters on television. When we don’t look as good as they do, we feel like failures. We have a list of “shoulds” inside our heads—things we expect ourselves to be able
to do.

Guilt
Guilt is usually the result of aggressive acts, wishes, and thoughts. It usually results from violating a rule—either our own or someone else’s.

What to Do about Unfinished Business
If you want to move past the things in the past that are keeping you stuck—your unfinished business—you will need to acknowledge them and tell the truth about them. You don’t necessarily have to take any action; sometimes just writing or talking about it is enough to lessen its impact. Or, there may be an action you can take to close the circle on this unfinished business.  You can write about it in a private journal or talk about it with a trusted friend or therapist. Try journalling about your feelings, what you would chance if you could, and what you think (or know) you need to do to gain the peace you’re looking for. Here are some places to look for your unfinished business:
1. Risks I should have taken
2. People I treated badly
3. People who treated me badly
4. Something I did to someone
5. Not doing something I should have done
6. Messes I need to clean up (literally and metaphorically)
7. Things I should throw away
8. Things I want to buy for my home
9. Things I want to buy for myself
10. Things I need but haven’t allowed myself to have
11. Projects I’ve started but have not finished
12. Projects I want to start
13. Things I want to change
14. Things I want to stop doing
15. Things I want to be
16. Things I want to have
17. Experiences I want to have
18. Things I want to say
19. Feelings I have not expressed
20. Secrets I don’t want to keep any longer

Suggested Reading
Dr. Arthur Freeman and Rose DeWolf, Woulda, Coulda, Shoulda: Overcoming Regrets, Mistakes, and Missed Opportunities.

You can also read a previous newsletter on How To Forgive Past Hurts.