I Make Decisions, Then Often Look Back and Regret Them

By Dr. Robert Wallace

October 27, 2026 7 min read

DR. WALLACE: I'm not making good decisions these days. I lack conviction on all of the decisions I do make after fretting over them, and I'm constantly tormented by the "what ifs" that spin through my mind quite regularly.

For example, I was looking for a part-time job and three job offers came in all within four days. This four-day window occurred after a month and a half of sending my resume everywhere I thought was feasible and having filled out 25 to 30 applications around my town.

Of the three offers, I felt two of them were the strongest, so I dismissed the third one. It was a hard decision, but I finally chose one over the other.

Now that I've been working at this job for over a month, I'm feeling pangs of regret that I didn't move forward with my second choice. I'm now seeing merits to the third choice that I dismissed so quickly. I need the money, so I'm sticking with this job for now, but I can't seem to get unstuck thinking about what might've been had I made a better or more appropriate decision for myself when I had the chance to do so.

I suffer from the same challenge when it comes to my dating life. I go for long stretches without any dates and then suddenly I have more than one opportunity all at once, but I can't bring myself to date multiple people simultaneously, so I have to make a choice. If that choice doesn't work out almost perfectly, I regret the fact I didn't select one of the other potential individuals to go out on a date with. How can I best deal with this quirk of mine going forward? — I Look Back a Lot, via email

I LOOK BACK A LOT: My advice is to do your best to change your perspective as much as you possibly can. Try to look at your situation as one of gaining valuable experience, rather than having to be perfect at every decision you make at the time you make it.

It's often said that hindsight has 20/20 vision. To some degree, that's true for almost all individuals in certain cases. Going forward from here, each time you feel you could've made a better decision in the first place, carefully review and think about what was in front of you at the time. Seek in hindsight to determine what influenced you to make the decision you made and consider how you could've made a different selection that might've been more appropriate for you.

Each successive experience is now actually helping you in various aspects of your life. Stick with it, focus on the process more than succumbing to the temptation to look back and pine for something possible for a fleeting moment, but has dissipated.

Regarding jobs, aim to find one that makes you happy and that you feel comfortable with the environment you're working in. Write down all of the things that you do not like about the job you're currently working at and strive to leverage that experience into your selection process going forward. Do your best to be enthusiastic about new unopened doors that are yet in front of you rather than worrying about ones that have closed behind you recently. There are many opportunities for all of us if we simply keep moving forward, learning from experience and keeping our eyes and ears wide open.

I APPRECIATE HIS SUCCESS BUT DON'T WANT TO FOLLOW HIS FORMULA

DR. WALLACE: I'm a guy and a busy college student in my sophomore year at my university. I have a lot going on in my life socially and with my studies, plus a part-time job I'm holding down as well.

I have a really fun cousin who lives two states away from our family, but he and his parents come to visit our home a few times a year, usually over a long weekend. He's my age and also a college student, but he's quite the entrepreneur, as he has an Internet-based business already up and running.

The basis of his business is that he finds various items at garage sales, antique stores, discount stores or anywhere he can locate them. He then polishes them or fixes them up, takes pictures and resells them on his website. I made the mistake the last time he visited by asking him in detail how he does his business.

Now he's not only trying to get me to start one in a similar manner to the one he has up and running, but he's told me if that becomes too much, I can simply source items for him from our town and ship them to him. The truth is, even though he's quite successful, it's not something I really want to dive into right now.

He's always going on and on telling me about how much income he makes, how he finds "untamed" gems of products, or items that look ugly, but that he can "peel back" to look much better, so that they will sell at a nice profit. I think he mistook my original curiosity as an invitation for him to teach me the "ropes" of this genre of business right away.

We've always gotten along great together, so I don't want to damage the family friendship I have with him, but I don't have the time, energy or interest in getting involved in his business in any way at this point. How can I delicately let him know this in a way that won't put our friendship on the skids? — His Reselling Isn't Jelling With Me, via email

HIS RESELLING ISN'T JELLING WITH ME: Simply compliment him! Tell him that you are amazed at how talented he is with his business ventures and how much you realize what he does works so well for him.

Let him know that you're extremely busy in your own life these days and that you definitely know you wouldn't have enough time to be a reliable enough partner for him, so you feel it's best to let him know that upfront so he won't be disappointed that you don't engage in this venture.

Then immediately ask him if it would be all right if you ever needed any business or career advice from him at some point in the future. Changing the subject in this manner and requesting his help and guidance should play directly to his personality and the way he looks at things, especially when business is involved. End by saying that you're glad that the two of you are relatives, because it gives you hope for yourself that you'll be successful in whatever venture you eventually discover as your career path down the road.

Sometimes intentionally using this type of self-effacing perspective can help you smooth the wrinkles out of a difficult situation quite diplomatically.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected]. To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

Photo credit: Jan Kop?iva at Unsplash

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