Seven Questions That Will Prevent Regret

By Alex Shalman

September 26, 2008   •   Fact checked by Dumb Little Man


One of the most fundamental and most difficult things that many of us have to do is to make a decision. It only takes a yes, or a no, to change the entire course of our lives. I’ve recently had to make a decision that put my relationship with my family, my girlfriend, and myself on the line — there were some questions I had to ask myself.

“I would much rather have regrets about not doing what people said, than regretting not doing what my heart led me to and wondering what life had been like if I’d just been myself.” – Brittany Renée

I recently made a decision to move to Israel for a year of learning about Judaism. My family is not very religious, and you can say they’re ‘afraid’ that I will be. Their fears aren’t rational, but they’re real, so their consequences on their emotions and stress levels are real as well.

They used a few justifications as to why I should stay:

  • I won’t be able to get to Dental School interviews from over there.
  • My girlfriend won’t wait 9 months, and won’t like the new me.
  • They assume I will completely change, and not be myself after the trip.
  • I’m upsetting my parents too much.

As you can tell, these fears are in my life as challenges so that I can over come them and be stronger than I was before. As Brittany Renée says, I’d rather follow my heart than someone else’s. Despite that quote, I’d still rather not live my life with regret and so I used a little exercise that helps me to eliminate all thoughts of regret from my life.

The Ten Year Dream
When you go to bed tonight, I’d like you to try something on. Get ready, brush your teeth, and snuggle up just as you would. However, instead of entering a normal dream sequence, you’re going to have a dream where you will meet your future self. You’ll go for a walk in your neighborhood, and you’ll discuss all the major events that had transpired in your life over the next 10 years.

Your future self is going to be quite ready and willing to fill you in on the joys, sadness’s, and major milestones that had passed for him, and are in store for you. This future self will share with you his regrets and plead with you not to make the same bad decisions again.

If you could do 10 years over again, would you? It might not be realistic to go back in time and do ten years over again, but it’s possible to prevent regret from occurring in the next 10. I know you’re not going to really meet your future self, but you can pretend you did. You can know some of the things that will happen because if you keep doing the same things you are doing now, you will keep getting the same results.

Seven Questions That Will Prevent Your Regret
Say that dream sequence with your future self happened. Would you follow your own advice to make sure the next 10, 20, or 30 years of your life were void of stupid mistakes? Ask yourself these seven questions and see if you’re willing to make the decisions that will prevent that regret.

  1. Would you make sure you exercised every single day?
  2. Would you read more books and expand your mind?
  3. Would you floss your teeth, and take care of your gums?
  4. Would you let go of a friend or end a relationship?
  5. Would you change jobs, or go back to school?
  6. Would you say I love you more to your parents or children?
  7. Would you settle for a good life when you know you can have an extraordinary one?

In the case with my family, and moving away to Israel, I think question number seven was the most instrumental. I already have a really good life, surrounded by people I love, I’m healthy, I’m going for an exciting career, and I have a popular personal development blog where I get to share my soul with the world. I’m good, however, I’m convinced that I was built for extraordinary, not good, so there are certain sacrifices I will make and challenges I will overcome in order to get there.

If only. Those must be the two saddest words in the world.“~Mercedes Lackey


Alex Shalman

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