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6 Critical Questions to Ask Before You Screw Up Your Life (or Feel Like You Have)

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You know that old adage, “Hindsight is 20/20”? 

If you’ve ever made a decision which you later regretted, you’ll deeply understand what this means (and may have heard it from more than a few well-meaning people). Faced with the result of a bad choice, you likely grumbled, “If I’d only known then what I know now, I’d never have done it!”

It’s an awful feeling to find yourself living the consequences of bad decisions. Wouldn’t it be nice if you could avoid making decisions you later regret? Or have 20/20 vision now to make decisions that improve your life, instead of screw it up and wear you out? 

As we head into this, let me just say: I don’t feel like (generally) you can totally screw up your life (but you can certainly feel like you have). Experiences happen for a reason, and often we learn lessons that are necessary for a better life from even the worst experiences. However, using these questions to evaluate any decision you are pondering might give you a level of awareness that allows you to learn the lesson without having to actually go through the bad experience, and that’s enlightenment I can really get behind.

If you stop and evaluate any decision you face with these six powerful questions, you can start making decisions that you’ll love: 

1. Would I be doing this out of obligation or guilt? 

If you were raised by parents that used guilt to get you to bend to their wills (or if you went to a religious school or attended a conservative church), it’s likely you’re susceptible to agreeing to things you would not otherwise agree to due to the overwhelmingly awful feeling of guilt or obligation. 

Take a moment to think about how many times you’ve done something out of guilt or obligation. Did you enjoy the experience? Or did you regret your decision and beat yourself up for your lack of willpower, all while suffering through until it was over?

Agreeing to any experience due to a sense of obligation or guilt takes valuable time and energy from experiences that are good for you and rarely ends well. Whether it’s as minor as deciding whether you have dinner with an old friend who wears you out or as major as mulling over whether you should end an unhappy engagement, recognize guilt and obligation for what it is, disengage from it, and listen to your gut instinct on what is best for you. 

2. Do I enjoy being with this person (or people)? 

There is almost nothing worse than hanging out with someone whose company you don’t enjoy or whose values are dramatically different from yours. It’s even worse if the person is highly critical of you, either overtly or passive-aggressively. It’s worse yet if the person undermines you and your goals.

The exhaustion you feel after dealing with such a person takes away vitality from you and depletes your ability to put time and effort into good things in your life. After all, when you’ve been with someone who wears you out, are you feeling energized to keep on with your goals? Or do you just want to take a nap? 

I think you know which it is. 

Make a list of people in your life. Notice how you feel after being with each person. Are you energized, happy, and feel valued? Or do you feel drained, worn out, and ignored? 

If it’s the latter, dial back (or eliminate) time spent with that person. Life is too short to be with people that wear you down.

3. Am I just forcing this being the right thing, even though it feels wrong? 

A friend of mine really, really wanted to be married. Every relationship was heading to that goal, whether or not the guy would make her happy in the long run. She finally got her wish and married a guy that was clearly not a good person and didn’t love her like he should. Fast forward five years: She ended up in an ugly divorce which left her financially and emotionally depleted.

My husband was offered a promotion at work which would require a move to a place where we had both said we would never, ever want to live. Somehow we talked ourselves into that move—after all, it was the next logical step in my husband’s career and it was a nice pay increase—and it was the most miserable year of our lives.

Sometimes the desire to attain a goal over-rides our intuition that the current experience isn’t the right one. It’s easy to do, especially if you are really trying to grow your business, take that next step in your career, or meet a big life goal. When an opportunity presents itself, it’s tempting to talk yourself into it, even if your gut is telling you that something is not right. 

If you have that situation presenting itself to you, it’s a good idea to write out what you are feeling about the opportunity and why you think you need to move forward. List what you truly want in the situation, then look to see if this opportunity matches with those desires. If the lists do not sync up, then you know that this is not a step forward you want to take. 

Look for the right thing—the one that truly matches your highest goals and desires on all levels—not the thing that only checks off the box on your goal list. 

4. Am I afraid of looking stupid if I don’t go forward? 

We’ve all done it; we announce to the world some grand plans to start a business, lose weight, write a book, or have a kid, and then realize that it might not be what we really want. For most of us, the fear of losing face with all those people is so overwhelming that we stick with the plan for way longer than we should. We end up miserable, worn out, and sometimes even broke. 

So what if your dad will knowingly tell you “I told you so!” when you announce that you’re not marrying that guy he always hated? Who cares if your friends will laugh at you when you say you’re walking away from a business that’s draining you on every level? Your happiness and health are more important than other’s opinions, and, at the end of the day, staying connected to something that’s not truly right for you keeps you from being able to take advantage of the right thing when it shows up.

If your motivation for staying the course is worry over other’s judgement of you, that’s a big red flag that it’s time to throw caution to the wind and decide a different path.

And the next time you have a big dream or goal, only share it with people who will support and love you whether or not you accomplish said goal. Anything else is self-abuse.

5. Am I afraid of looking stupid if I DO go forward? 

Contemplating quitting your day job and taking an internship in your dream field? Thinking about adopting a baby as a single parent? Mulling over going fully mobile and traveling the world?

There is no human who has ever existed that made a great step forward for mankind (or just themselves) that wasn’t criticized, laughed at, or targeted. What if Einstein had given up because one of his teachers said he’d never get anywhere? What if Gandhi hadn’t begun a peaceful movement 

Do yourself a favor: If you want to go forward on an unconventional plan that’s calling to you from deep in your soul, go for it. The more people who make fun of you or tell you that you’re crazy, the more likely it is that you’re on a path to something really awesome. 

6. Is it just that I hate quitting? 

Many of us have been taught that “quitters never win,” which causes a great amount of incentive for people to stay in situations way longer than they ever should. This is never more apparent than when you’ve realized that a prior decision was a bad decision, but now you fear letting go because you “shouldn’t quit.”

Don’t do it. I know you might have put a ridiculous amount of hours into a new business or spent endless hours writing that novel you know you have in you, but if there is a point when you are no longer passionate about going forward or it’s taking a serious toll on you or your life, it’s time to walk away. 

I can tell you of at least 3 different times in my life when I KNEW that I should walk away from a project, but kept trying to make lemons out of some seriously sour lemonade. In one case, I had put two years of my life and passion into a start-up that I truly believed could make a huge difference in the world, but knew that the president of the company was a hot mess and could not be trusted. But, I believed so strongly in our mission that I doubled-down and worked even harder, thinking that I could somehow bypass her and pull this off. I also didn’t want to let down my co-workers, who also had put a lot of passion and time into this. I really thought a handful of us could somehow pull this off. I just did NOT want to quit on something this important. Needless to say, one of my greatest regrets is not walking away earlier. 

If you feel like you HAVE to stay with a certain project because you don’t want to let others down, or that you’ve put a crazy amount of time/love/creativity in and are having a hard time letting go, just ask yourself: “How is staying with this project depleting me? How is staying with this causing me stress? If I was able to let go, what might improve in my life? Why do I think I cannot quit?”

I also love a practice from a favorite author and inspiration of mine, Tim Ferris. He suggests that, when looking at a situation like this, to do a “fear-setting exercise.” To do this, imagine quitting the experience/job/relationship/whatever, and go to the absolute worst case scenario. So, for ending a bad engagement, it might be, “I’ll end this relationship and all our friends will hate me. I’ll lose the money I have put down on the wedding venue, because it’s too close to the marriage. Everyone will think badly of me because I did this. I will be alone for the rest of my life and die alone.” That’s certainly pretty grim. Then, on a scale of 1 - 10, rate how likely that scenario is. In this case, it might be a 3 or 4, at best. Next, think through the best-case scenario. “I will finally be free of a miserable relationship and will stop feeling stressed all the time. I will be able to do fun things I like to do just for me, and I will learn to love alone time. When I am ready, I will find a wonderful person who will be my soulmate, and we will love and support each other for the rest of our lives.” Rate how likely that scenario might be; in this case, it’s probably a strong 8 - 9. Then, rate how much better you would feel overall if you did this. If the worst case scenario is a lot less likely than the best case scenario and you’d feel lots better moving toward the better scenario, then it’s a great indication that you should make that move. 

If you realize that you are freaking miserable staying with the current experience, opportunity, or person, then let it go. You aren’t quitting; you are making a decision to let something go that isn’t for your best, and that’s very different energy. 

I can tell you from experience that when you are able to do this, you’ll be amazed at how much stress and worry releases from you. You’ll feel alive and unburdened, and that’s pretty great. 

Best of all, when you use these 6 critical questions to help you make good decisions about your life and your time, you’ll avoid experiences you’ll later regret and have more energy for you and for all the positive experiences in your life.

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