Life & Work Skills

5 Reasons Why You Are Doubting Your Decisions (and Why It Has to Stop)


Last week I grabbed takeout with my friends from high school. As we huddled together on someone’s couch in our oversized sleep tees and face masks, we tearfully broached the subject of regrets. One by one, we talked about how we were too young to doubt our life trajectories, but how we often indulge ourselves by thinking about the ‘couldas, wouldas, and shouldas.’ I was surrounded by incredibly smart and successful women; each one with personalized career paths and incredible personalities. But the only thing we could talk about was what we lacked. One of my friends lamented the fact that she ‘should’ve moved out to NYC when she had the chance.’ Another complained about how she ‘could’ve dated Mr. Right, but now he’s with someone else, and it’s just too late.’ When my turn came around, I listed things off my list that I had been curating for as long as I can remember.

Days passed, and randomly when I was in line at Starbucks, I overheard a woman and her friend talking about how they felt like they made the wrong decision to go to law school, and I was taken back to that night with my friends. I began to wonder why we, as millennial women, doubt our personal decisions. After all, we are the ones who made them. After talking to a bunch of loved ones and conducting extensive emotional research, I’ve figured out the reasons why you doubt yourself, and why you desperately need to stop.


1. You’re living in the past, and that’s no way to live.

If you are doubting why you took a job offer, or if you moved out too early, or if you are regretting anything that you may have gotten yourself into, you are living in the past. It’s only human to wonder what would have happened if we got a chance to rewrite our stories, but you have to realize that hindsight bias is 20/20. Stay true to your decisions, because, at one point, you thought it was the best thing for yourself to do. Even though things may look different now, it’s impossible to go back and give yourself a heads up.


Why It Has To Stop

I don’t think anything amazing has happened from thinking too much about what ‘should have’ happened. If you ever get in a rut and start focusing on the past, start thinking to the future. Every single thing in life can change in a heart beat. In the wrong relationship? Fix it. In the wrong career? What steps do you need to take today to change that? Need to break up with a toxic friend that you decided to tolerate in the past? Cut them out. You have the power. Use it.



2. You’re expecting the worst to come… but it’s not on its way.

I used to think that I could prepare myself for anything just by thinking about it. I used to mull over my decisions just by outlining every single possible outcome. Whoops, I chose the wrong major, I guess I am going to be unemployed and unhappy for the next 20 years of my life. Uh-oh, I moved to the wrong city, guess I’m going to be friendless and alone until I move back home. Ugh, I picked the wrong apartment, guess I’m going to hate myself every morning during my 45 minute commute.

I only have one word for that pattern of thinking. Yikes.

Expecting the worst to come is like gearing up for failure. You are more than that. Why are you preparing to be unhappy if you haven’t even given yourself a chance to succeed?


The Solution

Give yourself a chance. You’re going to meet a lot of people that will convince you that happiness is impossible. Don’t be one of them. Don’t doubt the decisions that make you who you are because you are afraid of the future. Let things play out the way they are supposed to.



3. You’re underestimating yourself.

Remember when you made that big life decision? How you went through the pros and cons? How you stayed up at night thinking over the alternatives? How you put your heart and soul into making the right choice for yourself? You picked the right decision for yourself back then. You did what was right for you because you know that you were strong enough to deal with the consequences. Do not underestimate yourself now.


Why Underestimating Yourself Is Unhealthy

By doubting yourself, you are undercutting your ability to think for yourself, which can severely hurt your self esteem. Do yourself a favor, and be your own cheerleader. You made the right decision. Relax.



4. You’re comparing yourself to others, and it’s stealing your joy.

The easiest way to doubt even the best of decisions: comparison. I mean, raise your hand if you have ever talked to a friend who is living her ‘best life’ right now, and you immediately thought about how your life choices should have mirrored hers. It’s not fun to constantly compare yourself to your friends or peers, and ultimately it can make you miserable. You are your own person, with your own dreams, mind, and heart. Even though the grass may look greener on the other side, remember that you planted and watered your own, so it’s completely yours.


You’re a chronic compare-er. What should you do?

Remember that life is full of high and lows, and when you were living your ‘best’ life, someone was jealous of your decisions. Tell yourself you are just trying to figure it all out, and trust yourself. It will eventually work out.



5. You’re aren’t in the right place right now, and you aren’t accepting it.

Okay. Bad decisions happen. You end up turning a corner in life, and end up somewhere you thought you would never be. You aren’t in the right place, and you need to back track and get the heck out of whatever situation you got yourself into. But for some strange reason, instead of thinking ahead, you keep on hating yourself for being in this sucky situation. Feel familiar?

The thing about bad life decisions is that, if you recognize that you are in a situation that isn’t too great, you have to accept it. Then you have to move on. You have to get yourself to the place you want to be. You can’t dwell on the unhappiness or self-hate. You have to pick yourself off the floor and get yourself what you deserve.


How You Get Good At This

Practice acceptance of all your emotions, even the bad ones. It’s okay to feel like you didn’t make the best decision. It’s okay to feel unhappy. It’s okay to feel anxious about your future. Accept your emotions, and then think of the next best step. Remember that you need the negativity to value the positivity in your life.


Do you doubt your life decisions? How do you deal with comparison?