Shoulda, Coulda, Woulda

Guest Blogger:

Jessica Walker

Financial Services

New York Life 


Image of a hand holding a clock

I’ve said it. You’ve said it. We’ve ALL said it at one point or another. 

“I shoulda done that differently, that way I wouldn’t have ________” 

“I coulda been this, if I’d only done __________” 

“I woulda been amazing at that, if I’d only_______” 

Sound familiar? 

Hearing it out loud makes me shudder. I’m not even kidding. Along with “it’s not fair,” these  phrases are the ones that make me break out in annoyed sweats. They are curse words in my  house. There is something so final about them. So definitive. And what’s even worse, the victim  mentality that accompanies it. Maybe I’m overshooting here but think about it this way; These  statements indicate that somehow you had less than, and because of that, you have been  slighted. Do you hear it, too? 

These ugly little phrases can hold us back and give us a license to accept things the way they  are. At the end of the day, they provide such a massive disservice to those that are looking for  growth, both personally and professionally.

Though I beat up the sentiment, in my heart of  hearts I know that what is MEANT to be said is, “If I only knew then what I know now, I would  have made a better choice.”  

Now, that didn’t seem to carry the same connotation, did it?? There’s real promise there! Let’s dive in a little more, shall we? 

Working in finance, one of the “shoulda’s” I hear the most is related to saving and planning,  specifically the lack thereof.

Now I may be bolder than most, but my response to this is always,  “you’re right, the best time to have started with your planning WAS 20 years ago, but the  second-best time is right now.” Taking a step in a forward direction, even a small one, is a  positive move. It’s to be celebrated. Who cares what’s in the past! If anything, it’s made you  aware just how important it is to start making changes now because you know how fast time  goes.

Perhaps you would have made different choices 20 years ago that weren’t as wise as you  would today. I’ve seen it happen. People make bad investment choices being young, arrogant,  and naive, which have yielded less than exciting results. I’ve also seen others that started later  in the game, but time and experience have taught them the pitfalls to avoid, and to seek wise  council from professionals. All of this to say, your decisions have placed you right where you are  today, good, or bad. Own them and move forward. No room for “shoulda”. Try this instead…

“I WILL start my investments today, because I know that doing so will get me closer to where I  want to be in retirement.” 

Ahh, feels good, right!? 

Coulda. Ugh. The pitiful one of the bunch, if you ask me. 

I once heard someone that I love say,  

“I coulda gone to art school if I hadn’t had to work so much.”  

Me: “Well, you aren’t working now. Go to art school.” 

“I’m too old now.” 

Me: “Well, you’re not dead.”  

They still aren’t in art school.  

This is the one that has the “Debbie Downer” feel to it. It reeks of victim mentality. It’s saying  that time has somehow plotted against you, and situations out of your control have prevented  you from accomplishing greatness. Come on, now! We could go into a whole thing on this but  the fact is, if you have a pulse, you can move toward your desired future.

There is nothing you  COULDN’T do if you truly wanted to. We’ve all seen people push past all kinds of roadblocks to  achieve their dreams. My word, I had an 89-year-old man pass me up in a 10k like I was  walking! Don’t tell me he was too old! He was determined, had stamina, and he put in the  work! Time stands still for no one. This should light a fire in you to move and fight and  persevere. This is the wisdom we see in stories of people knocking off their bucket list, item  after item, when they get a terminal health diagnosis. They aren’t leaving any “coulda’s” on the  table. They know the secret. 

“Because I know that I truly want to be an artist, and I don’t have to work right now, I could  finally sign up for that art class.” Atta, girl! 

Last but not least…. “woulda”.

This is all about what was, or better yet, what is still to be. If you  had it all to do over again, THIS is how you would have done it. That’s at least showing  reflection, and honestly, I can get behind that!  

So, here’s my challenge to you. Take the “wouldas” of your life and make them learning  opportunities. Do things differently NOW, sharpen your skills, grow, and be better, because you  CAN. 

The Bible tells us that the power of life and death is in the tongue. Our words shape our worlds.  What are you saying to yourself? 

Rephrase the couldas, shouldas, and wouldas with “I CAN, I  SHOULD, and I WILL.” Speak life and watch what happens! The possibilities are endless!