Letting Go of the “Should Haves”

Letting Go of the “Should Haves”

There comes a point in life where you have to find a way to move forward, especially when you are a student mother. Starting over is hard, but holding onto the past will not make it any easier. Leaving the should haves behind, and moving forward will be a breath of fresh air.

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I should have done this, I should have done that. The dreaded “should haves.” We’ve all been there, right?

There comes a point in your life where you sit there and you think, “Wow, I wanted to do so much more by now. Where did I go wrong? Do I still have time to achieve these things?”

We all will have regrets in life, but some of these we should learn to let go of and move forward. If for nothing other than the sake of our sanity. I’ve been there, multiple times actually. I’ve always been a BIG dreamer. To be completely honest, my childhood dream job was to be a NASCAR driver, haha. Crazy dream for a little girl, I know.

Letting go of your regrets is not an easy task, but once you do you'll be able to live your life.

Time gets the best of us, life throws us for a loop, regularly.

But it’s okay to be in the position.

That position is where you might find that you can still get to those crazy dreams and reach them. It just may not have been in the timeline you had first imagined. When it comes down to it, there are some major “should haves” that we all face, but if we learn to release them, we can reduce our stress levels drastically.

We all should have done something different at this point in life, but it's important to embrace the mistakes and forgive ourselves. Let it go and move away from regret.
  • “I should have saved more by now.”

The truth is, if we went through life knowing how to avoid all the pitfalls of saving money and what we could do with all of the money we “could have” saved, we wouldn’t learn the strength it takes to make ends meet and have pride in what we are able to accomplish in life’s lowest points.

I actually sat down one day and calculated how much I could have saved between the ages of 16 and 21 years old if I had only saved $100 a week out of my part-time job income. It was a lot, to say the least. I couldn’t have purchased a house with a pretty decent down payment, AT 21 YEARS OLD! Yeah, that’s upsetting.

Here’s what I calculated. And I didn’t mention that I started working at age 12, so the number could’ve been MUCH higher.

I got my first part-time job exactly one week after my 16th birthday. So we’ll say that 259 paychecks (counting the waiting week when you first start working) are what I received between that day and my 21st birthday.

At $100 per week, I could have had a savings account with $25,900.

  • “I should have bought a house first.”

Maybe you should have, maybe I should have. But we didn’t. That doesn’t mean it cannot happen. My goal was to buy a house by the time I was 30. I’m not there yet, but the 3-year timeline is not going to fit my current situation. I have recently come to terms with this and have given myself 5 years to get everything (from career to savings, to credit scores) straightened out so that I CAN buy a house. And I’ll only be 2 years behind schedule.


  • “I should have waited to start a family.”

It’d probably be an easy guarantee that many of us did not plan to start a family when we did. I don’t think you would be reading this if your life followed your “life plan.”

My son was born 7 1/2 years ago, making me a mother at the age of 19. Motherhood is amazing, but it sucks at the same time.

I know that there are certain things that I will not be able to give my boys because I had them so young. Stability is a major factor in this should have for me.

Stability is crucial for children. But our sanity as parents is even more important. If we drive ourselves nuts with all of the things we wish we could have put off in our past, our sanity no longer exists. Children are much more understanding and aware than we, as parents, give them credit for.

To be brutally honest, I had to move in with family for a couple of years recently. It was the hardest decision of my life, but I made that decision so that my family could be in a better financial position to give my kids the stability that they deserve. Just know that it is definitely okay to have to take a few steps back in order to move forward. Life does, in fact, go on, and you can make it work. You just have to be willing to work.

  • “We should have gotten married first.”

My boyfriend and I (yes, I said boyfriend) have been together for going on 9 years. Our anniversary is in August. We have had so many amazing times together, but also some very tough times. I couldn’t have asked for a better person to share my life with, or for a better father for my littles.

That isn’t to say that we haven’t had our issues. For some, these issues would have been the end of the relationship. But we were lucky enough to stay strong throughout relationship struggles. Even if you’re in the middle of a relationship struggle, help is available to you.

But with that said, I do wish we would have gotten married before having children. Signing forms for school and having to write out both of our last names is not fun. I would have loved the chance to be Mrs. before my kids were born. But hey, now I get to have these awesome little gentlemen in my wedding when the day comes.

You can plan and plan your life, but if you only count on that plan for your life happiness you will be disappointed. Having a tentative plan is a much better idea, this way you can make adjustments as things change and unexpected things happen.

  • “I should be further in my career by now.”

This is a HUGE should have for me. Huge. I have been a college student for 9 years. Yeah, you read that right, 9 years. I have accomplished one Associates degree in that timeframe. Although I’m sure I have enough credits to have way more than that.

You see, I had no idea that the career I started going to school with would be something I would let go of. I started college as an Interior Design major. Moving from there, I’ve gone to school for Medical Office Management and also Psychology. It wasn’t until I got to my Psychology program, 3 years ago, that I found my true passion for life. There’s a major reason for this passion that I will cover in another post.

I still, from time-to-time, look back and wish that someone would have stopped me from pursuing those majors. After way too much debt, and now a great deal of frustration, I have never been more motivated to continue my career as a student. I’m pretty sure you could call me a professional student at this point, haha. But that’s okay, the whole time I have been pursuing my love for knowledge, and I have learned to do so many things that maybe one day will come into play.

  • “I shouldn’t have taken so many student loans.”

Student loans, as any student mom knows, are a burden and a blessing all in the same token. To date, I have racked up over $50k in student loans. This is one of my biggest life regrets. And to think I’m only 26. Coming to terms with that debt, and acknowledging the fact that I made the choice to carry that debt, has been a real eye-opener.

Had it not been for my excessive debt, I wouldn’t want to provide a college education to my littles as much as I do now. Giving them an educational foundation would not mean as much to me if I didn’t put myself through this.

Student debt is almost a necessity in this day and age, and I’m sure many of you will agree. But when we’re done with this role in life, we will be thankful that we took those loans and gained the knowledge that we gained. It won’t be easy, but letting go of the regret from your loan debt will allow you to focus on your education and your family much more.

If you’re looking for scholarship opportunities you should check out my posts:

These are just to name a few that I have crossed in my short lifespan. This is by no means a comprehensive or scientifically created list. These are just some of the things that, when it comes down to the bottom line, I felt so much better after I learned to move past the “should haves” and onto the “I still can.”


Have any “should haves” that I didn’t cover on this list? What about any suggestions for coming to terms with your regrets in life? I’d love to hear your feedback in the comments below.


Don't hold on to the things you can't change. Let go of regret and live again.

11 thoughts on “Letting Go of the “Should Haves””

  • “Motherhood is amazing, but it sucks at the same time” I can totally relate to that sentiment. There is so much I have put off to raise our 3 kids. This year I was determined to make a change and got myself back into college. I am so much happier now that I have something to work toward. Great post! I will be back soon! 🙂

    • That is so awesome! It’s not easy tackling college as a parent but it’s so worth it. I love that my kids see the value in education through my own efforts. I think that is the biggest motivator for me at the moment.

  • Hats off to you Mama for raising your baby at 19, I found motherhood tough when I started at 27. I think ‘should have’ thoughts are completely natural though especially being a parent as you want the best for your family! I often think I should have saved my money instead of buying clothes, make up etc etc . I wish you all the best with your studies, soon enough you’ll be paying those loans off and enjoying your career ⭐️


    • It definitely wasn’t easy at 19. Although I had grown up well before my time so it made it easier. I had a good job and my own apartment and everything so that helped a lot. But saving money is something I am still consistently working on.

  • Wow, should haves…I guess the biggest really is buying a house. I am now 55 and rent, and house prices are way more than I can ever achieve, but it wasn’t really always like that, I just took the easy option. My bad.

    • It happens. I have to make a conscious choice to move past these regrets on a regular basis. But the fact that I am aware of them makes this task somewhat easier. Buying a house is no longer easy, credit takes more time to build and it just isn’t a great time to be buying if you compare to the previous housing markets.

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