If You Could Rewind, What Would You Do Over?

Back to the Future Time Machine A few weeks ago, I wrote a post where I shared my biggest financial mistakes and asked all of you to share yours. When I began the post, I prefaced it by stating I wouldn’t change too many things–mainly because of the immense learning experiences all of my mistakes have afforded me (plus, I do live with no regrets).

But after thinking about this more, I realized that if life had a rewind button (could you imagine?!), there are some things I’d definitely do over again–both financially and personally.

If Life had a Rewind Button…

I’d avoid digging myself into credit card debt

Yes, I had a massive amount of credit card debt and yes, I paid it off years ago and haven’t looked back since. While I’m happy to have cleaned up that part of my finances at a relatively young age, I can’t help but wonder what I could have in the bank had I not been so careless with my money.

I remember going to the ATM with a friend in college. After he withdrew his money, for whatever reason he asked me to hold it and the receipt (details are fuzzy at this point). I’ll admit that I did look at his total balance on the receipt, and I remember feeling as if somebody punched me in the stomach. I don’t remember the exact amount but it was upwards of tens of thousands of dollars. I think at the time I might have had $100 to my name. If only that would have been enough of a kick in the pants to get myself on track earlier!

I’d make an effort to network more

I’m a horrible networker, but I’m an absolute people person–how’s that for an oxymoron?! Instead of hiding in the shadows at functions or standing quietly on the sidelines, I’d push myself to introduce myself to more people and learn how to network as early as possible. I’m learning now more than ever that you truly are your network when it comes to your professional life.

I’d educate myself about personal finance at a much earlier age

I essentially had no positive financial role models when growing up. Sure, I was given a modest allowance ($5 or less) when my parents could afford it, but that was for doing laundry for 6 people, cleaning the whole house and getting my little sisters ready for school in the morning. I earned every penny of that and then some.

But I remember my mom making a few poor choices when it came to money, and I think some of those stayed with me for far too long (one poignant example is her announcing one day that she didn’t care if she had the money and proceeding to spend hundreds on my little sisters at the Disney Store for new school clothes. This story should be continued at another point, but I have to decide how much I’m willing to share in such a public way).

I’d rebuild burnt bridges

As I said above, I’m a people person. But I’ve also been through some extremely difficult experiences that have somewhat hardened me when it comes to truly letting in other people and trusting new friends. I’d love to rewind and not make some of the mistakes I’ve made in the past when I had a wall bigger than the Great Wall of China built around me.

I’d teach myself that material objects charged today aren’t worth the finance charges and missed savings tomorrow

This is a huge one–for far too long I defined my self-worth in terms of how many courses I could take, how many jobs I could work and how many material objects I could amass. I filled voids and reduced stress by shopping instead of dealing with the problem head-on. Thankfully I’ve changed my super consumer ways, but I wouldn’t mind the opportunity to rewind and not buy all that crap!

I’d tell my family I love them more

Recent struggles and not so good surprises have reminded me that life is fragile and your family is your rock. No matter how messed up our families may be, there’s usually at least some members of it who will stick by our sides through thick and thin.

I’d like to rewind and tell all of the family members I’ve lost how much I love them and how much they mean to me. While I can’t reverse time, I can absolutely get better about telling the ones who are still here with us just how valued they truly are.

I’d start saving for retirement earlier

I was recently talking to a younger friend about money, and I was floored (yet very proud!) to hear how she’s socking away crazy amounts of money in her retirement accounts and has done so since she was 23 (!!!). I started saving a wee bit at 25 and really focused my efforts at 26, but I can’t discount the earning power I lost by not starting at 22 or 23…

I’d forgive myself (and others) faster and more often

This will always be a work in progress, but I’d like to rewind and not be so hard on myself. I’d also like to not have such crazy high standards for some of the people in my life. It’s a balancing act and one that I’m getting better at, but I could certainly do some things differently if I was ever given the chance to drive my little time machine back a few years…  :)

But the reality is that life has no rewinds…

All this said, I of course know that life has no rewind button no matter how much I might want one from time to time. It’s all a matter of coulda, woulda, shoulda at some point but there are always opportunities to learn from your mistakes, stop repeating them and replace them with much better habits. You just have to be willing to process what’s happened and put in the hard work to make those necessary changes.


What would you do over if you could rewind?


Photo credit: AdamL212

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Freelancer; reformed spendaholic; risk taker; adventure seeker; world traveler; rose smeller; debt destroyer. My mission is to inspire others to live a healthy, balanced life one cent at a time.


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  1. great post! I think if I could rewind I would reconsider college. it was nice and fun but on a daily basis I don't use my 5 years degree and probably would be at the same point or better if I had started working right out of high school.
    My recent post Buy my method, not my lifestyle

  2. I'm not really sure what I would do differently. Mostly because in order to things differently I would have to have had a different background. Which means my parents should have done things differently.

    Probably enjoyed college more. It's a once in a lifetime opportunity, and I think I worked more than played.

  3. I wouldn't have left the job I had throughout university. The position was a student position, working in the Academic Support office. I worked there for 4 years, 20 hours/week. After 4 years, the programs I was running (and others in our office) were doing so well that they restructured the whole system on campus. My position was changed into a full-time position, with several added responsibilities. Because I (foolishly) decided to take an extra year of school and remain a student for another year, I walked away from a pretty much *guaranteed* position, with a university. DUMB DUMB DUMB!
    I ended up pursuing a career that had a little to do with that position, but more to do with my major (theatre). And now that' I've been working in theater for 4 years, I realize what a huge mistake I made, and I'm trying to get back into academic support instead.
    My recent post So, I Guess I’m Doing This Thing!

    • Oh man…I'm sorry to hear this! I've had my part-time job at a local university for almost 7 years, so I understand where you're coming from with this. Good luck with your search—I hope it works out for you!

      • It's kinda funny that it wasn't until I started looking for a new job a few months ago that I realized it. I saw a posting for "academic support" and my heart jumped into my throat, and it all came back to me.

        (Unfortunately that specific posting was in a specialized field in which I am not qualified, but I'm still holding out for one that will work out!)
        My recent post So, I Guess I’m Doing This Thing!

  4. Good post Jen! There are a few that I would that rewind that are just like yours…not getting into debt and educate myself about finances much earlier. I really wish that I would've focused on saving for retirement more at an earlier age, but you can't allow that to hold you back and just focus on it more in the current. We're really trying to do that ourselves now.

  5. The good thing for you is that while you wish you had known better sooner you have nipped it in the bud in time to really do well for yourself now and in the future. I probably would have majored in Creative Writing in College. Not a so called "real" major but then again neither was the social science I actually majored in and have never used. I should have just went with my passion. Job wise, I'm not sure I could do much better then where I'm at. I do wish I hadn't wasted 8 years in a job I hated but I'm not sure I'd have ended up in a much different place right now.
    My recent post Amazing Quest & The Guys

    • Thank you! I hope that's what I'm getting across here–lots of mistakes made but it's never too late to fix things and make the future better for yourself.

      And I love the idea of a creative writing major! Could you do something now on the side to fulfill that dream?

  6. Great post! I too, wish I'd started saving for retirement at an earlier age. But at the time I was in over my head in student loan debt, so I guess one of the two had to be stalled a little. Everyone makes mistakes so I don't beat myself up over it. Now I just have to work at little harder to catch up. I also wish I had been a more careful spender when I was in college. I certainly didn't need a lot of the material things I was buying (purses, jewelry etc.).

  7. I really have no regrets! I guess I would have kept my Amgen stock is one. I made 500% return, but I didn't realize they would split the stock in the future and multiple times. I really not complaining, but you asked.

  8. I would have not gotten that oh-so-useful Fashion Design degree. I would have purchased more houses to renovate before I had children. I would have started investing much earlier.
    With my own children, I am starting at age 6 buying them one share of stock in a company they like and can relate to, such as McDonalds. They can watch the stock price, know when it goes up or down that they are making money, and we purchase the stock that they choose for birthday and Christmas. They don't need any more toys or clothes, and this helps them learn about purchasing stocks.

  9. Where do I start? Ugh, well for one I'd stat saving for retirement earlier. I'd also have a budget. But let's just go back four years when I started freelancing. I needed to scale back my lifestyle for the sudden shock of my income decreasing. Instead I spent the same. That is probably my biggest mistake.
    My recent post One Step at a Time: Part Two

  10. I had choices along the way and I want to trust that I made the right choices even if they didn't work out as planned. I learned from my wins and losses and have become a better person because of it. Life has been good to me, not perfect who's life is? I agree with Lena, the past is the past, take the knowledge we have gained and make it work for us this round. Great post!
    My recent post PF Weekly Reading List #10-Can I See Some Stolen ID Please?

  11. Awesome post! True there are no rewind buttons, but it's nice to learn from the past. No regrets here as our past shaped who we are today, but for me, I would spend less time and energy worrying about what people thought and focus on what I needed to do. I also recently wrote a post called Thank Your Family. Seems like we're on the same wavelength!
    My recent post BI 041: Fixes Trump Workarounds

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