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A Financial Do Over: Hindsight is 20/20

What Would a Financial Do Over Look Like for You?
What Would a Financial Do Over Look Like for You?

A reader asked a question of me recently. The question was, “If you could go back in time to your early 20’s, what would you do differently to build a better financial safety net and grow your net worth faster?”

I thought it was a terrific question, so I’m putting it into a post today. Hindsight is 20/20, as they say, and having learned much about money and life over the last 25 years 2 years and 4 months, I can think of a number of things I’d do differently if I could go back to my early twenties and have a financial do over of my finances. Here are some thoughts:

1. I’d stop caring what people thought. So much of the financial mess we’re dealing with now is because we cared what people thought of our “status”. We wanted to be viewed as being successful, and we mistakenly thought that material possessions = success. If I could go back to my early 20’s, I’d dump that mindset ASAP instead of waiting till I was in my forties.

2. I’d have saved a set percentage of my income each paycheck. There’s a good book out there called The Wealthy Barber, Updated 3rd Edition: Everyone’s Commonsense Guide to Becoming Financially Independent . The book is full of great stories and financial wisdom, and I’d highly recommend it to personal finance aficionados, but the main takeaway of the book is that if one commits to saving 10% of their income from the get-go, that the savings results will be plush enough to cover all other financial errors – even a boatload of debt.ย  Love the concept, and if I could go back in time, I’d commit to saving at least 10% of every paycheck no matter what.

3. I’d commit to living within my means and refuse credit card use.ย  No amount of “stuff” is worth being saddled down with thousands in credit card debt. The peace of mind that comes with owing no man is unbeatable.

4. I’d put a minimum of 20% down on house purchases and pay for cars in cash. In other words, I’d leverage myself better so that if I was put in a situation where I needed to sell my house or car, there would be a net profit instead of a loss or a “come out even”.

5. I’d ramp up retirement savings. I’d contribute a minimum of 5% to retirement savings. Everyone can live on 5% less of their income, and the long-term results would be well worth the sacrifice.

6. I’d dump the broke mindset a lot earlier. I lived for years with a broke mindset. Now that I’ve traded that broke mindset in for an abundance mindset, I’ve opened the door to a wealth of blessings, financial and otherwise.

Friends, while these are all great ideas, we cannot for reals go back in time and have a financial do over. We can, however, take control of our finances TODAY and start implementing changes that will put us on the road to debt freedom and financial independence. So stop living in regret of past mistakes, and start building a better YOU today!



  1. Although I try not to dwell on the past, I often say I wish I knew then what I know now, but all about moving forward for us these days, but since our children are just starting their financial lives we are teaching them as much as we can to be so much better with money than we were at their age.

    • Laurie says:

      We’re doing the exact same thing, Brian. We can’t go back in time, but we can give our children a new future and change our family tree, as Dave Ramsey often says.

  2. I think these are some great thoughts of what many have done and in hindsight wished they had done differently. I did save a set amount back when I first started working but it was just a small amount. Many of my peers weren’t even saving at all so I thought I was doing fine. But I definitely could have saved more and now wish I did. And caring what others thought…yea I think that would be hard to convince my younger self to stop caring about that. It is tough especially when you are still young and easily influenced by others.

    • Laurie says:

      I hear you, Andrew. It is difficult! We are working hard to teach our kids that they are here to lead, not to follow, in the sense that we don’t want them to be careful who they allow themselves to be influenced by. I spent way too many years working to be accepted by too many people.

  3. Vanessa D. says:

    If I could go back in time there is an entire boatload of stuff I would do differently. I grew up in a household where frugality or thriftiness was evident, but talking about money was taboo. I didn’t know that my dad socked away a set amount every week to pay for Christmas gifts. I didn’t know that there was an amount put away every month for vehicles. I’m only just now starting to figure this stuff out and I really wish I had known then.

    So I guess if I could change just one thing – I would have educated myself sooner and talked about it more – to my kids and to my now ex-husband.

    • Laurie says:

      I hear you, Vanessa. Money was such a taboo subject back then, and it seems like only now are people starting to open up about it. Education is key – this is why us bloggers are here. Thanks for the comment and for visiting the site!

  4. Debt Hater says:

    Good points, and I’m glad I’ve been able to stick to your points in my early 20s without needing a do-over! I’d like to go back an educate my past self more on the consequences of student loans and hopefully steer myself towards making a smart decision – maybe going to community college for two years and then transferring.

    • Laurie says:

      You’re lucky to have been going through your twenties relatively unscathed! Yes, I hear you about the student loans. There definitely needs to be more education out there about how to reduce student loan amounts from the get go. Great comment!

  5. Great points! I’m really happy I took my mom’s advice, those small things that she did because she rarely spoke of frugality. She taught me to value every penny and eat meals at home and that a simple life is still a wonderful life. It’s helped me put my financial house in great order so that hopefully I don’t need a do over later on!

    • Laurie says:

      Amanda, your mom sounds like a very wise woman!!! What a blessing. Smart of you for taking her advice, too. ๐Ÿ™‚

  6. Laura Harris says:

    I love love LOVE this list, Laurie! So insightful and exactly what I’ve been learning, too. I especially love how things like “I wish I would have studied investing more” or “I wish I would have gotten involved in the stock market” didn’t make your list. That’s what I always thought “being smart with your money” meant. Definitely not anymore. Being smart with your money is being brave enough to say no to things your peers still say yes to.

    • Laurie says:

      “Being smart with your money is being brave enough to say no to things your peers still say yes to.” LOVE that, Laura! You should write a post on that!

  7. Mario says:

    This is a great list!

    There are many things I’d change if I could do it differently, but because I can’t go back in time, I’m living in the moment and always looking forward.

    Still, there are plenty of lessons for the younger folks so I’m sure they’re happy we’re laying out the things we’d do differently if we could ๐Ÿ™‚

  8. Numbers 2 and 3 have been big ones for us! Living beyond our means was a big part of what got us into so much debt in the first place. Now that we have changed our mindset and are living well below our means, the debt is leaving. And more importantly, we are determined now to never have that kind of debt again!

  9. When you are 60, you’ll look back and be SO glad for what you did in your 40s. It would be nice to have had it all figured out at age 20, but it puts you in a minority to have it figured out at all : )
    (Is that a Tim Hortons cup I see in your photo?)

    • Laurie says:

      LOL, might be. Found the photo on Flickr and don’t drink coffee, so I’m only vaguely familiar with famous coffee house logos. ๐Ÿ™‚

  10. There are certainly some financial choices I made in my past I wish I could make differently, but Iยดm glad Iยดm still young enough to steer my financial life down a different path now. Better late than never, right?

  11. I don’t know why some people care what other people think of them. It’s our life and we have to be responsible for it. Others may not care about us. So, we’d better do the same way. Doing this wouldn’t bring us to our goals. Now, let’s stop thinking what others think of us.

  12. I sometimes imagine how different things would be today if we’d implemented the things you mentioned. Boy were we clueless. My mom would buy savings bonds every payday throughout the years. When she cashes in a $50 bond now and ends up with $3000 in her hand, I sure wish I’d done something, ANYTHING, similar. Great post, Laurie. It will help a lot of younger people see that the time to start getting in super financial shape is NOW.

  13. As you know, Laurie, I have had a similar past to you and I can honestly say that I would echo 100% of this list. It’s sometimes painful to look back at the past and know where you went wrong, but I truly believe that from the pain comes great and lasting lessons that are not only meant to help us but others as well. I think a big reason why I can help my clients so much is because I was so similar to them and I know how to help them before they get completely sideways like I did and I take comfort in knowing that my mistakes are helping other people.

    • Laurie says:

      Ditto, ditto, Shannon!!! We cannot go back and have that do-over, but we can use what we’ve learned to help others, and we are doing it, and isn’t that a great way to overcome our mistakes? I believe it is, my friend. ๐Ÿ™‚

  14. Lisa says:

    Whenever this subject comes up, I always say that I wish I started saving right when I got my very first job. Even though I was part-time and in retail, I really think I could have squeezed some savings in. Compound interest is something you just can’t make up for!

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