Updated on 02.09.10

Hindsight Is 20/20

Trent Hamm

When I look back at my overspending days, it’s easy for me to see the many, many mistakes I made. My life was littered with them. There are some old journal entries of mine that are absolutely cringe-inducing to read. I still have quite a few items in my closet that are just the result of blind conspicuous consumption. I didn’t save. I didn’t invest. I didn’t plan. I didn’t focus on building the career I truly wanted.

Looking back, I see all of those mistakes and missed opportunities and poor choices. I want to smack my 23 year old self on the head and yell, “Get a clue!”

Yet, I also know that hindsight is 20/20.

Back then, I had a sense of what I wanted – a nice home, a marriage to Sarah, kids, a job that gave me the flexibility to spend lots of time with them – but I didn’t have any idea how to get there. Today, though, I have the knowledge and time to reflect – and I now see all of the mistakes I made.

Here’s the real key, though: those mistakes are done and over with. I don’t have a chance to repeat those days and make better choices.

Instead, I have two things I can do today.

First, I can strive not to repeat those mistakes. I know now that my life is perfectly happy without having all of the latest and greatest stuff. I don’t need to go out to eat constantly or go golfing or buy nice clothes or own a new gadget or go on ridiculously expensive trips (like a week in a hotel room in London with a view of Hyde Park and the Royal Albert Hall like we had on our honeymoon, for example) to be happy. I know what I value and love and need in my life.

Second, I can share what I’ve learned. For some people who are eager to find a better path, it’s easy for me – that’s what The Simple Dollar is for. When I learn something new about personal finance and the great life sensible money management can build, I can share it here.

There’s also a need to share things with people who aren’t at that same stage in life. How exactly can I reach out to them without being overbearing? For me, it’s usually a matter of just dropping a book in their hands or just asking what they want to do in their lives and then asking them what things they’re doing today helps get them there.

Don’t waste your time beating yourself up over the mistakes of the past. Those choices have already been made – no amount of anger or disappointment at yourself can undo what’s already been done. Instead, focus on the choices you make today and revel in making good choices now.

You can never change the past, but you can certainly learn from it. Better yet, you can take what you’ve learned and apply it to improve the present – and drastically improve the future.

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  1. Stephanie says:

    I think this is very true. And it’s something that you have to remind yourself sometimes. I can look back and say, “Why did we go out to that super fancy restaurant” or “Why didn’t I try for more scholarships so I would have less student loan debt now”…the questions I could ask myself like that would go on and on. The key is, as you said, to learn from those mistakes and help others avoid those same pitfalls. It doesn’t matter how you go into debt, as long as you recognize how it happened, and that you will not do it again.

  2. asithi says:

    This concept can be applied to other areas of our lives.

  3. BirdDog says:

    Great post, Trent! I’ve beat myself up quite a bit over decisions that I made in my early to mid twenties. Thankfully, I learned from my mistakes and I’m able to move on and do better from here on out.

  4. Maggie says:

    As the parent of a nearly 20 year old, I am also learning that there are some things a person has to learn for themselves, no matter how much we want to spare them that.

  5. getagrip says:

    Handling your own mistake is easy.

    The real trick is watching your children walking the same path, and having the ability to guide rather than try and step in and fix, and being able to let them fail and learn when necessary.

  6. almost there says:

    Life is like that. Different things are important at each stage of our lives. The older one gets, the more one looks back and asks “why did I do those things?”, I wouldn’t do them now. “Our House”, though dates is a good song too (CSN&Y).

  7. Sandy says:

    I soooo needed this post today. I received e-mails and a catalog on the great “sales” at Eddie Bauer and was really having to work to talk myself out of needing that turquoise blue sweater that was only $20…. I don’t need it, I have more clothes than I know what to do with already! Thanks for hitting the nail on the head today!

  8. So now that you realize that taking an expensive vacation might not have been the best financial decision, when do you think you will update us about your plans to travel to Italy (I think it was Italy)?

    I’m often perplexed by people who think travel is so expensive. Sure, it CAN be expensive but if done wisely you can find yourself in some amazing places on the cheap. I’d be more than willing to write a guest post about this topic if you’d like. I’m not a world traveler by any stretch of the imagination but I’m becoming quite saavy on how to get to places (and survive very well) while there.

    I’ll be leaving for Germany in about a month and have no intention of spending more than $1,000 for the entire trip, including airfare, food and room. I also have no doubts that it will be an incredible trip.

    I hope that your self-describe comfort isn’t turning into complacency and you find in 10 more years that you wish you’d have captured life a little more aggressively than in front of a computer. There is a great big world out there waiting for you and I hope that you take my words as I intend them, as a gentle nudge to get you to move forward on your trip.

    I await an update!

  9. The 20K Mom says:

    Learning from our mistakes is one of the great challenges of life. Growth only happens through challenge and struggle.

  10. Matt says:

    Excellent post once again Trent. So many times we beat ourselves up emotionally over the past. Once it’s over and done with, the only thing productive to do is learn from what happened so when faced with a similar situation you can develop a fresh outcome.

    We spend a lot of time with this concept with our daughters. They often want big ticket items to buy, yet get lured in by the smaller, impulsive purchases of the world. The only way I think it will connect with them is to weigh the options better and the subsequent big purchases are easier for them to negotiate.

  11. triLcat says:

    @steven #8 – yeah, my husband & I & 2 kids are planning on going to Finland this summer on a shoestring budget. One thing that saved us a fortune was that my mom immediately suggested, when we mentioned Finland as our destination, checking flying through St. Petersburg – flights were 40% of the cost of flights to Helsinki.

    For those who juggle, the European Juggling Convention often ends up being cheaper than the US one, even when you include airfare, because it’s on campgrounds rather than in a fancy convention center. This year’s in Finland!

  12. Oskar says:

    We all made ‘mistakes’ in our younger years but that is what we learn from. I think we have to stop and think that we probably would not be were we are today if we had not made the decisions we made when we were younger…however bad they might seem in hindsight…

    good post!

  13. This may not seem like a big deal, but it really can be for those starting out down the road of financial security.

    More than likely, you will make mistakes, and its very easy to let these get you down.

    You can’t do that, it is simply counter-productive

  14. mehrzahl says:

    You sound like you never make any mistakes anymore… I still do though I think I have my fundamentals right.

    I fully agree with Maggy, everyone needs to experience some mistakes themselves to really learn from them.

  15. Tammie says:

    You can’t change shoulda, woulda and coulda, so you might as well go on.

  16. Geoff Hart says:

    Learning to move on without forgetting the past is an important survival strategy. M. Scott Peck’s “The Road Less Traveled” is a brilliant book about spiritual and emotional development, though not everyone is comfortable with the final section on “grace”. Nonetheless, it’s an important and life-changing book. Among other things, it illustrates how important it is to forgive the errors of the past (including your own) and move on.

    Sadly, we poor souls learn better from making mistakes than from anything else, and we have to learn to forgive ourselves when we err. Best you can do is try to make amends, hope not to make the same mistake again, and keep trying. You’re gonna mess up now and again, but that’s how the game is played.

  17. Kevin says:

    Good food for thought.

    This actually got me thinking. Many personal finance blogs like Trent’s and JD’s are based on trying to educate their readers and help them learn from the authors’ mistakes. They seek to teach their readers the lessons they’ve learned, without having to suffer the consequences the authors endured.

    But the more I think about it, the less I think that works. There are some lessons you don’t truly appreciate unless you’ve lived through the negative consequences personally. Perhaps the BEST personal finance blog would be one that encourages its readers to make mistakes that have the biggest “bang-for-the-buck” in terms of correcting negative behaviours (balanced against the long term negative side effects).

    Hmm. I wonder what such a blog might look like. :)


    Jeremy writes: “I just graduated university. I have $35,000 in student loans, and I just got a job that pays $50,000. I want to buy a new Volkswagen. The dealer is offering me 7.9% financing. Should I do it?”

    Yes, Jeremy, you should definitely do it. Finance that car for 5 years. Then please write back in 5 years and tell me how you feel about financing brand-new vehicles.

    I’d be willing to bet that, 5 years from now, Jeremy would have a much stronger aversion to financing expensive cars than he would if Trent just told him “don’t do it” right off the bat.

  18. I’m a big believer that we make our decisions based on only the experiences we have and the circumstances before us.

    As our experience grows, and our circumstances change, we see the decisions of days past in a different light, but nevertheless–we cannot change them.

    We can only continue to make similarly well-informed decisions in the present, again based on our current experience and circumstances.

  19. Ruby Leigh says:

    Yeah, I am glad I am not the only one who went on a rediculously costly Honeymoon. I guess we just thought we had money to blow. You know what though – it was super fun, and while I think we could of spent less – I just try to appreciate the enjoyment of it and make better decisions going forward.

  20. Lou says:

    Since you like music so much, check out Willie Nelson’s “Nothin’ I can do about it now” It starts with “I’ve got a long list of real good reasons for all the things I’ve done” and ends: “I could cry for the time I’ve wasted, but that’s a waste of time and tears, and I know just what I’d change if I went back in time somehow, but there’s nothin I can do about it now.

  21. ZyAnn says:

    I have no idea as to how I stumbled upon this post today but I am extremely grateful that I did. I’m 22 years old and have been working in a Multi National company for the past 2 years. To be very honest I can’t say that I have been wasteful till now but when I think about it the path that I’m walking would definitely lead me to what you described above. It’s made me want to stop, think and then act. So thank you very much Trent for this article as I wouldn’t want to smack my 23 year old self on the head and yell, “Get a clue!”

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