Hindsight and Our Personal Life Lessons

life lessons

There are literally dozens of famous quotes that begin with “If I knew then what I know now…” In fact, there is even a book by that name.

What are we really talking about when we start a sentence with: If I knew then what I know now? Think about that for a moment. What kind of perception and feelings would prompt us to use that phrase?

* The perception. Anytime we compare the present to the past we are doing so with the advantage of hindsight. We are looking back on our life course with knowledge that we did not have at the time and speculating how that knowledge would have altered our situation or outcome.

* The feelings. If we are pleased with some part of our personal history we generally don’t think about how having more knowledge at the time would have made it better. So, I think it is a fare assumption to say that the feelings behind the phrase “If I knew then what I know now” are rooted in regret or dissatisfaction. In some way we wish things had been different, right?

There will always be hindsight

The fact is, hindsight can only benefit us in the present, it has no application to the past. You can never change what has already happened and thinking about it is a complete waste of time. You can, however, use the knowledge you’ve gained to make better decisions right now. That’s what hindsight is for!

Now, here’s the kicker. In the future, when you look back on the decisions you make today you will have new knowledge that you don’t possess right now. That means that from that vantage point you will probably see possibilities that you do not see at present.

Life lessons are cumulative

If we are paying attention, life becomes a continuous learning experience. At any given point, the life lessons we learn are exactly what we need to learn to keep the process going. Admittedly, some of those lessons are painful and costly. The higher the price of a life lesson the more likely we are to remember it and to benefit from it in the future. Every experience has value if we learn from it.

With that in mind, we see that wishing we had acquired certain knowledge earlier than we actually did is unrealistic. One life lesson leads to the next and we can’t skip ahead. But we can, and should, learn from the experiences of others, especially from their mistakes. If we allow it, their life lessons will put us way ahead of the curve, but it still doesn’t change the process.

Is hindsight really 20-20?

We have all heard that hindsight is 20-20, but is that really true? Yes, but only for a moment because continued learning updates everything. Remember, the whole process is cumulative and knowledge is ever changing. We keep building on what we know and as long as we are alive the process never stops (hopefully).

How can understanding and accepting this process help us now and in the future?

3 Ways to make practical application

1. Don’t waste time thinking about “if only.” Your life is busy unfolding right now, that’s where the majority of your focus needs to be. Instead of fretting over how the past might have been “if only,” think about all the valuable life lessons you have learned.

2. Apply what you have learned. Use those life lessons to help you make wiser decisions now and in the future. Knowledge becomes wisdom only through application. You have spent years learning. Always strive to put what you’ve learned to good use.

3.Turn hindsight into foresight. As you look back on your decisions and outcomes you should begin to notice patterns. When you did things one way you produced a certain type of result. When you did them differently, what kind of result did you get? Identifying the patterns that led to good results will improve the quality of your decisions. This is how hindsight becomes insight.

What led me to write this?

This article is my response to an Invitation to “Write about Stuff that You Wish You Had Known Earlier in Your Life.”  While it sounds like an interesting topic, my problem is that I don’t relate to it. I understand the premise, but I honestly don’t relate to it in my personal life.

Are there painful and costly life lessons from my past that could have been avoided by knowing then what I know now? Absolutely! Super heavy lifting has caused me more chronic back pain than I care to think about. Foolish investment decisions have cost me more money than I am willing to talk about. And the list goes on.

Speculation is worthless

Sure, I can see plenty of ways that my life might have been more comfortable if I’d had the knowledge to make better decisions in the past. But who is to say that one of those uncomfortable situations didn’t save my life somehow? Maybe my life would have been better on some level, but that is just speculation. I love my life and every experience has contributed to making it what it is, even the painful ones.

Life is an individual journey and we all experience different things and learn different life lessons right on schedule. I believe that experience is the greatest teacher. Even when academic knowledge initiates a profound life change, it is usually because our journey led us to a situation that made us receptive to that kind of learning.

How do you feel about your life lessons?
Are there things you wish you had known sooner?
How valuable is experience compared to head knowledge?
The lines are open!

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  1. Debbie October 5, 2010 Reply

    You really make it all come together here. The only problem that I have is seeing my children make some of the mistakes I made and they to are learning the hard way, because they think they know best. that one is hard, but I am learning to just be there when they fall down.
    You are right we all learn by things we have done in the past. I have found in life if we don’t learn the first time many of those mistakes will happen again. ( I like to call them learning experience rather the mistakes)
    thank for the nice article.

    • Jonathan October 5, 2010 Reply

      Hi Debbie, seems we always hope that others, especially our children, can benefit from our mistakes. Then we need to ask: “How often did I allow myself to learn from my parents mistakes?” It’s almost like a right of passage thing. We always think that we know better when we are young. I like to say that “at 18 I knew everything there was to know and now I am almost as dumb as my dad.”

      • Debbie October 6, 2010 Reply

        Love that Jonathan, “at 18 I knew everything there was to know and now I am almost as dumb as my dad.”
        I do know what you mean. I always thought as we get older we are suppose to get smarter, but not so much when it comes to the young adult in our lives, should I say.
        thanks for the smile you gave me.

        • Jonathan October 6, 2010 Reply

          I like to reason with them like this. Let’s say we are talking to an 18 year old who is feeling especially knowledgeable.
          Q. When you were 12 were you smarter than when you were 10?
          A. Of course I was!
          Q. When you were 15 were you smarter than when you were 12?
          A. Way smarter!
          Q. Now that you are 18, how much smarter are you than when you were 15?
          A. Much, much smarter!
          Q. When you turn 21 do you think you will be even smarter than you are now?
          A. I’m sure of it.
          Last question – At what point do you think that process stops?

  2. Sandra Lee October 5, 2010 Reply


    I wholeheartedly agree with the reasoning and insight you present in this article. I too believe our lessons arrive in perfect timing when we are ready for them to appear and they present exactly what we need to learn in that moment.

    I think it’s important to see and acknowledge mistakes we’ve made in the past for the purpose of learning, but not to dwell in the realm of regret, which is pointless. The point of life isn’t to be comfortable. As you wisely point out, discomfort is often a key part of the learning process.

    I also respect the fact that people need to learn their own life lessons in their own time – not on my schedule and not in my preferred way!

    I appreciate how you always offer an authentic and unique perspective. It’s very kind of you to link to my Life Lessons post too. Thanks so much! I am honored.

    • Jonathan October 5, 2010 Reply

      Hi Sandra, learning to “respect the fact that people need to learn their own life lessons in their own time” can be a huge step for some of us. But learning to do that is also very liberating and a lot less irritating for those other people.

  3. Farnoosh October 5, 2010 Reply

    Jonathan, you are a very clever one! You write a fantastic post about regrets, lessons, foresight and hindsight and still refrain to get too personal ;)! – which is what we were hoping – and I hope that someday you share more of your own lessons but your perspective is invaluable and you raise great questions. I think even if I knew then what I know now, I would have not listened to me and would have had to make some mistakes and take some tough roads. It’s just human nature sometimes. Of course there is no way to know and there is only the present and the future to live for….thanks for participating in our series!

    • Jonathan October 5, 2010 Reply

      Greetings Farnoosh, I really did struggled with the original premise of this series. While I have learned many things over the years that I could share from a personal perspective, I couldn’t relate to wishing that I had known them before I was ready. That discrepancy put me in a position to write about the concept rather than the specific lessons.

  4. Nea October 5, 2010 Reply

    You made some excellent points here. I think it’s a great idea to just appreciate those past mistakes. After all, what would be the point of life if we already knew everything & there was nothing to learn. There is room in life for mistakes…mistakes that we can learn from and mistakes that allow others to learn from us. Great post!

    • Jonathan October 5, 2010 Reply

      Hi Nea, in my case, it is a good thing that there is plenty of room for mistakes because I have made more than my share. Then again, the lessons they taught have been extremely valuable.

  5. Lance October 6, 2010 Reply

    I love this line you’ve said about hindsight becoming insight! So true – when we can look back and somehow apply what has happened in our past to our life now (or in the future) in a positive way – that is truly a great lesson in our life. And that we’ve had experiences that may have seemed less than ideal (as each of us has) – they are what has made us what we are today. And had we not had those…it just so impossible to even know where that might have taken us.

    ….which reminds me that what really matters is the present…

    • Jonathan October 6, 2010 Reply

      Hi Lance, I am always amazed when people refuse to learn from their personal past. Much of life is trial and error. So, the only way to avoid the things that don’t work and do more of what does work is to reflect, analyze, and apply. That’s how we gain insight, we learn from experience. That includes all of our experiences as you pointed out, those that are ideal and those that are something else.

      Congratulations on running a successful marathon. That is an awesome achievement.

  6. Abubakar Jamil October 6, 2010 Reply


    Thank you so much for your participation.

    I loved you article as a whole but when I reached this part—”My problem with the premise of this series is that I don’t relate to it. I understand it and wanted to participate in it, but I don’t relate to it in my personal life.”—I couldn’t stop smiling.

    You know why? Because I don’t either.

    Yet, I chose to run this series and you chose to write for it.

    I can relate to you on this one for sure. Thanks again for writing. :)

    • Jonathan October 6, 2010 Reply

      Greetings Abubakar, I must admit, your comment came as a surprise. How funny that we both felt compelled to participate and that we both share similar feelings. Thanks so much for expressing how you feel about this. I was a little concerned that others might not appreciate my perspective here.

  7. John Rocheleau October 6, 2010 Reply

    You said:

    “wishing we had acquired certain knowledge earlier than we actually did is unrealistic. One life lesson leads to the next and we can’t skip ahead.”

    And that says it all really. We have to see each moment we are in as an opportunity to experience and to learn. Those moments will then create a future that has no need for hindsight.


    • Jonathan February 8, 2011 Reply

      Nicely said John: “We have to see each moment we are in as an opportunity to experience and to learn. Those moments will then create a future that has no need for hindsight.” That is exactly how I see it also!

  8. Christopher Foster October 6, 2010 Reply

    I love what you say about being thankful for your life and for everything that has brought you to this moment. I certainly wouldn’t want to change a thing, because…

    I have the opportunity right now to be with the greatest teacher of all, which for me is stillness. In the stillness of my own being an amazing thing is possible, awareness of who I truly am. Thanks Jonathan.

  9. John Rocheleau October 6, 2010 Reply

    I have often wondered what it would be like to have the ability to physically go back in time to do things differently.

    Of course, if I did, I couldn’t guarantee that I’d be here wondering such things so the whole idea just falls apart.

    As a result I have decided not to build that time machine. I realize that I am here BECAUSE of the past — not in spite of it.

    Although …..?

    : )

  10. Frank October 8, 2010 Reply

    I can say confidently that the things I look at in hindsight have given me insight into how I make decisions currently. Some of my foolish decisions has created my current opportunities. If I never got burned in a multi-level marketing scheme I would have never opened up a book about investing. If I never read that book about investing I never would have become a stock broker. So I appreciate my younger, greedy, and unwise self. It has made me who I am today.

    I enjoyed this post thoroughly Jonathan. Thank you for sharing.

  11. Marion October 13, 2010 Reply

    I did enjoy this Jonathan

    I often see people who beat themselves up with the hindsight stick instead of enjoying the ah ha moment that hindsight can give and move on with the new learning.

    I think life is full of lessons – if we choose to accept them. Mine was a simple lesson – love yourself more – but it took me a long time to learn. Yes it would have been great to learn it sooner but would I have been ready for it? There is much to be said about when the student is ready the teacher appears.

    Knowledge v experience is an interesting question but the answer I believe lies in what you do with it. It is a bit like theory and hope. Theory is based in knowledge and often in theory certain things “should” not work but from experience I have seen people make things happen – often from the power of hope.

    Thank you for an inspiring post.

  12. John Duffield October 21, 2010 Reply

    Hello Jonathan. Here’s a little “hindsight” trick I employ to help me learn from my own (past) life. I learned it by writing my book. Here’s how it went. First off, the book took a very long time to write. Okay, so there I was, ten years into it one day, looking back at the first chapters. It’d been so long since I’d written it, it was like reading something somebody else had written. In fact, I found myself learning new things from reading it…. that I didn’t know before. Like I was learning something from somebody else’s book? But wait a sec here. I was the author. If somebody asked me “what do you mean by this or that?” in my own book……I normally would’ve said “that or this”. But now I wasn’t sure what my own words meant. Matter of fact, if I went back with “fresh eyes” (like I was somebody else), and read my own work, I’d begin to discover all kinds of new things I’d never thought of before. As if my own writing was a kind of diamond mine I could keep on digging up new treasures in. Okay, so here’s the “hindsight insight”. Truth be told, our lives are like a kind of book. Call each a “Book of Life” if you want. And yes….each of us is the author of our Book. But each of us is also a completely separate “observing learner” too, who can profit from studying our own Life. In fact, if you can detach yourself from the “author” role you’ll see that every chapter is like a separate Booklet of Life. And….wonder of wonders… that means you have an entire library to study….not even including the other Books of Life around you. But here’s the thing. To really get a huge sense of wonder about your own life, (to make you study it because it’s like a new book to you) you have to realize you’re not the author….even though you are. You’re actually “THE AUTHOR and NOT THE AUTHOR” at the same time. “Nuts!” you say? Not at all. It’s just like that famous half-empty glass that’s also half-full…at the same time. It’s called “wholeness” and wholeness by another name is called “love”. And so. Learning from your past life is really called “loving thyself”. Ciao Jonathan.

  13. Suzette April 15, 2011 Reply

    It is good therapy to go online and read what other people have to say about life. learn to value your own life and try to listen to others who are trying to give you good advice about how important you are. Life is amazing! Try to see the bright side of it :)

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