Regret Is My Motivator

It is very easy for me to sum up the reason I choose to do anything in one word, “regret.” A short simple word that needs no defining yet powerful enough to get me to do practically anything. A little background might be in order now.


The year was 1998, I was about 24 and I was still in graduate school going for my M.S. degree in environmental science while the dot com revolution was in full swing. It seemed that every newspaper and finance show on television was touting the amazing potential of this new mainstream media, the Internet. While happily studying in school and perfectly content where I was in life something nevertheless was tugging at me inside. Having a pretty solid amateur understanding of computers and networking in general I began to think if my place somehow belonged in this new media rather than the environmental sector. And so, article after article I began to read about other 20 something CEO’s running their own dot come start up from a garage or dorm room and thought to myself, “Why not me?”


Thus began my quest into figuring out what I wanted to do online and whom to do it with. I got in touch with a college buddy of mine who was a computer science major along with an elementary school friend who was also in graduate school at the time. As we met and discussed various options about what we were looking to do and the type of computer and networking equipment needed I began to question if this was the appropriate route I should be taking. After all, I was close to finishing up my Masters degree and most likely had a decent job waiting for me soon after I graduated. However, a stronger force quickly squelched any question I had regarding my decision to start an online business. And that force was regret. I remember vividly the conversation I had with my elementary school friend discussing the viability of this potential business and whether or not we should go for it. The question was quickly answered for me as I knew that no matter what happened I did not want to feel regret. The regret of not even trying. The regret of not giving this new business a chance. To me, it did not matter if our business succeeded or failed. I just knew deep down that I had to do it because the feeling of regret would be much worse to me than the feeling of failure.


I could somehow see the future at that moment and did not want to stand idly by while someone else would potentially create the same business as I had envisioned. And so, almost a full seventeen years later our venture is still online and still providing me with cash flow. You can bet, today, I feel zero regret in my decision to start this venture as I view it as a success no matter how much longer it remains viable.


Too often we read about or hear about the people who state, “That was my idea!” Or the all too common I should have/could have (you fill in the blank). One must ask why do our future selves often times regret the choices made by our past selves? Why does it seem rare to hear statements from our future selves declaring joy for a past choice made rather than regret?


All of us are on personal quests to achieve some measure of financial independence whether from passive dividend income, peer to peer lending, real estate or other income producing entities. The question inevitably comes up from time to time from friends or relatives even as to why you we doing what we are doing.


I get the sense that our community is very well aware of time travel and realize that our three selves (past, present and future) are really three separate and very different individuals that essentially affect each other. We all know that our past selves give rise to our present selves which sets a path and direction for our future selves. If you have an opportunity to start a business, invest, buy real estate or whatever, take action and never let regret extort a better life from your future self. After all, who among us in ten, twenty or even thirty years from now would want to utter the words, “I wish I bought KO, PG, CLX a decade ago. I should have invested in PEP or PM.” For me, the feeling of regret is much worse than the feeling of failing. Let ‘regret’ be your motivator to take action.


What motivates you to take action and limit or entirely eliminate regret from your future self? Please let me know below.

74 thoughts on “Regret Is My Motivator”

  1. I regret starting investing the way I did and not paying attention to the lesson that my Grampa gave me with WMT at the age of 15. I remember thinking that buy KO at 2.5% seemed crazy, when you could buy this or that company with a 8% yield. To this day, I still get the I should have bought that as I read about positions here and there.

    Live and learn though. Sometimes it is hard to decide if I will regret whether or not I did something. Or at the time your just to naive to understand that you will. I wish that I payed more attention when I was learning Spanish in high school and was fluent right now. At the time I just wanted to get it done, now I live and would like to go to places where Spanish is spoken!

    Great post and congratulations on your success! A lot of people lost their shirts then!

    Take care!

    • Hi ILG,

      Happy to hear you enjoyed this post. I guess everyone at some point in their life declares a ‘should have, could have’ moment and regrets not taking action whether it was learning Spanish in high school or some other event. As you said, ‘live and learn’ and that story about not buying into KO way back when resonates with many. I guess it’s human nature to look back and feel regret about not taking certain action. Of course, hindsight is always 20/20 so it may not always be the best example. The key is to always look forward and realize that your decisions today will always affect your outcome, for better or worse, down the road. Thank you for stopping by and commenting.

  2. DivHut,

    Great post. I don’t know who said “Life begins just outside our comfort zones.” but I love this quote. I think action is the only way to eliminate not only future regrets, but also our current fears. What motivates me is the thought of unrealized potential, both in me and those that are close to me. I hate the idea of being the person who takes the road most travelled, which is the crowded road full those who wished they had taken action instead of seeking safety.

    My Dividend Pipeline recently posted…January 2015 Income and ExpensesMy Profile

    • Hi MDP,

      I believe that great quote comes from Neale Donald Walsch and it speaks to me as well. We all know that in order to get anything done and improve our life we have to exit our comfort zone. Only then can we realize our full potential and improve. Sure failure is always a possibility when you leave your comfort zone but to me there is no better way to improve and realize your potential and in that manner leave all regret behind as you know you ‘gave it a shot.’ I’m glad you enjoyed this post and as always I appreciate your comment.

  3. Keith,
    Interesting post. Funny, I started my senior year in high school in 1974 (which is about when you were born).

    I went into business with a partner because I didn’t want to spend my life working for someone else, but it ended badly. His son was diagnosed with MS or MD, I don’t remember which, but I do remember finding his wife and son in the shop one morning. I asked the wife what was going on and she said my partner/her husband left town and told her I would figure something out. Trying not to get emotional while typing this since it has been over 3 decades, but that son-of-a-b did something that I still find unfathomable/unforgivable. Not ditching me and the business, but ditching his wife and son.

    Long story short, I closed the shop and used my engineering degree to make a comfortable living without taking the risk of being a business owner. I have no regrets, though, about trying to run a business. Taught me a lot about life and love and about myself.
    Be blessed,

    • Hi KeithX,

      Your comment really highlights some of the lower points of humanity and, of course, the lessons learned from those experiences. I think it’s great that you and your partner had the vision to start a business because you did not want to work for someone else and in that respect I applaud you. Too bad your story continues to take an unfortunate turn with your partner essentially abandoning everyone, friends and family alike. I bet that experience has taught something about yourself and humanity. Though painful all these years later as you recollect, you seem to have turned this sad experience into a positive one for yourself as you moved on and built up a comfortable life for yourself. The key is to have no regrets which you stated and that’s really what looking back is all about. Thank you for sharing this personal story with us.

  4. Very nice post, DivHut. There have been plenty of times that I have let an opportunity go in the past and regretted later. Even to this day, sometimes I let go after weighing all the pros and cons and realize that I made a bad decision, but try to learn from that experience. Its all part of living and learning I suppose.

    Congrats on keeping your idea and baby going for so long. Im glad to hear that you started something while you were in your final year of masters and dont regret that decision now. Kudos to you.

    Thanks for sharing
    Roadmap2Retire recently posted…Chatter Around the World – 83My Profile

    • Hi R2R,

      As you mentioned, it’s all about learning from past experiences and if you are always looking back and feeling some sort of regret it just means that your present self needs to adjust its decision making process. No one is perfect and hindsight is always 20/20 so I guess the key is to really reduce the number of times and degree of regret one feels. Believe me, I wish I would have been a dedicated dividend growth investor many, many years prior to me starting out. In fact, my first stock I ever owned back in 1988 paid a dividend but I was too young and naive to understand what it really meant. I can only imagine where my dividend income would be today had I simply bought PG, KO or MMM almost thirty years ago and just reinvested. Again, hindsight is 20/20. All I can do is be happy that my recent past self and present self is investing for the next 20 or 30 years for a happier future self. Thank you for stopping by and commenting.

  5. Well written DH – I think this is something that motivates me as well, whether or not I conceptualized it quite this way or not. Failure and regret are so closely intertwined, in that one leads to the other. Fighting the urge to be lazy, to quit, to not stretch as far, all is derived from not wanting to fail, but more importantly not wanting to regret the actions or inactions that led to that failure. I would be lying if I didn’t have some regrets in my life, so the key is forge ahead and resolve not to regret again.

    Think about eating something bitter and what is worse… the initial bitter taste, or the long-lasting after effects that linger for a while. Failure comes and goes quickly, but regret can last a lifetime.
    writing2reality recently posted…Trades – Emerson Electric (EMR) and Johnson and Johnson (JNJ) PurchasesMy Profile

    • Hi w2r,

      Thank you for the kind words regarding the post. I have to say that I think your last line summarizes the concept of regret and failure perfectly when you say, “Failure comes and goes quickly, but regret can last a lifetime.” It’s true that sometimes we are our own worst enemy when realizing a full potential. Laziness, fear of failure and simple inaction are often the symptoms of a disease called regret. While I believe everyone feels regret at different points in their life, the key is to manage it accordingly and to mitigate it in the future. As I mentioned in another comment, the key is to always look ahead and make sure your present self takes whatever initiative is needed to ensure a better and happier future self. Thank you for stopping by and sharing your thoughts.

    • Hi LAH,

      Your comment highlights the point of taking action rather than inaction and regretting the decision down the road. I fully agree with you that it’s better to say ‘oh well’ which translates to failure rather than the infamous ‘what if’ mantra which equates to regret. Keep seeking those opportunities and always think of your future self when making any present day decision. Thank you for stopping by and commenting.

  6. Great post! I totally agree with this. After finishing up my MBA recently I decided to venture out and start something. I have been in an industry for 9 years and felt like I needed a change otherwise I would regret it. And thats exactly what I am doing. No matter what happens, at least I’ll know in my heart I followed my passion and I wont wonder “what if”. So far so good.
    Mabel @ Teach Me To Invest recently posted…Radio Shack: The End of an Era {how bankruptcies have shaped how I approach investing}My Profile

    • Hi TMTI,

      Good for you. I think it’s always a bold decision when one leaves their comfort zone and ventures off into another aspect of life that is largely unknown. As you stated, no matter what happens you’ll never feel any regret and never ask yourself the dreaded “what if” question. For better or worse you will find out on your own. Congrats on venturing out and starting your own thing. Thank you for stopping by and sharing.

  7. Interesting story, thanks for sharing. Sounds like the fear of regret can be used as a motivational tool to succeed. I remember the dot com boom and how quickly things were changing at that time in the I/T sector. What was (is) the business and do you have any tips for anyone looking to start a small business from their home?
    Dan @ Our Big Fat Wallet recently posted…Lessons from the Wealthy JanitorMy Profile

    • Hi OBFW,

      I fully agree with you that even the ‘fear of regret’ can be a motivational tool. Actually, that’s exactly what is was for me. I just knew that no matter what happened I wanted to simply avoid the feeling of regret which was all the motivation I needed to actually go for it. Success or failure was not even a consideration for me as I ventured into my business. The fear of feeling regret was much stronger. I never wanted to ask myself the ‘what if’ question down the road.

      To answer your question, back in 1998 my buddy and I started an online video on demand service. It was a time when streaming video was jerky, postage stamp size and fuzzy. Granted we started small but as video compression improved and broadband penetrated more homes our business grew. I can tell you that the one thing that kept us going and to anyone who wants to start a business from home I will say be “CHEAP.” Keep things small when you start, do EVERYTHING yourself (as much as you can), don’t hire staff, let computers/servers be your workforce. In other words, stretch your dollar big time. We stayed in a garage for years and outsourced only professional help such as legal or programming. We harnessed LAMP (Linux, Apache, MySQL, PHP) as it was all free and reliable and grew organically. Don’t spend on advertising or other shortcuts to gain traffic/sales etc. I think you get the gist of how we ran our business. As always, I appreciate your comment.

  8. Today is the first day of the rest of our lives, so doing things now in order for our future selves to not regret our present decisions makes a lot of sense. 😀 I find other people’s regrettable stories are motivational as well. I read an article where really old people were asked what they most regret in life. Some common things were not spending enough quality time with friends and family, and not saving and investing earlier enough. So I try to make sure that doesn’t happen to me. 🙂
    Liquid recently posted…Wharton School’s Financial QuizMy Profile

    • Hi Liquid,

      As cliche as it sounds it’s so true that the actions we take today will surely affect our future outcome and there’s no time like the present to take that action. As you stated, “Today is the first day of the rest of our lives.” It’s funny how many of us “smarter” younger people (20s, 30s, 40s, 50s) somehow dismiss listening the wisdom of our elders. After all, they would have the longest perspective when looking back at how they lived their lives and it’s true that you could learn a lot form what they have to say. I find it interesting that a common regret they stated was not spending enough quality time with friends and family. It’s kind of telling to us as to what’s truly important in life. Thank you for stopping by and commenting.

  9. In philosophy class, I learned that “the decision that has been made is the best decision.” I graduated with $100k in debt, but I have $40k in savings. I only pay the one that charge 5% first, which knock it down to $60k, after that I slowly pay it. I could have used that $40k to invest in AAPL, but that 2006, who would be in the right mind, invest everything you got in an overvalued market? Of course appl had a great run even in the economic down turn. The thing is we wouldn’t know what’s best, but we made the best the decision for that circumstance. We live and we learn, so that history don’t repeat itself. 🙂
    Vivianne recently posted…Taking advantage of freebies from US banksMy Profile

    • Hi Vivianne,

      Your comment highlights the phrase that ‘hindsight is always 20/20.’ Sure investing in AAPL back in 2006 would have been a great call but as you stated you would have been out of your mind to invest all you had in that stock rather than pay down your debt. All we can do is take action and make a decision based on whatever we know at the present time. But the key, as you mentioned is to actually make a decision. Too often we get scared to make a choice as we fear the outcome or fall prey to analysis paralysis and over think and analyze a decision to death. Thank you for stopping by and sharing your thoughts.

  10. DivHut,

    I totally agree with that sentiment. Regret is totally worse than failure. Regret does have a silver lining, it is a powerful motivator to change your future for the better more so than any failure.

    Side note, you still in the environmental science type business? Been in the environmental consulting / clean energy world myself since I started working.

    Thanks for the post,
    Dividend Gremlin recently posted…Side Job IdeasMy Profile

    • Hi DG,

      I think most people fear failure and don’t want to feel/experience that sentiment, but, as you mentioned, the feeling of regret, for me at least, is much worse and can often be the catalyst to modify your future decisions.

      I never went into the environmental sector after school as I started my business soon thereafter and basically almost seventeen years later haven’t looked back. I guess I’m just another one of those college graduates that have a degree and is totally not using it. Thank you for stopping by and commenting.

  11. Good article! When I discussed the pros and cons of moving to the USA for my dream career with my best friend, he advised me to take the chance. He mentioned that he had a chance to do something “out-of-the-box” many years ago — and he’s regretted not doing so ever since. His message was essentially what you write about.
    FerdiS recently posted…10 Dividend Growth Stocks For February 2015My Profile

    • Hi FerdiS,

      Unfortunately, the story of your friend regretting his decision to not do his “out-of-the-box” idea is more common than not. I am sure his feeling of regret constantly comes up even though many years have passed. Kudos to you though for taking a chance and moving to a new country to follow your dream. We need to hear more of those stories and celebrate the successes and the failures too as the outcome is not as relevant as the decision that has actually been made. Thanks for sharing your story and commenting.

  12. I don’t have regrets. There might be some choices I’d do a little differently, but then I would not have learned from them… I 100% follow you with that article! There is one thing though that slows down action a little: having a family. Before having a wife and kids, I would question myself less and move a lot faster. Responsibilities slow me down a little but also make me think about what I’m aiming to do, which is a good thing in the end. Thank you for sharing your thoughts! 🙂
    DivGuy recently posted…Is Telus (T.TO) Done Growing Yet?My Profile

    • DivGuy,

      Having a family definitely changes your perspective and, at least in my case, altered my goals. Before I just thought about my future but now I’m responsible for the future of three others as well. If anything it adds to my resolve.

      As for regret, we all experience it to some extent, but it’s how we learn from those decisions that will help guide us in the future.

      Dividends with Children recently posted…January 2015 Income and Expenses OverviewMy Profile

      • Hi DwC,

        Well said. A family simply changes one’s perspective but should not paralyze you to essentially not take any action which will ultimately manifest itself in the form of regret down the road. Success and failure are are simply learning tools for future decisions we make. Thanks for commenting.

        • I think the difference is that you are not alone to assume your decisions once you have a family. When you are alone, you can easily quit your job and jeopardize what you have to follow your dream for example. Once you have a family, you do not only jeopardize your future, but your kids future. That’s something different.

          On the other side, having kids is the most amazing thing that ever happened in my life 🙂
          DivGuy recently posted…Build a Dividend Growth Portfolio in 6 Questions + a real exampleMy Profile

          • Hi DG,

            You are very correct in your statement regarding having a family or not. That’s one of the reasons I started my business at age 24 because it was just me. No wife, children or even home to worry about. Failure would only impact my life and I was OK with that. It’s different if failure can impact your family life though. Thanks for commenting.

    • Hi DG,

      I think it’s great that you can declare that you don’t have regrets. That certainly puts you in the minority of individuals and just goes to show that you are not afraid to take action no matter the outcome. That being said, I fully agree with you that once you start a family and have other responsibilities it may make your decision making process a little more difficult but still shouldn’t stop you from taking action one way or another. The key from all of this is to avoid the feeling of regret whether the choices you make succeed or fail. Thanks for commenting.

        • Hi DG,

          That’s good advice in general. That’s the point of this article, take action. Don’t be afraid to act or take a chance. Prior to regret the biggest distraction one feels before attempting something new or different is fear. Fear of failing. Fear of the unknown, etc. Conquer fear and you’ll have little future regret. Thanks for the comment.

  13. DivHut,
    This is a very good article about some of the mistakes we make. I can say that I regret not getting into stocks back in 2009 but then again I had no idea how the stock market worked. It amazes me that they don’t teach anything about the stock market in school. I am glad that I was able to learn and continue learning about investing in general. I definitely don’t want to be one of those guys that say I regret not putting more money into a KO or PEP! Thank you for the timely post.

    • Hi DM,

      Looking back seems to be humankind’s favorite past time. We all do it at some points in our life. The key though is when looking back one must be happy with the choices and decisions made that got them to their present self. Like you, looking back I should have piled everything I had back in 2009 in stocks. But that’s hindsight. I can be happy knowing that I stuck to my plan and did continue to invest in stocks throughout 2008 and 2009 following my monthly investment goal just as I do today. So in that respect I’m very happy with my past self for not panicking and selling when everything was down. Thank you for stopping by and commenting.

  14. Great post! It’s awesome that you took advantage and pursuit the internet business. Like you said, even now you’re seeing the cash revenue which is great. Too often we look back in our lives and regret things that we didn’t do. It’s important to take as many opportunities as possible so you don’t look back and regret it later.
    Tawcan recently posted…How to start dividend investing todayMy Profile

    • Hi Tawcan,

      Happy you have enjoyed this post. I think it’s important for all of us to examine all our selves (past, present and future) and realize that every choice we make will affect us in one way or another. There’s the saying that people mostly regret the things they did not do rather than the things they did do and I fully agree with that statement. I guess the trick is to always ask your present self what will your future self think when he/she looks back. I know when I buy into high quality dividend growth stocks I can see my future self being happy with my decisions today. As always, I appreciate your comment.

    • Hi Adam,

      As mentioned in other comments you can’t be too hard on yourself because hindsight is always 20/20. The key is to learn from those past experiences and take a different course of action when similar opportunities present themselves in the future. As we all know, a market correction is inevitable. Whether that occurs in the next month, year or decade it’s important to remember how your past self behaved and how your future self regretted your past self decision. As you stated the second best time to start anything is today. Thank you for commenting. Much appreciated.

  15. Great post. It brings up all types of different thoughts and feelings. One of these days, I’ll get around to writing up a similar post of my biggest motivator… Fear. Fear of uncertain future, Fear of not making enough money to support my family, just Fear of failing to pay off my debts and not live the life I want. The reason I’m like this stems from seeing my parents continue to struggle after the recession over 6 years ago. My dad was the sole breadwinner at the time in the mortgage business and that career essentially vanished when the housing market blew up. He now works at Lowe’s making just above minimum wage and my mom had to go back to work as a daycare provider. It has been tough on their finances and their relationship. I started investing because I never want to end up in that situation.

    I’m trying to make as much as I can while I can, save the most I can and lift the burden of not being able to support my family off of my shoulders.

    Thanks for the post!
    American Dividend Dream recently posted…401K Update – February 2015My Profile

    • Hi ADD,

      Regret, fear, insecurity, doubt are all related in some manner when looking at the decision making process each of us have to make going through life. I can fully understand where you are coming from not wanting to be in a similar situation as your parents as my family has gone through the same situation the last several years. Like you I swore to myself to never get myself into an unsustainable situation which partly involves living well within my means and really having an insanely large safety cushion if things really go south. It can be scary when one lives a life with lifestyle creep and over the years expenses can really get out of hand when compared to income. It becomes such a delicate balance that can be easily thrown off. Live large, fall harder, live small, fall softer. Thanks for sharing your story with us and your motivation to lighten your active income and slowly grow your passive income.

  16. DH,

    In that I have reached my sixties, I have had plenty of time to accumulate regrets. There are many, no doubt. After discovering DGI a few years ago, I chose to move ahead with it. I knew it would take some time to see results on the income side of things. If I hadn’t started the process though, I knew that 10 years into the future when I thought about how much income I gave up, I would yet again have huge regrets. I’m likely to have regrets in the future, but establishing a flow of dividend income is on the “no regret” list. Nicely written article.

    Dividend Gravy recently posted…Dividend Progress – 2014 Year EndMy Profile

    • Hi DG,

      I’m happy to see you on board the passive dividend income train and no doubt in ten and even twenty years from now you’ll be thanking your past self big time for the actions and choices you have made today. It’s perfectly normal for everyone to feel regret to some degree in their life. After all, we are faced with a number decisions every single day and often we don’t act on each rather simply kick the can down the road which eventually leads to a regretful feeling for not taking action in the future. Glad you enjoyed the article and look forward to reading your DGI updates.

  17. DH,

    Rage. When I was in college I was offered a 40k a year job with no benefits. But being an idiot I rejected the offer and told my boss I was going to try out for Army JAG….to learn my first lesson in life: You are not special nor the cream of the crop. After working at two low paying job, I finally got my current job…a 40k job not in my field.

    I dividend invest out of rage. I made stupid choices in life and now they’re coming back to bite me. I dividend invest to hopefully make the next mistake a lot less painful.

    • Hi TBDI,

      I have to say that your reasoning, rage, for not wanting to feel regret is definitely unique. In fact, I don’t think I ever heard anyone give that as a reason. Kudos for originality. After reading your comment I can understand why you feel the way you do realizing that, as you stated, ‘are not special nor the cream of the crop.’ I always held the belief that there will always be people smarter than you and ignorant than you. Richer than you and poorer than you. Healthier that you and sicker than you. I think you get the idea. The key takeaway is to focus on ‘you’ and not on others and take whatever course of action needs to be taken today to mitigate any potential future regret. Judging by your comment I think you are very set in making sure your future self will be as regret free as possible. Thank you for stopping by and sharing your experience.

  18. DH,

    It’s great to hear that you took action upon your idea to start your own online business. I’m sure every time you reminisce back to that point in time you are SO glad you took that leap of faith. Not many people are able to live a life without regrets since hindsight is always 20/20. I also have made decisions in life that I regret, but I just try to look forward and learn from my regrets and mistakes. Props to you on your decision to start your site!

    • Hi ACI,

      Your comment highlights a very healthy attitude towards regret and decision making, looking forward. Too often people feel regret and look backwards without realizing that a potential future exists to make things better. Like anyone else, I too regret certain choices in life but focus on the future and realize that looking backwards is always 20/20 which is not a fair outlook. I appreciate your comment and for stopping by.

    • Hi DFG,

      It’s true that sometimes our past choices don’t turn out the way we want but a key event occurred that should mitigate some of the regret. And that event was that a choice has been made. I would imagine the feeling of regret being compounded as a result of indecision. One cannot dwell on past occurrences rather look at the present with an eye towards the future and hope things work out. Dwelling on the past for any reason is never healthy and, as you stated, always leads to a feeling of unhappiness. Happy you enjoyed this article. Thank you for stopping by and commenting.

  19. DH, great article. I remember learning about human development, psychologically and how a lot of people end up bitter in their golden years. The reason was regret, I suppose a feeling of a wasted life. To me, I learned not to regret my decisions because in doing so I am somewhat rejecting who I am today. Since I love my life for the most part, it would be illogical for me to have any real regret. I of course have thought back before about wishing I would have done this or that differently, but nothing really too serious. The best part for me is realizing I have time to do almost anything I wish to do, the hard part is deciding exactly what to do. I’m glad to hear you made the right decision in following your gut, it seems to have served you well, all these years later.

    – HMB
    HMB recently posted…Stuffing MoneyBags – January ’15My Profile

    • Hi HMB,

      I think we can learn a lot from our elders. After all, who better than an elder to give you a long perspective on life. Regret often can make one feel bitter and sad and while we are still young it is our responsibility to mitigate these potential feelings by taking action so as to not feel regret in the future. We need to realize that it’s OK to be wrong and make a mistake. It’s not OK to be indecisive and later regret not taking a course of action. “Walk on road, hm? Walk left side, safe. Walk right side, safe. Walk middle, sooner or later get squish just like grape. Here, karate, same thing. Either you karate do “yes” or karate do “no.” You karate do “guess so,” just like grape. Understand?” – Mr. Miyagi. I think this quote says it all. Thank you for stopping by and commenting.

  20. What motivates me the most is people around me. When I was in an accounting firm, everyone was so amazing and inspiring. They still enjoy their lives but at the same time are very determined to achieve their career goals. Before I knew it, I became like them. Thanks for the great read!
    BeSmartRich recently posted…How to simply invest for dummiesMy Profile

    • Hi BSR,

      Whatever motivation works for you to not be regretful in the future you should use. I think it’s great that your coworkers had such a positive influence on you. You know the saying, “Tell me who your friends are and I’ll tell you who you are.” I think this applies here very much. Glad you enjoyed the read. Thank you for stopping by and sharing your thoughts.

    • Hi DD,

      Your comment highlights a great point that lessons can be learned from past blunders. I think it’s important to look backwards just not dwell on the past. You seem to have a very positive attitude about your future which will no doubt guide you to a brighter tomorrow. Keep looking forward and leave the feelings of regret to someone else. I appreciate your comment.

    • Hi IOT,

      Congrats to you on taking that leap to work for yourself. Your comment highlights exactly as I felt many years ago when I did the same thing. I figured, If I fail at least I tried and would not have any future regret and be bothered by the dreaded ‘what if’ question. Thank you for stopping by and sharing your story.

  21. A very interesting post there DH, thanks for sharing.

    However, for me, ‘regret’ is not my motivator and similar to Div Guy, I would go so far as to say that I pretty much live my life with no regrets. No sense for me in looking back and asking “what if…?” when you can’t do anything about what’s happened in the past.

    Of course, in my youth, I took various paths and directions that changed my life and at times, those choices were not the best ones I could have made.

    But even if the decisions were bad ones, I don’t regret any of them because they shaped me into the person I am now. If I make a wrong decision, I just try to learn from it and move on.

    I even had a similar situation you had when I was at uni – in my 3rd year, I was given the option to major in either the unknown and relatively new IT route or the safe Finance route. I took the Finance route, obviously not realising there would be a dotcom boom around the corner.

    What are my motivators? A combination of success and happiness.
    weenie recently posted…Chinese New Year and PredictionsMy Profile

    • Hi weenie,

      I think it’s great that you can say you pretty much live your life without any regrets. There are very few people that can state that. You also have a healthy attitude about not dwelling on the past as there is really nothing you can do to change it and at the very least you should just use the past as a learning tool. You seem to have a good grasp and attitude in your life. I can see that your motivation will have you reaching for greater successes in the future. Thank you for stopping by and commenting.

  22. Great post, DH. Regret is an extreme motivator for me as well. No matter what it is, if you don’t take a chance that’s really tugging at you, you could always fall back to it in the futre and say, “Damn, what if?” This is a big thing in my life right now, as I decide to balance the direction in where I am going. Do I want to invest most of my cash into my Roth? 401k? Dividend portfolio? Do I want to take a higher but more desirable risk and spend a bigger amount of cash to start a small gym/personal training business, or perhaps make a purchase on my first home and plan to rent it out for income down the road? All of these questions, and no matter what happens and what choices I make, there will always more than likely be a shred of regret with one or the other, regardless of whether or not I made the choice or not. Definitely opens your mind and makes you think.

    Good post and I wish you the best –

    • Hi Bloodstone,

      I’m happy you enjoyed this post and got something out of it. The dreaded ‘what if’ question seems to haunt most people at some point in their lives. As you stated, regardless of whatever choice you make there still may be some small factor of regret but take solace in the fact that you had the nerve to make a choice in the first place. I think indecision is probably the worst form of regret that one can experience in the future. The bottom line, as I quote Mr. Miyagi in another comment, “Walk on road, hm? Walk left side, safe. Walk right side, safe. Walk middle, sooner or later get squish just like grape. Here, karate, same thing. Either you karate do “yes” or karate do “no.” You karate do “guess so,” just like grape. Understand?” I think that statement is very telling. Either do or do not and deal with the consequences later. As always I appreciate your comment.

  23. Keith,

    Thank you for sharing your story, very inspirational. While I don’t have regret as my main motivator, I definitely understand where you are coming from. The feeling that my future self has to miss out on something great simply because I’m too lazy to get off my butt or because I made a bad decision would kill me.

    I wish you could share your online venture with us!

    No More Waffles recently posted…The Case for Health Care StocksMy Profile

    • Hi NMW,

      Always happy to hear that my words can provide some inspiration to others. The general question of what motivates an individual is very personal and while regret is a big pusher for me I can understand other reasons for motivation for others. As you know, I always look at my future self and ask if he’ll be happy with the decisions my present self is making. If I can envision a happy future self it will mean I’ll have little or no regrets when looking back.

      To answer your question about my online venture I can tell you that I started an online video on demand service. It was a time when streaming video was jerky, postage stamp size and fuzzy. Granted we started small but as video compression improved and broadband penetrated more homes our business grew. Thank you for stopping by and commenting. Always appreciate the support.

  24. Great post. I never worry about failing because to me, when I fail at least I tried. When I regret it is because I never tried in the first place and then I have a 0% chance at succeeding. At least if I try, I have shot at succeeding, even if I also have a shot at failing.

    • Hi MSG,

      Well said. Your comment highlights exactly as I feel which is why regret is my motivator more than anything else. I can accept success and I can accept failure. I cannot accept regret for not even trying. Thank you for stopping by and commenting.

  25. Great post! I’d almost say that your quality of life (and I don’t mean in a material sense) in determined by whether your fear of regret is greater than your fear of failure. My greatest regret, in the context of achieving financial freedom, is not starting sooner. I remember putting off investing for almost two years because I was too lazy to research stocks (I had important video games to play!), letting the money sit in CDs that I knew weren’t earning anything. All of that was taken care of by the time I was 29, but I still wished I started earlier. I could only imagine how far along towards financial freedom I would be.

    ARB–Angry Retail Banker

    • Hi ARB,

      I think your desire to invest earlier is a sentiment that everyone shares. Better late than never of course and as long as you are looking forward and not stuck lamenting decisions of the past you’ll be just fine. It’s funny how often we look back at our past lives and realize how much time/money/energy/resources was wasted on nonsense. As always, I appreciate your comment.

    • Hi DC,

      Thank you for your kind words. I think it’s important for our present selves not to forget that one day we’ll have a future self looking back and wondering if our past self made the right choices in life. At least now you can realize that law school was a good choice for you and regarding CAT, I wouldn’t worry too much. CAT is a classic cyclical player that goes from boom to bust cycles every few years. I’m in the same boat with you and all I care about is that the dividend is maintained. In the meantime, I won’t fret and just get paid to wait. Thank you for commenting.

    • Hi DC,

      Everyone thought it was the end of the world for TGT at the time. Think about the world economy growing again in a few years and you may regret not buying more CAT. Thanks for commenting.


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