Regret and Hope

My feelings while engaging in investing, seem to exist on the spectrum between these two extremes:


I've only been investing outside of my 401(k) for a couple years. Once I started (a year before turning 40), and began understanding what I was doing, my initial feelings, beyond the initial excitement of "getting in the game", were feelings of regret.

I was virtually kicking myself multiple times for starting this so late.

First off, by this time I could have had a much bigger portfolio, paying much higher in dividends by now, if I had started upon employment after college. I might even be close to that early retirement number by now.

Second, I think of all the money up to this point that was spent on nonsense that is either gone down the drain, or tied up in things that are sitting in my place of residence that I no longer use (my girlfriend and I will be soon starting a de-cluttering activity for my place to rid myself of such items).

Now, I understand that one ought not to live in the past, but it is oh so difficult not to do, when I see the current opportunity in front of me. The opportunity to earn income just by doing some research on companies and making the right choices on which ones to invest in. Plus, the opportunity for that income to grow just by these companies choosing to increase their dividends, essentially giving you a raise, much higher than you would get in a typical job. It can be intimidating when looking at the small payments now, knowing that they could have been much larger by now, and comparing them to the value needed to cover my expenses to be able to reach financial independence.

Instead of this I chose to chase a couple of business opportunities and was too naive about it and sunk lots of money into them as well as other things with very little to show for it (I actually ended up in the red for years, even bleeding my 401k at the time, before digging myself out, which definitely slowed any progress I could have made)

I constantly think of all the compounding I missed out on. Although, not constructive at all, I keep thinking what might have been.


Then on the other hand, now that I have been investing for a couple years (this is outside of my 401(k), I actually restarted my 401(k) investing about 5 years ago), and am starting to see some real momentum, my dividend train is picking up steam. I have also been seeing some good capital appreciation (then again, who hasn't in this current bull market?).

I still have a good 25 yrs until the conventional retirement age. I have been recently able to max out my 401(k) contribution, and next month I anticipate a personal best in crossing the $100 threshold in dividend income. So I definitely have hope for the future, as I see things building up.

Though I continually have thoughts of what might have been, I also have thoughts of what could be for the future.

I have a good 25 years from this point to compound, but am thinking I might be able to get it done within 15 years as I have been able to build up my savings rate to just below 50%. I am also looking at potential side hustles to add income to help move things along. At this point, I am very hopeful and faithful that I will get it done. I am also getting better at saving, understanding necessities vs. wants, and trimming down what I spend in a typical month.

As I become more knowledgeable about my investments and money in general, I think proceeding in a better than linear fashion with respect to income and overall poftfolio value is very possible. I'm excited now to see how this turns out!

On this "Regret vs. Hope" spectrum, I feel like I am now slightly beyond the midpoint, headed toward the side of hope. With each increasing month of dividends received and other positive developments, however, I am moving ever so much closer to that "Hope" end of the spectrum, leaving a little bit of regret behind.

Somehow I feel I am not alone in this, as we all have made mistakes in our younger years which we might regret, but are making amends for better future. Am I right?

Where are you on this Regret vs. Hope spectrum?

Let me know about it in the comments below.


  1. You are correct that you are not alone and if anything far from alone. I am 48 now and went through a similar process of regret & hope abut a decade ago.

    In regards to where do I fall in that spectrum today, fortunately I moved beyond that spectrum and now my regrets have become experience and hope is replaced with controlling my future.

    It took me awhile to figure it out but regret & hope are emotional and emotions are something you want to strive to eliminate from investing decisions.

    At least you are not wallowing in self pity and trying to take control. This is a great step and keep it up!

    1. Great points Ken, I see your point about these being emotions and not allowing them to cloud investment decisions. I have used my past blunders as lessons learned, and pushing forward. Thanks for the comment!

  2. Realize mistakes will happen and put it behind you. You will make more but you are in the game. I used to beat myself up constantly but no more. As my portfolio has grown the hope took over ! Good luck !

    1. Thanks PandP, great point. I can feel a real momentum now, and am super excited to keep it going, thanks for the comment!

  3. Look forward not backward nothing you can do about the past but keep investing. Once you hit a certain point those wasted years will mean nothing.

  4. Look forward not backward nothing you can do about the past but keep investing. Once you hit a certain point those wasted years will mean nothing.


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