Lessons Learned About Setting Goals

It is that time of the year.  To me, December means finishing out the year strong, racing towards the finish line, and setting the table for a successful year going forward.  For the last few weeks, I have been thinking long and hard about my life, investing, and our blog goals.  What should I focus on?  Where should I be at this point next year?  Questions like these have racing through my mind and I am trying to process and make sense of them all.  I’ve been thinking a lot about the goals I have set from the prior year and trying to leverage them as much as possible, including both the successes and the shortcomings.  I thought it would be helpful for me, and hopefully some of you, to write down my thoughts and lessons learned over the last few years about setting goals.   Time to dive in.

Before I set in, I thought I  should mention this to all of you that are new to the “setting goals” process.  This is an acquired task for me and my first ever formal goal listing was in 2014.  Of course, you guessed it, it had coincided with the founding of our website.   That’s when I saw the light.   I found the goal setting process was extremely helpful in the beginning stages of my portfolio, forcing me to focus , buckle down, and push my portfolio/dividend income higher and higher.  I was determined to hit the mark and I had fun along the way.  Aiming for a certain benchmark was way more fun than the “Well, I feel like investing now” approach I had taken earlier in my investing career that saw my dividend income grow sporadically.  Once I started setting goals, my income grew steadily…exactly how I like it.  Now, setting goals is second nature to me and a process that I look forward to annually.

The following lessons have been on my mind a lot recently, as I mentioned in the introduction.   I’m trying to use my past experiences as much as possible to help shape the goals of the future.  A goal might seem like an amazing idea at the time, only to find yourself asking questions two months later such as “Who was I kidding?” or “What on earth was I thinking?”  There will be amazing goals that you set every year and there will be duds.  Just like investing and the rest of life, it is going to happen.   The important thing is taking the right lessons from your experiences and using those experiences as a foundation for better ideas.   Here are the lessons that have learned about setting goals and this amazing process.  I’m going to try to keep the clichés to a minimum here, but just a heads up, there will be several throughout the article.

Lesson #1: Focus On What You Can Control – This was the very first lesson I learned in the goal setting process.  I think your goals should be focused on actions you can control.  An easier  way to explain this will be to discuss how this impacted me.  The first time I set investing goals for myself, one of my goals was to end with a portfolio market value in excess of a certain dollar amount.  I thought that I could achieve this goal by trying to invest as much as possible and watch the market take care of the rest.  WRONG.  I was close to hitting this mark, and you guessed it, the market started to turn south.   Come November, knowing my cash balance and the funds that would be available pver the next couple of months, I had the realization that the only way I was going to cross this mark was if the market would start to appreciate… a lot.  There I was, victim to the market, having the helpless feeling knowing that there was nothing I could do to change the result.

That’s what I am referring to with this lesson, and it doesn’t apply just to investing either.  In order to succeed and achieve this goal, I was dependent on forces that I could not control.  I hated it.  When I reflected on why I was not able to cross the certain market value, I realized the flaw in the logic. The purpose of setting the goal to increase my market value was to increase the overall size of my portfolio (obviously).  In an overly simplistic picture, I realized there were two ways my portfolio was going to increase: by investing more and by market appreciation.  Which one of those methods did I have complete influence over?  The answer is obvious.  That’s why I changed my thought process when I set my goal for the next year.  Rather than aiming for a certain market value, which needs a healthy dose contributions and market appreciation, I instead focused on trying to invest certain dollar amount in the market over the next twelve months.    Transferring cash into your investing account is a goal that you can control and hitting that mark is completely dependent on your ability to save money to invest in the market.  To me, that was a much more solid goal than the previous year and made a huge difference.

Lesson #2: Push Yourself – I think the best goals are the ones that are difficult to obtain.  What’s the point of jumping over a hurdle that is barely off the ground? What’s the point of setting a goal that you know you can achieve with minimal effort?   You should be pushing and sweating every step of the way.  If you set a goal to invest a certain amount of capital during a year, then you should still be trying to figure out how you are going to scrape together the last few dollars to hit that goal.  If your goal is  run X number of miles during the year or have X number of steps, you should still be trying to hit that mark through the end of the year.  You shouldn’t set the bar so low that you run enough miles by the end of June and are sipping drinks on the beach for the last six months.  Push yourself, force yourself to be uncomfortable.  If you want it bad enough, you will find a way to make it happen.  That is just a part of human nature.   Lanny and I were having a discussion about our 2017 blog goals and we stumbled on the ultimate cliché/quote that inspired us to increase our targeted income by a significant of dollars.  “If you aim for the moon and miss, you’ll land among the stars.”

Lesson #3: Make Sure It Is Achievable –  This is a perfect follow-up to the previous lesson.  A goal should be challenging. A goal should make you push yourself.  But in the end, you have to be able to achieve the goal or there has to at least be a realistic chance that you can accomplish the goal.  If you set too ambitious of a goal, what’s going to happen when you realize after one month that there is no way you are going to achieve it?  To piggy back off of the last example, of course Lanny and I would love for our website to earn $10,000,000 next year.  Could that be a goal of ours? Sure.  Would it be effective? No, considering we would learn after one day that the likelihood of that occurring next year.  But that didn’t stop us from pursuing a super aggressive income total that we know we can achieve with enough hard work and dedication  (No, I won’t spoil that amount for you in this article – sorry folks).   You need to push yourself, you need to aim high.  But you need to make sure that you can get there.

I’ve given you examples so far of goals that involve a lot of numbers, so I wanted to apply this to one of my life goals from 2016.  When I set my goals, I entered the process thinking that I wanted to begin the process of re-teaching myself how to play piano.  Through high school, I practiced daily and was pretty good by the time I graduated.  Then, well, life happened.  I stopped practicing as frequently and my skills fell off a cliff.  I miss it tremendously, which is why I decided to set a goal that involved playing piano.  When I set the goal though, I wasn’t honest with myself.  I had the image in my mind of me playing at my peak level, not my current state.  My goal wasn’t simply to re-learn how to play.  My goal was to teach myself a song that I could barely play back in my prime.  If I couldn’t master this song when I practiced an hour or two every day after playing for ten consecutive years, why on earth would I be able to learn this song when working full-time, blogging, and trying to live the normal adult life?  OF COURSE I FAILED.  I didn’t set myself up for success because I wasn’t honest with myself and set the bare astronomically high.  The problem wasn’t the concept of the goal, because I really wanted to play piano and get back in the habit of playing piano.  The problem was that I was aiming for something that I had no chance of achieving.  I should have found a difficult, achievable goal instead of an impossible one.  Let’s just say I am hopefully going to correct this when setting my goals for next year.

Lesson #4: Allow Flexibility and Don’t Box Yourself In – The title of this lesson probably sounds different from the message I am trying to get across.  I’ve made mistakes in the past where I created goals that were so specific/so narrowly focused that I would have been engaging in an action just to satisfy the goal whether or not that was the correct decision at the time.  Hopefully that makes sense.  For example, one of my goals last year was to investing in two dividend stocks with yields below 2%.  In order to achieve that goal, I would have had to purchase stocks that were overvalued and didn’t meet the normal metrics of our stock screener or were not necessarily the best deal at the time.  Looking back, I should have set my goal as “invest in two stocks that are below my portfolio’s dividend yield” or something that would have provided me with more flexibility.  I know this isn’t true for all goals and sometimes being specific is the right answer.  But in my brief goal setting history, I don’t think I have accomplished a goal that forces one activity.  Please let me know if you have had a different experience.

Lesson #5: Have Fun – I’ll end with the simplest lesson I have learned…have fun and set goals that you are going to enjoy battling for over the course of a year.  I promise you that you will be more motivated, determined, and more likely to achieve the goal if you are having fun along the way.  Life is too short to force yourself into actions that are going to make you miserable.  So enjoy the ride and the journey,

Hopefully you find these lessons helpful as you set your goals for the coming year and many years going forward.  I know we all have different lessons, pieces of advice, or tricks of the trade we have learned over the years.  So please, share your stories and lessons in the comments section so we can all learn from each other and set the best goals possible!  I can’t wait to read your comments.


12 thoughts on “Lessons Learned About Setting Goals

  1. Great article, Bert. I really enjoyed Reading it.
    I think that all those lessons are important but at the same time, I think the most important one is lesson 5. As long as you have fun doing something, it will come to you more easily even if the underlying task is actually challenging. I think that Warren Buffett calls this ‘tap dancing to work’.
    Regarding lesson one, there is this great zen flow chart (you can google for it) it goes along the lines of when there is a problem you have two options:1) the problem is within your control, so you can do something about it meaning go ahead and do it and don’t worry. 2) the second option is that it is out of your control, so don’t worry about it.
    Either way, great article. Thank you for sharing!

    • Thanks DIB,

      I just looked up that chart and it summarizes Point #1 exactly. Too often I feel like we find ourselves trying to find ways to solve problems that we cannot control just for the sake of doing it. I’m sure it is harder to distinguish whether or not you can do something about it though in the heat of the moment, especially if you are convinced that you can figure it out.

      Appreciate the compliments about the article. Very kind. Have a great weekend.


  2. This time I think “Lesson #4: Allow Flexibility and Don’t Box Yourself In ” resonates with me. This ability to be flexible when things are coming at you and turn it into an opportunity is a great tool to have. I was setting a goal to achieve “dividend income”, but I ended up achieved “passive income” by having the real estate property totally manage by someone else, but it 5-10x more in passive income for the years to come with the same amount of money invested. The willingness to adapt is key. 🙂 Although, I’m looking to get back into stock soon after everything is settle.

    Great advices!

    • Vivianne,

      Great story. Its funny how much changes in a short period of time. You do your best to map everything out and put together a stable path forward. But ultimately you need to be able to adjust when a change emerges. You are in a better position today than you were yesterday because of it.


  3. Great post, Bert. I’m relatively new to the goal setting process so those tips you gave are great. I think setting goals that are realistic, that you have control over and that are fun are the most important aspects but all of your points are valid. Looking forward to reading about your goals for next year.

  4. Yea setting goals that are realistic is a must. I set a dividend goal late this year without really looking into whether I had a shot in of hitting it(I don’t) and I know for sure I’ll be a bit more realistic with my investing and life goals next years. This’ll be the first year I’ll have real life and investing goals I’ll set for myself and I hope the blog helps me follow through on them!

    • Time in the Market,

      You have to be able to accomplish the goal. It can be challenging as heck, but you still have to be able to cross the finish line. I’m excited to see what goals you set for yourself this year. Blogging is a huge help, especially for investing goals, because you are documenting your every move. Plus, all the other people you are interacting with serve as great motivation. It becomes very contagious, especially with everyone cheering you on along the way!

      Thanks for the comment!


  5. Hi Bert,
    Lots of good advice there, thanks for writing it up. #4 stuck out the most for me as I’m always hesitant of goals which drive specific investment purchases. Similar to the low yield goal you mention, a goal to generate xx level of dividend income might drive a late-year spending spree on high yielding stocks to beat the goal. So I suppose I end up at goals driving how much money should be invested whereas your investment strategy / plan dictates how the money is invested.
    Best wishes,

    • DL,

      Thank you very much! You mentioned the risk of the dividned income goal right there. It isn’t worth achieving the goal if you are sacrificing quality along the way. Sure, you will hit that goal in 2016, but 2017 may see a huge step back. Imagine if you wanted to hit that goal last year, saw KMI’s stock price falling and their juicy dividend yield increasing, and deciding to jump in and accomplish your goal. Heck, they said they are trying to increase their dividend 10% annually through 2020, seems like a great investment. Then, the rug is pulled out from you, the dividend is slashed, and you are now miles away from your goal. So yes, the goal is garbage if it forces you to chase yield and forget about the quality of the dividend income stream.

      Enjoy your weekend!


  6. Hey Bert,

    Another point I’d like to add about goal setting, make sure your goals are measurable and have a time frame against them. This way you can track progress.


  7. I’m with you on finding the balance between pushing yourself and finding something achievable as well. I gave myself realistic and then enormous stretch goals. I think even seeing the big goals out in cyberspace is helping me achieve them.

Leave a Reply

Your email address will not be published. Required fields are marked *