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Year End Self-Assessment – This is a Tough Love Article!

Another year of your life has just passed. Are you happy? Are you prosperous?

Are you happier than a year ago? If not, why not?

Are you more prosperous than a year ago? If not, why not?

If you answered “no”to a question above, you should take this article very seriously! How seriously? So seriously that you will stop reading right now, get a pen and paper (or open a new Word file) and start writing answers to questions that should motivate to make the changes in your life you probably know you need.

If you are not willing to write down the answers to the following questions, stop reading right now because this article is an absolute waste of your time! Just know that “if it ain’t writ, it ain’t thunk!”

If you write your answers in a Word file, simply copy and paste the questions below, then write your answers in bold red font. Do it now!

Let’s start with your financial situation, then we’ll move on to your personal life. Be aware that these questions are not meant to be comprehensive and I am not a licensed financial advisor, marriage counselor or anything else that requires a license, so I am not providing any type of advice, just friendly questions for your own introspection.

Prosperity Questions for Self-Assessment

  1. Did your income and/or net worth increase by year-end this year compared to year-end last year?

  2. If so, by how much?

  3. If you do not know your numbers for this year and last year, why not? When you write down the answer to this question, you will come to a very important realization about why you are not making the progress you deserve.

  4. If your answer to Question 1 was ‘no’ (i.e., your net worth and income did NOT increase from a year ago), then why not? Be honest and write as much as you need to make your case for ‘no’ that cannot be torn to shreds by your coach.

  5. If your net worth increased from year-end last year to year-end this year, congratulations! If that net worth increase was less than $100,000, why?

  • Was it because you didn’t have the skills? If so, why didn’t you get the skills in the past year? Are you willing to vow to yourself to acquire those skills in the coming year? Really? Are you going to do it? For real?

  • Was it because you didn’t have the resources? If so, write down a list of potential sources for funding. If you have no idea how to approach this, consider options such as partnering, private lending, hard money loans. There is a lot of money out there waiting to be deployed and if you don’t know where it is, you need to learn that. Are you going to learn that in the coming year? For real? Write down your answers or stop reading right now!

  1. Is your active income (such as from a job at which you actively work) enough to cover your living expenses? If not, then why not? What do you need to do to increase your income to the point that you can cover your living expenses? Write it down now or stop reading!

  2. If your active income is enough to cover your living expenses, do you have passive income? Passive income is income that flows into your bank account with little to no ADDITIONAL work by you after having done the advance preparation work to generate passive income. Examples of passive income are social security payments if you’re old enough, rental real estate, private lending (as the lender), buying discounted notes, generating royalties from creative work (music, writing books, streaming video training), pension payments if you’re old enough and a wide variety of passive income generators.

  3. If you have passive income, is it enough to cover your routine living expenses plus 30% cushion? If not, then what do you have to do to reach that level of passive income?

  4. Do you have a liquid emergency fund that can cover your next big financial event? Have you even estimated how much liquid emergency fund you need for things like non-covered medical expenses or happy events such as your kid’s future wedding or college?

  5. Is the liquid portion of your net worth sufficient to cover most reasonably anticipated special expenses such as medical emergencies, vacations, car down payments, kids’ college, etc. If not, then write down what you must do to build the liquid portion of your net worth to cover most reasonably expected special expenses (be aware that medical expenses that are not covered by standard Medicare are estimated to average about $260K per couple after age 65).

  6. Is more than 75% of your net worth invested in only one investment category such as stock market, real estate, bonds, precious metals, etc.? If so, write down what would happen to your financial security if that investment category drops 30% in value. Would you be devastated financially?

  7. Write down the percentage of your net worth that is liquid and the percentage that is not liquid.

  8. Write down the percentages of your net worth that are in each investment category such as stock market, real estate, bonds, cash, precious metals, private equity, etc.

If you are having any trouble with these questions, you should watch the video in our Smarter Investing home study course shown at If you don’t care enough about your future and are not willing to adequately invest in yourself to buy this extremely valuable training, then at least invest your time to read the article at

Happiness Questions for Self-Assessment

  1. On a scale of 1-10, what is your general happiness level? Be aware that we will be coming out with an app “Be Happier” that will actually measure your happiness level on an ongoing basis. The goal is to serve as a roadmap with measurable milestones for how to improve your happiness from where you are today to where you want to be at a defined point in the future. If you are interested in this app, please contact Marc Halpern to be notified when the app is public and/or if you want to be a tester for the app before it is formally launched.

  2. Are you happy in your relationships?

  3. If not, which relationships can you “fix” (through counseling, intervention, therapy, simple discussion, etc)?

  4. Which relationships can you live with?

  5. Are there any toxic relationships in your life? If so, can you disengage SAFELY from any of those relationships?

  6. What are the sources of happiness in your life? Write them down or stop reading.

  7. Can you increase the time you engage with those sources of happiness? Write down practical changes you can make to invest more time in happiness activities. It can be as simple as listening to music or audiobooks during your travel to work.

  8. What are the sources of unhappiness in your life? Write down what you can do to SAFELY minimize the sources of unhappiness in your life. For example, do you waste too much time arguing with your significant other? Let’s say that you are a real estate investor and you have certain tenants that cause you aggravation, do you file for eviction promptly when they violate the lease?

  9. Sometimes, unhappiness is beyond your control, such as the death of a close family member. Even then, sometimes you can find meaningful activities in which to engage that can help mitigate some of the unbearable loss. It’s not easy. For example, my father’s parents were murdered when he was a teenager and he was put into slavery for 3.5 years. Upon his liberation from slavery, he dedicated his life to making the world a better place through teaching over the next seven decades.

  10. Do you enjoy your primary occupation? If not, in which occupation would you like to engage on a daily basis that you would enjoy, if money was not a barrier? Then write down the barriers to engaging in an occupation that would greatly enjoy.

Again, this is far from a comprehensive list and I am not a licensed advisor of any type, so no qualified advice is being given here. These are simply questions that provide food for thought, especially if you are one of those people who make new year’s resolutions on January 1st and toss them aside on January 2nd. It’s your life. If you want to live life to its fullest, you should really take a hard stop and think strategically about what you are doing.

If you took these questions seriously and wrote down answers to the toughest questions above, take this one step further and add your own questions to customize a plan for your personal situation since your life is unique and different from everyone else’s life.

This time of year is the perfect time to reassess your basic assumptions in your strategic life plan for happiness and prosperity. Most of you don’t even have a written strategic life plan, yet you spend 99.999% of your time executing that plan that doesn’t exist. That makes no sense. You do want to be happy, don’t you? You do want to be prosperous, don’t you?

If you read this whole article and did not write down anything, shame on you. It’s your life. Stop wasting decades of your life like most people do. But in the end, it’s your choice.

If you want to review the answers to your questions or even if you are just looking for an accountability coach, check out the 1-on-1 coaching services offered at

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