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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?