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How To Set and Achieve Measurable Goals for Simultaneous Happiness and Prosperity

by Marc Halpern, Part Time Investors LLC

June 15, 2024


In preparation for the “Offshore Goals Retreat” (Nov 10-17, 2024) during which I will be presenting advanced strategies and practical guidelines for setting and meeting your goals for simultaneous happiness and prosperity, I created some very simple tools that will help you:

  1. Define your needs and wants to achieve happiness.

  2. Differentiate between those needs and wants that require not much more than changing your mindset and those that require more significant resources such as additional cash flow and/or additional net worth.

  3. Making purposeful investments that match the amount and type of resources you need to engage in activities that you enjoy without causing harm.


One purpose of this article is to help you focus with clarity on your endgame goals while preparing you for your customized practical path to reach those goals.


The second purpose of this article is to help you prepare material customized for your personal situation that you will use in workshop sessions that I will conduct offshore in November 2024 and onshore starting in 2025.


Happiness Goal


It is essential to start this discussion by stating how to set the overarching measurable goal for happiness. The measurable goal for achieving happiness is to MAXIMIZE THE NUMBER OF SECONDS THAT YOU ENJOY WITHOUT CAUSING HARM TO YOURSELF OR OTHERS from this moment until the end of your life.


You can learn the full details about the definition of happiness and how to measure happiness in my book “Now Be Happier” available on Amazon and described in my TEDx talk “How to Measure Happiness and Be Happier.”



List of Activities You Enjoy Without Causing Harm


Since the goal is to maximize the number of seconds that you enjoy without causing harm, the first step when setting this goal is to IDENTIFY every activity that you enjoy that does not cause harm. That includes activities that you anticipate you will enjoy at any time in your future life. It is crucial to compose this list of activities that you enjoy since we need a target to shoot for or else we will be leaving unrealized enjoyment on the table and never even know it.


For that reason, you should really invest at least 15-30 minutes writing down every single activity that you enjoy to any degree whether it is daily (reading?), occasional (going to a concert) or once-in-a-lifetime (skydiving? travel to the North Pole?). Don’t be surprised if you add 100 activities to your list of things that you already enjoy or plan to enjoy in the future on your bucket list.


After you create your initial list of activities you enjoy, be sure to add to your list additional activities you enjoy as you think of them. For those of you who will participate in the “Offshore Goals Retreat,” take the list with you during your two days on shore in Bermuda and add to your list since you will be in such a relaxed state of mind that you will likely come up with more activities you enjoy that you should add to  your daily list as well as your bucket list. 


Get creative! Did you include overseas travel? Did you include celebrating your 50th anniversary with your life partner? Did you include writing and publishing a book? Did you include changing your occupation to the one you always dreamed of?


Ask yourself what enjoyable activities should be on your bucket list.


At the same time, don’t forget your routine activities that you enjoy. Did you include daily meditation or prayer? Did you include winding down watching your favorite sitcom at the end of a long day at work? Did you include consensual relations with your partner? Did you include eating a good meal? Did you include exercise? Did you include reading to your kids at bedtime?


The list of activities you enjoy MUST meet the criterion of not causing harm to yourself, to others or to the environment. For example, having a couple of beers with your friends is enjoyable, but drinking too much to the point of intoxication is NOT OK for this list because it could cause significant harm to you or to others by bad behavior.


Enjoying your work is great but if you work so hard that it often reduces your quality time with family, then you must recognize that you are causing harm. Another example of activities you might enjoy that could cause harm includes posting on social media that can be enjoyable but cyberbullying or politically attacking others on social media cannot be on your list because it causes harm to others, even if you derive some sort of twisted satisfaction from this activity.




As you probably know, goals must be measurable so that we can know if and when we achieve our goal and be able to monitor our measurable progress along the journey to achieving the goal. You have probably seen the acronym SMART for goals that must be 1. Specific, 2. Measurable, 3. Achievable, 4. Relevant and 5. Time-defined.


The question is how can we set and achieve SMART goals for happiness that include quantifiable metrics?


As I explained in the book “Now Be Happier,” a key component of your Happiness Score is measured by the time during which you are engaged in activities that you enjoy without causing harm. I use the word “INVEST” time to describe time during which we are engaged in an activity that we enjoy without causing harm. We even have an app for iPhone “Be Happier” that keeps track of the number of seconds that you are INVESTING = enjoying without causing harm. Download “Be Happier” from the Apple App Store here.


We found that it is very practical to measure happiness by aggregating the total time we are INVESTING = engaging in activities that we enjoy without causing harm. Thus, we can set a SMART goal for achieving happiness and actually measure progress.


The app “Be Happier” provides the ability to track the amount of time you INVEST in each of the activities that you enjoy that do not cause harm that you add to your list. You can also choose to aggregate the time you INVEST without entering the details. It’s up to you.


To be sure, you do NOT need the app “Be Happier” to measure and track your Happiness Score and I write a dedicated chapter in the book to this entitled Chapter 17: How to Track Your Happiness Score Manually.


I would like to introduce here a concept for goal setting that I have not disclosed before that helps integrate goals for prosperity with goals for happiness.


The new concept relates to the fact that some goals require resources beyond mindset, time and discretionary money.  So, we will now divide activities into two additional categories:


  1. Activities that require mostly mindset change

  2. Activities that require additional non-discretionary money to perform


Activities That Require Mostly Mindset Change


The content of the book “Now Be Happier,” already covers setting and meeting measurable goals for happiness that only need a mindset change to be achieved. Please refer to the book for the highly detailed descriptions of how to increase your happiness:

·       in relationships

·       at work

·       in health

·       in self-actualization

·       in spirituality

·       in community

·       in other life activities


Activities That Require Additional Non-Discretionary Money


In the years leading up to the real estate bubble that burst in 2008, there were quite a few gurus who created late night infomercials about real estate investing, especially for rentals and flips. Many of these informercials were filmed at upscale resort locations with palm trees in the background and often featured the guru riding up in a very expensive luxury car. In one of the infomercials, the guru wore a Hawaiian lei (wreath) over his suit. The message was always very clear that you will achieve great riches by investing in real estate.


While the imagery of “rich” or “filthy rich” was prominently implied in these promotional videos (sometimes explicitly using those exact words), the concept of “rich” was never defined.


The underlying qualitative concept is that if you are filthy rich, you can BUY WHATEVER YOU WANT. I am suggesting here that we approach the notion of prosperity by first defining WHAT DO YOU WANT? Once you actually know what you want, you can set SMART quantitative goals then figure out a well-defined and efficient path to achieve the SMART goals.


In other words, instead of starting down a path to accumulate an unknown number of millions of dollars that can buy a bunch of unknown toys, it is a lot more efficient in terms of both time and money, to know what you want and how much it will cost, then pursue the targets. On top of that, not everything you want needs a huge pile of cash. Some things do, but some things need a steady stream of cash.


The figure below shows a practical set of steps to:

  1. Define what you want based on activities you enjoy that do not cause harm.

  2. Differentiate between those activities you enjoy that require only a mindset change and those that require additional resources beyond your discretionary income or net worth.

  3. Further identify which activities can be done if you just had some extra cash flow and which ones require an additional big pile of cash.

  4. Choose between active, passive and semi-passive investments that are specifically targeted to match the needs for additional cash flow and/or additional liquid net worth.



Once you set specific quantitative goals for the activities you enjoy that are differentiated by requiring additional cash flow or requiring additional liquid net worth, that is the best time to determine whether you are in a position to target meeting those goals through active real estate investing or passive investing.


Active Real Estate Investing Versus Passive Investing


Active real estate investing is often more appropriate for newer investors who don’t yet have large net worth OR for veteran investors who want to maintain direct control of their investments and/or are resistant to change and/or enjoy managing tenants, contractors, code officials, property managers, etc.


Passive investing is often more appropriate for veteran investors with a higher net worth (often with accredited investor status or higher) who are tired of managing tenants, contractors, code officials, property managers, etc.


Active real estate investors often use rentals for incremental cash flow in the short term and large growth of net worth in the long term or flips for short bursts of smaller increases in liquid net worth.


I was able to achieve financial freedom without driving myself crazy by buying only 1-2 single family homes per year, mostly rentals and flips, when I was an active real estate investor before I transitioned to passive real estate investing in private placements. I teach efficient active real estate investing in my Smarter Investing home study course. My course is particularly suited for part-time investors who, like me, have primary occupations outside of real estate.


I successfully made the transition from active real estate investing to passive real estate investing by exiting single family home investing and redeploying the proceeds into private placement investments. I still have two single family home rentals left, so I haven’t totally exited single family home investing, but I must say that life as a passive LP (limited partner) investor is sooooo much easier as a daily lifestyle. I teach passive investing in my course “High-Return Private Placement Investing: Best Practices & Risk Management.


Truly passive private placement investing is best executed after performing DEEP due diligence, mostly for effective risk management that results in higher returns. That is why I founded the DEEP Due Diligence Mindset Club, currently with 56 private investors who organically form teams to perform DEEP Due Diligence before investing in private placements.


Passive private placement investing is effective for generating both cash flow and net worth. Learn more about this in my article “Strategy for Managing a Private Placement Investment Portfolio: Income & Growth Considerations.”


The most tax-efficient path I took in building my cash flow and net worth was investing in single family home rentals and flips using my self-directed Roth 401(k). “Roth Tracks” is a turbo-charged path strategy for making the transition from single family home investing to truly passive private placement investment investing. A track is a sequence of real estate investments that roll over the proceeds from one investment to another and executing this strategy with a tax-free Roth account is extremely powerful! I teach this strategy and execution in my lecture “Smarter Investing Using Roth Tracks.” As I show in this lecture, I achieved compounded annual tax-free growth rates of both net worth and cash flow in the 30’s, over periods of 5 years or longer. In my opinion, long term growth of cash flow and net worth is the truest way of measuring your progress, not to mention the most practical.


Today, my Roth 401(k) is totally free of single family home investments and is currently invested in 12 private placements in 9 sectors with 7 sponsors. Since I am older than 59 ½ and my Roth has been open for more than 5 years, I am able to use the tax-free cash flow from my Roth and the tax-free proceeds from investment exits (growth) to fund my family’s activities that we enjoy in both categories of “additional cash flow” and “additional net worth.” The proceeds from exits are actually practical as sources of liquid net worth for special activities such as vacations with increased frequency and quality.


The point of the approach of matching investments to specific enjoyable activities that require extra resources is to avoid wasting precious years and decades of your life pursuing a vague amorphous idea of amassing some non-defined pile of net worth, then spending it down on stuff you might want that you figure out later. You can start to engage MUCH SOONER in the activities you enjoy the most if you know what those activities are, how much cash flow and/or net worth you need for those particular activities and then learn and apply the most efficient investment strategies to achieve that cash flow and net worth WITHOUT DRIVING YOURSELF CRAZY!


If you are hesitant to perform this analysis, consider the fact that you will likely avoid wasting a decade or two of your life by participating in a 2-day workshop. It’s your choice. It’s your life.


Before concluding this article, I would like to highlight a point related to businesspeople who focus huge time and energy to “scaling their business” as a paramount goal. There are many ways to achieve self-actualization and massively scaling a successful business is a great way to achieve that sense of accomplishment. But, scaling of their business is sometimes (not always) the opposite of what they want, since scaling often means even more time and headspace at work and less time for enjoying family and other joys of life. We all know successful people who scale their business without thoughtful and careful planning for their personal time and family lives. This can increase the probability of divorce and going a lot less to the kids' sports activities and recitals.


I work with businesspeople who get to the point in life that they are more interested in increasing happiness. In those cases, I encourage active businesspeople to consider shifting at least some of their time from active business management to passive investing that provides similar or better income and growth without slavery to the grind.


In summary, in this article, I suggested that you consider adopting and implementing several concepts to increase your happiness in a resource-efficient manner by first recognizing that happiness is all about engaging in activities that you enjoy without causing harm. Make a list of these activities, including your daily routine activities that you enjoy and your bucket list items. Identify which activities that you enjoy that require additional resources other than mindset. Then quantify the resources you need while differentiating between needs for cash flow and net worth. At that point you can thoughtfully and efficiently design your investment activities (passive or active as appropriate for your situation) to match the specific needs for cash and/or net worth growth so you can circle back to increasing the amount of time to engage in the activities that you enjoy without causing harm.


Does this approach make sense?


If so, I hope to see you on the Offshore Goals Retreat. Register HERE for the Offshore Goals Retreat before July 1, 2024 for a 20% early-bird discount.


Alternatively, watch for my onshore workshops that I will be conducting periodically starting in 2025. They will be announced on our Events page.


Be Happy! Be Prosperous! In that order.


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