How to Think About Time and the “$5,000 Question”

There is no way to become an expert in time. Meaning? It is difficult to know with 100% certainty if you’ve made the right decisions until you’re 80 and look back saying “I have no regrets”. If that is the case then you’ve absolutely made it (visit a hospital and you’ll see that the vast majority are unable to say this). Time can only be understood or bucketed into segments and we’ll take a stab at outlining some key things we’ve learned (or think we’ve learned) about time.

Time and Value

Time is Second Only to Health: Largely speaking, the only thing more important than time is your health. Why? It can buy you more *valuable* time. If you’re eating healthy, working out and avoiding unnecessary stress (probably the most difficult of the three) you’ll increase your health. By increasing your health you’re elongating the amount of time you have and also increasing the quality of the time you have left! A year of life in a hospital bed at 40 is definitely not equal to a year of life for a man who can still play every single sport on the planet. In addition, time is certainly more valuable than money since $$$ can eventually become perpetual (Financially Independent).

Time is Not Valued Equally:  Now many of you see the conundrum here! Why do we focus on making money early if time is more valuable than the money? Well, if you get rich early on you can take advantage of *more valuable time*. A full year of free time to do as you please at age 30 is not equal to a full year to do as you please at 60. There is no real debate there since the human body degrades over the years. Knowing that time is not treated equally, somewhere around 40-45 (guesstimate) is when each subsequent year is less valuable than the prior year (capacity for new life experiences). To avoid negativity, yes there are millions upon millions of things you can do at 45+. Ignoring the fact that you’re less malleable when compared to 30 is preposterous.

The Masses Do Not Value Time: The masses value their time at nearly zero. They will look at the highest “hourly wage” as the best way to earn income and the best way to maximize their time. In addition, instead of looking at ways to create recurring income, they will look for ways to reduce one-time costs. This is the exact opposite of the correct way to get rich. If you’re creating nothing but recurring long-term income the one-time costs become meaningless… For fun here’s a quick way to see if your colleagues understand the value of time. Ask them the $5K question “Would you rather work all day today and make $5,000 or would you rather work all day and generate $1 per day forever?”. The correct answer of course is $1 per day forever. At a 4% interest rate assumption (not even risk free!) $365 a year is equal to $9,125 vs. the $5,000 one time outlay. Now… ask yourself if you can work all day today and create something that makes you just $1 a day forever (if you can your “annual wage” is $3.33 million!). The fact that no one reading this blog will trade their time for money (long-term) is the greatest thing about time (others are willing to happily do so). Another way to put it? If you can really find a way to generate just $1 a day for life and do this for a year… Your income is $133,225 for life.

Time Can Increase Your Long-term Value: The second greatest thing about time is that it rewards you handsomely for making the right decisions. If you made the right moves early then the rewards compound for you. This is pretty simple and the rule of 72 is the best way to do back of the envelope math. All of your assets should double in value every ~10 years assuming it gets a 7.2% growth rate. Taking it a step further, correctly used time allows your future utility to increase since it works in your favor to increase leisure and increase the set of items you can do with your leisure time.

Time and Risk

Risk is Almost Always Related to Time: We don’t know if we’ll wake up tomorrow and get hit by a bus. We don’t know if we’re making the right decision at all times (long-term utility). What we do know is that risk is primarily related to time since you could be doing something else. Given that backdrop, the biggest risk people take is doing nothing. Indecision is the worst use of your time since it leads to a 100% failure rate. The faster someone can make quick risk adjusted decisions, the more likely the person is to maximize their time over the course of 80 years.

As Time Passes Activity Risk Increases: If there is something you want to do today, we suggest doing it now if you won’t be able to do it ~3-5 years from now (stated this many times in the past). This is specific to anything that won’t ruin your financial life forever. The reason? Activities go away as years go by. If there is a specific recording artist you love, it is best to go and see them ASAP (their careers are shorter) similar to sports if that is your hobby.

Reliance Risk Increases: As time passes by your employment risk will increase. You’re going to be earning more money (more cost effective to be fired!) and you’re less likely to replace that income at another company. To put it another way… reliance risk goes up over time. Even in items outside of employment if you rely on any single item for either happiness, sense of life meaning or income, the risk of it going away goes up over time. Many people become suicidal after earning large sums of money and seeing their company go bankrupt or being let go from their high paying investment banking career. Risk related to *Reliance* on one specific item (for anything) goes no where but up over time due to a large amount of psychological factors.

Risk to Adaptability Increases: As time passes by our ability to adapt decreases. This is also due to psychological factors. If someone believes they have made the right decisions their entire lives they would have to admit they made a large mistake over 5, 10, 15, or 20 years. Stuck in their own minds. This works both ways. If we try to convince a retired millionaire that he wasted his time working a career for 50 years just to retire at 70…. It wouldn’t work. Similarly, there is no point in telling him such a rude thing because there is nothing that can be done to reverse the decision in the first place! When you’re in your 20s? You’re a jet-ski that can move and change directions rapidly. In your 30-40s? You’re a standard boat… and by 60? You’re a tanker ship with the decision already made. As a rule of thumb, if someone is hard set on a belief and has maintained the same thoughts for more than 5 years… go with “smile, nod, agree” to avoid confrontation.

Unproductive Use of Time

Arguing With People: This is still prevalent on every single platform you can find from Twitter, to Facebook to internet forums etc. It takes a long time to master this skill since it requires “quitting”. This is not something in the vocabulary of ambitious people, so it is rarely mastered! Arguing with people isn’t a good use of time because at the end of the day around 50% of people just won’t like you anyway. The presidents (Trump, Obama, Bush or Clinton etc.) all of these people don’t have a 100% approval rating. Just call half of the population a wash and chalk it up to the “numbers game”. There are 7 billion people in the world, it is better to find one of those 3.5 billion who will at least be neutral to you and have a real discussion on any given topic.

Doing *Everything* for Money: The best way to burn time is to focus 100% of it on money. That’s a strange comment given our website draw but it is true. No one wants to be around someone who is constantly worried about earning more money from ages 20 to 50… It eventually becomes meaningless. These individuals usually have trouble socializing and making long-term friends which is not a productive use of time (there is an eventual cut off). This blog and our book are no different, earning a few bucks selling an e-book is significantly less productive (maybe we’ll blow it all on throwing a party for our favorite commenters!).

Giving Up Time to Cut Costs: Re-read the first paragraph under unproductive use of time and you’ll find that no frugality blogger will ever agree with us. This is fine. We won’t argue. We just outline the points here which show skills are learned when you earn; no skills are learned when you do nothing. If you’ve already cut your costs to the bare minimum it’s not going to go any lower… so why would five hours of research to save money on coffee outperform $2 spent meeting a potential customer for coffee? We give up.

Worrying About Opinions of Other People: Unless someone has what you want, their opinion shouldn’t be that meaningful to you. If you admire someone’s ability to earn money it makes sense to listen to their money advice. If that same person can’t do a pushup, probably best to ignore his fitness advice. So on and so forth. Lots of time is wasted worrying about living up to other people’s values. Create your own values and live according to those. If you’re not engaging with people who dislike you and you have some fun activities outside of making money, the chips will fall into place over a long period of time that will delete opinions from people you don’t respect in the first place. It’s a “win win”. The people who will never like you? Well they never get a chance to meet you either!

Thinking About the Past: It is one thing to learn from the past it is another thing to dwell on it. Everyone will make a wrong turn here and there. Maybe you take the wrong career or join the wrong firm. Maybe you jump at the wrong time. It doesn’t really matter anymore since it’s in the past. What really matters is learning if there was a “blind spot”. Find the blind spot and don’t let it happen again. Finally, maybe the decision was actually the *correct* move and it just didn’t happen to work out! If that’s the case, thinking about anything negative from the past is a colossal waste of time. Only positive things from your past should be remembered to improve your focus and emotions.

Time and Excitement

Time Spent to Achieve = Dopamine: Anyone who isn’t financially independent yet (but is serious about it) will receive an enormous amount of dopamine when they cross the finish line. We’re not joking when we say we’re jealous of those people that are on their way and have a clear path there. Becoming financially independent can take up to 10-20 years (standard version) and there are very few things in life that take such a long time to achieve. Think about other events where an immense amount of joy is shown and they are directly related to the time it took (athletes winning championships, parents watching their kids graduate college, so on and so forth). Once you experience something like this your views on time change forever.

First Time Experience Excitement: Generally, the first time you do something new from an experience perspective it has the most value. This is different from the large amount of dopamine obtained from achievement or success since it’s a repetitive task. If you go out and get drunk for the first time it’s typically a lot of fun… do this 200 times and it certainly wears you down. This is seen in drug addicts as well where they need more of it to achieve the same “high”. Knowing that dynamic, having a long list of interests is a great thing since you can get the “first time experience” hundreds of times over the course of your life (it also prevents you from developing a plain and boring personality as well!)

Time and Consistent Excitement: You’re a lucky person if you find five things you can do every day that constantly give a baseline level of dopamine rush. This can be anything from athletics to music to travel to reading. We only say “lucky” because it takes a good amount of effort to go through many first time experiences (second point) and find one that remains relatively constant. You’ll find that the main ones that create constant dopamine levels to rise rarely cost thousands of dollars to maintain.

Concluding Remarks on Time

Overall, life is a big balancing act. In order to obtain money you have to give up time (building recurring income streams of course!) and you also have to recognize that the time you’re using could be spent doing other exciting things that will become harder to do as we all age. We would really summarize this into 10 key points: 1) since health can improve both time and money we’d focus on activities that maximize this – athletics, clean diet etc., 2) consistently review activities to make sure life doesn’t pass you by and you don’t become a boring guy, 3) always look for ways to create recurring income and realize that 99% of people will trade their time for money happily – will fail the $5,000 question, 4) fail a bunch of times as early and as often as possible, this way as risk increases in the future you’ll be well positioned to avoid big mistakes, 5) diversify your life as there is no need to rely on any singular item for meaning, money or emotional support, 6) Don’t bother arguing with people – easier said than done!, 7) realize that money is only a tool and eventually loses utility, 8) the amount of time it takes to achieve something is directly related to the dopamine obtained, 9) have a growing list of first time experiences – things to try and 10) unlike money, time cannot be taken back choose wisely


  1. upper says

    “1) since health can improve both time and money we’d focus on activities that maximize this – athletics, clean diet etc.”

    And avoid things that deteriorate all three!… heavy alcohol, partying, and watching tv.

    Most I’ve seen all realize the alcohol/party thing in mid 20s and significantly cut down – its a weird cycle though because when you’re crushing it in your mid 20s it makes you want to party more, but then you realize it sets you back a few days and even more if it was a long “run”.

    Awesome post!

  2. Nick says

    Forgive me if I’m missing something, but wouldn’t the $5000 over time outpace the $1 per day assuming it was invested?

    • Wall Street Playboys says

      Nah man. 4% on $5K is just $200 a year vs $365 a year. Risk free is actually closer to 1-2% so it’s really $100 versus $365!

      Most people never get it and never create recurring income. Broke for life.

      Only 1% of people will understand the significance of that question. That’s why we have no problem putting it out there.

      The point of the question *HOW* are you earning is what matters. Not how much over the long-term.

      • Nick says

        Oh wow, that’s interesting, I didn’t think of it that way. I ran the numbers and it looks like you would break even around the 20 year mark, then exponentially increase from there!


        40 years
        30 years
        20 years
        10 years


        40 years
        30 years
        20 years
        10 years

      • Gene says

        4% return? That is horrible! You need to go somewhere around the 7% range (which is pretty accurate for long term investing.

        That number gives you something like this for the $5000 investment.

        5 years: $7,013
        10 years: $9,836
        15 years: $13,795
        20 years: $19,348
        30 years: $38,061
        *40 years: $74,872
        50 years: $147,285

        vs $1 (which we will also invest since it would not be fair otherwise)

        5 years: $2,169
        10 years: $5,209
        15 years: $9,472
        20 years: $15,453
        30 years: $35,604
        *40 years: $75,246
        50 years: $153,226

        So if you factor in that this money will simply be invested, you will never touch it, and it can grow for years to come at a rate of 7% (a much more likely investment percentage), these are the numbers you would get.

        Please note that this does not take into account taxes, investment fees, etc. that would obviously affect both numbers, and arguably the $1 would be hurt more because those fees and taxes would end up taking a bigger percentage of their money out each year.

        My analysis is that $1/day would be fine if you lived in a tax free world, your investments charged no flat fees and an equal percentage fee based on portfolio size, and you had years and years to invest and were not planning on using these funds for 40 years (i.e. someone 30 or younger). Otherwise though, the $5,000 today makes more sense from an investment standpoint.

      • Wall Street Playboys says

        As stated the $1 a day is *guaranteed* ie it is risk free.

        So comparing it to 7% (no where near risk free) isn’t a fair comparison.

        But we don’t mind the analysis, the more people willing to trade their time for money the better! More people to outsource work to! (Half joke) We hope more take the $5K option, for selfish business purposes

        One last way to explain… would you invest $5K for $365 a year guaranteed or 7.3%? (notice that is higher than 7% we did that on purpose)

        We would liquidate all of our assets and buy it if it was risk free today

  3. VD says

    First time commenter. 10 figure business owner. Phenomenal post.
    My priority goes like this : Time > Health > Reputation > Energy => Creativity > Money

    In order of renewability. You can use time to gain health. But not health to gain time.

    • Wall Street Playboys says

      True the Renewability point makes a ton of sense.

      We’ve always taken health a tad more seriously due to our own bias… that being fit and jacked at 35 is better than being a slob at 28 because the life expectancy likely already took a hit and it takes a long time to flip it around.

      Renewability is an interesting concept consider it stolen for our day to day life convos! Hahaha!

  4. V says

    This post is brilliant in the most pragmatic sense, in particular the context.

    Greatly appreciate “sending the elevator back down”.


  5. Jack says

    8) the amount of time it takes to achieve something is directly related to the dopamine obtained

    Beware of the deadly dopamine which is released from porn, video games and other outlets designed to give you easy instant gratification.

    Once your brain is hooked on these easy pleasures, it is highly unlikely for you to achieve greatness in any other area of your life.

  6. Sisyphos says

    Health is easily fixed, you only need the right habits. It’s automated for me (eg I really enjoy spinach and quark). I find it harder and more complex gaining the right habits for moneymaking.

    You made me think of the euphoria I got the first ten times i got drunk. Now it’s just banal (maybe I should try ‘new’ drugs!?).

    • Wall Street Playboys says

      Probably not, no point in overloading on drugs. The whole point is that those don’t give lasting dopamine I.e. Feel free to do Something bad for your body once and awhile (drinking)… but beyond that it’s not that great.

      No matter what we say people will do drugs and chase temporary highs… hence why we don’t argue about such topics anymore (the addicts never get it) Good luck!

      • A says

        Have to say. I started Mod usage and feel like a million bucks…definitely useful for grinding.

  7. D-Train says

    Man, this website has really made me see the world through a different lens (for better or for worse at times).

    1. Health: went from “trying to eat well” to juicing 5x a week and subscribing to a meal service that delivers fresh healthy meals with an accurate macro count. This essentially automates my health from a nutrition standpoint. Sleep is a different story.

    2. Time: I always knew the value of time but becoming more *efficient* in my time has made me a more well rounded individual. During my 30 minute commute each way I read on a book on my iphone using the kindle app so I get an hour of reading every single day (while the regulars are playing candy crush). I pay up a little bit more to go to a powerlifting gym where my routine is automated, and a coach/ other experienced lifters are there to check your form. Started playing guitar. The free resources online are incredible and structured in a way that you know exactly what exercises, routines, and practice schedules. Started in August and 30 minutes a day has been all I needed for drastic improvement. Meditation 10 minutes a day has helped me tremendously. Also learning Spanish (use apps on the phone and go to language learning meetups).

    When I incorporated all of these things in my life I thought that it would leave me know time for my social life, but my social life has sky rocketed. Two phenomenons I’ve noticed:

    A. When you make less time for people and have a busy schedule, people tend to gravitate to you more and want to spend time with you more (both men and women)
    B. When you make beneficial changes to your life a lot of these changes stack. For instance, I like latinas. When I go to a spanish learning meetup I can learn a language, while flirting with a latina. Also two good excuses for a date are teaching them guitar, asking them to teach me salsa dancing (trying to learn also). You quickly start killing two birds with one stone. Overall, when you use your time efficiently to pursue interesting and worthwhile endeavors that will enrich your life, people will want to become a part of your new life.

    3. Work: I got crushed on office politics believing performance was a much bigger piece of the puzzle and office politics was petty and not worth playing the game. Got steamrolled for this and started networking heavily externally and leveraging relationships within the company. Currently chalking up my losses and planning my next move. No need to dwell in the past will hit the ground running at my next gig.

    4. Starting a business: Realized the important of this and how it is non-optional. Currently researching this every chance I get and hope to have a revenue generating website up within a couple months.

    5. Women: Last on the list for a reason. Completely stopped putting effort into attracting women and got better results. I think any guy who is in shape, can speak another language, has interesting hobbies, and is well dressed will be just fine. Had a few girls ask me if I could teach them guitar. Makes for a great date.

    Sorry for rambling! Looking forward to the book. Keep up the great work!

  8. 5K says

    I would still rather have the 5K… I’m young and would simply plow this into my online business and aim to generate 10K.

  9. RE Guy says

    On the risk to adaptability, it’s a strange sort of balance between ego and action, that no matter what it is we do we will in some way come to believe it is correct and to see things from that limited perspective.

    You can be totally ego-less and maintain a meditative state while doing nothing but breathing, and believe yourself to be completely humbled by the universe and have a pure “beginner’s mind”. (I read the book on your recommendation)

    But then the moment you act you immediately start to create that ego again.

    I think journaling and meditation, and focused action are two sides to the same coin and two ways of discovering that nature of reality. And that everyone has to find their balance.

    I also think your point about definitely not explaining to a 60 year old “where they went wrong” is very true and I’ll add that that is one of the reasons these days I refuse to discuss religious beliefs with people.

    A major problem of “smart” people is thinking that arriving at what is most logically consistent, what is likely objectively true, is the single overriding principle to their interpersonal relationships.

    Thankfully I’ve been breaking that habit (along with arguing with people!).

    • RE Guy says

      It struck me after writing this how much healthy contempt for other people can come from humility.

      What I mean by that is if I am honest about my own failings, and my own ability to harbor incorrect beliefs, then I am forced to act to fix them, which takes time and energy.

      And if I don’t spend that time and energy on myself, then I become a less valuable person to the other people around me.

      So in a sense not arguing with Regulars is the natural result of not wanting to be an angry person, because to argue with them is to be frustrated.

      And in a cyclical sort of way, because I know I’m just going to “smile and nod” I can be more pleasant around them, since my goal is just to maintain a positive (or at least not negative) relationship with them using the least energy possible and not to convince them of anything.

      I do this with the understanding that although it is possible I could help them with my knowledge greatly in the long term, the relative investment of my time and energy to change them is so much greater if they themselves don’t have a humble and knowledge seeking attitude.

      And because they are not me, and don’t owe me anything, and could decide to leave my life completely, freely and at any time, I am largely making an insecure investment by attempting to help them, which degrades my sense of purpose.

      What occurs is that I require someone first prove they are invested in me and my needs, and loyal (all in addition to the right attitude), before I spend any significant amount of time trying to improve their beliefs.

      This is again a “smart person problem”, and I’m reminded of a commentator here from a long time back who tried to have a conversation with an attractive art student about what was “practical” for her to pursue (and was frustrated by her lack of receptivity).

      A “smart” guy failure with people (men as friends, women romantically) is to try to help someone intellectually before the person has shown themselves to be invested in them emotionally (with women this means talking to them about their problems before you’ve had sex) and to help that person when they don’t have the right humble attitude.

  10. Roark says

    I’ve made it, but probably turned into that “boring guy”. I have a serious relationship (am happy with it) so going out seems kind of like a waste. I definitely need to change some things or so I’m not wasting my 20s.

    Still want to work a ton, because I’m not worth $3.5M yet, but I probably need to diversify my hobbies and how I spend my time so I’m not just working and reading.

    Planning on going to toast masters, picking up golf, and also learning to dance.

  11. Abe says

    This must be the law of attraction at work, since I was looking to pull 5000 out of a retirement account. That much took me four years though.
    It was interesting the comment about a dollar a day, and candy crush. A few years ago when I spoke with people everyone raved about that, and Clash of Clans. I downloaded Pokemon Duel recently and they have the same method of having one thing that you could buy (gems). It occurred to me after reading this for something like that made by a small group, one person would have to buy your in-game item once a day…

      • Abe says

        Apologies, that’s on me for lack of clarity. It was the amount, yes, 5K, I put into a government retirement account while I was military based off of the recommended “save X%” advice. I was one of the better ones financially as well.

  12. Playing Catch Up says

    By far the number one life lesson I have learned has come from reading this blog and that is about time. That very life lesson pushed me to make the right steps and go from an unemployed college grad forced down a certain unprofitable career path by his parents to landing a decent offer (I did go to a good university and picked a profession after reading this blog thoroughly) and pursuing a profitable career thanks to this blog.

    Looking back at it, the one thing that kept me going when I was in my early 20s waking up to all of this and keeps me going now as someone in his mid 20s is that very concept of time. In the grand scheme of things, I think about how much little time we have on this planet to truly enjoy life.

    I used to do research in college and found how so many professors who had these phDs from prestigious schools were such depressed and generally bitter people, exceptions existing of course.

    We really only have a select window of opportunity to enjoy life and collect those moments that can make life fulfilling. I am going to guess that window of opportunity begins in college when we are free from parental guidance (parties at the widest at this stage) and probably ends at some point in our 30s.

    That window of opportunity to build on your skills/talents, experiment with fun things in life, see the finger things in life, have some fun, have enjoyable moments, pursue that dream that corresponds to your talents, and make it happen. Just that window of opportunity to have moments we can look back on in life and be proud that we experienced them before we become “too old”.

    It made me want to get up every day and fight, rebel, and make something of my 20s.

    The value of time and that windows of opportunity in a man’s life for him to truly live. I want to experience it to the fullest before I get too old for it, got a few years left but time flies!

  13. Jacob says

    I think I took your advice on not being frugal a little bit too far and have probably been spending 2x what I should. Working on reducing it. Didn’t realize how much my status items were really costing me until I calculated the spread between investing it (+7%) and not investing it (-2% from inflation)

    There is one contrary point that you guys might agree on… if you do some research to reduce a recurring cost you can cut down on total cost per year significantly. For example if you spend $2-3k on food but find a way to make it $1k and also clean up your diet that’s pretty significant. I 100% agree that spending more than 15 seconds on your decision to buy coffee is a waste though.

    Assuming that you have most of what you need but not enough to “feel rich” (say 1-2M) does it make sense to trade time for money? 7% returns on this money isn’t enough to pay for my lifestyle. Only makes it about half way there. My income should cover the other half for at least the next 5+ years and I could always spend less.

    I’m currently in a position where I have a bunch saved up, am in my mid 20s, and moved to a new industry. I’m a top 1-2% performer but it’s dollars per hour. Thing is, it’s pretty decent dollars per hour, but nothing incredible. Let’s say 20k/mo conservatively.

    It’s going to decrease over time though. I’ll either work less or the industry will get more competitive. Most likely both.

    Am I being stupid? I feel like starting a biz would not yield the average return I’m getting now from my work. (Counting in all the failures, like say you had a 10% chance of making $1M/yr that would be 100k/yr) I’m also basing that 20k figure on working only about 4-5 hours a day. So while I’m sure that there are better options out there, it might not make sense to try them when I already have something solid to lean on.

    Creating an income stream that makes $1/day FOREVER is pretty tough. I have found that my income streams don’t last longer than a few years. Am I just missing something here? Better to make an income stream that generates $5000 per day for a year NOW that lasts 2 years than have an asset that makes $1 a day forever right?

    • Wall Street Playboys says

      Lots of issues we won’t repeat but we’ll outline it since it seems our items were not Interpreted correctly:

      1) you never trade time for money, ever over the long-term
      2)being employed long-term increases income risk, they would love to fire high earning employees
      3) until financially independent… not allowed to spend on status items ***unless it offers a return***. Buying a customer dinner at a fancy place usually leads to more profits than the cost as an example (we use a coffee example in the frugality post as it specifically says earn a return on getting coffee with someone, spending money on expensive items with no return… well that just doesn’t make sense if not independent yet)
      4) we disagree, learn to make recurring income or get eaten alive long-term. That has been covered 100x on the blog. If you feel it’s harder to earn $1 a year forever… it proves the value of recurring income. All that said, if you believe your path will work we can’t add much… not everyone gets rich in the same way.

      All of this is outlined in various posts, this is not a Q&A, we are only responding becuase it looks like a lot of this was not clear.

      Good luck and we recommend starting a biz asap! If you’re making $20K a month you definitely have enough value to start a company that just seems practically impossible to ignore!

      • Jacob says

        Thanks for the response, I might just do this for the short term and start a biz after I sort out health.

      • Jacob says

        BTW I have noticed that some status items have directly gotten me connections with people who may have not paid attention otherwise. This has led to $$$. That’s the upside. Downside is that people expect you to spend a lot and try to extract resources from you. Overall my status items have probably been profitable financially speaking. Might be a rationalization, but then again might not be.

  14. MM says

    Got lucky purchasing small multi’s in Brooklyn 2007-2011. Worked hard for 15+ years, ~2-3M. Its been a whirlwind of losing hair, gaining weight, and dependent on sleep meds. Most of the money tied in real estate. Can’t sell because taxes will eat you alive, can’t 1031 into larger multis with these rent stabilization laws, and don’t trust people enough to hand over my money. When you specialize, you live and die by your sword. I did it wrong. Health, mental and physical, is more important than anything.

    • OwnMyHood says

      A couple partial solutions:

      1031 into RE in areas that don’t have rent control.


      Sell and hold paper making sure to sell at higher price but lower interest rate than the market to take advantage of cap gains over income tax rate. This benefits the buyer as well (higher basis) as long as he doesn’t pay the loan off early.

      As far as the health goes, if being a landlord stresses you out that much, sell (just making sure to minimize taxes due).

      Eat right. Get a lot of exercise and do something to calm you down before going to bed (reading or meditation).

      Great post and a lot of great comments.

  15. JP says

    Very solid article, thanks!
    B/E is essentially year 30 assuming a 6% IRR….


    365-annual payment

      • JP says

        Much of the readers seem to be young professionals so I was just making a rate of return assumption based on long term equity returns. If you gave us $5k, it would likely be earmarked towards (LT) equities.

      • Wall Street Playboys says

        Yes it was a joke. Meaning that was part of the reason we phrased it that way.

        Recurring income is stable stickier and more valuable than a volatile stock market return.

        Example it can’t go negative like the stock market returns can in years.

        Maybe we should write a post on that as well!

        “There is no negative to recurring income”

  16. matt kobus says

    How I stay motivated:

    (un)Fun fact – if you are 25 years old, you have approximately 18,250 days left.

    Carpe diem time!

  17. says

    While I was still climbing the mountain to financial independence, my mentor would tell me he’s jealous.

    I never understood why. I thought to myself “You’ve already made it? Why would you want to switch positions with me?”

    He told me I’d understand once I got there. I do. Without a fight, life becomes meaningless. The first fight is the best. Now, we look for novelty to find that first fight again. It will never stop.

  18. Larry says

    “A full year of free time to do as you please at age 30 is not equal to a full year to do as you please at 60. There is no real debate there…”

    Actually, there is debate there. They are equal. “As you please” at 60 is going to be different than “as you please” at 30 based on a variety of factors, beginning with interests. I agree with the general premise of the piece about “carpe diem”, but you seem to have the distorted view of aging that all young people have, including myself when I was your age.

    Due to taking care of myself by exercising, eating right, and few bad habits (everyone needs one or two bad habits to make life interesting), I’m in better physical condition (strength, flexibility, blood work, etc) at 45 than at 25.

    • Wall Street Playboys says

      Great perspective Larry!

      Just building off of lessons learned from a hospital, watching people near the end of the road and their opinions on where they went wrong.

      If you’ve kept your energy levels up at the age of 45 that’s outstanding and we salute you!

      We agree life is never over, simply saying to keep track of things that may not be doable as we all age

      Believe there is a book on this, top five regrets of the dying. Something along those lines.

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