Regret Minimization Framework

Level 2 - Value Investor

Welcome Avatar! We’re going to walk though some high level ways to avoid regrets later in life. This is a distinct topic since “mistakes” vs. “regrets” are entirely different. The way to think about it is relatively simple.

A mistake is something you failed at but doesn’t move the needle later in life.

A regret is something you can’t change and is permanent.

Currently, happy to say that regrets on currently not on the table (so far!).

Mistakes? Could probably run an entire bullet list that will extend 70,000 pages. Some big ones include: 1) not cashing in on ring tones - $1.99 per sale - many beach front properties in California are purchased from this hay day, 2) selling Netflix stock far too early, 3) spending too much time partying in the USA, 4) not starting an online biz sooner, 5) taking too long to figure out the corporate politics game and 6) arguing with people on the internet who were complete and utter failures - if you argue with an idiot online the world only sees two idiots.

This is a bullet oriented way of saying, most decisions don’t change the course of your life at all. Older people commenting on the post below suggested that it really boils down to just 1, 4 and 7 (work, kids, health).

All of the above is largely age dependent as well. If you’re turning 90 with a couple years left to live, it really doesn’t matter if you are learning about AI, crypto, VR/AR etc. Similarly, if someone is 35-40 you better be sure/certain if you will have kids and with who (no need to post the random exception to the rule 50 year old centi-millionaire). The general point is the same.

Regret Minimization - Go to End of Life Care

If you’re in college, this is the ideal time to work as a volunteer in end-of-life care. If you are not? Then you should take a couple of days to talk to older people nearing death. An alternative (to remove excuses) is to meet some people in a luxury assisted living neighborhood in your city. This one will filter for wealth which forces respect in a world where “money is god” (heavy US culture belief)

For those that have read the book “Regrets of the Dying” here is the summary (source)

“1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

2. I wish I hadn’t worked so hard.

3. I wish I’d had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish that I had let myself be happier.” - Bronnie Ware

If you want to add to this list, Felix Dennis all time favorite writer, stated that he regretted not having kids (he spent ~$100,000,000 on drugs and women!). He also suggested that he worked far too hard after roughly $20-30M (forget the exact number). You can discern that this was basically admission of point #2 above. Bonus: if you read the book closely, you can see that when he was broke and on the come up, he had a lot of issues with dating/women. Combine that with an extreme addiction to sugar babies and it’s quite easy to see how he avoided kids for life. The most impressive part is the self awareness to realize he made a mistake with both kids and money chasing.

Now that you have the summary, it’s most likely that trap #2 is the biggest for most. We’re probably falling into the trap right now and only time will tell if the work vs. live balance was properly aligned. Hence “no regrets for now”.

Work Backwards - Framework by Age

Once you have the big picture written out, you can solve backwards for what you might regret in the future. Every decade or so there are certain things you can do/can’t do and should do. If you miss the window it is closed and locked forever since Time is more valuable than money!

20s Age Band: This is directionally a game of accumulation: knowledge, skills, experiences, etc. The tricky part here is most people are quite unhappy. They are unhappy because they think they deserve more than they have (don’t have any results). This creates a lot of anger since patience isn’t really something the majority possess.

On the other side of the spectrum, if someone is incredibly type A, they end up *losing* their entire youth. There are people out there who have never had a wild party, never tried any drugs, never lived on the edge even once. While you there is no requirement to do these things, being the boring dude with no funny life stories isn’t going to work. Type A people get older and unsurprisingly realize there is no way to turn back the clock.

The answer is simple (you all already know), go out 2x a week Thursday and Saturday. Do all your vacation weeks international. Generally speaking, all the nights out should be focused on the things that you shouldn’t do in your 30s: 1) going to dive bars/post college bars, 2) any concert/event tailored to the age band - except Coachella which is a disaster, 3) any spring break type party atmospheres, 4) most Vegas pool party scenes and 5) standard house party type events.

If you don’t do all of these things, you really can’t get the time back. All of them can be done without losing a *significant* step in your career, business and health.

As a short note, the notion that you will “lose your health” by working long hours is insane. You can sleep 6 hours a day and be fine. Maybe one weekend you need to sleep in but your energy levels are so high it just doesn’t matter. Around your late 20s this starts to come down. Anyone trying to tell you “don’t work so hard” in your 20s is giving you terrible advice. The regret related to work is not within this age band at all.

Skill Development: Every year you should also learn a random skill. Could be basic golf. Could be a new language. Could be an instrument. Could be cooking. All of this prevents you from becoming the overly type A person with “nothing to talk about”. There is no such thing as boredom. However. Boring people are a dime a dozen.

30s Age Band: If you’re a guy, this is typically the best decade in terms of options across the board. You’re making a lot more money, your first biz is likely a success and you’re on the *steepening* section of the income curve. All of this is just based on probabilities/statistics.

You’d think that the dopamine is higher when you’re at peak earnings but if your earnings are flat from 42-47 you don’t really feel excitement. Excitement is when wages + biz earnings + investment gains are all growing at the fastest rate (percentage gains).

The downside? In a state of pure excitement you have to make a few significant decisions: 1) where you will settle long-term, 2) are you going to have kids and with who?, 3) what type of work are you going to dedicate to since your skill accumulation is nearing its peak - statistically and 4) do you really need to keep running digits up on a screen?

While it’s by far the best decade (if you’re a guy), the responsibility here is enormous unless you want to end up with the same regrets as Felix Dennis himself (chasing digits for no reason - addictive and nihilist life views).

Everyone here already knows our views on America. Degeneracy is only going to accelerate which means a large chunk of people should not be parents (being realistic). That said, this is one of the major decisions to make since you won’t have time to vet the future mother of your kids (every single relationship in the world is honeymoon phase for 6-9 months so you don’t have infinite shots on goal to solve this one).

As a point of emphasis, we’re not telling anyone “what to do” simply that this is a stage in life where you better plan for some major decisions. The other ones are just as important. If you choose the wrong line of work to focus on you might hate every day of your life for the next 10-20 years. If you choose the wrong place to live? It will impact you negatively for years.

If you hit it big? Running up digits to just give all the money to charity or the government makes little logical sense. Guaranteed regret of “working too hard”.

40s and Beyond: Can basically toss this all into one bucket. You either have kids or you don’t. You’ve already chosen your profession/biz line of focus and you’re officially a quasi tanker ship.

For those that recall, in your 20s you’re a Jetski that’s easy to change course, 30s is more like a 65 foot boat and 40s and beyond is largely a tanker ship.

Onto The Smaller Stuff

That’s the general big item stuff. There are a lot of other decisions that make life significantly easier (or worse). The majority is related to health.

Health Basic Adjustments

There is a pretty large decision to make here. Do you care more about quality of life or the length of life. We’re not going to make that decision for you. We’ve already publicly stated that HRT (Hormone Replacement Theory) is something we believe in. This suggests quality of life is better than a couple extra years in your 80s or 90s (making it up).

In addition to that, there are other ways to lengthen your life statistically. Most people go into repetitive motions (cycling, walking, lifting) and not much else. If you do actual research you’ll learn that picking up a racket sport is effectively a *must*. If your goal is to live a healthier life you’ll end up playing: tennis, racquetball or squash. While the official winner is tennis, all the racket sports are close

Glory days of heavy lifts, basketball, fighting, American football etc. should be avoided. Don’t psyop yourself into thinking that you still got it.

While we’re sure this controls for wealth a bit (tennis is a more expensive sport), the standard deviation is large. Continuing to focus on muscle mass/dead lifting and other such activities is pretty much a waste of time.

Study Death Rates: There is no reason to go overboard (similar to the view of simply taking up a racket sport). That said, basic research will give you a few simple answers.

Since the majority of you will be financially stable, you should structure your life to be pretty central. Draw a simple 15 minute radius by car around your home and figure out how common you’ll be going over 40 mph. This alone will reduce your chances of death by a significant amount!

Another good example is skiing/snowboarding. We dunk on this hobby all the time since it is not only expensive and freezing but one of the fastest ways to end up in a wheel chair for life. *yes we’re biased as we know three people who have had this happen. All had families as well*

Also. If you’re a speed fanatic, get the sports car if you must, just don’t get on the motorcycle.

Before signing off on this sub-section please don’t go insane with pills/supplements and plans to live forever. This likely defeats the point of life itself and creates more stress that shortens your lifespan “need to take 15 pills and fall asleep at exactly 9:01pm!”. Just look at the real issues (death, severe injury) and reduce the probabilities there. There is a 100% chance you’ll get injured doing something, just make sure it doesn’t upend your life.

Studying the Next Generation

If you grew up pre-internet you know that parents had crazy beliefs such as “don’t stare at the TV too long”. Now? We all stare at smartphones, laptop screens and TV screens 24/7.

There is a big difference between becoming low key vs. uninformed. Being uninformed means you’re falling behind the times on new things that are coming out. Could be AI, crypto, VR, new peptides etc.

If you study the next generation, you won’t pass down terrible advice. If you want a concrete example from the 2000s it would be hardware vs. software engineering.

While both are extremely hard to master, it didn’t make sense to focus on hardware engineering after the internet came out. While you can say hindsight is 20/20, there was enough information to show that software was becoming more and more valuable. The cloaking software back then was absurd and made a lot of people disgustingly rich (legally too at the time!).

Hope for the Best Plan for the Worst

One downside of all this stuff after you make it? You’ll become insanely paranoid. Rational optimism is probably the best you can do. No matter what you’ll get the paranoia.

Write down the absolute worst case scenario for everything (finance, health etc.). Then try to line it all up to prevent disaster. Once you get to this point and feel safe *never* make a decision that gives you any sort of pause/anxiety.

As the saying goes “if you have to think about it the answer is no”. This only applies after you’ve hit your exit number though.

You do have a rock solid exit number don’t you anon?

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Disclaimer: None of this is to be deemed legal or financial advice of any kind. These are *opinions* written by an anonymous group of Ex-Wall Street Tech Bankers and software engineers who moved into affiliate marketing and e-commerce.

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