I started saying that I was semi-retired in 2020, I was 22 years old then… what the fuck am I doing using the word “retired” before half my childhood friends made their first $?
Well, it was often hard for either my ‘normal life’ friends to understand and it was similarly hard for my “hustle” friends to understand so I thought I’d write this article and share ‘what retirement means to me.
What is work?
You can’t use the word “retire” unless you first define what work is. Because what are you retiring from?
As I’ve said earlier on this site, work to me is everything I don’t want to do.
I never had a traditional job in my life, I did odd freelance jobs in 2016/2017. Had a remote job from 2017-2018 and after that, I never worked for anyone else just ran my business.
In 2020 when I semi-retired, I didn’t work at all for 2 years. I let my business die, I didn’t check emails for 2 years and the business collapsed entirely.
“But Jeremy you left money on the table”
Of course, that’s what every retired person is doing. They’re saying no to money cause freedom is more valuable.
With “freelance work” & “remote work” almost everything is “work”. (Some exceptions some people like what they do)
With your own business, just like a job, you might enjoy some parts but you may not enjoy other parts.
So it’s a simple question, “would you do this thing even if you weren’t getting paid” if yes, it does not work. If not, it’s work.
Even the “it’s not that bad” work. Everyone who says it’s not that bad only says that as long as the upsides are better than the downsides.
But if you can get the upsides without the downsides why should you put up with any downsides?
So retirement to me is just not doing all the “work” aspects and just spending all my time doing what I want to do.
If I had to make a spectrum of retirement it’d be:
living completely off investments> living off passive/semi-passive businesses/rental income > living off a business where 90% isn’t work
They’re obviously more antifragile ways than others. For example, if you need $10k/mo for your family, it’s more antifragile to earn $20k (yes double) divided equally from 4 different kinds of business and investments vs just making $10k from one.
Its s curves all the way down.
You Lazy Fuck
There’s a large camp in the world that believes that people should “pay their dues”. That you need to wait until you’re 65 and can’t touch your toes before you consider not working.
Cool I don’t think about people like that.
I’m someone who believed that he should be able to travel the world for a living when he was 18 years old 😂 Definitely the wrong person to talk to about “paying dues”. You do that, I’ll just ignore that. Chat with you when you’re 65.
But there’s another camp. It’s the hustle people who have an unconscious fear of not working because all the “retired” people they see are just old and sad.
An example I shared with a friend is that he probably was afraid of being perceived as the village drunk who does nothing but pass out on the sofa the entire day.
wow really? Those are your only pictures of people that don’t work? Drunks and old people.
Let me share what I think about when I think about ‘retired’ people:
1. Austin Hill (check his first interview on whatbitcoindid)
Austin is an Og cypherpunk. What does his past 20 years career look like?
Well, he built a company and ran an investment firm from 2007 to 2010. I think he “retired” around 2010.
Fast forward to 2014 and he came out of “retirement”, helped start Blockstream (currently valued at $3.2B), was the CEO for 2 years, and then “retired” again in 2016.
In 2024 he’s a bit out of “retirement” and visited the project down in El Salvador and even gave a talk at the school that I’m helping with.
Next, let’s look at
2. Balaji Srinivasan
Worked as a professor at Stanford, the started a genomics company in 2008 and sold it.
Started earn.com in 2013, then pivoted and then acquired by Coinbase and worked at Coinbase for a year.
Later just quit and spent most of 2020-21 on Twitter, podcasts, and Angel investing here and there. And now in 2024, he’s publishing a book that’s coming out this month.
That’s what I think about when I hear the word “retired”.
You don’t “have to work” so if you work you only work on things you care about.
The “FIRE” (financial independence retire early) community always seems to have discussions every couple of months around “yeah get fi” but “re” is probably not good cause retiring early kills you/loses meaning etc.
Yes, if you go from 40 years of a shitty job with no meaning to doing nothing, yes retiring will kill you.
But if you’re young, maybe don’t put yourself in that position in the first place 🤷♂️
What’s the problem with waiting until your 60s to retire? Well for starters you’re old and you enjoy life less vs if you retire for 2 years every 3 years or even more often.
Also if you work at the same thing for 40 years and don’t spend time doing nothing you wrap your identity completely in what you do and you can never reinvent yourself.
Also if you don’t “retire” often, eg. Work 2 years, take 2 years off. Work for 3 years, take 5 years off. Retiring becomes a big deal vs just a normal cycle.
”But that’s Balaji, Austin, that’s not me. I’m not like them”
Cool, believe that and you’ll just make it your reality.
My larger point is to ignore the majority of categories of people. Ignore the “retired” people who do nothing when they’re old, ignore the retired people that have no meaning, and pay attention to the Naval’s, the Balaji’s, and the Austin’s.
Why not use the word, “break” instead of retirement?
When you use the word break, you’re giving ourself an ‘out’ from letting go of your identity and the work. Aka you hold onto something that you can ‘go back to’.
“I’m not a nobody, I’m a writer on break trying to find inspiration, I’m somebody”
It doesn’t mean that you can’t go back to something if you retire from it but more precisely you aren’t planning to and hence can quit it entirely. Stop playing the game/keeping ‘doors’ open.
How many years of freedom can you buy?
One good metric I like when thinking about work is this:
If you work for 1 year, how many years of freedom can you buy?
For example, if you earn $5k/mo post-tax and your expenses are $3k and your investments grow just as much as your lifestyle+ inflation (so they cancel out for simplification).
You’d have saved 0.8 years of freedom for every year of work.
That multiple is a good metric to look at the world. You want that multiple to grow.
I have friends who if they work for 2 years could probably buy themselves 2 decades of freedom.
While I have friends who could work for 2 years and lose freedom cause they will have more debts at the end of those 2 years than at the beginning.
”But Jeremy I don’t like thinking about money the way you do, I don’t want to put in the work to understand it.”
Well, if you don’t think about money you’ll probably just have to work your entire life for it instead.
You can ignore reality, go right ahead. But then you just have the consequences of ignoring reality.
Who has the time?
Last winter I had just landed in Tirana and right after immigration and checking into the Airbnb and connecting to the Wifi, I opened Spotify to see that The What is money show had released a total of 10 hours of conversation with Balaji.
A day or two later I told my girlfriend, “A 10-hour podcast of Balaji just came out.”
She jokingly said, “who even listens to that? who has the time?”
”haha I do! I listened to the entire thing twice in the past 2 days.”
If you had to take a 6 months break and reinvent yourself… can you? How about 6 weeks? How about 6 hours where you stop letting other people, including yourself, tell you who you are?
I remember when I was living in a tent in the mountains of India I asked myself a question, “who am I when I take away everything everyone has ever told me about myself? Including what I tell myself”
I had a funny conversation with a cousin where he said, “Oh Jeremy can’t work because he has to spend all his time going down rabbit holes and figure out how things work”
I remember thinking, “well someone has to😂”
Someone has to read all the best books in the world, visit all the coolest places, why shouldn’t it be ME? Or YOU (yes you!) for that matter?
This is where having optionality matters.
It’s much easier to leave NYC, move to a village in Mexico, and keep your costs low while building your business vs living in NYC and have to work just to make ends meet.
Spending 2 years building a biz in Mexico will be much easier than 2 years in NYC.
There’s a Dystopian short story I’d like to share. It’s titled “For the benefit of mankind” by Liu Cixin. (It’s actually for free on Google Books)
A above is a small snippet from the story.
Right now people are spending so much time wasting talking about the cost of college I just ignore that entire box because the real ”education” is “time + ability to learn + reinvent yourself”
The smartest and most interesting people I know are ones who can spend most of their time doing things that they’re interested in. They spend 6 months reading all the books in once topic just because they’re fascinated by it.
They go to El Salvador on the ground and spend weeks and months there before commenting about bitcoin as legal tender vs journalists who haven’t left their apartments.
Again money (not much) but still the freedom money gives plays a role here. You can learn so much better if you combine the infinite resources of the internet + being on the ground and talking to people and seeing for yourself.
That’s the “super computer in the brain” as described in the story above. The internet + real world experiences.
But I did everything I was supposed to
One of the excuses I respect the least is “I did everything I was supposed to”.
A lot of people have gone through life never questioning the “water that they swim in” and they did “everything they’re supposed to”.
Notice how religious that sounds, it’s almost like someone bargaining with god to be let into heaven because they went to church everyday.
The most fragile people I know today are people who did everything there were supposed to because they never took initiative, they never took responsibility and they never grew up.
Many people use that idea, “everyone did it” as an out. As a justification, like that makes it better. I don’t, I don’t care if you did something stupid just because millions others did it. It’s still stupid.
I don’t get why it’s so weird, it’s almost like people saying things like, “I’m eating exactly like all these fat people, why am I fat?” What do you expect?
If you blindly do something without questioning it that’s not making a choice. No matter what you may think so.
A friend of mine decided not to do his masters and instead decided to work online and travel.
We were once in a group and he started talking to the other people about how ‘you didn’t need to go to college’
I laughed and said, ‘you mean second college right (masters) or first college?…cause you did do that… remember?’
He realized what I meant and said, ‘yeah wow both’.
I shared the quote from Pirates of the Caribbean, “Dead men tell no tales”
Well, in your case, “Dead people make no choices”. (Ik it doesn’t roll off the tongue 😂)
You never made the choice when it came to ‘first college’, you just did what you were supposed to. You convinced yourself that it was your choice but there wasn’t ever a choice.
But with the second college, you happened to actually be ‘awake’ a little. And guess what? You made a choice.
”why are you so against college?”
I’m not, I just don’t care much about zombie choices. For example a kid from India dropping out of engineering to go study cooking cause they love. I would call that a choice, so I’m not against college I’m just saying that obvious that is that zombie choices aren’t choices.
If this above friend decided to go back to college but in something they were actually interested in studying I’d be the first person to push them to do it.
There’s a reason I have “money” as my first section in my book recommendation, because if you solve money first you have more free time.
A rich kid might be privileged to be able to wait 6 years for their startup to turn profitable but today it’s also the blogger who has the freedom to write once a week and spends the rest of their time reading and learning new ideas.
Life isn’t fair some people are lucky enough to have time due to circumstances while other people have to hustle for a year or two to have optionality to then have the free time.
Money by itself isn’t enough tho. You can have enough money to have the freedom but then culture wars, political & status games or social media might take away all your time.
So while the Money and optionality can give you freedom, you can be sucked back by the siren calls of ‘keeping up with the Instagram jones’, ‘hustle culture’ and then Money becomes your new cage.
It’s okay to spend savings
Most people never get into the habit of saving. However once they do they often go to the other extreme of obsessing over savings.
Note: savings = savings + investments for this section.
Doesn’t matter if it’s the fire community or the start up bros or bitcoiners stacking sats.
Now I do believe as a society we probably should have a bigger savings mindset. But at the same time most individuals in the above community go to far in the other extreme.
In what way?
Well, everyone know that compound interest grows so ‘time in the market’ is better than timing the market so you need to start young blah blah blah.
So, if you have a net worth goal of Eg, 25x yearly expenses, ‘you shouldn’t stop until you’ve reached that goal because you’re sacrificing so much money if you take a break when you’re young’. That’s the narrative.
That’s not wrong, but that’s not always a useful framework.
1. You could die
Just saving money for a hypothetical future isn’t a good strategy cause you never know if you’re going to be around to actually enjoy that money.
Doesn’t mean you should just go crazy and spend it all tonight either. It’s a balance of both those extremes.
2. You’ll actually reach your goal quicker if you take a break.
This is a hard concept for most people to get so I’ll use numbers, I’ve seen this happen multiple times with many people so it’s a good hypothetical:
- you make $500 a month and manage to save 6 months expenses.
- take 6 months break and you learn new things
- you now make $3000 a month with the knowledge, you save 2 years expenses
- You take a 1 year break
- you now make $20k a month, you save 10 years expenses
- Take a 4 year break
- you now make $50k a month and reached your goal faster vs trying to achieve it with $500/mo
Jump. That’s always my mentality.
In each ‘break’ you let go of your previous world. Kill your community, kill your reality.
Take a step back, take a break maybe a year maybe two as much as you can afford. Reinvent yourself and jump ahead.
3. Unless you spend savings you’ll always be afraid.
Money is stored freedom, but it’s not active freedom unless you use it.
Most people save to protect themselves from bad things happening (Eg. Job loss, failure of business) and their insecurities get wrapped around the amount of savings they have.
Not seeing their investment portfolio going up would create fear.
so why not pull from the other extreme and make your portfolio go down intentionally by actually spending it?
Realizing that you can always top it up and live life and use that freedom to actually do all the things you want to do.
So what’s retirement for me?
In fitness there’s an idea called Muscle memory. Dorian Yates described it best on Joe Rogan:
You see that body, it look me 10 years to grow it that much. Now if I took 3 years off and came back to it, I could get the body back in 6 months.
“That can’t be true.” Well the exact details might be off but the idea and trend isn’t.
There’s a really cool experiment where a guy gained, 63 pounds of muscle in 28 days.
Why do I share this information about muscles?
Well if you’re in the right industries it works the same with Money.
After dropping out of college it took me nearly 3 years to make >$3k/mo. Now if I started working I could easily make over $3k/mo in less than 2 months.
Same logic as muscle memory. MM is just a baseline. If you want to increase your MM you still have to work just as hard, but your baseline obviously goes up over time if you put in the work.
Eventually you just jump s curves when you learn more and more with every break you take.
Imposter syndrome will probably come in the way for many people here where they’re too afraid to stop making the $ cause they’ll be afraid that they’ll never be able to recreate it.
This is why I recommend retiring often. Leave things when they’re good and come back to them so you realize it’s always reproducible.
Nat Eliason has a good tweet and article on the second aspect of this which is, The Life-Changing Magic of High-Speed Career Sampling
Testing potential careers at high speeds and shameless quitting bad fits should be encouraged.
In the last 9 months I tried being a YouTuber, real estate developer, normal software engineer, then found a home in crypto.
Took a few tries, but so happy where I ended up.
— Nat Eliason (@nateliason) August 9, 2021
When you’re independent and have optionality you can pick to spend one year trying 5 different careers because you’re not in the position to say yes to every single opportunity that comes on your plate.
And can wait, relax until the right opportunity comes on your plate.
Or as Derek Sivers said, It’s hell yeah or no.