Back in 2012, when I left my finance job, I worried that I had made a huge mistake. The money was good. The work provided a good atmosphere. But I was exhausted from the grind. So I did what any sane person would do when faced with one, limited life: I chose a better way of life.
It would be completely unreasonable to stay miserable just to collect a paycheck, especially when the long-term health costs become apparent. However, leaving a high-paying job without another job lined up is scary. Freedom always sounds better in theory than it does in practice.
So I made emergency plans.
I wrote about creativity financial buffers my financial buffers. The idea was simple: build so many walls that if a tsunami ever reached my money, it would lose momentum before destroying everything. Only if all those walls fail will I have to put on a wetsuit and go back to the grind.
One of the most important safeguards was investing.
With just a chip and a chair, anything is possible. And now, as AI guardians approach millions of ways to make a living, guardians strengthen their power, and capital is becoming increasingly concentrated, learning how to be a skilled investor is no longer optional. It is essential for survival.
Why Talent Investment Is More Important Than Ever
We know that artificial intelligence will eliminate or suppress millions of jobs.
At the same time, traditional routes to the top are closed. The details are not that important. Relationships are very important. And the rich, who are rationally self-interested, don’t line up to redistribute their money to the rest of us.
The less valuable the work, the more powerful the capital.
You can fight this fact, complain about it, or be nice about it by showing the goodness of the investor. Or you can adapt. I prefer to adapt.
Being a good investor is how you give back agency in a world where wages are uncertain, jobs are fragile, and loyalty is rarely rewarded. Investing is one of the few skills that balances without asking for permission.
An Important Goal All Skilled Investors Should Have
There are countless goals and benchmarks that investors can set. Beating the S&P 500. Will retire at 50. Saving enough for college. But while you’re still working, there’s one goal you should follow:
Try to make your investment always match or exceed your daily income.
If you can achieve this goal at least 70% of the time before you LEAVE, you are probably a good investor. You have developed a skill that gives you a choice. Don’t lose your job and don’t panic. You can take risks that others cannot. You can wait instead of begging.
When it’s HOT, the goal naturally evolves.
Your next goal would be to always get enough money from your investments to cover your basic living expenses againor your income already covers it.
This may sound unnecessary, but it is done on purpose. My definition of FIRE, which I proposed back in 2009, is when your income covers your basic living expenses. Anything above that is the safety margin.
Protecting Your Retirement By Continuing to Grow Your Wealth
The goal of an investor in retirement is to save money to build so that your margin of safety expands over time, not shrinks.
Goodness knows your costs can go up due to inflation, children and medical expenses. The more money you have working for you, the less likely you will need to go back to work out of necessity.
If you want a realistic stretch goal in retirement, try to generate more from your investments than the average income you earned during your last three working years. When you do, you buy even greater peace of mind.
And if you achieve this, it is probably not because of you the need order, but because you enjoy the process.
Investing Is Stressful Because It Takes So Much
When you no longer have a day job, you will naturally find new ways to stay engaged. Since I started investing in 1996, and spent 13 years working in the equities departments of two major investment banks, investing has been a part of me.
Since my son was born in 2017, I set myself a personal challenge: I’m trying to get more out of my investments than my biggest income year in 2007. It gives me a great sense of purpose as a provider.
I failed to do that in 2018, 2020 (close), 2022, and 2023 (close). But I made it through 2019, 2021, 2023, 2024, 2025. A 50% success rate so far isn’t great, but it’s a fun challenge that keeps me sharp. The challenge also gives me endless things to write about, which helps support Financial Samurai.
Managing family finances can seem like a full-time job. Negative mood swings.
When markets change, mood swings can be sharper than they should be. Ideally, a skilled investor should have the calmness of a monk. Bad market day it must be it is not visible to his spouse and children. Sadly, I’m not there yet, but I’m working on it.
The upside, however, is logical.
You can make a lot more money. And if you have a lot of money, you should worry less – at least in theory – about running out of money. When you become a parent, the pressure to make more money increases. If you don’t have a day job, that pressure just spills over into your investment.
What gives me peace is knowing that even if something goes wrong, I have a realistic chance of recovery by investing.
What makes a Skilled Investor
Being talented does not mean being smart. It means having the ability to do something well enough, consistently enough, and to be trusted with responsibility over time.
A good investor doesn’t need to hit a home run. They need to avoid strikes in order to keep growing their wealth in a consistent manner.
Here are the key characteristics of a good investor:
1) They understand the risk before rushing to return.
Skilled investors know exactly how much they can lose without panicking or being forced to sell. They size positions accordingly. They are heavy first, then they grow. Improper risk management is the biggest mistake I see in DIY investors.
Skilled investors don’t have big blowups with their money. Because if you end up losing a lot of money, you end up losing a lot of time. And time is the most precious commodity of all.
2) They have a repetitive structure.
They don’t invest based on vibes, headlines, or social media buzz. They have a process for evaluating opportunities, allocating money, and exiting when the thesis breaks down.
3) They differ in intelligence, not blindness.
Skilled investors diversify across asset classes, income streams, and time horizons. But they also understand the connection to concentration. Diversity is a tool, not a religion.
4) They control behavior better than most.
They don’t panic by selling near the bottom or chasing near the top. They know that emotional mistakes are more expensive than analytical ones.
5) They measure results honestly.
They track performance against reasonable benchmarks, after fees, after taxes, and after inflation. They don’t lie to themselves like Coast FIRE fans sometimes do.
This is where most people fail. Rising balances create the illusion of success, but few investors know their true returns after fees, taxes, inflation, or excess exposure.
That’s why I use the free financial dashboard from Empower. It puts every account in one place – value, distribution, payments, and performance – so the truth is unavoidable. You can’t improve what you refuse to measure.
6) They are always learning.
Markets are volatile. Technology is changing. So should investors. Being skilled is not a place; it is a stored skill.
I didn’t spend three hours researching and writing a post about how different fund structures trade for fun. Sleeping in on Sunday morning after having the kids for two days was better.
I wrote this post because I needed to fully understand what to do and what to expect with my $700,000 position Fundrise Innovation Fund.
If You Don’t Want to Be a Skilled Investor, Outsource a Job
Not everyone wants to spend years learning how the markets work, tracking portfolios, or thinking critically about asset allocation and risk. That’s right. And I understand.
But what not well he’s doing nothing and hopefully things will magically work out. Decades from now, you may end up with a lot of money, or you may be wondering where all your money went.
If you’re busy, disinterested, or honest enough to admit you don’t enjoy investing, the smart move is to without managing your money that it does take it seriously. Just as you wouldn’t perform your own surgery or defend yourself in a complex legal case, you shouldn’t be taking on something as important as your family’s financial future.
The key is to post with intention.
You want to work with professionals who have programs, incentives, and experience aligned to help you make solid, long-term progress, not just sell products or chase hot trends.
Getting an outside job doesn’t mean abdicating responsibility. It means choosing the highest probability outcome if you know your limits. I don’t get into my roof to clean my gutters, so I hire a professional to do it.
A good investor understands himself first. If your limit is earning, building, or creating, let someone else focus on growing your capital.
Investing as a defense and offense
In a world where job security is shrinking, income inequality is rising, and institutions are faltering, investing is no longer just a matter of wealth creation. It’s about self-defense.
That’s right you reduce dependency for any one employer, industry, or program. It’s how you buy time when things go wrong. It is how you maintain dignity when circumstances change.
You don’t have to be different.
But you do skill is required.
Because as the future becomes more uncertain, the ability to make your money work for you may be one of the most important skills you ever master.
Readers, how important do you think it is to be a good investor in order to become financially independent in the future? And do you believe this is a skill most people can realistically develop, or should practice externally? Do you think investing will be a more important life skill for our children than it is for us?
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