How to Plan Your Life Like an Investment Portfolio to Achieve Ultimate Freedom

What would you invest in if you are to live to 120?

Most people live life not looking too far ahead. That’s why their options shrink over time.

If you want to live a long and free life, you want to plan it like a long-term investment portfolio. Here’s a 6-part framework of how to do that👇

1. Get into a growing field with steady cashflow

Choose your first profession in a field with growing demand.

This should be a field unlikely to be replaced by tech for the next 20 years. Eventually most professions will be replaced, but buy yourself time as much as possible.

If I were to pick today, I’d choose bioscience, software engineering, or data analytics, in that order. The entry barrier for the latter two has dropped dramatically with the internet, so competition is higher. But that tells you demand is also high.

Years ago I picked macroeconomics. It’s a field a lot like medicine. Stable demand, but you need large upfront investment to get in. Once you’re in, the cashflow is decent, but the upside is not big. Overall an ok choice but not the best.

Pick a field with increasing demand. Rising tide lifts all boats.

2. Solve housing expense ASAP

Own a house in full equity as soon as you can.

Rent/mortgage is the biggest expense outlay for most people. It’s a heavy shackle on financial liberty. Once you solve it, you have the safety to explore riskier bets.

You want to buy a place and pay it down ASAP. It doesn’t have to be where you live if that’s too expensive. Remote work will prevail. It’ll be less important where you live in the future. And there’re plenty of places in the world with cheap real estate and good internet. So if you can’t afford your current location, buy cheaper elsewhere.

I bought an apartment a week after I got my first job, paid it down, rented it out, and moved to a smaller and cheaper place. This way my housing outlay became zero.

3. Build another stream of income

Once you solve step 1, you want to diversify your income sources as much as you can to be more anti-fragile.

This means things like freelancing, consulting, selling small software, drop-shipping, selling content, etc. Pick something that does not require lots of capital upfront, can be done part time, and leverage your skills.

It doesn’t take much to start making a bit of money online. (You can make 40 bucks a week playing Axie Infinity for God’s sake!)

But you want to choose carefully because you have limited time. You want to pick something you enjoy doing, and allow you to improve skills, so it doubles as an investment in human capital (see below), even if it’s the not the most profitable choice in the short term.

In other words, pick things that expand your options and leverage over time, not the opposite.

4. Invest in your own human capital

It used to be that you go to college / grad school once, and you’re done with education for life. Not gonna work anymore.

Human lifespan is increasing. Retirement age adjusts accordingly. Adding to the fact that knowledge creation cycle is accelerating, it means you can’t expect to stick to one career for your entire life.

If you’re ambitious (or crazy, depending on your worldview) like me and expect to live to 120 – 150, you won’t retire even in your 90s. If you’re going to work that long, you will likely need to have not 1, but 2 or 3 full careers, as how we currently define “careers”.

You’d be delusional to think that could happen without additional investment in your human capital.

A good friend of mine decided to change career in her mid-40s. She went back to school for three years to get a master’s in this completely different field. That’s a huge investment most people don’t dare to make in their 40s or 50s.

It was a tough three years because she had to juggle full time job and full time school. But she pushed through, and is now free to start a new career that can last 30+ years. (She’s in counseling psychology, so older is actually better.)

To all the people who laughed at her for being “too old”, “too late”, “too financially irresponsible”, who’s laughing now?

Even if you’re in a career you love right now, allocate 20% of your free cashflow and your time to invest in a new one. You’ll likely need it. This applies to everybody regardless of age.

5. Invest in a real business

Most people unhappy with their job and paycheck have a false, romanticized idea about entrepreneurs.

If you think entrepreneurship is cool, flashy, and an easy way to make money, you haven’t owned a real business. By a “real business”, I mean a going concern that has employees, accounts, vendors, investors, i.e. a hub of production activities that generates values.

Having been on both sides of receiving and giving paychecks, I can tell you the latter is harder. Way harder. This is true whether you’re operating a neighborhood dry cleaner or a Fortune 500.

On the flip side, if you can make the business work, it can create predictable cashflows and have higher upside if it scales. But it is a risky bet. So if you want to attempt this, do it after you take care of steps #1 – #2, and ideally #3.

Soundwise is such a bet for me. Right now it generates enough revenues to pay the team and our operating costs, but it’s not creating any cashflow for me, the owner. I sure hope this will change. But if it fails completely, at least it would not endanger my finances and lifestyle.

A real business can be a worthy investment, once you build your safety net. But don’t bet your life on it.

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6. Invest in long-term growth themes in financial markets

You’re better off making long-term bets in the market rather than trading in and out.

Investing in financial markets does not require any overhead. You don’t have employees and customers to manage. In that sense it’s simpler than a real business.

But simpler doesn’t mean easier. Otherwise why hasn’t the whole world become rich like Warren Buffet?

Being a successful market trader takes a lot of skill, and requires a certain personality, which most people don’t have, including me. (To get a sense of what it takes, check out Jack Schwager’s Market Wizards books. They give an excellent overview.)

It’s much easier predicting what would happen in 20 years– e.g. Currencies will be digitized, energy cost will drop, lifespan will be extended further— than predicting what will happen next week or month.

So unless you plan to spend all your life studying the markets (you still have steps 1 – 4 to take care of, remember?), you’re better off betting on long-term growth trends that would play out in the next 10-20 years.

Identify the trends and the investments that will benefit from them, get in at good entry prices or do dollar cost average, try not to FOMO, and hodl for the long term.

Allocation

Once you solve steps 1 and 2, save 10% of your free cashflow in an emergency fund on which you can live for 6 moths – 1 year. Do not touch it. After that, you’re free to allocate cash to steps 3 – 6 however you please. In summary—

How to plan your life like an investment portfolio to achieve personal freedom:

1 Get into a growing industry

2 Get housing expense down to zero

3 Build another stream of income

4 Invest in your human capital

5 Bet on a real business

6 Invest in growth themes in financial markets

Liked this? Follow me on Twitter 👉 @realnatashache, for more ideas to help you become wiser, richer and happier.

In Episode 119 of the School of Intuition, I talk about my 6-part framework for planning your life so that your options and freedom expand, not contract, over time.