Have you ever lay awake in bed on a Sunday night, dreading the coming morning?

I know I have, along with a disappointingly high percentage of the American workforce. But that anxiety isn’t a given. 

In my years working as a CPA, I studied dozens of my clients that managed to escape the 9-5 grind and live a fulfilling day-to-day life.

Today, I’m going to show you how you too can achieve financial freedom and use it to create lasting happiness. Let’s get started.

The Four Foundations of a Life Worth Living

First, let’s talk about why financial freedom is so important.

People are endlessly chasing what they think will make them happy. And let’s be real, it’s usually something to do with money.

We dream of paying off student loans, buying a new car, or getting a promotion at work because we instinctively understand that financial success is connected to happiness. Sadly, it’s hard to nail down what that connection really is.

Don’t worry, I’m not going to sit here and tell you that nice things are evil or that vacations are a waste of time. We both know that isn’t the case.

Plus, it’s easy to tell people what won’t make them happy. But what will actually do the trick?

There’s a pleasantly surprising amount of research on the topic of happiness. Definitely check it out. When I dug through it, there were four fundamental concepts that showed up repeatedly. 

In no particular order, they were: 

  • Security
  • Freedom
  • Self-esteem
  • Connection


First, what do I mean by security? Does everyone need to pay a bodyguard of questionable physical fitness $16/hour to skulk around behind them in order to be happy?

Might be fun. Until you have to pee and turn around to find them still hovering over your shoulder.

No, a sense of security is as simple as managing your fears with purposeful action.

The three most common areas of concern are financial security, physical health, and relationships. You need to be able to sleep comfortably at night, knowing that you have a good plan to manage at least those three.


Nobody likes to be told what to do. The stereotype of the rebellious teen exists for a reason. As soon as we reach a basic level of competency, we want to be in charge of ourselves and what we do with our time.

That desire for autonomy doesn’t go away when we get a job somewhere. We usually just accept that we have to give up a degree of our freedom in the name of practicality.

Everyone needs to pay the bills, and that usually requires playing by someone else’s rules in exchange for a paycheck.

Of course, there’s a sliding scale of tolerance for this. Living the corporate life made me want to bash my head through my cubicle wall, but I’ve definitely met people who were happy to clock in and out each day.

Figure out where you fall on the freedom spectrum. Whether you want to start your own businesses or just avoid a micromanaging boss, you shouldn’t settle for anything less than you need.


Okay, now we’re getting into the more interesting stuff. Can you actually learn to like yourself more?

It’s easy to think that your self-esteem is just a part of your personality. But the truth is, it’s a habit like anything else.

Have you ever met someone with unshakeable confidence and wondered where it came from? They built it. With action.

I’ll be honest – I hate mindset gurus. “Think bigger, get out of your comfort zone, shift your perspective, blah blah blah.” These are all pretty much meaningless. In reality, people are defined by their actions.

That’s the key takeaway here: do things you find admirable until you can’t help but admire yourself.


Connection can be the hardest need to define, since people have such different social expectations.

I’m a lifelong introvert and have always preferred the company of a few close friends to a crowded party. Still, I get a lot of benefit from being a part of communities that I admire and spending time with loved ones.

Whatever your particular needs are, I’m sure you know the feeling of wellness that comes from a genuine connection with others.

Humans are social creatures. We need quality relationships in our lives. Make time to nurture the ones you have, and always be open to the possibility of making new friends.

Optimize Your Finances for a Happy Life

At this point, you’re probably saying “Okay, Nick. Your ideas sound nice. But what do they have to do with financial freedom?”

Glad you asked. Everything.

My working hours are all dedicated to creating three financial “assets,” each of which contribute towards one or more of the four needs I discussed above. Let’s take a look at them. 

Asset 1: Satisfying the 4% Rule

The first asset is the most straightforward, but will probably take the longest to achieve.

If you’ve done any sort of retirement planning, you’ve probably heard of the 4% rule. It’s a simple rule of thumb that says if your net assets > 25 times your annual spending, you’re financially free.

This is based on the Trinity studies performed in 1998 by a group of economic professors at Trinity college.

They found that the vast majority of stock heavy portfolios will survive an annual withdrawal rate of 4% or less over 30 years. If you’re interested, you can look at their studies in more detail here.

What does this mean for you?

In simple terms: if you have a million dollars invested, you can spend $40,000 of it every year and be confident that you won’t go broke, even if you adjust each year for inflation.

It’s easy to see why building a portfolio like this would change your life. 

Your basic lifestyle is paid for, and any job you take is just icing on the cake. That’s a massive win for freedom and security.

Increasing the rate at which you satisfy the 4% rule is all about optimizing your earning, spending, and investing. 

I currently live a comfortable life in San Diego spending roughly $18,000 a year. Since I’m a cautious man, I inflated that number by a quarter to $24,000 and multiplied it by 25 to reach my paper portfolio goal of $600,000.

You might pause at this point and think… Isn’t this all you need? If you have the ability to retire, shouldn’t you be able to go live on a beach somewhere and be happy?

Maybe. Maybe not.

There are drawbacks to relying solely on the 4% rule:

  • It can take you upward of a decade, even if you’re hyper-disciplined
  • It doesn’t provide any opportunities to build self-esteem or connection
  • Your investments are at the will of the market (sequence of returns)
  • There’s no guarantee that future stocks will behave as they did in the past

Those last two are the issues we’ll address first. After all, we’re looking for security here. Can you sleep at night with no back-up plan? I can’t.

That’s where the second asset comes in.

Asset 2: Reinforcement through Real Estate

A lot of people are intimidated by the real estate game, mostly because it’s not as passive as paper investments. But that’s actually a good thing.

Stock picking is a game where the odds are stacked against you. The more you try to dance in and out of the market, the more likely you are to fail.

But real estate is the opposite. Unlike stocks and bonds, real estate encourages you to take control.

You pick the properties, you execute the strategies, and you bear the responsibility for your success or failure. Knowledgeable and intelligent investors can create returns far better than the stock market average.

My personal goal is to create another complete source of financial freedom through real estate. That means another $24,000 a year, this time through rentals.

That could be just four rental properties at $500/month each.

Think you could find one of those a year over the next four years? I know I do.

Check out this post for a detailed discussion on the real estate strategy that can get you all four of those properties by recycling the same down payment.

Now let’s dive into the third piece of the puzzle. This is the real holy grail, but it’s not exactly an asset in the same way as the other two.

Asset 3 – Find or Create Your Dream Job

All too often, we settle for jobs that slowly grind the soul out of us.

I’m not the guy to tell you to abandon everything to recklessly pursue your dream of being a pop star, but there are responsible ways to work towards a job you enjoy.

My story is a good example.

I graduated from college with double majors in Finance and Accounting. Mostly because I liked business, and people told me it would “open a lot of doors.” Which was good, because I had no idea what I wanted to do.

I started my career with an international public accounting firm as an auditor. It was a decent gig, but it wasn’t perfect. There was too much travel for me, the hours were rough, and I couldn’t relate to the enormous clients.

So I eventually took a job with a local accounting firm on the tax side and specialized in real estate.

It allowed me to stay in my hometown of San Diego, have a better work/life balance, and work with smaller businesses. 

And things were… better. But I still wasn’t happy. I wanted to write, create, and be my own boss. And to be honest, I was never cut out for corporate office culture. So I made my plan to get out.

How? I got my savings rate up to 50%. Then 55%. Then 60%. Pretty soon, I realized that I had enough saved to go without work for 5 years if I wanted to.

With that kind of cushion, I felt comfortable pursuing a freelance career as a copywriter. And let me tell you, finding a job you enjoy is worth the effort.

I wake up every day feeling excited to work on my projects. I’m motivated, passionate, and happier than I previously thought possible.

Best of all? I no longer lay awake on Sunday nights, dreading the coming morning.  

Why Does This Work?

One of the best ways to come up with a plan is to work backwards from your desired endpoint.

Maybe you used this strategy to figure out those mazes that restaurants put on the back of their kids menus. The same idea works here.

I took a clear picture of what I wanted: freedom and security, a sense of self-worth, and good people to share the journey with. 

I worked backwards from that picture and created a plan to build each of those pieces.

Meeting the 4% rule will give me a fundamental level of freedom and security. Of course, the future is uncertain, and the back-up plan of real estate provides me with true peace of mind.

Even if there’s some sort of stock market disaster (maybe a pandemic hits), my financial freedom will be strong enough to weather the storm.

And finally, having my dream job gives me purpose, a community I admire, and a sense of pride in my work. I’ll be able to rely on it for structure and purpose each day, even after I have the means to retire.

So I guess that’s one asset down, two to go.

How You Can Start Today

All three layers of my plan are long term projects that take years to grow, but I’m not putting happiness on hold until they’re done.

I already strive to take on work that I can be proud of, to take comfort in my growing independence, and to connect with communities of like-minded people.

Whether you copy my strategies or come up with your own, I hope you find happiness along your journey.

Do you like the plans I’ve outlined above? Have you developed some of your own?

I’d love to hear your thoughts. Tell me your story in the comments below!

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