The Jared Dillian Letter

There’s plenty of opportunity once you pass survival mode

Human instincts haven’t changed much since we moved out of the cave. We’ve just modernized our fears.

Today, instead of worrying about saber-toothed tigers, we worry…

  • What if I lose my job?

  • What if I wreck my car?

  • What if the stock market crashes?

Humans are still stuck in survival mode, but now it’s all centered around money.

Personal finance orthodoxy plays into these fears. It’s all about pinching pennies and scraping by. It’s about surviving (which you are already pretty good at). But it stops there.

Today we’re going to talk about how you can move past all that—and go from surviving to thriving.

Step #1: Eliminate Your Debt.

You can’t thrive if you’re paying $5,000 a month for stuff you bought three years ago. You need to eliminate that debt (but you already knew that).

Maybe you’ve considered the snowball method, where you pay off your smallest debt first and work your way up. I’m not a fan of this method—it infantilizes people. Even worse, it can cost you thousands of dollars in extra interest.

Instead, sit down and look up the interest rates on your credit cards and other loans.

Of course, you have to keep up with the minimum payments on everything. And do it on time—always. From there, start eliminating your highest-interest debt first. This will probably mean credit cards, followed by your car loan, and finally, your mortgage.

How quickly can you do it? I’m a fan of the Damn, This Hurts test. You want to pay off enough every month that it feels uncomfortable.

That discomfort won’t last forever. Because once the debt is gone, you get to keep the money you earn. And when you do buy something…

Step #2: Pay Cash.

Pay for things with the money in your bank account (or with literal, cold hard cash). Don’t put it on a credit card. This will keep you from returning to debtors’ prison.

You will also need to plan for surprises, which inevitably happen.

Your first goal is to save $10k in an emergency fund. After that, work on saving six months’ worth of living expenses and then one year’s worth.

This way, when the check engine light comes on, or your dog is rushed to the vet, or something even worse happens, the money is there waiting for you.

The first time you handle an emergency with cash and not credit feels really good. You are one step closer to thriving.

Now it’s time to...

Step #3: Maximize Your Earning Potential.

Not all jobs come with stock options and a clear path up the ladder. If you have a job like that, great! You have exposure to the upside.

If you don’t, have a conversation with yourself about what you’re worth and how to maximize your income.

If you think you are underpaid, you can request a raise. If you don’t get it, nothing is stopping you from seeking employment with someone who will pay you 20% more for similar work.

What if the problem is your skillset? If it can’t bring in the kind of money you want or need, consider expanding it—or just learning a new skill, period.

That might mean getting your real estate license, or starting a junk removal business, or getting certified as a welder. If you’re into tech, maybe you learn a new programming language.

The extra money might not come from the things you are good at now, but I’m sure there are lucrative things you could excel at if you invested the time.

Step #4: Take Some Risk.

Once you’ve wiped out your debt, built up your savings, and boosted your income, you are free to take a few risks to increase your wealth even further.

This comes with a disclaimer: Do your research first.

If you want to invest in the stock market, do your homework. If you want to invest in real estate, learn about it first.

That does not mean listening to family and friends unless they are experienced professionals. Everyone has a neighbor/cousin/brother-in-law with “hot tips.” Virtually all of that is crap advice. And if you hear someone say, “Buy Gamestop!” just run the other way.

If you aren’t sure how to start investing, this short report I wrote will help: How Do I Start Investing? It’s free, by the way. Just download it.

Step #5: Learn How to Spend Money.

Alright! You are debt-free, cash-heavy, and taking calculated risks.

You have plenty of money for a better lifestyle. But for some reason, you don’t feel comfortable spending it. Instead, you just keep stashing it away, waiting for bad things to happen.

That is not thriving.

Hard work is supposed to hand you a reward. So, it’s time to figure out what makes you happy.

Personally, I’m not much of a car guy. My everyday car is a Toyota Highlander. But part of me has always wanted a Corvette.

Because I completed Steps 1–4 a long time ago, I have plenty of cash on hand, and I finally bought one. The decision to buy the Corvette made me happy. Paying cash for it made me even happier.

But it’s taken me years to get comfortable spending.

When I worked at Lehman Brothers, my base pay was in the high six figures. What I made on commissions pushed me into seven figures. But in the seven years I worked there, I only took one vacation. (That alone is a bad sign.)

It wasn’t even a fancy vacation because I was cheap. My wife and I rented a place for $250 a night on Cat Island, one of the most deserted places in the Bahamas. It’s basically a strip of sand.

Cat Island, The Bahamas—aka The Barren Strip of Sand

I’ve since learned my lesson. We recently got back from Greece, and though I didn’t blow my money on a yacht, I did spend the right amount of money for my income level.

What Does Thriving Look Like to You?

Is it taking short trips whenever you like? Putting in a backyard pool? Maybe it’s as simple as buying as many books as you like.

Not everyone thrives in the same way. One of the best things about building up your wealth is you don’t have to fit into some rich-person mold. There isn’t one.

You get to do what makes you happy.

If you haven’t gotten there yet, you do not have to remain stuck in the same spot, endlessly treading water just to survive.

There are plenty of opportunities out there.

Jared Dillian
Jared Dillian


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