You’ve done everything “right” but you’re still worried about money. Why?

You’ve done everything “right” but you’re still worried about money. Why?

Our product team has been working on something so interesting, I asked them to share some of the insights we’ve discovered.

Alistair Clark, one of our product developers, has been speaking with people who have already done the basics of personal finance: These people have already set up automated savings accounts and invested. Many have accumulated considerable amounts of money in the hundreds of thousands (or millions) of dollars.

So what’s next? What do you do when you’ve already done the basics of personal finance?

Alistair got the kind of behind-the-scenes access that few of us have. He spoke to wealthy people about their hopes, fears, and dreams around money — and discovered that once you’re at a more advanced level, your concerns change. Your goals change. And whether you intended to or not, your lifestyle changes.

Let’s see what he found.

Alistair, take it away…


Every week, Ramit gets thousands of emails with questions about personal finance.

99% of the time, his answer is the same: “Go read my book, I Will Teach You to be Rich.

But 1% of the time, he gets a really interesting email that doesn’t have a simple answer, and he’ll forward it over to the IWT product team to see if we can help.

For example, check out this email a reader sent to Ramit after reading the IWT book:

It’s too beginner for me. I finished because of the entertaining style and I like to vet books before recommending them. My stage is this:

  1. Zero debt… pay credit cards to zero, twice a month. Paid off my mortgage 25 years early ($230k). Haven’t paid a car loan in over 5 years. And my twins are now in school (so no more $1,500/mo child care any longer).
  2. I’m self-made with a video production/photography business + my wife is a psychologist with the VA, so we have a decent income.
  3. We each have contributed $18k into our 401ks (mine is a solo-k) for years.
  4. We have maxed our ROTHs for about 7 years each (more on this later).
  5. We are very frugal (our two spending items are 1. quality food (groceries) and 2. travel).
  6. I’m about to turn 38, wife is 34.
  7. We have $750k-$775k invested/saved and adding our house puts us over a million.


At IWT, we love seeing emails like this. Here’s someone who actually took action, implemented our personal finance advice, and is now in a great place with their finances.

From the outside in, there’s absolutely nothing to worry about! And yet, we continue to get emails just like this from people worrying about their finances.

What’s going on here? Why do we worry about money even though we’re doing everything right?

The psychology of why we worry about money

In Ramit’s book, he outlines what we call “The Ladder of Personal Finance.” People loved having a clear roadmap telling them exactly what to do next.

“The Ladder of Personal Finance” from Ramit’s book, I Will Teach You To Be Rich

But eventually, you get to the end and there are no more rungs on the ladder. You’ve checked all the boxes. All you’re left with is that same empty feeling we had after finishing our favorite video game that we spent hours trying to master. Except… you don’t have another game to play. With your finances, it can seem like the only thing left to do is sit and wait for the next 30 or 40 years until you retire.

I don’t know about you, but that sounds boring as hell.

I’m impatient. I want to be optimizing, tweaking, and doing something to keep getting better every single day. If someone came to me tomorrow and said, “OK Alistair, you’ve checked all the boxes for your business. Now you just have to put it on autopilot and go sit on a beach for the next 30 years,” I’d tell them they were crazy.

Humans are problem-solving machines. We aren’t good at sitting on our hands and being patient. For example, just look at this video of a woman in a self-driving car for the first time. Does she look relaxed? No! She is freaking out and worrying because she has nothing to do.

If money is supposed to buy us peace of mind, then why do some of us act just like this woman in the self-driving car? And what is the “last mile” that can get us to be more zen about our finances? 

3 things we noticed from people who don’t worry about money

As I mentioned above, I’m on the product team here at IWT. We’re in the course-making business, which means solving some gnarly problems for our readers. And this is the type of big question we LOVE to tackle to see if we can find interesting, counterintuitive solutions.

Over the past month, we’ve been digging into the tactics and mindsets of the wealthy to find out what they do once they’ve “checked all the boxes” and mastered the basics of personal finance.

How do they get to that enviable position where they never have to worry about money again? What do these carefree people know that we don’t?

Today I’d like to share three examples:

1. They are prepared for everything

Earlier this year, the New Yorker ran a fascinating article titled “Doomsday Prep for the Super-Rich”. In the piece they described how some of the smartest, most successful people from Silicon Valley and Wall Street are preparing for the apocalypse (yes, you read that correctly). They are buying remote property, building self-sustaining bunkers, and sometimes even stockpiling ammunition to prepare for the eventual breakdown of civilization.

When asked the simple question of “Why?” here’s what Yishan Wong, the former CEO of Reddit, told the New Yorker:

Most people just assume improbable events don’t happen, but technical people tend to view risk very mathematically … The tech preppers do not necessarily think a collapse is likely. They consider it a remote event, but one with a very severe downside, so, given how much money they have, spending a fraction of their net worth to hedge against this … is a logical thing to do.

Maybe you’re not ready to drop a few million on a bunker in rural Kansas, but that doesn’t mean you can’t be prepared for the future.

In speaking to our students who worry about money, I’ve noticed that a lot of people are afraid of unpredictable things that might happen in their future. Some people refer to these as “the things you don’t know that you don’t know” or “unknown unknowns.” Here’s how one student described his fear:

What worries me isn’t job loss. What worries me is the million other things that could pop up. What’s hiding around the corner that I don’t know about?

This type of fear can be incredibly powerful, because your imagination runs wild with worst-case scenarios. It’s like when you are walking down the stairs into a pitch black basement of a rickety old house. It’s terrifying. Anything could be lurking in those shadows.

But there’s a simple solution: Turn on a light.

You can do the same thing with your finances. Instead of being afraid of “unknown unknowns,” you can shine a light on your financial future by learning from people ten years older than you who can tell you exactly what to expect.

We call it the “10 Year Savings Strategy” and wrote about it here.

2. They protect the money they already have

Ever see a news story about a rock star or athlete going bankrupt and wonder, “How is it even possible to lose that much money?” ESPN’s documentary Broke investigated the phenomenon of very rich athletes going completely broke. The statistics are shocking:

According to a 2009 Sports Illustrated article, 60 percent of former NBA players are broke within five years of retirement. By the time they have been retired for two years, 78% of former NFL players have gone bankrupt or are under financial stress.

One of the primary causes of financial problems for these athletes was not extravagant spending. It was mostly due to bad investments, ranging from real estate to restaurants to car washes.

It’s an interesting cautionary tale because one of the most common questions I get from students who have “mastered the basics” of personal finance is “How do I make my investments grow faster?”

As your wealth grows, you’ll find the investing opportunities start to grow as well. Instead of just a “boring” target date fund, now you can buy real estate, invest in start-ups, and take sizable positions in individual stocks. At a certain level, the world of hedge funds and private equity start to open up as well. It’s tempting to throw your money at these exciting opportunities and promises of outsized returns and it’s easy to develop an obsession with growth and moving faster.

I find this fascinating, because the research I’ve done revealed that the most successful wealthy people have the opposite approach. Instead of asking “what can I gain?” their #1 question is “how can I avoid losing money?”

For example, Warren Buffett has two rules of investing:

Rule 1: Never lose money.

Rule 2: Never forget rule 1.

So what does this mean for you?

This is more a matter of mastering your own psychology than any new tactic or fancy asset allocation. There’s a reason at IWT we consistently recommend boring, simple investments like lazy portfolios and target date funds.

But we’ve also spent enough time studying the psychology of personal finance to know that being a 100% disciplined monk with your investments is near impossible. No matter how much you read about the merits of basic index investing and why stock picking never works, there’s still a little voice in your head saying, “Yeah, but what if I find the next Amazon stock? I’d be a millionaire in five years!”

Here’s what we recommend: instead of suppressing that voice in your head, embrace it. Take 5% of your portfolio and put it aside for whatever crazy idea you have for making your money grow faster. Invest in Bitcoin. Buy $5,000 in Tesla stock. Invest in your cousin’s car wash if you want.

Do whatever you want, because while you might lose that 5%, you can sleep well at night knowing 95% of your money is still safe and protected.

3. They don’t do it alone

There’s a great scene in Entourage where the agent Ari Gold is introducing the management team of actress and singer Mandy Moore.

(Heads up: You may want to put in headphones for that link, there’s some NSFW language in that clip.) 

It’s kind of eye-opening as he goes down the line introducing this super-team of six people who are required to manage the career of just one person: manager, music agent, publicist, attorney, music manager, theatrical agent, etc.

It’s also possible to develop the same type of super-team to manage your finances and literally outsource your worry to someone else. Attorneys, accountants, life insurance specialists, financial planners, investment advisers, and even a psychologist or psychiatrist could all be part of your financial super-team.

You might be thinking, “Wait, what? I thought Ramit hated financial advisors. Doesn’t he spend an entire chapter in his book telling me NOT to hire a financial advisor. So what’s going on here?”

I asked Ramit about this incongruence, and he pointed out a really interesting and counterintuitive insight: Once you reach a certain point, the basic personal finance rules no longer apply.

Normal people with ordinary financial needs don’t require an advisor. That’s why we tell most people it’s not worth their time. But once you’ve conquered the basics, then the basic rules no longer apply.

Here are a few scenarios where it DOES make sense to pay an advisor:

  • When you have a lot of investable assets (~$1MM+) and have much more to lose if you make a mistake.
  • If you have complex situations (imagine having three kids, planning for college, and buying a house at the exact same time).
  • When you just want a second set of eyes to make sure you have everything done right and aren’t missing anything.
  • When you’re short on time and want to pay for convenience (e.g., you can hire a bookkeeper who you forward bills to and who pays them for you).
  • When you run your own business, an accountant is a no-brainer who can “cover your ass” and also look out for things you don’t know about.

Is hiring an advisor expensive? Yes, of course. But ask yourself, how much is constantly worrying about your finances costing you?

If you’re looking at getting help with your finances from a professional, then we recommend beginning your search at the National Association of Personal Finance Advisors ( These advisors are fee-based (they usually have an hourly rate), not commission-based, meaning that they want to help you, not profit off their recommendations.


If you read I Will Teach You to be Rich, applied everything, and you’re now running into new, more advanced problems where there aren’t clear answers… it can feel weird to bring stuff like that up to friends. “Hi, do any of you know what to do after you max out your 401k and pay off your house? Thanks!”

But here at IWT, you’re with your fellow weirdos. It’s safe, we promise. In the comments tell us how you’ve “leveled up” and what you need help on next. We want to help.

You’ve done everything “right” but you’re still worried about money. Why? is a post from: I Will Teach You To Be Rich.



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