I’ve Seen Worse: Your Money Fears Are Not Special

You may feel alone in your confusion, but let me assure you, everyone around you is in the same boat.

Key Takeaways

• Your money fears are completely normal; don’t let them control you.

• Momentum beats perfection.

• Having a clear goal and a timeline attached to it will help get your savings on track.

The thing about being a professional is that you see the same thing over and over again. You do the same thing at first dozens, then hundreds, then maybe thousands of times. A surgeon can remove a bullet and stitch up a gunshot wound like it’s nothing. “I’ve seen worse,” they say, where you or I would be frozen in fear and terror even if we’d studied how to perform the surgery for hours. Practice makes perfect.

In my profession as a financial advisor, I’ve seen hundreds of patients. Not with gunshot wounds, but with fears and anxieties about money. I’ve seen dozens of couples have the exact same fight about money in their marriage. And I’ve witnessed hundreds of people wake up with an extra three million in net worth because the company they work for went public.

This is why you should trust professionals. Because your emergency is not an emergency to them. They can react calmly with thousands of hours of training and years of institutional knowledge behind them. They can remove the bullet, or help you sell off your stock in a tax-efficient way. And you’ll sleep better at night knowing you’re in good hands.

The point I want to make is this: you’re all the same. We’re all human, and we all struggle with money issues. Whether we grew up with it or not. Whether we’re interested in how it works or we couldn’t care less. So while many of the clients at my firm settle into their first call ready to tell me the wildly unique circumstances of their financial and personal lives, I sometimes chuckle to myself, because I’ve heard it before. Over and over again.

So let me share some of the most common money fears, circumstances, and opinions I hear, in the hope that it normalizes how you approach your own relationship with money.

“Are we too late?”

There’s an annoying adage in my profession that goes, “The best time to invest was yesterday, the second best time is tomorrow.” Which means just start, there’s no value to dwelling on the past. You might be a little late, but that’s life. You went to grad school, you had loans, you took care of a sick parent. Life interrupted your master plan of saving 20% of your income every year. I like the simplicity of “better late than never.” If you’re investing your first dollar at 50, yeah, you’re a bit behind and it will be harder, but we can do it. You’re here now. Sometimes this devolves into anger and self-loathing and reflecting on choices that were made.

And yes, technically you’re right. You should have done this sooner because compounding is real. The eight years you spent not contributing to a 401(k) cost you actual money that I cannot get back for you. You feel bad, maybe even a little embarrassed and that feeling is expensive in its own way, because shame is what kept you from booking a call with a financial planner for three years. I’ve written about this before in Don’t Wait for the Asteroid. Shame fuels avoidance. And avoidance is the actual asteroid.

The fix: I ask what changed. Something always changed. A baby, a diagnosis, a divorce, a liquidity event, a divorce, a parent who died without a will. Nobody wakes up and calls a financial planner without a good shove of a major life change. First, we triage: what’s on your mind that brought you in the door. Let’s get some next steps for that and move on. When I notice that someone feels behind on reaching their goals, I know our relationship is fragile. They are putting so much faith in this working that one wrong step from my or my team could scare them off. So we handle the gunshot wound first (the trauma that brought them in the door) and then next week, we start to make bigger plans. One thing I find helpful is to take one positive action towards their goals, like automating savings contributions. We can run the numbers later, but let’s start. Maybe they’ve been avoiding this for years, I have this one opportunity to sit with them, and actually set up the bank transfer. They took an action, it wasn’t scary, and now they are on the right path. Momentum beats optimization every single time. Man, I love my job!!!

“I didn’t grow up with any money; this is all new to me, so I’m behind.”

Two things can be true in the above statement, however people often conflate them.

First of all, you are not behind on the money stuff, even if it feels like it. What you might be behind on is the financial jargon. Nobody is born knowing what a 401(k) is. The people who seem fluent in this stuff most likely had parents who said the words “index fund” at the dinner table. That’s just exposure. So you didn’t have that. But guess what? VERY few of us did. You can close that vocabulary gap in about six months. Subscribing to this newsletter and reading a book or two is a great way to start. Beth Kobliner’s sweeping vocab recap is also good.

The second thing is that growing up without money leaves permanent marks and it can take much longer to try to remedy this. I see it constantly. It shows up as hoarding cash in a checking account earning nothing, because a big balance is the only thing that feels safe. Or the opposite, spending money the second it arrives, because in your childhood house, money that sat around got taken. Or being scared to invest a dollar because watching your account drop $500 in a bad week feels like the electricity getting shut off.

But there is some good news: people who grew up without money are frequently the best savers I work with. They are unbelievably resourceful. They just don’t believe they’re allowed to be good at saving, so often what they really need is a cheerleader.

The fix: First, we name the specific knowledge gap. It’s usually five to ten things that they have always felt self-conscious about not understanding. I.e. Lady, what ARE you talking about when you say index fund? But we’re not talking about a lifetime of education—all you really need is a few hours with Claude and my newsletter. Write down every word you’ve nodded along to without understanding: Vesting. Basis. Backdoor Roth. Then ask the dumb questions to me, or your favorite AI chatbot, or read a great introductory book. I mean, mine is amazing, but if you can’t wait till it comes out in November, I think Beth Kobliner’s book is a great starting place for financial vocabulary building.

Coming November 10th. Pre-order here.

Once we’ve brushed up on our vocabulary, we look at where the cash is sitting, because that’s where money issues from childhood usually start to show up. And then we start with the savings order of operations like everybody else, because you aren’t that special and everyone needs a high-yield savings account.

“I’m saving up to buy a home, but I’m pretty sure I’ll never be able to afford it.”

There’s a chapter in my forthcoming book called “The Great American Lie of Homeownership.” It’s about how the realtor lobby has outspent the pharmaceutical industry lobbying Congress for tax benefits and to convince you that homeownership is the best way to build wealth and status in this country. Spoiler alert: it is most definitely NOT.

Homeownership is not for everyone. It’s a pain in the ass. Prices are out of control relative to earning potential. So before we talk about the numbers, I make sure clients interrogate this desire and confirm they’re doing it for the right reasons. Is it because they think they should? Because they think it’s a good idea? Or because owning this particular type of home in this particular part of this town is the deepest desire of their heart?

The third of those is a very valid reason to upend your life to save for a down payment. The other two are not.

The fix: After my rant, some goals get defined. I think goals are incredibly important for action, and I like to put real numbers and a real timeline on them. So I tell clients to go find a home on Zillow. An actual listing with a price and an address. Then we do the math together.

For example: Here’s a home in LA. It’s listed at $1.25 million. Assuming a 20% down payment and another 5% of the purchase price for closing costs, you need $312,500 in cash. But let’s round up and call it $315,000.

Now we look at income. Say you and your partner take home $180,000 after taxes and you’re saving a heroic 20% of it. That’s $36,000 a year, which gets you to $315,000 in roughly nine years. Nine years. But say you already have some savings, so let’s add that to the pile and shorten your savings timeline. Now we have a goal and a date.

So in just one discussion, we now have a clear goal and a bunch of different paths to get there. Want it sooner? You buy a less expensive house. You put less than 20% down and pay PMI (private mortgage insurance), which is not a moral failing. Or, you extend the timeline and make peace with it. Or if it’s available to you, you present your case and ask for help from relatives who may have some cash to spare.

Yes, it’s true, a huge share of first-time buyers get down payment help from family. Many of the people who insist they did it themselves did not do it themselves. So if you have a parent or a grandparent with the means and the inclination, the conversation about a gift or a family loan is worth having while they’re alive, and there are clean ways to structure it.

Sometimes, after looking at all these numbers can reveal something you didn’t really want to admit: you don’t actually want the house; you want the feeling you think being a homeowner will provide. What you really want is SOMETHING to work towards. But you can instead rent, invest the difference, and free yourself from the tyranny of homeownership.

“Why should I invest money when the world is going to end due to the melting ice caps and tyrannical governments?”

Sure, it could happen. But what if it doesn’t?

If you have the capital and if it will help you sleep at night, go ahead and build a bunker in Kansas or Canada or whatever. I’ve heard this sentiment more times than I can count but I don’t think we’ve had a single client actually break ground on the bunker yet. But if you strongly believe it might help you survive whatever nuclear or climate-driven apocalypse is coming, that’s valid and you should do it.

However, what I want you to see is the shape of the trade. If the world ends, your account balance is irrelevant, and you lost nothing by investing. If the world does not end, and you sat in cash for twenty years waiting, you will have paid a very real price for a hypothetical. The asymmetry runs entirely against you. Also, every generation has had its version of a hypothetical doomsday scenario. Nuclear annihilation. The end of the world in 1999. Peak oil. The financial system dissolving in 2008. Some of those were close calls. And yet, the market compounded through all of them. I’m not saying that as a promise (I can’t predicit the future, no one can). I’m saying it’s a real pattern.

The fix: I take the doom seriously. If catastrophe is a real part of your worldview, put five percent of your portfolio toward it. That can mean literal Cash in the safe, land, a very nice generator, whatever version of resilience is meaningful to you. This way, you get to hedge your worldview, but you just don’t get to make it your whole plan.

“I don’t trust the stock market.”

What you mean is that you can’t see it, and you can’t fully understand it, so you’ve avoided it. You can see a house and made-up value on Zillow, that’s fairly easy to grasp. I’d wager that most people know what a down payment is but very few can actually explain what “The S&P 500” means. (It’s a stock market index that tracks 500 of the largest publicly traded companies in the U.S.).

But when I dig into this with clients, their distrust usually attaches to a specific memory. A father who lost half his retirement in 2008 and never got back in. A grandmother who was sold a variable annuity with no way out of the expensive contract. Or just graduating from college into the 2008 financial crisis and realizing that greed is destructive. That grievance is legitimate. It’s also aimed at the wrong target. It wasn’t the stock market’s fault; it was human greed.

The fix: We separate distrust of the market from distrust of the financial industry, because the second one is thoroughly earned. Then I explain what a fiduciary is, what fee-only means and why nobody at my firm makes a dollar based on what you buy in the stock market. Then we build a low-cost and diversified stock market portfolio, which is boring and is supposed to be.

And then we start small, on purpose. We hold hands and go slow. I find that many clients initially expect us to move all their money in the stock market on day 1. (I mean, that’s what I would like them to do, but after years of this, I know that won’t work). We start with a small amount in one account. We watch that amount drop, because it will. But notice that you survived. Hey, after a drop, maybe it went up 5% since our last meeting!? You cannot think your way into trusting the market, you just have to experience it for yourself.

After that, you stop looking at it. Checking stocks daily is how people who trust the market turn into people who don’t.

Parting shot: your money fears are not unique, but they are solvable.