She’s hardly alone — a quarter of Millennials believe they will never save enough money for a down payment and they also spend more on cosmetics and aesthetic procedures ($2,670/year) on average than any other age bracket.

It’s the “Millennial Glow-Up” and it’s causing some critics to age prematurely in frustration.

They view it as shortsighted and lamentable: Botox instead of budgets, micro-needling instead of micro-investing. Bustle connected the dots with this unforgettable headline: ‘I Can’t Afford a House, so Why Don’t I Just Look Gorgeous?’

The article takes a probing and empathetic look at several millennials who are putting serious money into self-care and aesthetic procedures, having decided that homeownership is too steep a climb.

What’s it like to live in this moment where you might have a decent income, but major necessities like housing, healthcare, and childcare have inflated far beyond wages in recent years?

What are you supposed to do with your money?

It is tempting, as spectators of other people’s finances, to fall back on a simple moral hierarchy that says you can spend your money in two ways…

1. Needs (which are justifiable) and

2. Wants (which are indulgent and should be viewed with suspicion).

Formulations like this are how guilt creeps into spending.

As a wizened millennial myself, there are two pieces of advice I’d give a spry thirty-something with enough money to spend on themselves, but not enough to purchase a home:

1. You are free to spend your money as you wish.

You don’t have to follow family or cultural norms around spending money. Several years ago, Stephen, a YNABer in San Francisco, realized how much money anxiety ruled his life.

“I was in the habit of making fear-based savings and financial decisions. I’d inherited my parents’ thriftiness and a judgment on money and those who have it. Now, I’m untangling guilt, shame, and practicality to forge my own financial philosophy.

YNAB helps me be realistic about money and remove unhelpful emotion surrounding saving, spending, and worrying about it.

When my dog needed emergency surgery that was well beyond the amount in our vet category, it was simple to prioritize him and clear how to cut back in other areas.”

Spending on you (or a dog) now, without judgment, can be a beautiful thing. But it’s only part of the picture. Ideally, your money is there for you now and in the future. So, my second piece of advice:

2. Be a good friend to your future self.

May you live a long life! And when you do, your future self will inherit the financial choices you’re making right now.

Tabitha, a court stenographer from outside New York City, said:

“Saving always meant deprivation to me. I didn’t have good financial role models growing up and, due to my habits, I found myself wondering whether I could ever retire!

Once I started using YNAB, I could finally plan for the future… For the first time in my entire earning life, I have GOALS!

I drastically downsized, eliminated my long commute, and found an adorable, and very inexpensive studio apartment that I’m not stressing about renovating to my heart’s desire because all my bases are covered.

None of this would have been possible if I stayed on the path I was on.”

Personal finance is a boat on the seas of the greater economy. Currents may push us one way or the other — to smaller housing, multi-generational living, or spending more on how you look.

Both Stephen and Tabitha found new directions and stopped worrying about money well into their adult lives. They couldn’t have imagined exactly how they’d be one day spending their money, but getting good with money gave them choices later on.

You can’t change everything, but you can decide what you’re going to do with your money. The returns of getting good at money last a lifetime.

Until next time,

Dan

Hana is a research oncologist. By nature of her work, she has to be precise and data-driven. So, decades ago, when she felt “huge” amounts of stress managing money with her young family, she experimented with every tool she could find, all the usual suspects: Excel, Mint, even the tagging feature inside her banking app.

But each software had the same blind spot: they “focused mostly on forecasting,” which meant she could put off hard decisions and avoid making trade-offs.

She wasn’t learning how to be intentional with her money.

For a long time she just managed cash-flow, keeping enough in the accounts and making sure nothing bounced.

Hana grew up in a home shaped by Depression-era frugality. Saving was common, but planning how to actually spend your money was never taught. For decades she would struggle with understanding how to spend with intentionality.

While in academia, managing research grants felt surprisingly like managing a small business… which she had absolutely no training in. But, she said, “With time, I got better at managing the money side of research.”

Then she left academia, and literally doubled her paycheck overnight.

“I know that sounds awesome,” she says, “But we seriously, seriously underpay academics.” (No argument here.)

Suddenly, she was stretched in a new direction, learning to manage her new cash flow. With two young children, it was chaos.

One thing she did do right was maxing out retirement accounts every year without fail. And she’s proud of this, but at some point she went back and did the math on those years where her income jumped after leaving academia.

If she had actually been proactively directing her money, there would be an additional million dollars in her portfolio today.

That’s a lot more dollars.

“That one I very, very much kick myself for,” she said. “It’s a lesson I share with mentees and young people whenever this topic arises… don’t make my mistakes.”

Which is why Hana reached out to the Budget Nerds after a recent episode, so she could share what she’s learned about the unique financial challenges facing women.

She said it felt like many women she knew were burying their heads in the sand about their financial future. Maybe they have a good income or life seems stable, but what they don’t have is a spending plan.

“And every financial advisor will tell you, the biggest impact on the viability of your retirement plan is your spending plan.”

Here’s an example of one of those financial challenges unique to women that rarely get discussed:

“I realized that my husband was planning for a retirement through his lifetime, not for whichever of us lived longer... which, based on family medical history, was statistically going to be me.“

Women live longer1 and yet they retire, on average, with 25 to 30% fewer financial resources than their male peers2.

Many of the other statistics are equally as stark:

• Women earn on average 15% less than male counterparts3.

• They’re 14% more likely to be single parents4.

• Over their lifetimes, they’re 43% more likely to take career breaks to care for family (children, aging parents—sometimes both)5 which has compounding effects on Social Security6 benefits that most people don’t fully understand.

• They face more barriers to credit and capital.78

• More than 43% of women in single-parent households live below the poverty line.9

“I don’t believe women today have it harder than men with managing finances,” she told me. “But I do believe we have it different. And the shame element makes us stick our heads in the sand. We can’t address what we don’t see.”

It’s only been a few years since she started YNAB, which helped her see the full picture. She’s been able to make a plan both for lots of family travel and a strong financial future.

“It has made a great difference,” she said. “As I built a sense of where I stood, I started to feel like I was taking control. It was empowering! And that feeling of empowerment, it was exciting. That’s where we start. Figuring out the actual, accurate, state of affairs. And then using that to build a plan.”

Peace, presence, and joy— that’s what she wants from retirement. And while she hasn’t entered that stage of life yet, for the first time, she told me, she can actually see the path.

Until next time,

Dan

I did look odd stretched out on the floor while everyone else sat on their cushions without complaint. But I had my reasons, which I began relaying as she frowned down at me.

Chronic pain in my neck and arms had sidelined me for over a year. My hands and arms couldn’t function properly, so I was also out of work. Downstairs, to get into the building, I had to wait for someone to press the elevator button because I couldn’t do it myself.

What this glorified gong ringer did not know was that lying down was the only way I could practice meditation with others.

It was the least painful posture available to me. I wasn’t intending disrespect; just getting on the subway from Brooklyn to Manhattan in my wobbly condition felt like its own kind of pilgrimage. But she wasn’t having it and sent me away like an unwelcome thought.

The funny thing about meditation is that you can’t tell what’s going on in someone else’s mind when they’re sitting quietly. They could be dwelling in deep concentration or replaying the intro to Perfect Strangers. Because mindfulness doesn’t look one certain way from the outside. It’s an ongoing practice, not a posture you take. You can practice mindfulness in an attic, on a submarine, and with or without a mustache (confirmed).

Similarly, being mindful about where your money goes doesn’t depend on how much you earn or what your financial life looks like from the outside.

You can make intentional spending decisions at any income level, in any circumstances (even when what you do with your money looks nothing like what your neighbors do).

But nobody has told you this. Instead, they’ve handed you a set of rigid, inviolable rules:

• “Renting is throwing your money away.”

• “Never take on debt.”

• “Buy a used car, don’t lease a new one.”

• “Pay off your mortgage as fast as possible.”

• “Skip the latte or you’ll be dumpster diving in retirement.”

Personal finance has reformulated these basic chords a thousand ways, but this kind of advice is surface level. Any of these might be right for you, but there’s a better way to drive your decisions.

Being mindful with your money means deciding how you want to spend it before you get to the register, before your online cart is loaded.

Be intentional with your money, not just reactive.

As your paycheck comes in, put some of it toward next month’s rent—money you are obviously not putting toward something else. Now ask yourself about that rent: does the flexibility to move when your lease ends feel like a gift? Does not paying for yard care and roof repairs suit you? Or do you wish you were channeling more money into a home you owned? Do you yearn to mow your own lawn?

These aren’t trick questions, and there are no wrong answers. But the act of asking them begins to reveal something important: what you actually value, as opposed to what you think you’re supposed to value.

Most people never ask because they’re too busy following the rules, or too stressed to look closely.

But the moment you start directing your money with intention, your money will show you what you really value.

Maybe you realize that renting feels like freedom and you’d rather put that money toward travel. Maybe you discover that you resent writing that rent check every month and something in you is ready to put down roots. Maybe it’s neither and you realize you just need a bigger emergency fund. All of that is useful information and all of it moves you forward.

With every decision about where to send your money, you’ll feel the pull of the life you want. Listen to that voice, not the scared one telling you to conform or get out of the shrine room.

I’d love to hear from you:
What’s one money “rule” you inherited from family or culture that you’ve since decided doesn’t apply to your life?

Leave a comment

Until next time,

Dan

Last night as I was putting my eight-year-old daughter to bed, I was stressing about the kitchen cleanup I still had left. But she wanted to pull me into her current obsession: the original cast recording of Les Miserables.

Sitting up with a flashlight, reading the liner notes for the double-CD (as one does), she grilled me hard: what happened to Cosette’s mother? Why did Inspector Javert chase Jean Valjean for 20 years over a loaf of bread? These are difficult but important musical theater questions. 🙏 But mentally, I was already out of the room.

It turns out that being an American worker often means wrestling with much heavier distractions.

In 2022, 57% of U.S. employees reported feeling financial stress at work. What’s more, over half of those employees spent 3+ hours each week dealing with personal money issues during office hours.

One patently obvious solution is for people to be paid a living wage. But, there is a very large swath of workers for whom the problem isn’t just income. Consider that 40% of Americans earning more than $100,000 are currently living paycheck-to-paycheck. This kind of stress makes it so hard to be mentally in the room—at work or at home.

Sure, being financially responsible is important, but that’s just the minimum. Let’s set the bar higher.

The real goal isn’t just to stop stressing about money, it’s to stop chasing it.

There’s a big difference between earning more and actually knowing where your money is going. One is an endless sprint and the other is an intentional practice.

Think about what it would feel like to open your bank app and actually feel calm.

To make a purchase without any guilt following you around afterward.

To know, without obsessively calculating, that your essentials are covered, your priorities are funded, and the money left over is genuinely yours to enjoy.

Many people fantasize that feeling calm about your financial situation is only possible when you’re earning 10x what you have now. However, it’s possible to feel better about money today by getting off the treadmill of “just make more money,” and paying attention to where your money is actually going. Only then can you decide, on purpose, where you want it to go instead.

You don’t want to just be chasing that bread for 20 years without a raison d’être.

YNAB has been helping people get off that treadmill for over 20 years, because we believe your money should work for you, not the other way around.

I’d love to hear from you:

Was there a moment when you stopped feeling like you had to chase money and started feeling more at peace with it? What changed?

Leave a comment

Until next time,

Dan

I had been dealing with neuropathy and a pain condition in my arms and neck that had forced me to stop working for a while. It made life a lot more difficult, and I was searching for a way to carry things around New York City without hurting myself any further.

I didn’t really have a job and I constantly worried about money, but that didn’t stop me from pouring countless hours into the search for the perfect backpack! I learned more than I ever thought I’d know about seam construction, carrying capacity, and ventilation systems (back sweat being one of the great under-diagnosed problems of our time.)

What I could not figure out was one fairly important question: how much was I willing and able to spend on this backpack?

I generally felt panicked about money, but what’s a couple hundred dollars for a bag when you’ve got thousands in your checking account?

Except, I knew that every month, the initially plump account balance I shared with my wife would slowly drain until we were shuffling money around to avoid an overdraft. So on one hand, I knew our finances weren’t good. But on the other hand… didn’t I deserve a good bag?

Without a clear sense of where all that money was going, I had no context for this spending decision. When every purchase exists in a vacuum, one of two things occurs:

1. You either wave any concerns away, promising you’ll figure it out later (”What’s a couple hundred dollars?”) or

2. You spiral, and simple spending decisions become torturous: Should I buy lunch today? Is it responsible? Am I responsible?!

I’ll share a happy update: I don’t really think this way about spending money anymore. Because I’m rich! I use YNAB. Here’s why:

There is no such thing as a single spending decision.

Every purchase exists inside a web of trade-offs, and the YNAB method makes those trade-offs visible, which really helps when you’re trying to figure out if you can spend a couple hundred dollars on a backpack.

When I glance at the app in the morning, I see that I’m making progress on funding a tennis weekend with my brother-in-law in the Catskills. I see I’m almost done saving for my daughter’s birthday party. That brief check-in means I can go through the day knowing where I want my money to go (and where I don’t.)

Which brings me back to the backpack. Hauling myself around those Manhattan outdoor stores, I was looking for more than the perfect bag.

Sometimes we buy things hoping we’ll become someone else in the process: healthy, active, organized. But that puts too much pressure on a single purchase.

The backpack wouldn’t make me into a different person, but it could help me carry things without pain. And as it turned out, that was enough — it was one of the smartest things I ever spent money on. I just couldn’t see that clearly at the time, because I didn’t understand how it fit into the context of all my other spending.

Without knowing what else my money was doing, every spending decision felt equally loaded and uncertain.

Buying the world’s “best” backpack might have meant one less Yankees game with my dad, or one fewer acupuncture session. Those were real trade-offs worth knowing about.

When you can see your trade-offs clearly, some purchases get an easy yes, some get a clear no, and you stop exhausting yourself over the difference. You make the best decision with the information you have and move on, because time is also finite and I wouldn’t want to spend too much of it browsing for backpacks on a beautiful day

I’d love to hear from you:

What’s a purchase you agonized over that turned out to be completely worth it?

Leave a comment

Until next time,

Dan

I acclimated to a persistent low-level stress around finances in a similar way.

When I felt stressed and overwhelmed about money, I treated myself to Thai take-out to cheer myself up and promised that next year was going to be The Year of the 401(k). But, afterward, I’d feel guilty and bad at money all over again.

Nobody beats themselves up for being bad at origami. You don’t lie awake at night thinking about the paper crane you couldn’t fold, or feel a hot flush of shame when someone mentions the word “origami” at a dinner party. If you’re bad at it, it’s just something you can improve with practice. No big deal.

But if someone thinks they’re bad at money, something completely different happens. A lot of shame happens. Money feels less like a skill you can learn and more like an assessment of your character—which, apparently, is someone irresponsible and impulsive who can’t be trusted.

And while you may feel as fragile as an egg if you think you’re bad at money, it might also just be the information you need.

The gift of realizing you’re bad at money is that now you can change. You don’t have to stay on the same stressful, unsatisfying path. Admitting that you feel bad at money is the first step to getting good at it.

Too many mean-spirited loudmouths have given being bad at something a bad name.

Carrying shame or defensiveness about a lack of skills can keep you preoccupied for a long time, or be so painful that you pretend it’s not true. It’s completely understandable and unhelpful.

The seductive narrative is that you struggle with money because you lack willpower, confidence, or are a hopelessly bad decision maker.

But here I would say, snap out of it! The trance you’ve been under has been spun by authoritative money gurus who create reality-TV style content out of people’s struggles.

It’s abetted by a culture in which hardly anyone shares details about their money, even among friends and family. The idea that spending and saving money is unlearnable is demonstrably false.

The millions of people who’ve stopped worrying about money with YNAB don’t all share a common genetic trait or all happen to have rich parents.

They’re people like this

Or this.

And they do stuff like this:

When you treat money as a skill to be sharpened:

• You can learn what it actually costs to be you.

• You can set aside money for the surprise expenses that *whispers* actually happen every year.

• You can spend big on the stuff that makes you or your loved ones happy and you’ll learn to quickly pass on “forgettable” spending.

Again, what is important is snapping out of the trance and remembering that the shame of feeling bad at money is never going to help you get good at it.

Instead, notice the discomfort you’ve gotten used to: worrying about bills or the car payment, the tension with a partner. That stuff is bad, not you.

I’d love to hear from you in the comments:

Was there a moment when you stopped feeling bad at money and started feeling good at it? What changed?

Leave a comment

Until next time,

Dan

You know exactly what you need to do: Open the app. Check the balance. Look at what came in, what went out, what’s overdue.

It’ll take ten minutes! Maybe fifteen, you tell yourself. This is what you always tell yourself, and yet, it never seems to work.

Instead you fritter away two hours on Instagram, watching strangers on vacation and before-and-after kitchen renovations. Suddenly it’s late and you’re tired and the moment has passed. Again.

Then, the shame spiral commences.

You feel lazy and irresponsible; yet, what’s happening to you is neither of these things. It’s what ADHD educator Brendan Mahan calls “The Wall of Awful.”

The Wall of Awful gets created, brick by brick, with every repeated failure, disappointment, rejection, or instance of guilt. It’s an emotional barrier which makes starting objectively simple tasks excruciatingly difficult. You’d rather do anything else.

From the outside, the Wall is invisible. No one can see what you’re struggling with, and it just looks like inaction. Yet, the avoidance of the task leads to more disappointment and guilt.

Money management might be the ultimate brick-making factory for the wall of awful.

The time you charged your way through a vacation without paying attention to the amounts.
The debt you took on before you were old enough to legally drink.
The way your partner doesn’t trust you around money.
The impulse spending that seemed so minor at the time.

The bricks build up until it takes so much effort to just look at your retirement account, to start a conversation about money, to pay those late fees, that you stop trying to scale the Wall at all.

Eventually, you lose not just the ability to tackle individual tasks, but any motivation to work on your overall financial status or improve your financial skills. But no one wins if you can’t get over the Wall.

Money touches almost everything in your life, so to turn away from it is to live a smaller, restrained life.

It’s like sitting in a world-class Italian restaurant and never turning past the first page of the menu. Do you only want to eat antipasti for the rest of your life?! (Nevermind, don’t answer that.)

Assuming that you don’t want to live in the paralyzing shadow of the Wall of Awful, what can you do? Brendan Mahan has some helpful suggestions:

1. Create handholds to climb the Wall.

Become aware of the emotions that come up around money and acknowledge them out loud. Take action on the feelings: talk to a friend or therapist, and try being kinder to yourself about the resistance you’re feeling.

2. Or, forget climbing the Wall and look for a door!

Mahan recommends changing your emotional state with music or altering your environment. He writes, “The Wall of Awful is often strongest at home because we’re surrounded by our responsibilities, struggles, failures, distractions, and concerns.”

The wonderful part of this metaphor is that it doesn’t absolve us from dealing with our money. Instead, it acknowledges the struggle as an obstacle instead of pretending it’s not there.

For me, Mahan is putting his finger on why I was able to stick with YNAB even though I had previously struggled to implement basic personal-finance advice. Willpower is overrated, but self-awareness is gold.

I’d love to hear from my ADHD friends in the comments:
What’s the one thing (a tool, habit, mindset shift, or even a weird trick that works for you) that finally made money feel a little easier to face?

Leave a comment

Until next time,

Dan

After spending too long trying to craft the perfect text message, I nervously send something like this:

Hey 👋
[This emoji says I’m chill, right?]

Great to see you last week!
[Just affirming that our friendship is more important than money!]

Just thought I’d check in about your share of the hotel bill!
[But I am toooootally not thinking or worried about it at all. ]

Thanks!
[Not actually sure why I’m saying this!]

While this affliction may disproportionately affect people-pleasers, I know that asking someone to pay you back is complicated for a lot of us—even (especially) when it’s with family and close friends.

I asked a few folks here at YNAB how they handle it when someone owes them money and why it can feel so hard to navigate. Here’s what they recommended:

Tactic 1: Clarify expectations upfront

If it feels awkward to ask for money, it might be because you’re not 100% sure what was actually agreed to.

My colleague Kathleen finds that clarifying the agreement solves most of the weirdness. Ideally, the conversation happens before the payment happens. Expectations are spoken ahead of time like: who’s covering what? When is repayment expected and how will it be sent?”

When everyone is clear going in, there’s nothing weird about following up later. You’re not “asking for a favor,” you’re just closing the loop on an agreement.

So speak up and confirm the details you need! Even a simple, “Just making sure we’re on the same page—you’ll send your half by Friday?” can make a huge difference.

Tactic 2: Let Venmo do the talking

Kathleen again, “I send Venmo requests, and it’s key to send the request as soon as it’s warranted. If someone owes me for dinner, I send the request that evening. Waiting a day or two or longer makes it more awkward.”

Sending a request through Venmo, bank, or e-transfer in Canada, makes it clear what you are asking for and easy for the other person to pay right then. This is a good option if you are exhausted by trying to strike the right tone of asking for what you want, but also pretending you totally don’t care.

Tactic 3: Eliminate expectations altogether

It surprised me, but several folks at YNAB said they never loan money or pay for dinner unless they’re okay with not being paid back at all.

Hillary wrote, “If I do get paid back, wonderful! If not, it’s fine because when I loan money or pay for something for someone, that money is gone. I know my financial situation is very different than friends or family, and that this is a privileged position. But when I wasn’t in this position I just wouldn’t offer to pay or would say, hey, I can’t cover both our parts.”

A related version from Ashley G: “Sometimes I say, ‘Hey! Did you want to Venmo me for dinner last night, or do you just want to cover it next time we go out?’”

I was impressed by the thoughtful and straightforward responses from my coworkers. I also had the sense that talking about money is profoundly difficult if you think there’s a way you’re supposed to do it.

I keep thinking of the Barbie movie monologue, in which Gloria (America Ferrera) lists the many conflicts of being a woman: “You have to be thin, but not too thin. And you can never say you want to be thin… You have to have money, but not ask for money because that’s crass.”

Talking about money is similar— it’s a collision of too many taboos for us to think we can do it in a ‘perfect’ way.

We live in a culture where talking about money is frowned upon, and yet almost everything in our lives interacts or depends on it. So, I say find what works for you (before the spending occurs, if possible). Say how you’d like to split it, or not split it. Resist the impulse to upset no one.

I’d love to hear from you: How do you usually handle the awkward art of asking someone to pay you back?

Leave a comment

Until next time,

Dan

Welcome to My Two Cents, an occasional postcard with two small riffs, rants, quotes, or recommendations I think you should know about.

1. There’s no such thing as bad weather, just bad clothing.

A friend from Maine once told me this, and after many long, crunchy walks through the ice and snow in the frigid Northeast this winter, I can confirm it’s true.

This sleeping bag of a coat got me through the cold stretch. Every time I threw it on to run outside for firewood, I was grateful I didn’t talk myself into the cheaper option. The plentiful pockets suit my packrat nature.

And these boots are the ultimate in waterproof, fashion-backward comfort.

Prioritizing winter gear that’s comfortable and well-made has been 100% worth it and reminded me of a quote from Patagonia founder Yvon Chouinard’s memoir Let My People Go Surfing:

“As individual consumers, the single best thing we can do for the planet is to keep our stuff in use longer… We live in a culture where replacement is king… These conditions create a society of product consumers, not owners. And there’s a difference.

Owners are empowered to take responsibility for their purchases—from proper cleaning to repairing, reusing, and sharing. Consumers take, make, dispose, and repeat—a pattern that is driving us toward ecological bankruptcy.”

– Yvon Chouinard

Given the context of this winter, it’s really got me thinking:

How can I spend money on things that make me an owner and caretaker, not just a consumer?

Is there something that you’ve decided to “own” instead of just “consume?” Let me know in the comments.

Leave a comment

2. “We give our children our genes and our love, and we don’t have any idea of what, in the end, they’ll do with them.”

– Nicholas Thompson, The Running Ground

I just finished this beautiful book about a son who follows in his father’s path as a runner, but tries to avoid his father’s mid-life meltdown. (The author is the CEO of The Atlantic.)

He says, “We give our children our genes and our love, and we don’t have any idea of what, in the end, they’ll do with them.”

To Thompson’s quote, I would add that we can also teach our children how to be good with money and we won’t have any idea of how, in the end, they’ll spend it. Which is fine as long as we’ve taught them how to spend it well.

Until next time,

Dan

At the most inconvenient times, your past intrudes.

It happens when you’re scrolling through houses on Zillow, or when you park next to a really nice car. Bumping up against your financial constraints can make you feel a surge of frustration or disappointment at the doofus you once were.

We inherit the choices and circumstances of our past, whether we like it or not.

I have a family member who declared bankruptcy in his early 60s. What began as a job loss was followed by physical and mental illness, years of unregulated spending, and increasing isolation. Other family members tried to talk to him, to help him—but though he could talk at great length about almost anything, he would not talk about money. The size of his debts grew, the collectors became more aggressive, and eventually he was forced to declare bankruptcy.

The consequences of our past are very real, but the stories we tell about ourselves often aren’t.

Even without the extreme experience of bankruptcy (more than 500,000 Americans filed last year), many of us imagine it would’ve been simple to take a different financial path. How could we have missed those opportunities? As if “personal responsibility” were a test announced in advance to be taken with a #2 pencil. As if my family member wasn’t fighting illness, stress, and the unpredictability of life itself.

Of course, compassion doesn’t erase the fact that what we did yesterday affects today, and what we do today will affect tomorrow. That part is undeniably true.

But judgment is like an invasive weed, creeping into every moment of disappointment or underwhelm.

Judgment creates villains and simple stories, when the past is usually far more complex. Look back on your own history: regrettable choices, yes. But bad intentions? Probably not.

At the risk of invoking Stuart Smalley, part of what makes a healthy relationship with money is learning to enter a loving relationship with your past self. Why? Because if money is an extension of us, hating our past spending is just hating ourselves. And how can you fund the life you really want if you don’t even like the person living in it?

I’d love to hear from you:

What’s a money decision you used to see as a “mistake” that you understand differently now?

Leave a comment

Until next time,

Dan

There, under bright lights and a stadium-style audience, you would find out-of-control teenagers, wayward parents, and warring siblings. The host (mind you, whose enormous salary depended on their misfortune) paced the stage, feigning disbelief and moral outrage.

Can you believe people like this? Tune in tomorrow for more!

Fast forward to today, while I’m no longer procrastinating homework on the couch, I see new versions of this same format play out all over the personal finance space.

Here are a few real quotes from popular personal finance voices:

“Are you done f’ing around and don’t want to die on the Walmart floor?”
“Stop doing poor people things!”

Why is it acceptable to get your financial advice with a bunch of insults and eye rolls?

My car mechanic doesn’t talk to me that way.

My doctor doesn’t either.

My lawn guy isn’t performatively banging his head into a microphone when I tell him my grass is under-watered.

It reminds me a lot of how the weight loss and fitness industry operates – another space where people searching for help are routinely shamed into behavioral adjustments.

“If it mattered to you, you’d find a way.”
“It’s not supposed to feel good.”
“If they can do it, why can’t you?”

To be clear: many people have real financial problems that need to be solved. But does shame actually help? Not much. Social psychology research shows that when people feel shame, they tend to isolate and withdraw—not change.

I wrote more about that here:

And I can already hear some of you: Some people need tough love. Someone has to tell them the truth.

That’s fair.

Money is hard to talk about. But you don’t have to be mean to yourself in order to be honest with yourself. Who among us hasn’t made regrettable decisions? Who hasn’t struggled with habits they wish they didn’t have? 🙋‍♂️

The “self-made” story popular in personal finance circles suggests that discipline and hard work are the only things separating you from success. This, by the way, is the same claim we often make about people who’ve lost a significant amount of weight, too.

Psychologists call this survivorship bias.

Survivorship bias works like this: because Facebook is worth hundreds of billions of dollars, every startup could do it too… right? Obviously not. Facebook is called a unicorn for a reason.

We look at the 0.01% who “made it” and assume we can copy and paste the same formula and it will work for us too, all the while ignoring why the other 99.9% didn’t.

This doesn’t mean people are doomed to stay stuck. But it does mean we should be skeptical of simplistic, judgment-heavy explanations for complex lives.

So why is personal finance advice so mean?

One obvious answer: marketing. A reliable way to grow on YouTube is to highlight someone’s extreme decision (“Dude Goes Into Debt to Mine Crypto”) and pair it with a shocked or angry face. It’s good for the algorithm.

When people feel humiliated or like failures, they lose confidence in their ability to help themselves. They start craving authority – someone successful, maybe even someone willing to punish them a little.

Some people believe that being bad with money means you deserve to be yelled at. Or maybe judgment is just entertaining. Maybe it feels comforting to think, Well, I’d never do that.

But I hope we don’t give up on people who are struggling or accept shame as the price of learning and growth.

In my twenties, my financial life was more chaotic than most of my friends’.

I felt ashamed long before any national figure could yell at me on YouTube. I thought you were just supposed to be good with money, like fish just knowing how to swim.

But I didn’t know. I had to learn. And I’m grateful I found a community that preserved my dignity instead of profiting off my shame.

No one needs content that feeds the harsh voice already living in their head. Encouraging ourselves and others to forgive past mistakes, build better habits, and celebrate small wins is far more effective long-term.

I’d love to hear from you in the comments:

How have you started to overcome shame and build more confidence with your money?

Leave a comment

Until next time,

Dan

At this point, you’ve said it so many times that you’re pretty sure you’re the hopeless case, doomed to be bad at money for the rest of your life.

This all-or-nothing thinking—next month will be completely different—is destructive for anyone, but especially for a perfectionist. Perfectionists need a lot of reassurance and confidence that they’re on the right track. This helps us soothe a core belief that we’re not enough.

Charlene, one of my colleagues here at YNAB, told me when she started using our software, it led to an unexpected discovery:

“I was trying to be ‘perfect’ with my income, but that was an impossible task given the amount of student loan debt I had and my goals for my money. So, I sought out part-time remote work that I could do while maintaining my day job.”

She began working as a Seasonal Support Specialist at YNAB back in 2016 and now she’s the People Ops Lead here.

By paying attention to your money, you might start seeing that something bigger needs to change.

When Charlene asked what her money was for, she realized she needed more of it to reach her goals. This was not her original plan, but she came to the process ready to learn instead of judging herself for not having it all figured out.

If you have the mindset, “What can I learn?” you’ll naturally start getting good with your money, the same way an athlete or musician optimizes their performance by paying attention to the little things.

You’ll learn what spending brings you joy or regret.

You’ll learn to live in balance with your income.

Speaking from experience, it’s hard to know how you actually want to spend your finite amount of money, until you’re seeing trade-offs like paying off your debt or going on a vacation.

Like a toddler learning to walk, figuring out what you value can be a messy, sometimes stumbling process. Only you can decide how strongly you feel about the $15 Boar’s Head sandwich or visiting microbreweries or how warm to keep your house during the winter.

But if you regularly give every dollar a job, you will find out what your money is for. And it’s the finding out part that I find the most exciting.

The perfectionist inside of you may be trying to turn money into a test (that you’ll probably fail.) But money isn’t a test and there is no teacher’s manual. Process goals and little wins will give you the reassurance and confidence that you’re on the right track.

I recommend starting with a simple, proven process goal: every time you get paid, give every dollar a job. It’s the most transformative money habit I’ve come across.

And remember that everywhere you look you’re surrounded by a lot of learners 👋

I’d love to hear from you:

What are you in the process of finding out about your money right now?

Leave a comment

Until next time,

Dan

From the window of his shack, he had a perfect view of the ocean and, in the distance, the mainland.

One night, as he washed his mug and plate after dinner, he stared out the window at the twinkling lights along the coast. They seemed to say, Come, join us.

But, he liked his little island because it felt safe and predictable. No one could judge him here or make him feel more behind in life than he already did.

He told himself he’d go to the mainland someday. Maybe next week or next month.

Logistics weren’t the issue; he had a sturdy rowboat, and the trip would take less than half an hour.

The problem, he told himself, was his money.

He’d made a few regrettable purchases recently, like financing Metaverse VR goggles and then finding out that no one is ever actually hanging out in the Metaverse! His credit score wasn’t where it “should” be, thanks to a back injury that kept him from working for a few months; the expenses just piled up on the credit card.

He wasn’t destitute, exactly, but when he looked around at his shack, his boat, and the seashell-lined paths, it didn’t feel like much of a life.

Keeping things this way felt responsible and safe. But it also meant staying still, if not stuck.

But, every so often, reminders slipped through, like a friend posting on LinkedIn that she was “thrilled to announce an exciting new food and beverage partnership!” He rolled his eyes, but it stirred up a mix of jealousy and longing. It wasn’t even the life he wanted! But it was proof that she had momentum and belonged somewhere.

He couldn’t think of a single thing he’d want to brag about on social media!

Sure, he’d built an impressive chess set out of driftwood, but he would gladly dropkick it all into the sea if he could just get his hands on a solid paycheck to help him reach his first $100K in retirement.

And yet, even those milestones felt slippery. He couldn’t remember a time when he’d actually felt satisfied with his financial situation. Someone was always doing better. In his mind, the mainland was full of dutiful savers and people who had figured it out. He didn’t belong there.

Staying on this island protected him from that kind of embarrassment, comparison, and risk. But it also kept him invisible and adrift.

Suddenly, as he rinsed off the last bubbles from his nightly washing, he heard a shout.

“Help! Help me!”

A man was flailing in the water, thirty yards offshore.

Hours later, the two men sat wrapped in blankets, warming themselves by the fire.

As the sailor shoveled bowls of oatmeal and berries into his mouth, he told his story: years lost at sea, drifting from place to place, desperate to reconnect with his family, especially his brother in San Francisco.

Without much hesitation, the man decided that in the morning he’d row the sailor back to the mainland. He’d help him get home. He might even pay for a flight back if that’s what it took.

Suddenly, he wasn’t worried about what it would cost, let alone the credit score or the financial benchmarks he hadn’t reached. He had something to do that made him feel like he mattered. Tomorrow, they’d head to the mainland.

As he climbed into bed that night, the man realized then that the island had never truly made him safe. It had only kept him in a state of permanent waiting for his life to become perfect before he could belong. The purpose he felt from the moment he pulled the struggling sailor out of the water had knocked loose something that financial perfection never could:

It softened his shame, loosened his self-criticism, and reminded him that he mattered now, not later when he had all his ducks in row.

Perfectionism promises safety, but purpose actually moves your life forward.

According to social psychology research, the antidote to perfectionism isn’t flawlessness—it’s mattering.

Psychologist Dr. Gordon Flett describes mattering as a more sustainable path to self-worth: knowing that you are important to someone, that your presence and efforts make a difference.

In Parts 1 and 2 of this series, The Perfectionist’s Guide to Getting Good with Money, we explored how financial perfectionism keeps people stuck, distorting both their understanding of how money works and their sense of self-worth. When you believe you don’t measure up, it’s tempting to hide, wait, or isolate until you’re “better.”

Dr. Flett calls the opposite of mattering anti-mattering: feeling invisible, unimportant, or undervalued. That feeling fuels perfectionism; and perfectionism, in turn, deepens isolation.

That’s exactly what was happening on that island. Because the man could only see what was unfinished or unimpressive about his life, he withdrew. And because he withdrew, no one could appreciate his creativity, his generosity, or his willingness to help.

So for all you mainlanders: yes, keep your goals.

• Make a realistic plan to pay down debt

• Start saving for a down payment

• Have regular, honest conversations about money

But remember, it’s also vital that you matter to someone or to a community.

You don’t need to hide behind your financial imperfections—that can be the adhesive that helps you bond and matter to each other.

Make sure that you have support and friend networks that aren’t contingent on how much money you have. Purpose, contribution, and mattering don’t come after you get your financial situation perfect. They’re often what make progress possible in the first place.

Next week, we’ll discuss the messy, sometimes clunky ways that former perfectionists have achieved liftoff.

I’d love to hear from you:

Have money worries ever made you pull back, hide, or isolate yourself? What did that experience teach you about money or about yourself?

Leave a comment

Until next time,

Dan

One man, an actor in his 50s, had almost been carried out to sea by a rip current off a beach in Queens. Another woman was thrown in the deep end by a parent in a sink-or-swim exercise. Coincidentally, this is how most people are introduced to the wide world of bills, credit cards, and debt. You’ll learn, eventually.

But the problem is very few people “figure out” how to swim on their own, because swimming isn’t an act of willpower. Trust me, I’ve seen hundreds of smart, resourceful adults try to overcome their fear of water by squeezing their lips and eyes shut, forcing their face underwater, only to splash and exhaust themselves without moving forward at all.

Swimming is a skill (duh), and so is money.

If money was simply about trying hard, then perfectionists—who often have motivation and willpower aplenty—should surely be able to land themselves in a place of never having to worry about money again.

But is that the case?

Research shows that perfectionism actually lowers performance.

For instance, psychology professors who hold themselves to a perfectionist standard are less likely to produce publications, receive citations, and get published in high-impact journals.

Even Andre Agassi, no slouch at tennis, was told by a coach that his perfectionism was making him miss shots because he wanted to “hit a winner on every ball.”

This is what my swim students would try to do when they’d attack the surface of the water in a furious approximation of “swimming.” They were just trying to get across the damn pool.

It should be so easy. Other people make it look so easy.

In life, it’s easy to look at other people in the next ‘lane’ and think:

I should be able to stay on budget.
I should be further along on my financial goals.
I should have more to show for the amount of money I make.

These recurrent thoughts make you feel frustrated and impatient with yourself. All you can think about is getting across the pool, to your goal. But fixating only on your goal means you stop paying attention to the process, you know, the way you actually get there.

When my terrified swim students arrived on their first day, the very first thing I had them do was dip their chins in the water and practice breathing calmly.

This could take a while.

I’d encourage them to relax their arms, maybe even smile. Then, they would put their lips in the water and exhale gently, proving to themselves that they can control the flow of water in and out of their mouths. If you can’t feel safe with your face under the water, forget getting to the other side of the pool.

The same goes for money. If you don’t have some foundational skills, forget climbing out of debt or saving for college. This is why focusing on incremental process goals will do far more for you than the big, audacious goals you think you need to set.

For all the perfectionists out there (as well as all the misfits resigned to imperfection), here are some process goals to focus on:

• Give every dollar a job. This has been the Maori face tattoo of YNAB for 20 years and it’s how millions of people have learned to get good with money. It’s simple; don’t rely on your bank balance as an indicator of how much money you have available to spend. Proactively set aside money for your rent, groceries, gas, health insurance, Netflix, etc. (Learn more here.)

• Treat your non-monthly expenses like monthly subscriptions. Nothing trips people up more regularly than unexpected car repair, taxes, holiday spending. YNABers learn to fund these expenses each month so they always have the money right when they need it.

• Adjust your plan as needed (probably often). Life never goes the way you expect it, and so it would be an exercise in stubbornness to stick to a plan you once believed was the right one. Your money is a pile of potential; it has no particular spending destiny.

When you do these regularly, soon you’ll find you’re in a different financial situation than you were at the start. You’ll see yourself crossing the pool and it won’t feel like a battle or a character test. It might even feel fun, which is what you forget when you were so focused on not messing up.

You just had to trust the process.

I’d love to hear from you – what kind of small, incremental process goals have helped you get good with your money or even just build a more comfortable relationship with your money?

Leave a comment

Until next time,

Dan

Many people struggle with money for the same reason: they think being good with money is a club reserved for perfect people.

Maybe you can relate: you make a budget, try a no-spend challenge, or finally face your fears and start learning about investing. And when one of those efforts falls by the wayside, it’s easy to conclude that there must be something about you that’s incompatible with being good with money.

Welcome to the perfectionist’s guide to getting good with money.

For the next few weeks, we’re going to examine how perfectionism sneaks into your relationship with money, keeps you stuck, and convinces you that progress is impossible.

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If you’ve ever felt this way, remember that money is not (and never was!) a test of your character.

Money is for funding the kind of life that sits right with you. It’s also for getting your bacon, egg, and cheese sandwiches when you’re too tired to make breakfast!

But if you’re a perfectionist, you’re likely having a tough time enjoying (let alone feeling content with) your financial situation.

Psychologist Dr. Samuel Mikhail, who co-wrote a book on perfectionism, described how perfectionists can take a difficult situation and make it impossible.

When discussing a patient experiencing debilitating chronic pain, Mikhail said, “Another patient who could no longer play on the floor [with his children] might focus on other ways of connecting with his kids, such as reading in bed or sharing an ice-cream sundae. But perfectionists live in an all-or-nothing world: because something has been lost, everything has been lost.”

“That attitude is likely to carry over into recovery, with the perfectionist thinking, I need to be just as I was before, rather than appreciating partial progress.”

Yet, as I’ve written recently, we live in a treacherous personal-finance landscape.

Teenagers are offered hundreds of thousands of dollars of confusing student loans, Klarna and Afterpay are dangled on every checkout page, and we often struggle to have honest conversations about money—even with loved ones.

So many of us have financially stumbled at some point, and then we drag this all-or-nothing thinking into our financial situations. “Something” may be lost when we take on hefty student debt, tank our credit scores with unsatisfying purchases, or find ourselves fighting about money with our partners more often than we’d like. Sure, something may be lost, but not everything.

I once heard the writer Joyce Carol Oates say, “Every story has a beginning, a muddle, and an end.” If you’re feeling stuck around your money, maybe you’re just in the muddle.

Like the father learning to be a good parent in spite of his chronic pain, we have to resist perfectionism’s conclusion that difficulties and setbacks mean we’re hopeless and all is lost.

We all have unique situations where incremental progress is not only possible but incredibly important for how we see ourselves. I can only get good with my money, not someone else’s more ideal-seeming financial situation.

Research on perfectionism shows that process goals are far more effective than outcome goals.

For example, instead of saying, “I’m going to get my credit score to 800,” a more supportive goal might be: “Every Sunday, I’ll review my spending, look at the week ahead, and make sure I have enough for groceries, gas, and rent.”

For perfectionists, big, one-time goals (like saving $10,000 by December) can subtly set us up to feel like we’re failing. Here’s why:

• There are too many factors outside your control: market swings, car repairs, health issues, etc.

• “Success” only arrives at the very end, which means months go by without any sense of progress.

• Perfectionists, especially, need frequent feelings of competence to stay motivated.

Feeling like you’re getting somewhere with your financial goals isn’t always about having more discipline or willpower. Sometimes it’s about choosing more appropriate goals that let you see your progress along the way, which is exactly what we’ll be digging into next week.

Until then, I’d love to hear from you:

Where do you notice perfectionism in your relationship with money—and how does it affect the way you set (or avoid) financial goals?

Leave a comment

Thanks for reading.

– Dan

Less than two hours later, the movie ends with Bing and Danny Kaye at a Vermont inn performing a huge song and dance number with their new sweethearts. Snow is falling in the background and their beloved general’s resort has been saved from bankruptcy.

From Rudolph to Home Alone, the essential message of Christmas movies is that everything works out in the end.

In It’s a Wonderful Life, George Bailey was so worried about money that he threw himself off a bridge. He returns to his house to find a town full of admirers singing “Auld Lange Syne” and dumping cash into a collection bucket to save his hide and the bank.

Even in my Judeo-Christian-Buddhist household I love Christmas movies, but that’s not why I’m writing this post.

I’m writing because many of us are actors in another movie, written and produced by credit card companies and retailers in which the moral of the story is: Don’t worry, all your holiday spending will work out!

With our hearts and wallets open, we get the message that only the Scrooges and Mr. Potters of the world are counting their money.

Exhibit A: Every Hallmark movie ever made, in which the heroine decides to leave her big paycheck or rich boyfriend for the small-town hunk who teaches her that money isn’t important. What’s important is finding love and finally opening her own bakery!

But at the same time, holiday shoppers in the U.S. are planning to spend $1,100 on presents this year.

31% of 2024 holiday shoppers who used a credit card are still paying off the debt.

So which is it…? Is money an important part of the holidays or should it be left outside, like a pair of dirty boots that we dare not track into the house?

When most of us grow up seeing that money is stressful and should be avoided in conversation, why would you want to bring it up during a season of ‘magic, hope, and light?’

Exhibit B: my unsold screenplay, A Very On-Budget Christmas.

Many of our most memorable Christmas grouches are obsessed with money. In Elf, James Caan isn’t able to love his elf-ling son until he learns to put family ahead of his big job and salary. To spell it out further, Christmas is the time of year where we can finally rise above the petty concerns of paying attention to our spending. You know, don’t be a Scrooge.

But can’t you see that this directly benefits MasterCard and Klarna and all the other companies who want you to take a seasonal shopping spree?

When I was a waiter, we loved a table where the wine was flowing because they would order more food than they could reasonably eat and a big check was sure to follow. This is us. Drunk on the holiday spirit, millions of consumers will bestow gifts on their loved ones with the hope that all the bills will get sorted out in the end.

I wish we could rewrite our script for the holiday, while keeping the yule logs, Mariah Carey, and Hallmark movies.

I also appreciate how the holidays invite us to step out of our comfort zones. We are offered a chance to transcend our usual self-centeredness and share something with loved ones. We are asked to stop hoarding our resources and to somehow, unbelievably, find good cheer during the coldest, darkest time of year (up here in New York at least).

But there’s a difference between opening up to the love of a handsome single dad who owns a toy store in a Hallmark movie and opening a credit card with Target, thinking it will all work out in January. And maybe it will. But the way we are discouraged to take care of ourselves financially during the holidays causes real problems and stress.

Instead of a pressured scramble to answer the question, What should I buy?

The greater question is, What is my money for?

It might be to buy Legos and Weird Al Yankovic tickets for your kids (shhh!) this holiday season, but it’s also for your rent, utilities, and taxes. These different parts of you have to live together in one beautiful spending plan.

And if you’re thinking, “Cool, thanks for sending this out three days before Christmas.” Don’t beat yourself (or me) up. I went overboard on gifts this year as well. It’s easy to do, which is sort of the point.

As with all personal transformations— and getting good with money is one of them— you can’t define yourself by a single moment or slip-up. Very healthy people take days off from the gym. Stephen King has turned out some real bad books, but is still a legend.

So take heart and remember that one concrete way to take the stress out of holiday spending for next year is to start putting the money aside way earlier. Think of your holiday costs like a subscription that you pay each month, and by December you’ll have a fat pile of spendable cheer.

I’ll close with a message that must have been cut for length from every Hollywood Christmas movie.

Being good with money isn’t a bummer, it’s a net positive in your life.

It’s as wholesome as a Hallmark movie, as transformative as a visit from the ghosts of Christmas Past, Present, and Future.

It changes you and opens the tap of goodwill and generosity in a sustainable, healthy way. You can give without depleting, be merry without worry.

Thanks for being here this year! Wishing you a cozy, restful end to the year, and I’ll see you in 2026.

— Dan

Author’s note: A careful reader and big fan of It’s a Wonderful Life correctly pointed out that actually what compels the despondent George Bailey to jump off the bridge is seeing Clarence in the water below. Thank you to Melissa and all the guardian angels of this newsletter!

1. A delirious new culture of consumption

“They Got to Live a Life of Luxury. Then Came the Fine Print.” — The New York Times

For Elysia Berman, the desire for high-end clothing and bags had been building up for years. She grew up surrounded by kids who casually flung Louis Vuitton bags into their Porsches while she decorated her L.L. Bean backpack with Wite-Out.

When she moved to NYC and got her dream job as a designer at a fashion magazine, with the help of Buy Now Pay Later she seized the moment. This is the story of her descent into high-fashion and high debt.

It’s a compelling exploration of a story that is increasingly playing out as BNPL seeks to normalize itself in consumer spending.

2. America’s Money Mood? Worried.

2026 Money Mood Report from YNAB

Why are women 12% more likely to feel guilty when they spend money to treat themselves, compared to men? YNAB’s 2026 Money Mood Report asked Americans questions about their financial lives that their friends, neighbors, and maybe even family might not know.

Read how Millennials feel about managing their money compared to Gen Z, and how much Americans can spend on a purchase before it no longer feels like “no big deal.”

3. Allowances for Adults?

“She’s 7 Years Old. Her Parents Are Saving to Support Her When She’s 30.” — The Wall Street Journal

Once you’ve made your bed and gotten a full-time job then you’ll get your (adult) allowance. The Wall Street Journal did a story on a trend of parents putting aside money for their children to receive when they become adults so they can afford the skyrocketing costs to be a grown up nowadays.

Some of my friends were nauseated by the story; some felt resentful that they didn’t get financial help from their parents or don’t expect to be able to provide an adult allowance for their children. My takeaway is that we are lurching toward unaffordability across many sectors of our economy—higher ed, healthcare, and housing— and we will continue to see creative and sometimes shocking responses.

What are your thoughts on this? Let me know in the comments.

Leave a comment

4. A Lonely Chef on the 100^th Floor of a Luxury Skyscraper

“At a Deluxe Dining Room on the 100^th Floor, a Chef Toils in Obscurity.” — The New York Times

A look inside the strange world of private restaurants in ultra-expensive apartment buildings.

The chef at 10 Cubed, which overlooks Central Park in NYC on the 100^th floor of an ultra-exclusive apartment building, has a menu that blends his African-Caribbean roots with classic French techniques. The only problem is that the restaurant is often empty because it’s closed to the public and the residents of the building are more likely to be zipping around the world than sitting down for a meal upstairs.

This line stuck with me from a manager at a similar private restaurant in NYC, talking about the $31 chicken breast with rosemary-smashed potatoes on the lunch menu, which residents can get delivered to their apartment via room service: “The definition of luxury has evolved into simple ease and convenience. The most important thing to all of us, no matter how much money you have, is time.”

It was interesting to reflect that money can get you a state-of-the-art apartment overlooking Central Park, but it might not buy you time.

5. My Mother’s Illness Changed the Way I Think about Money

“My Mother’s Illness Changed the Way I Think about Money” — The Wall Street Journal

The personal finance columnist for The Wall Street Journal wrote this very personal account about caretaking for her mother toward the end of her life. She chronicled how those realities burned through the comfortable money advice she had long given. A quote from the article reads:

“As a personal finance expert, I give advice on how to maximize wealth. At the end of my mother’s life, I realized there’s a more important question: What is our money for?”

6. Die with Zero

Die with Zero: Getting All You Can from Your Money and Your Life by Bill Perkins

I listened to this as an audiobook and it made a big impact right away. The author makes the (obvious but powerful) argument that some experiences, like going on a skiing vacation with your kids or taking a parent to visit their ancestral homeland, are only available to you at certain times of your life. Therefore, you should spend your money to create fulfilling experiences when you can and not hoard money until the window of creating good memories has closed.

My wife and I decided to take on a massive renovation of our house this year because I realized my oldest daughter might only have six years left before she moves out and I wanted her to have a restful bedroom… and a stairwell that wasn’t dangerous… and walls that weren’t flaking paint.

And so, kapoosh, we took out a home equity loan because we realized that being able to enjoy this house with our girls was worth the price of the interest on the loan.

It’s a thought-provoking book, especially on the subject of inheritances, and I wholeheartedly recommend it. (Bill Perkins has a companionable reading voice if audiobooks are your thing.)

7. Paying for College, Understanding the Price

The Price You Pay for College by Ron Lieber

Confession: I have tried to put the enormous sums of money I may someday need to pay for my daughters’ college tuition out of mind. I feel behind on retirement; I live in one of the most expensive parts of the country; yada, yada, yada. But this year I decided to stop hiding from the issue and picked up Ron Lieber’s excellent book, The Price You Pay for College.

Lieber spent years reporting on higher education and his book explores questions like: why is college so expensive now? What makes a good college for your specific child? I heartily recommend this book if you want a guide to navigating what Lieber calls “the biggest financial decision your family will ever make.”

I’d love to hear about something you read, watched, or learned this year that made you think differently about your finances and/or priorities! Share ‘em in the comments. I’m hungry for more!

– Dan

She was, understandably, pissed at me for not thinking through all the costs, for applying my habitual bright-side-of-life disposition to renovating a 200-year-old brick house. What could go wrong?

I learned a lot about money in 2025 and I suspect next year I will, too. As Alvy Singer in the movie Annie Hall says, a relationship is like a shark; If it stops moving, it dies. And whether we like it or not, we all have a relationship with money that has to keep moving, because our goals and circumstances are always changing.

So, here are the five most important things I learned about money in 2025:

1. Pessimism Can Pay off (Sometimes)

One of the things my wife is good at is anticipating the ways a project could go badly. I’ve theorized about why she leans this way when it comes to money and why I’ve tended to assume that most money problems will go away… eventually… somehow.

The first lesson is that when taking on a complicated project of uncertain length, like moving to a new home, adopting a pet, or God forbid a DIY home improvement project, assume that the costs will be higher than you expect. Depending on your psychology, you may imagine that this enterprise will go smoothly and stay on budget. Don’t fall for it.

When it comes to funding something like a big vacation or starting a business, you’ll be so much happier at the end if you look on the stormy side of life. Ask yourself, am I ready for unforeseen problems to emerge? Can I pay for them?

Don’t assume the best case scenario. Put that money aside now before you’re slumped on the kitchen floor wondering how you’re going to afford $3,000 of that beautiful paneling you thought you just had to have. At “worst,” you won’t end up needing the extra money and can put it to use on your next goal.

2. Focus on What You Can Control

It was about April of this year when Tariff-mania seized my news outlets. This, in case you don’t remember, is how the stock market was feeling when it seemed like supply chain chaos and a recession was around the corner.

Anxiety wafted through the public radio broadcasts and many of my friends and family were spiraling into a panic loop: prices will skyrocket > consumers will stop buying stuff > economy will fall over > jobs will be lost > feudalism.

But it didn’t happen, at least as completely and disruptively as many feared. To me, the lesson is not that big, bad macroeconomic events won’t happen—they will—but you and I can’t control them no matter how frequently we refresh The Wall Street Journal home page.

I learned to redirect some of my attention from macroeconomics to the micro-economy happening in my household. I assessed the money going to our non-negotiables like our mortgage, utilities, healthcare, and I looked at what we could cut in a pinch. (Here’s a helpful guide from my colleague Ben on how to do this.)

Like a surfer in a churning sea, I learned to find relative stability on my small board in an otherwise choppy situation.

3. People Can Spend Money on the Same Thing for Different Reasons

I read a very illuminating book (which I’ll write about more later) called The Price You Pay for College by The New York Times personal finance columnist, Ron Lieber. Among the many outrageous things I learned about our dysfunctional higher education landscape, one thing was clear: every parent and child is operating with different priorities and circumstances. College is not one-size-fits-all.

But Lieber’s project is even broader: to remove a sense of shame for parents who can’t pay upwards of $360,000 for four years of college and to lessen the pressure for students who fear that success is only possible if they can crack the code and get into a tiny number of elite schools.

After reading The Price You Pay for College, I felt more okay that my wife and I don’t have hundreds of thousands of dollars lying in wait for our kids’ college. I now feel confident that our daughters, should they wish to attend college, will be a part of honest conversations about what we can afford, the trade-offs of loans, and what is our goal for higher ed? At the end of the day, your financial priorities are about making the best decision for you, not imitating the herd.

4. Money Is Meant to Be a Conversation

One of the coolest things I saw this year was Sherry, a YNABer in her 70s getting her first tattoo next to her son, Michael, at YNAB Fan Fest in Minneapolis. It was a gathering on the banks of the Mississippi River in an old industrial building with several hundred YNABers. There was so much joy in the air. Why? Because when money is stripped of worry and taboo, you’re suddenly excited to talk about it. Money touches everything, so when you’re good with money, your life can really change.

5. Sleep on It

A blogger from simpler times on the Internet (circa 2009), Leo Baubata of Zen Habits, used to tell people to wait until the first of the month for discretionary purchases like books, clothes, music, home goods, etc. But this had nothing to do with waiting for payday.

It was a mindfulness practice that gives your brain a chance to reflect: is this really how I want to spend X dollars? (Your money is finite; remember that.) Once the initial excitement and lusting for gratification fades, you’ll know if those jeans or that novel is something that has lasting interest for you. But if, as is usually the case after a couple days or a week, the luster has faded, you haven’t lost anything; you’ve only gained the money to now spend on something you really do care about.

Over the summer, my wife and I were briefly enthralled with the idea of putting in some paneling in our living room wall during the reno. A designer friend mocked it up and showed how charming it would look. We had mentally said, yes, let’s do it, but the contractor was slow to give us the quote and when it came in at $3,000, we almost went ahead on sheer momentum.

But after about a week of letting the decision sit, we realized there were so many other things ahead of paneling that we wanted to spend that $3,000 on. We passed, and I bought a fancy can of paint for about 60 bucks and I almost never think about the paneling that could have been.

In talking about this post with someone who used to work in retail, she told me that two pieces of advice for people struggling with compulsive shopping are:

• Take whatever you want to buy at the store and ask a salesperson to put it on hold for you overnight. They can almost always do this.

• When shopping online, add the item to your cart and then close your browser. Sleep on it and see if the purchase still calls you the next day.

This is what I should do with the leftover apple crumb pie from Thanksgiving that I’m still ravaging — wait a bit instead to see if I’m actually hungry.

But I refuse.

I’m willing to be good with money and bad with pie.

As always, I’d love to hear from you in the comments: What did you learn this year about money?

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Until next time,

Dan

Let’s say you start a newsletter about a thorny topic like personal finance, because you’re tired of dudes in tight T-shirts dominating the conversation with “How to 10x Your Income.”

You’re tired of good, earnest people feeling like they’ll never get good with money. They think they’ll never be able to buy a house or help their kids with college because of financial mistakes they made in the past.

Now let’s say thousands of people start reading this newsletter and when they come across stories of uncles struggling with debt or busboys buying $3,000 art prints on their lunch break, they are moved to hit reply and share their own stories.

But here’s the sad part of this oddly specific scenario:

Readers couldn’t actually share their stories or learn from each other, because that newsletter was trapped on a platform built to send email blasts about cashmere sweater sample sales, not dialogue about how mother-in-laws should spend their money. I don’t want to sell you a sweater; I want to talk about mother-in-laws.

I started writing Loose Change over a year ago because I know a lot of people worry about money.

For many of us, just thinking about our financial situation is enough to send us into fight or flight with worry and shame.

But the best way to dissolve all that worry and shame is to actually talk about it.

And so today, Loose Change is officially on Substack, a platform designed for writers and readers to have a conversation. Now, all you cool and interesting readers can comment on posts and respond to other people’s comments.

With this transition, I can also send behind-the-scenes posts in which I share what I’m reading, listening to, trends I’m following, and (of course) stories about people being good with money in surprising and unique ways. Plus, all you’ll have to do is head to the comments and to tell me what I should write about next or if you think I’m dead wrong.

As you may know, some Substacks are behind a paywall, but this one won’t be.

We want to foster a community of readers who are getting good with money together; that’s why we’re settling in here on Substack (also my cashmere sweater sample sale business is floundering).

Thanks for being here, and make sure to subscribe for more practical articles on why we spend, save, and think about money the way we do.

I’m very grateful for your readership.

Dan

Like me, Jason was in his 20s and living at home. I was squirreling away cash for my move to Brooklyn, but Jason didn’t seem to have a plan.

Every night, we waited on people with way more money than us: students at Yale who could afford $150 dinners, adults who had remunerative careers (unlike working at a restaurant and saying you’re a writer). Often, they’d drop the credit card on the table when I approached with the bill, not even deigning to look at the price. I longed for that kind of laissez-faire attitude with my money.

And what scared me more than spilling a mojito on a rich person or getting yelled at by the kitchen staff was thinking that I might not ever get close to being like those people dropping their Amex’s at the end of a meal, looking completely relaxed and comfortable.

I was scared I might end up like Robert, an older bullying waiter who started working in restaurants as a young actor. Robert greeted me every afternoon from his hangover in a darkened corner of the restaurant, shouting “Chad!” (I had a passing resemblance to NFL quarterback Chad Pennington)

Jason’s big art purchase never made sense to me until years later, when I was dealing with a health crisis and feeling hopelessly distant from the life I wanted.

I’d always focused on the randomness of Jason spending $3000 on a piece of art, but never tried to empathize with what he may have been looking for when he spent that money.

Maybe he was thinking of the people we served in the restaurant, and when he walked by the art gallery that day he thought, why not me? When is it going to be my turn?

Maybe when the salesperson put the bill on the counter, Jason just dropped his credit card without even looking at it. He felt he needed this purchase, not because he needed art. (They sold art posters at the museum down the street.) Maybe he needed the certainty that this phase we were in—folding napkins in a basement restaurant—was just a phase.

Buying stuff is easy. Understanding why we do it is not.

Think about the loner who never invites anyone to his house but builds a bar for entertaining. Or, the person who freaks out about the price of eggs, but spends $600/month on their new car lease.

Some personal-finance experts make a living ripping people to shreds for decisions like this. They act as if spending money is simply an exercise in rationality. It’s not.

We spend to express who we are and who we want to be.

And sometimes, if people don’t believe they can get where they want to be by staying on course (planning, saving, etc.), they try to leapfrog the process and spend money in a way that seems crazy or irresponsible from the outside.

Maybe Jason wasn’t just spending money for the thrill of it. Maybe he was impatient with the distance between his current life and the one he imagined. I can relate.

Money isn’t just a tool; its a language. When we spend, we’re not just buying things. We’re making quiet (and sometimes not so quiet) declarations of what we value or who we hope to become.

The trouble comes when we try to shortcut the becoming part.

We want to feel like the person who’s already made it, not the one still bussing tables and waiting for life to happen.

So, sometimes we spend in ways that seem reckless and unthinking because we’re tired of waiting to feel better about our money. And when we do, it doesn’t help to shame ourselves for it. Money mistakes aren’t moral failures. We all make them, and usually they’re just moments of impatience.

The real work isn’t punishing ourselves into better habits as some finance experts (ahem) would have you believe.

The real work is learning to practice patience instead of panic, compassion instead of criticism.

Have you ever spent way too much on something you regretted later? What did you learn from the experience? I’d love to hear about it.

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Until next time,

Chad Dan