Money Advice Fails When Shame Keeps People From Facing the Math

Carrie Grimes’s operating premise is blunt: money is not just arithmetic. It is “math and feelings,” and in her view the feelings often matter more than the math because they determine whether people can face the math at all.

Grimes grounds that view in both personal experience and WorkMoney’s daily work. She describes years of believing she was “bad at money” because she was poor, living paycheck to paycheck, and sometimes standing at a register hoping her card would go through. WorkMoney, the nonprofit she founded during COVID, now has more than 9 million members and is in regular contact with people by text, email, and phone. Across those interactions, Grimes says, the recurring obstacle is not only that people lack financial information. It is that fear, shame, avoidance, exhaustion, and the need for some relief interfere with using it.

Grimes uses a mundane Target run to make the point. Someone goes in for a prescription and walks out with peanut-butter pretzels, a throw pillow, and a small solar lantern. The purchase was not in the budget, but the person wanted it. Grimes does not frame that as a moral failure. She asks why it happened. In her own case, the answer was often that she had had a hard week, felt there was “no joy in life,” and wanted a small bit of pleasure. The spending was a signal: the budget was colliding with an unmet emotional need.

Avoidance works the same way. Grimes says some people do not open the envelope or look at the bank account because the information feels like one more piece of evidence that they are failing. The practical result is that the math gets postponed. Her book begins, she says, with identifying a person’s “money story” and deciding what they want it to become, because that story can either make the financial mechanics usable or keep them out of reach.

Jeff Berman identifies himself as an avoider and says Grimes’s book helped unstick him on financial matters he had not wanted to face. The admission broadens the problem beyond acute financial distress. Even people with education, professional credentials, or income can be afraid of money decisions, can procrastinate, and can carry stories about what money says about them.

Grimes is careful not to let the emotional frame turn into a substitute for the material one. When Berman recalls his first job after law school as a public defender making $29,500 a year, living with two roommates, and timing grocery trips around triple-coupon nights at Safeway, he asks how anyone sets money aside in that situation. Grimes’s first answer is not mindset. It is that most people’s problem is that they do not have enough money.

That, she says, is the math problem. The economy deals people different hands, and people have to play the hand they are dealt. The hard part is holding both truths together: inadequate income and high costs are real; so is the need for agency inside whatever constraints exist. For Grimes, a useful distinction was changing “I have to” into “I choose to.” She stresses that she does not want that idea weaponized. It is not a way to blame people for constraints they did not create. It is a way to give a person some usable power inside them.

Grimes traces her own money reset to a small humiliating loan. When she moved to Ohio for her first union organizing job, she says she had “negative money,” shoes with holes in them, and a failing car she called Mo. On her first day, the organizing lead wanted the team to go out to dinner. Grimes had planned to return to a Red Roof Inn, eat ramen, and watch Law and Order. She did not have money for the meal.

Her boss saw the situation, paid for dinner, and handed her $100 to buy shoes and give herself a little cushion until the next paycheck. Berman notes that $100, 20 years earlier, with no paycheck for two weeks, was “godsend money” — and also a debt that created immediate pressure.

Grimes says the debt bothered her enough that she sat in the hotel room with a pen and wrote down what she had to pay, what she expected to make, and how she would repay him. Berman calls it what it was: a budget. Grimes says it became the basis of the budgeting method she still uses — not complicated, just what has to be spent and where any extra can go.

The important shift was not that she discovered budgeting as a technique. It was that she repaid the money and felt competent. Until then, she says, she had interpreted the facts of being poor as evidence that she was bad at money. That belief became self-reinforcing: thinking she was bad at money led her to behave like someone who was bad at money.

Repaying the $100 interrupted the loop. She began to tell herself she could be good at money, then applied that same logic to credit card debt and an emergency fund. Each time doubt returned, she pushed back: “Of course you can be good at money.”

That story also explains why Grimes is skeptical of financial advice rooted in shame. Shame may provoke a short-term reaction, but she argues it does not repair habits. She compares it to someone in the fourth row of a baseball game yelling at a player to hit the ball better. The yelling does not make the player better. It mostly reveals something about the person yelling.

Her first filter for personal finance advice is therefore emotional as much as technical: if the advice makes people feel terrible about themselves or their choices, walk away. Grimes says the shame-based advice is morally aggravating to her, but her case against it is also practical. It does not solve the underlying behavior.

WorkMoney began as a pandemic response, but Grimes says the idea behind it was older. She had spent roughly 20 years as a union organizer, talking with working people in homes, churches, bars, and union halls about their lives and money. That work trained her to listen, which she says she did not initially enjoy. “Really good organizing is listening,” she says, and she liked to talk.

The listening produced two conclusions that later shaped WorkMoney. First, many people did not have basic financial knowledge; nobody had sat them down and taught them how to “do money.” Second, people felt alone. They were navigating wages, benefits, bills, debt, and public programs as individuals.

WorkMoney was the organization Grimes says she wished had existed when she was trying to figure out money herself. It is a nonprofit with more than 9 million members. Its stated function is to help people earn more, save more, and spend less through programs, services, coupons, discounts, and information. Grimes likens part of the model to AARP: a large membership organization that can provide practical benefits and also aggregate power.

The first version was a website created in 2020, when people were trying to understand stimulus checks, PPP loans, unemployment, and other pandemic-era financial questions. Grimes expected the demand might subside as the emergency did. Instead, she says, signups did not fall. In some periods, they accelerated.

Her explanation is that the pandemic was not the underlying problem. It exposed a broader absence: no single trusted place where everyday Americans could go for straight, practical information about money. She also argues that the post-pandemic economy has not become dramatically better for most people. Even people earning what would traditionally count as a good living are squeezed by healthcare, education, housing, and childcare costs rising faster than wages.

Berman references a chart he and Grimes had been looking at that showed an unusually large gap between the stock market’s position and Americans’ feelings about the economy. Grimes agrees with the broader point: the number of people who feel squeezed is large, and middle-class families are stretched.

The result, in her framing, is that WorkMoney is no longer a temporary patch. It is an attempt to build a “permanent civic institution” where people can get individualized financial help and also use collective strength to bargain for better market outcomes and communicate expectations to decision makers.

WorkMoney’s mobile interface, shown during the discussion, presents that hybrid mission in practical terms: immediate savings help, budgeting and debt tools, planning categories, and prompts that tell users they are not alone.

Those examples are not presented as financial innovation for its own sake. They are the product expression of Grimes’s organizing diagnosis: people need basics, reassurance, and a way not to be alone.

Asked where WorkMoney hit scaling inflection points, Grimes first points to an organizationally modest but revealing marker: the remote team grew from one Zoom screen to two. That meant WorkMoney had moved from “passionate generalists” to a mix of generalists and people with specific expertise. It also meant work was leaving her hands.

Grimes describes herself as a “founder’s founder” who likes solving hard problems alone. Letting a team take over more of the work was one of the scaling moments. She credits the team with both doing the work and giving her grace while she learned to let go.

The more strategic inflection was less obvious. Grimes says WorkMoney considered narrowing around one specific high-impact problem — for example, car insurance costs. That could have meant focusing on insurers, regulators, and deals that lowered costs in that category. But the organization concluded that scaling fast required the opposite of a classic startup wedge. Instead of getting narrower, WorkMoney “leaned way back.”

The reason was intake. If the goal is to help millions of people put money back in their pockets, the organization must quickly understand what kind of help each person needs and route them to the best available version of that help. Sometimes that is immediate savings. Sometimes it is information. Sometimes it is a chance to influence broader economic decisions.

Grimes describes this as “full stack” money work. People should make good individual choices and play the cards they are dealt. But there are also ways to improve the odds.

One example is partnerships. Grimes mentions Upside, an app that offers gas discounts at participating stations. WorkMoney members using the code WORKMONEY can get an additional discount, and Grimes says she has saved 25 cents a gallon in some places. She does not present the partner as perfect. She notes that Upside may track user data and may not be the best deal in every market. WorkMoney’s standard, as she describes it, is not to pretend partners are flawless but to be clear-eyed about tradeoffs and offer practical value where it exists.

Another example is policy translation. Grimes says WorkMoney read “every word” of a new tax bill and explained to members what it meant, including which tax credits to watch, where the benefits were, and where the bill would not do as much good. The service is partly a marketplace of options, as Berman suggests, but Grimes says much of the work is interpreting the economy and policy in terms of a household wallet.

Carrie Grimes does not describe WorkMoney as a partisan project. She says she does not think much about left and right and thinks more about right and wrong. She also says that if politicians could solve the problems of the American economy by themselves, they would have. Politics, in her formulation, is an outcome.

Jeff Berman challenges the phrasing. Politics is also the process by which policy is made: tax bills are passed by politicians, signed by presidents, and shaped by large moneyed interests trying to influence fine print.

Grimes clarifies that political decisions are the end result of many forces. WorkMoney’s job, as she sees it, is to build power before and around those outcomes.

She says she thinks about WorkMoney having power in five ways. In the discussion, she clearly names and elaborates four: market power, constituent power, audience power, and entrepreneurial power.

Market power means people getting together to bargain for cheaper goods and services. Grimes says she wants WorkMoney to become large enough to bargain around healthcare costs and sees other areas where collective purchasing strength could reduce prices.

Constituent power means working- and middle-class people telling politicians, regulators, and elected leaders in both parties what they expect. Grimes’s formulation is direct: elected officials have their jobs because constituents put them there, and their job is to represent all of them.

Audience power is about deciding what to listen to, whom to trust, and what content to make. WorkMoney’s wallet-focused explanations of economic events sit in this category. The organization is not only distributing information; it is trying to shape an audience that can understand economic developments in practical terms.

Entrepreneurial power means building businesses and tools that make life better. Here Grimes reveals a new WorkMoney-backed service called Money Finder, at moneyfinder.com, designed to negotiate bills.

The service starts with cable, internet, and cell phone bills. A user uploads a bill; Money Finder analyzes it; negotiators try to lower it. Healthcare bills and health insurance are not yet covered, though Grimes says healthcare is “on deck.” She also says she wants to add car insurance and home insurance as the negotiation team grows.

The savings and fee claims are distinct. Grimes says Money Finder has saved an average of $400 per negotiation so far. She also says most people have saved $400 or more. Users pay only if the service saves them money, and the maximum fee is $75.

Berman describes the fee as a commission on savings: the user and WorkMoney “rise or fall together.” Grimes agrees. She distinguishes Money Finder from other bill negotiation services by emphasizing that it is nonprofit-backed and intended to put money in people’s pockets.

The benefit is not only dollars. It is also time and exasperation. Berman recounts spending months negotiating a five-figure healthcare bill that he says should have been covered by insurance. Even as a lawyer by training, with access to the internet, the process took forever. A service with pattern recognition, knowledge of trigger words, and negotiation capacity could therefore matter even to people who are not financially unsophisticated.

Carrie Grimes’s personal finance advice is mostly conventional, and she presents that as a virtue. The internet’s “cowboy investment culture” — crypto, housing speculation, stock trading — may appeal to some people, and she says without dismissing it that her husband enjoys crypto and puts real time into understanding markets. But her view is that most people do not have the time, skill, or industry knowledge to make that the foundation of financial security.

Her preferred order is plain. Build a $1,000 emergency fund. Pay off credit card debt, because ordinary investments are unlikely to earn more than credit cards cost. Then save three to six months of expenses. Only after that should people focus on investment and retirement. For retirement, she argues that everyday people should max out tax-advantaged accounts before putting money into other investments: 401(k)s, 403(b)s, and IRAs, with room for individuals to decide between Roth and traditional options.

The advice is not framed as the only valid life script. Grimes is equally forceful that nobody else gets to decide what matters about a person’s money. Buying a house, having children, or meeting some inherited marker of success may be right for one person and wrong for another. The title of her book, The Joy of Money, reflects that hierarchy: joy is what the money is for.

Jeff Berman closes by comparing the book favorably with Morgan Housel’s The Psychology of Money, which he says is the personal finance book he has most recommended and reread. Grimes calls Housel great, and Berman describes The Joy of Money as a strong companion to it.

Grimes’s practical steps are simple enough to state in a few lines. Her larger point is that people do not live inside financial mechanics alone. They live inside fear, debt, wages, bills, status expectations, family histories, and institutions that can either isolate them or aggregate their power. Getting better at money, in her view, requires both sides at once: the arithmetic that puts dollars where they need to go, and the emotional and collective conditions that make it possible to do the arithmetic in the first place.