A Good Life Can Look Bad on Paper

Throughout my career, I’ve talked to a lot of accomplished people living comfortable lives. Once their guard comes down, sometimes after a drink or two, the conversation gets to the same place. They feel behind in life, as though they haven’t accomplished enough. Some feel like failures. The reasons vary: Not owning a house or the house they wanted, not having enough money saved, feeling underpaid, or not scoring the dream job or job title their peers have.

I’ve felt that way in my own life, too.

Sometimes I’ve tried to argue with them, using statistics to show how much they have actually accomplished. It rarely seems to help. They nod, and then comes the “but.”

There is always another group of people they compare themselves with. People who are doing better by some measure that everyone seems to accept. And questioning either the comparison or what counts as success does not get me very far.

We’ve accepted a list of things we’re supposed to have done or collected by a certain age, often without asking who wrote it. Fall short, and we call it failure.

The writer Amanda Saint described how she had no house, no pension, no big salary or impressive job title, about to turn fifty-three, but loved the life she had. She did not consider missing any of these the evidence of a failed life.

She had no loans or credit cards, and no credit score. She owed nobody anything, but there was no grade for that.

Owning a home has helped build wealth for American families for more than a century, and could be a smart financial decision. In 1919, the U.S. Department of Labor printed posters urging Americans to “Own a home for your children’s sake.” Buying a home was promoted as something a good parent would do and was worth borrowing money for.

We are told that to be financially responsible we need to have saved a certain amount of money by a certain age. Fidelity, which is in the business of selling investment products, even published a table for it. It assumes you started saving at 25 and never stopped or paused. Anything below that, and you feel you are behind.

We are even told how much money we are supposed to spend on an engagement ring. De Beers spent a fortune telling us a diamond was forever and spending two months' salary was the right amount for a lifetime of happiness . You hear people at cocktail parties mention the two months' salary rule and many brides expect it.

The FICO score was created in 1989 to price the risk of lending money, and then in 2001, people got to see their score. Many started treating their FICO score as their personal finance grade, stressing over the number when it moved a little.

A lot of what is called falling behind has little to do with the parts of our lives that matter the most. Most reflect a decision not to take on extra debt. Not owning a home means you did not want to owe money on a mortgage.

Buying a house is a financial decision. Buying one later in life, or deciding to never own one, tells us very little about whether someone has lived a fulfilled life. The National Association of Realtors puts the typical first-time buyer’s age at 29 in 1981 and 40 in 2025.

Not having a high credit score could just mean you have decided not to live on borrowed money.

Not paying two months’ salary for a ring means you did not want to pay a large sum of money for a small stone that has no impact on your marriage's success. Spending two months’ salary on a diamond engagement ring does more to fill the pockets of executives at De Beers than to ensure a happy married life.

Fidelity’s chart or a FICO score are both useful, and measure a level of financial stability or ability to pay back a loan. But they should not be a verdict on how you are doing in life.

I have caught myself doing exactly that. Looking at my savings, credit score, or my home and treating them as a measure of how I am doing. It is very easy to push aside everything you have done and try to judge yourself through a narrow lens of a few numbers.

An account balance, a deed, or a credit score can tell us what we own and what we owe. They were never built to tell us whether our lives have been enough.

If you have found yourself questioning your life choices and whether you are behind in life, pick one milestone you are paying for right now. Write how much effort you are putting into achieving it, and next to it write how achieving the milestone will actually change your life.

Look at what you wrote a few days later and see if the answers surprise you. Chances are, all the work you put into achieving that milestone was more about checking a box you were taught to check than doing something that has a meaningful impact on your life.

You might have no house to your name, or no big savings account, and love the life you have built.

You may still want to own a home, save money to go on a dream vacation, or help loved ones, and work hard toward those goals without labeling your life as a failure.

I keep thinking about Amanda Saint, who had no house or pension, about to turn fifty-three, and loved the life she had. She could see what was missing from the list without deciding that the life she had lived was a failure.

Sources

• Amanda Saint, Substack Note, 18 September 2025. About to turn 53; no home of her own, no investments or pension, no big salary or fancy job title; no credit rating because no loans or credit cards; "I don't feel like I'm failing at anything." https://substack.com/@amandasaint/note/c-157219827
• Hoover Institution Library & Archives, Stanford University, "Own a home for your children's sake," poster US 4940A, United States Department of Labor, Information and Education Service, catalogued 1918/1919?, no known restrictions. Reproduced in the essay. https://digitalcollections.hoover.org/objects/38321
• Vincent J. Cannato, "A Home of One's Own," National Affairs, Spring 2010. The Own Your Own Home campaign, begun by the National Association of Real Estate Boards and taken over by the U.S. Department of Labor in 1917, which distributed posters and banners promoting home ownership. https://www.nationalaffairs.com/publications/detail/a-home-of-ones-own
• Fidelity Viewpoints, "How much do I need to retire?" Savings targets by age: 1x salary at 30, 3x at 40, 6x at 50, 8x at 60, 10x at 67, assuming 15 percent of income saved every year from age 25 (including any employer match), more than half invested in stocks, and retirement at 67. The chart in the essay is drawn from this table. https://www.fidelity.com/viewpoints/retirement/how-much-do-i-need-to-retire
• De Beers, "Our history": Frances Gerety of N. W. Ayer wrote "A diamond is forever" in 1947. https://www.debeersgroup.com/about-us/our-history
• De Beers advertisement, N. W. Ayer & Son, early 1980s, "How can you make two months' salary last forever?" Reproduced in the essay. Ayer's De Beers campaign records: Smithsonian National Museum of American History, Archives Center, N. W. Ayer Advertising Agency Records. https://sirismm.si.edu/EADpdfs/NMAH.AC.0059.pdf
• myFICO (Fair Isaac Corporation), "The History of the FICO Score": the first general-purpose FICO score was introduced in 1989. https://www.myfico.com/credit-education/blog/history-of-the-fico-score
• myFICO, 20th anniversary post: myFICO launched on 19 March 2001, giving consumers direct access to their FICO score for the first time. https://www.myfico.com/credit-education/blog/myfico-20-anniversary
• National Association of Realtors, "First-Time Home Buyer Share Falls to Historic Low of 21%, Median Age Rises to 40," press release, 4 November 2025. https://www.nar.realtor/press-releases/first-time-home-buyer-share-falls-to-historic-low-of-21-median-age-rises-to-40
• National Association of Realtors, "2021 Highlights from the Profile of Home Buyers and Sellers," forty-year table: first-time buyer median age 29 in 1981. https://www.nar.realtor/sites/default/files/documents/2021-highlights-from-the-profile-of-home-buyers-and-sellers-11-11-2021.pdf