Getting Ahead Is Easier than Ever

Everyone says you can’t get ahead these days.

That’s a lie that’s been told for 300 years. It wasn’t true then. It’s even less true now. Getting ahead is easier than ever.

Notice, I did not say “Everyone can get ahead.” That is not true. I said you. Doing what it takes requires less, pays out more, and the payments last longer than at any time in history. You, however, must be willing to do all those Go Ahead things that actually worked when others won’t. Take the right risks, and the odds are ridiculously in your favor.

Let’s start with being in America. I assume if you have this book you either live here or want to. You should. The United States is the wealthiest large nation on earth. Just 10 nations are wealthier, all very small: Monaco (39,000 people), Liechtenstein (23,000), Luxembourg (645,000), Bermuda (61,000), Ireland (5 million), Switzerland (9 million), Cayman Islands (67,000), the Isle of Man (85,000, and not a real country), Norway (5.5 million), and Singapore (6 million). Size matters for opportunity. The third-largest town in Alabama is more populous than five of those wealthier nations. Switzerland is smaller than Michigan.

Global wealth is wildly misunderstood, mostly by Americans. Mississippi, the poorest U.S. state¹, is wealthier than Britain, France, Italy, Spain, and Japan. The sheer scale of wealth surrounding Americans gets obscured because it is just life’s backdrop. Not so for all the people who want to live here. Tyler Cowen, the panoptic economist who identifies the globe’s most talented young minds, notes nearly all his award winners want to work in the United States. “I have written so many letters for O-1 Visas,” Cowen observed of the immigration designation reserved for Individuals with Extraordinary Ability. “It’s stunning to me how few say, oh, could you help me get into Denmark?” Assume if you can’t find opportunity here, you probably won’t find it anywhere else.²

Nor would you have found more opportunity in history.

The good old days sucked, no matter when those days were. Do you have a fondness for Colonial Williamsburg and scrappy immigrants with rap skills? Great. Me too. But early America was a terribly hard place to get ahead.

About a third of colonists arrived as indentured servants or convicted felons, and another third as slaves. Contrary to popular misconception, indentured servants obtained the right to land³, rarely the land itself. They still had to buy it. Then they needed tools to plow, seeds to plant, and livestock to graze, all of which cost more money. Money was what the landless poor didn’t have. So they moved forward renting for another seven years. It often took nearly fifteen years to truly own their American dream. Few lived that long.

American colonists were pretty grumpy about how hard it was to Go Ahead. The Governor of Virginia could barely sleep at night. “Oh how miserable is that man who must govern a people who six parts of seven are poor, in debt, discontented, and armed⁴!” Armed indeed. They burned his colonial capital to the ground 100 years before the Revolution. Americans were angry about not getting ahead from the very beginning.

You could take risks, but if they didn’t work out you might find yourself in jail. Yes, jail. People went to prison for being broke in the 1700s, and this happened regularly. Worse, if a man went bust, his wife and kids were imprisoned, too. They forgot to put that in Hamilton.

Or maybe you prefer your nostalgia from the 1800s? In 1870, food, rent, and clothing⁵ took 91 cents of every dollar made (today it’s under 40 cents). The typical American owned just one and a half shirts. That is an actual historical statistic. To make money to buy this expensive food and the other half of that shirt, the typical man worked sixty hours per week. Women worked more. And the dollars people were paid in could lose their value overnight, making them no more stable than cryptocurrency today.

If you could find work, that is. Newspapers regularly proclaimed the death of American opportunity in the twenty-four recessions that century. One in four years was bad, and some were really bad. Rather than the age of getting ahead, “Ours is the age of suicide and mysterious disappearances⁶,” which were so common New-Yorker ran an article dedicated to studying suicide notes in 1839. Why all the drama? Until late in the century, there was very little insurance to cover losses. If your bank collapsed, house burned, crops failed, or spouse died, you just lost everything.

No, the 1800s were not better and they certainly weren’t easier.

What about the twentieth century? The Greatest Generation. Leave It to Beaver. One-income households. Golly, gee, what a great century! Or not. Let’s bust some myths, shall we?

Teen pregnancy was nearly 10 percent in the late 1950s. Today it is barely 1 percent. It’s hard to get rich as a single teenage mom. But the wages were better, right? No, that’s not true either. Since the 1970s, the median income has risen⁷ by around 50 percent (yes, adjusted for inflation). Even left-leaning groups admit wages are up⁸ at minimum 29 percent. But working-class wages went down, right? No. The median weekly earnings of high-school graduates⁹ (no college degree) is up since the mid-1990s. In my birth state (North Carolina, which lost all those furniture and tobacco jobs) the bottom 10 percent of earners make 33 percent more than they did twenty years ago. It’s up in every other state, too.

Poverty rates, meanwhile, were horribly high. By some estimates, about half of Americans were poor during the Roaring Twenties, which was before the Great Depression. By 1950 it was nearly a third. Today it’s barely over one in ten.

You can make more money, working less hours, spending less to survive, while buying more luxuries than any one of your ancestors. You can marry whomever you want. As we’ll see, that’s a big deal; marriage is one of the largest predictors of financial success. Side hustle platforms are everywhere. Your savings are safe. Mortgages don’t involve questions about your sex life (they used to), and you don’t have to pay them off in five years. Debtors’ prisons are abolished, bankruptcy laws give second chances, and Social Security offers a built-in retirement annuity. You’ve got it harder than “back then”? Puh-leeze!

Moving is easier, too, and mobility matters a lot. Go Ahead starts with an action verb. Success belonged to those who went where the opportunity was, and getting there is easier than ever. Your ancestors climbed aboard crowded, hot, stinky ships. For 15 percent of Americans, those ancestors were forced onboard. Scottish immigrants spent nearly two months in wooden hulls. Travel from China took thirty days. Italian immigrants endured two weeks. Leaving the Dust Bowl for southern California lasted weeks if your truck didn’t break down, which you’ll know if you’ve read your Steinbeck. Driving cross-country took the U.S. Army two months. But you could, today, rent a U-Haul and arrive with everything you own anywhere in the country in under forty-eight hours. You probably know someone who has.

Here’s a big difference no one has told you: finance is simpler than it used to be. An army of advisors gets paid to convince you that this crazy financial world is complex beyond imagination. Let the professionals handle this. But that’s not true. Early Americans had to figure interest rates with pencils where you have spreadsheets. Individuals regularly issued mortgages to local homeowners that included payment tables and civil law procedure. Could you do that? The price of any security in the world is available, accurate, and on your phone. Nineteenth-century investors had to go to seedy bucket shops that served liquor at the bar—and pornography in the bathrooms—just to see what the ticker tape said. Moving money involved dangerous and expensive stagecoaches with two drivers, one quite literally in the shotgun seat. Now you wire it and pay the bank a small fee. Even 100 years ago, most budgets were vague guesses by families who might be math illiterate. Today software tracks spending down to categories like “kids’ sports.” There is nothing about modern personal finance that is harder than it used to be. If your great grandmother could issue mortgage documents, you can do this.

Here is the last, and perhaps most important difference. You live longer. Life expectancy was forty-five years in the Old West. You are already an adult, which means you are probably going to hang on to about eighty-four¹⁰. Your income and investments have longer to grow. You live two lifetimes compared to early Americans. Don’t waste them.

* * *

Starting in the 1970s, a cottage industry of academics published research bemoaning the lack of real “get aheadism” in the so-called land of opportunity. The basic summation of those scholars is as follows: despite our national myths, most people stay in the same income class as their parents. Born poor, die poor. Born middle class, die middle class. Born wealthy, die in a Tahoe skiing accident. This line of reasoning has been absorbed into a media narrative feedback loop, especially on social media. Nearly 60 percent of young people today say the American Dream is no longer possible.¹¹

Our culture swallowed a pessimism pill, and it isn’t doing you any good. If you scream at people that their lives are terrible for five decades, they may start to believe you. There is real—and really persistent—wealth inequality in America. We will tackle that in later chapters. For now, remember this: the question is not what type of economy you would build, but what you will build in this economy.

For everyday people, the goalposts are set where they are and it’s best to get the ball moving. The clock is twice as long as it used to be, but it is ticking.