Holding the office of the President of the United States of America is, arguably, the hardest job in the world. (At least that’s true as long as you have moral fiber, a system of values, and an understanding of history and the complexity of global politics.) The POTUS is the head of the government, the Commander in Chief of the military, and the leader of the American people, both technically and in spirit. Many former presidents have said that nothing on earth can prepare a person to be president; you learn on the job and do your best not to mess things up — or to even improve things.

While no pre-presidential career can necessarily prepare a person for the immense responsibility invested in the office of the presidency, many professions practiced in the pre-POTUS lives of American presidents can provide good head scratching fodder for the citizenry. Many presidents served in the armed forces, many were senators, and some were state governors. Quite a few presidents were one of those things (or more) and practiced law. A few were teachers. Some were farmers. One was a failed haberdasher. Long story short, not every head of state followed a predictable path to the Oval Office.

15. Ulysses S. Grant – Always a Soldier

Grant is one of only a handful of presidents who not only had a military career before taking the office of President of the United States, but who had no other career aside from serving in the armed forces. In his case, it was quite a career indeed. The 18th President graduated from West Point in the middle of his 1843 class, and would soon serve as an officer in the Mexican American War. He tried his hand at farming for a few years between that war and the American Civil War, but it was only at arms that he found pre-POTUS success. Like that time he was promoted to be the commanding general of the Union Army.

14. Jimmy Carter – The Peanut Farmer

There’s nothing inherently strange about being a peanut farmer, as was James Earl Carter, Jr. (that’s President Jimmy Carter, of course) for many years of his life. It’s just that peanut farming is not usually a stepping-stone to the Oval Office. Here’s the thing: as much as people talk about his farming career, Carter only became a farmer to preserve his family’s wellbeing after the death of his father, James Earl, Sr., who had run the farm for many years. Before take over the farm, Carter was a naval officer with advanced training in nuclear power and propulsion.

13. Harry Truman – The Haberdasher

Harry S. Truman spent most of his life as a politician holding various elected offices, including the office of President of the United States of America. He also served in the army for many years, seeing action in WWI, where he served with valour and distinction. But when not destroying enemy artillery batteries or winning elections to various offices, Truman mostly spent his time driving small businesses straight into the ground. He and a partner launched a haberdashery in 1919 only to see it go bankrupt in just two years. He was still paying off debts related to the failure more than a decade later.

12. Thomas Jefferson – Renaissance Man

Thomas Jefferson, the third POTUS, is a hard guy to pin down. He was a writer, a lawyer, an ambassador, a statesman, a slaveholder, a farmer, an architect, a theologian, and much, much more. It’s rather exhausting just to think about all the jobs this man held; now try to imagine actually doing everything from drafting the Declaration of Independence to designing Monticello to revising a version of the Bible to overseeing several plantations. It certainly helped that Jefferson inherited thousands of acres of productive land as a young man. His long life helped, too: Jefferson lived to be 83, which is like 143 in today’s years. (Not actually, FYI. Do not quote that in your term paper, kids.)

11. Abraham Lincoln – The Rail Splitter

While the arc of Abraham Lincoln’s life was shaped primarily by his years spent practicing law, his time as a state and federal congressman, and perhaps by his brief time serving in a militia during the Black Hawk War, it was his stint as a rail-splitter that we remember today. Why do we think of the 16th president as The Rail Splitter? Because that’s exactly the image his supporters cultivated during his run for office. Lincoln had indeed spent time clearing land and splitting logs to construct simple rail fences to help define the family’s ranch, but the experience was only a passing part of his youth until it was made into a part of his lore.

10. Herbert Hoover – Geologist in Chief

Before he was mishandling the response to the Great Depression, Herbert Hoover was a successful mining engineer. He earned a degree in Geology from the newly-opened Stanford University, and would go on to work overseeing mines in California, Australia, and China, and traveling around the world as a mining consultant. He amassed a personal fortune that helped sustain him as he pivoted into public life, helping repatriate American citizens living in Europe as WWI broke out and working with various groups to ameliorate hunger issues caused by the war. As noble and helpful as all that work was, he couldn’t do much to help people after the stock market crash of 1929 and ended up as a one term POTUS.

9. George W. Bush – Sports and Oil

History may partially vindicate the 43rd President of the United States; we’ll have to see what state the Middle East is in after many years have passed. But for now, it seems as though George W. Bush would have done more for the American people if he had stayed out of politics and instead had stayed in the oil business or stuck with owning a major share of the Texas Ranger’s baseball team. He could afford the latter thanks to money he made via the former. And how did W establish a successful oil speculation business? Largely with Saudi investment steered to him by his father’s connections.

8. Teddy Roosevelt – Rough Rider

When Teddy Roosevelt couldn’t find a war, he created one instead. Like, he actually kind of did, I’m not kidding. Tensions had long simmered between America and Spain over various contested territories in the Caribbean and the Pacific, and when an American ship, the USS Maine, exploded mysteriously in a Cuban harbor, open conflict soon followed. This was at least partially true because, without authorization, Assistant Secretary of the Navy Theodore Roosevelt ordered multiple ships to go and prepare for war, ratcheting up tensions. Roosevelt then resigned from his office and, largely with his own money, raised a volunteer regiment that would become known as the Rough Riders. They headed off to Cuba and forced their way into the action of the Spanish-American War.

7. Andrew Johnson – Runaway Tailor

Andre Johnson has the dubious distinction of being only one of two presidents to be impeached. Long before he was an embattled president, he was a reluctant tailor. Johnson was apprenticed to a tailor at the age of ten, legally bound to serve in the shop until he reached the age of 21. Instead, Johnson ran away at 15, taking odd jobs (as a tailor) for the next several years, during which he travelled around much of the south on foot. Ironically, it was as a self-employed tailor that Johnson would become prosperous. His business made him enough money to invest in land, which led to more wealth, which opened the door to politics.

6. Chester A. Arthur – Small Town Schoolteacher

As of the 2010 national census, the town of Schaghticoke, New York (pronounced EYE-M-NOT-SHORE-HOW) had a population of fewer than 8,000 residents. It was even smaller back in the middle of the 19th Century, when future president Chester A. Arthur was teaching at a school there. Arthur worked as a schoolteacher while on break from college, and took on a full time job as a teacher after he graduated. He eventually became a school principal, and then later moved into practicing law. He would become a partner at a practice noted for its abolitionist efforts. Good for him.

5. George Washington – Surveyor

The Father of America, as President George Washington is often and rightly known, was many things before becoming the first head of the fledgling American nation. He was a successful planter (reliant on slave labor, it must be noted), he was a successful military leader, and he was, for many years, a land surveyor. He began this career while still of school age, learning the trade through academic exercises, since surveying involving quite a bit of math and logic. Washington became a professional land surveyor while just 17, and would still conduct occasional surveys as a hobby up until the year of his death in 1799.

4. Andrew Jackson – Making Saddles and Founding Memphis

Yes, Jackson is the man that stares back at you from your $20 bill. Before he was ushered in as the seventh president of the United States, Jackson served a short stint as a saddle maker. During this early period in his life he juggled two jobs like many us by working for a saddle maker while teaching on the side as well. He eventually became interested in land speculation and formed a partnership with lawyer pal John Overton. Surprise, surprise, a lot of the land they claimed for themselves belonged to Cherokee and Chickasaw tribes. Jackson was as one of three original land investors who founded Memphis, Tennessee.

3. Dwight Eisenhower – 5 Star General

Throughout all of American history, there have been just nine five-star military officers, and there will likely never be another: the rank was officially retired in the early 1980s. The rank was most notably held by Dwight D. Eisenhower, the Supreme Allied Commander during WWII. Ike was where the buck stopped, as it were, as the allies battled to regain control of Europe and the Pacific from the Axis Powers; no one outranked him except for the POTUS, a position he himself would hold within a few years of his victory in the Second World War.

2. Woodrow Wilson – The Constant Scholar

Woodrow Wilson was the president of a university before he became President of the United States, and one might argue the former was a better fit. Though he would serve as a decent wartime Commander in Chief, Wilson’s life had always been focused on academics. He studied at Princeton and earned a doctorate from Johns Hopkins, going on to lecture at Cornell, teaching ancient history at Bryn Mawr, and joining the faculty of several other colleges and universities in his younger and middle years of life. He would eventually return to Princeton, this time as the head of the venerable institution. This role led to his entry into state and then federal politics.

1. Ronald Reagan – Actor

Ronald Regan rode into politics on star power and charisma. Born into a poor family, Regan used his natural talents to build himself into a known commodity, first starting out as a radio announcer and soon moving into film and television after he moved to Los Angeles in the late 1930s. While Regan was never noted as one of the true leading men of his era, he was featured in dozens of films and was widely respected as an all-American man. He moved into politics in the 1960s, supporting Barry Goldwater and eventually becoming Governor of California. After two failed runs for the presidency, he sailed into office in 1981.