Skip to main content

Failure and the Art of Overcoming it: The Story of Abraham Lincoln

When faced with adversity in life, many people cannot cope.

Sometimes the stress is too much. Fear and self-doubt take over.

It’s in these times when it is extremely beneficial to have a helping hand.

Someone to look towards for motivation. Someone who can help show you the way.

Not everyone has that though.

Abraham Lincoln was one of these people.

A self-made man with little supporting cast, his list of failures would be enough to make anyone run and hide.

And yet, he would learn to overcome this adversity on his own and become President of the United States of America.

Quick Bio

Name: Abraham Lincoln

Nickname(s): Honest Abe, The Great Emancipator

Birth: February 12, 1809 (Hodgenville, KY) (about an hour south of Louisville, KY)

Death: April 15, 1865 (Age 56)

Height/Weight: 6’4” 180 lbs

Claim to Fame: Ending Slavery via the 13th Amendment, Leading the Union through the Civil War, Vampire Hunter

Other Professions: Attorney, Surveyor, Illinois State Legislator, Member of US House of Representatives from Illinois

Strengths: Leadership, ability to control emotions, moral character

Weaknesses: Self-doubt, choice of theatre (too soon?), ability to choose a competent Vice President

Brief History

Abraham Lincoln’s life story is absolutely remarkable.

We’ll split this into two sections: His failures (or bad moments), and his successes.


Here’s the timeline:

Age 9: His mother died. Later would become estranged with his father.

Age 23: Ran for State Legislator, and lost (eventually won two years later). Also lost his job in the same year and attempted to get into Law school, but failed.

Age 24: Borrowed money from a friend to begin a separate business. By end of year it had failed and he was bankrupt and in debt.

Age 26: His sweetheart (girlfriend) suddenly died. This left him with a broken heart.

Age 27: Suffered a nervous breakdown.

Age 29: Sought to become the Speaker of the State Legislator, and lost.

Age 34: Failed to achieve party’s nomination to Congress (though would run again and win three years later).

Age 39: Stepped down from Congress, at his party’s behest, though he wanted to stay.

Age 40: Attempted to get the job of Land Officer in his home state (Illinois), and was rejected.

Age 45: Defeated for the nomination to the US Senate.

Age 47: Entered to receive the Vice Presidential nomination, and was soundly defeated.

Age 49: Once again, he was defeated for nomination to the US Senate!

You have to lose in a Senate race at least twice in order to get a memorial in DC 🙂

Just two years after this last defeat, at age 51, Abraham Lincoln would be elected as the 16th president of the United States.

This is an absolute laundry list of failures.

To think that one man could overcome all this grief, disappointment and heartbreak and become the most powerful man in America is absolutely remarkable!

As you’ll see, with each setback, he had success to propel him forward:


Age 23: After losing his job, he enlisted in a volunteer regiment during the Black Hawk War and was elected Captain by his fellow volunteers.

Age 24: When his business failed, he rebounded by being appointed as postmaster and a surveyor. One year later he would win election to the Illinois state legislature.

Age 27: Despite having a nervous breakdown, he bounced back by getting re-elected to the Illinois state legislature. He also received his license to practice law in Illinois after studying for years on his own.

Age 29: Now and in the next couple years Abe was admitted to practice law in the US Circuit and District Courts. He also became a partner to one of the most successful lawyers in Springfield (Illinois Capital).

Age 37: After his failure to receive the nomination 3 years earlier, he was finally elected to the US House of Representatives.

Age 40: After stepping down from Congress a year earlier, Lincoln was admitted to practice law in the US Supreme Court.

Age 45: Though he was defeated for nomination to the US Senate, Lincoln began to emerge as a leader to the newly formed Republican Party (a replacement of the former Whig Party). He was a strong voice in the anti-slavery movement.

Age 51: Elected as the 16th President of the United States and remained so for the rest of his life until his untimely assassination.

Also saw Abe up close at Mount Rushmore! (on the right)

How awesome is that.

This guy had adversity hit him at tough times throughout his life.

Instead of quitting, he focused on what he wanted to become, and WORKED to be that person.

Even though he did not get immediate satisfaction, in the end he could not be beaten down.

Lincoln played such a pivotal role is guiding our country through what some call our darkest hour.

Many say without him, the world would look a lot different today.

It is because of this, that he is usually considered among the greatest US Presidents in our history.

Other Interesting Facts

Enshrined at the Wrestling Hall of Fame. With a supposed record of 300 wins and 1 loss, you could say he was pretty good!

He created the Secret Service just hours before he was assassinated (crazy coincidence, right?) Though their original intent was not to protect the president.

He was the first president to have a beard.

Never attended Law school, and taught himself Law.

Lincoln battled depression most of his life. This is something many people can relate to.

He won the 1860 election, while not even being listed on half of the ballots! (All from the South)

Financial History

Early Career

Lincoln came from extremely humble beginnings.

As his father was a frontier farmer, he had very little money. What money he did make when he was young, all went to help out the family.

Setting off on his own at age 22 he found a job in a small town in Illinois.

After eventually losing this job (as the business failed) and coming back after serving in the Black Hawk War, Lincoln decided to start up his first business with a friend.

May or may not have had the beard his whole life

With no money for a down payment for the general store they purchased, Lincoln had to borrow his half.

This proved to be a big mistake, as less than a year later, the business had failed.

Abe had to work several jobs as a postmaster, surveyor, legislator and lawyer in order to help pay this off.

A year later when the debt was due, he was forced to sell his horse and other items to partially pay it off as well.

Worse yet, when his partner died, he also, honorably, agreed to take on his remaining debt and pay that off too. So much debt!

While it’s not known how long it took Lincoln to pay it off, this surely hamstrung him in the short term.

Later Career

Working in politics for most of his life, Lincoln did not make much money here. In fact, if anything, it was a financial liability.

Much of the political campaigning would come out of his own pocket, and travel costs in those days were very expensive.

Luckily, lawyers were well paid back then (and still are now!)

Ascending quickly to partner, and eventually starting his own practice, this served as the main source of Lincoln’s wealth.

Eventually, Abe went on to live a fairly normal financial life, investing in bonds, buying a house, and even becoming a creditor to a small number of people.

Of course being the upstanding guy he is, he would charge lower than average interest rates on his loans.

While never extremely wealthy, Lincoln was able to take hold of his Finances to help make a name for himself.

Estimated Net Worth

The tremendous debt that Lincoln found himself in after his business failed hamstrung him for many years.

He even coined this among friends and called it his “national debt.” (If only he saw the size of it now!)

Due to his humble beginnings, working in politics and as a frontier lawyer for most of his life, Lincoln was never among the wealthy elite.

At his death, his estate was worth nearly $111,000 in 1865 dollars. This translates to roughly around or slightly less than a $1 million dollar net worth in today’s terms.

This, of course, is just Lincoln’s estate, and does not include the famous debts of his wife, Mary. (Perhaps the subject of a future post!)

Though early retirement was not in the cards for Lincoln, I daresay if he had the chance to, he would have preferred to continue helping the nation instead.

Lessons Learned

Don’t Ever Quit

After early setbacks, Lincoln had many opportunities where he could’ve quit and settled down for an easier life. Instead, he never gave up and became the man we all know and love.

Have an Emergency Fund

If Lincoln had an Emergency Fund when starting his business or after, he would have been able to pay off some of his debts to prevent his only physical assets being taken.

Recognize the viability of a business venture

With no job setup after returning from the Black Hawk War, starting a business made sense. However, make sure it’s a viable business in a market that can support it.

By this time, the small town had failed to grow large enough to support three general stores, and there was little avenue to explore outside markets.

With little capital and little demand at their store, there was not much Lincoln could do other than watch it slowly fail.

Grind when paying off debt

With his personal debt (and business partner’s debt) at a high level, Lincoln worked multiple jobs to gather the income necessary to pay them off.

Acquire skills by whatever means necessary

Although he could not get into law school, Abe was an avid reader and taught himself law while working several other jobs. Eventually this paid off when he received his license to practice law.

If you’re looking to change career paths, acquire the necessary skills with any extra time you have.



When I was deciding which historical figure to do next, I realized just how many amazing people are out there that we can learn from.

It was tough to pick!

Thus, as part of my quest to mix history and personal finance, I’ve decided to do a recurring series on historical figures and their finances.

Due to the research involved and depending on how busy my schedule is, I’m going to try and do these once every other week if possible.

Let me know if there is anyone you’d like to see featured!

See my previous post on George Washington’s vast real estate portfolio!

Passionate about history too? Let me know in the comments, I’d love to hear feedback!


Personal Finances of Abraham Lincoln; by Harry E. Pratt

Abraham Lincoln; by George McGovern

8 thoughts to “Failure and the Art of Overcoming it: The Story of Abraham Lincoln”

  1. Hahaha too soon, too soon!

    Well, I’ve got the “grind when paying off debt” thing down, as I’m currently petsitting through Monday and will likely be working about 18 hours this weekend. Maybe I should go visit Lincoln’s memorial after this weekend and yell at him for how tired I am 😂

  2. It’s interesting how different of a person he sounds if you just read the list of failures versus list of successes. I’d hedge we all have these two lists, and while it’s healthy to acknowledge that the failures do exist, I think focusing on the highlight reel makes for a much happier life.

    1. That’s a great perspective to look at it. I think that’s definitely the case for most people, I know I have my fair share of failures. I agree though, I like to keep things positive over here as well 🙂

  3. Bahaha my time management skills largely consist of running around like my hair is on fire and hoping I manage to accomplish something in the meantime 😂

    Luckily the 18 hour weekend is a one-off. And I suspect won’t be repeated once I’m debt-free. Because sleep.

  4. I love the thought behind this series – Lincoln is a great moral role model, sure, but his perserverance should be first in mind too. The best advice I’ve heard so far this year is: fail often, but don’t fail so big that it takes you out of the game.

    1. I think that’s awesome advice. Especially while we’re young we should be taking risks and be prepared to fail, but it’s always in the best interest to not put yourself so far out that you have to start all over from scratch if it all goes badly.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.