A Confirmed Failure at the Age of 38

A Confirmed Failure at the Age of 38 post image

Ulysses Grant’s first stint in the military ended early. At the age of 32 he was forced to resign his post as a captain. Binge drinking was suspected. A string of business failures and separation from his young family (he couldn’t afford to bring them to his post in the western US) had surely contributed to his misery.

Back home in St. Louis, the next 6 years were financially trying for Grant, his wife, and 2 children. During that time he failed at both farming and real estate. He was in debt and without consistent income until his father, who owned a leather store, intervened. He was offered a job as a clerk.

Take it or leave it.

Grant was out of options. He took the job, and moved his family to a the quiet northwest corner of Illinois.

At the age of 38, Ulysses S. Grant was a confirmed failure.

*  *  *

On April 15th, 1861, following an attack on Fort Sumter, President Lincoln put out a call for 75,000 volunteers to join the military. Grant, being the only man with professional military experience in his quiet little corner of Illinois, helped rally volunteers and was given a ‘fluke’ promotion to colonel.

As a military commander in the new struggle he found quick success, later being described as a man with “dogged determination and iron will.” His straightforward manner and decisiveness on the battlefield created results.

An unexpected and early turning point in the war came at Fort Donelson where Grant confidently commanded a victory for the Union– and took over 7,000 confederate prisoners in the process.

Grant’s failings– his drinking, his forced resignation, his business muck-ups, his loser job– realities that would crush the desire of many to act, seemed to fade into the background.

His slate clean, and the stakes higher, he continued to make mistakes. Here’s an account of his attack on Fort Donelson, taken from Shelby Foote’s classic The Civil War : A Narrative (emphasis mine):

[Grant] had started behind schedule… men had frozen to death because of a lax discipline which let them throw away coats and blankets in fair weather, that individual attacks had been launched without coordination and been bloodily repulsed, nor that the commanding general had been absent from his post for better than six critical hours while one of his divisions was being mauled, the other two having been barred by his own orders from lending assistance.

[The only thing the public noticed was] the sweep and slam-bang power of a leader who marched on Wednesday …. and received the fort’s unconditional surrender on Sunday. 

By finding the right field of play, and deploying simple and confident instructions to those who needed them, despite many (deadly) errors, he went on to continued success and eventually was the one responsible for forcing the confederate surrender at Appomattox, ending the US Civil War.

He wasn’t done there. Grant’s deeds had made him the most popular man in America. In 1869 he was elected president.

In 8 short years, Grant had gone from a store clerk in northwest Illinois to the presidency of the United States. He spent his two terms in office working successfully to maintain the union he had fought to preserve.

*  *  *

I love stories of people changing their lives radically through hard work and determination. If you have any other good ones, please share them with me!




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Published on 12.11.12
  • HuntsHewett

    Great post, Dan. Everyone talks about the trial and error of Lincoln, Franklin and others but this was inspiring for a different perspective. Grant had literally nothing going for him and still persevered by continuing to put himself out there, regardless of the obstacles.

  • There’s something about good history that just gets me jacked up. The American Civil War has always fascinated me, largely since there’s so much good history out there done about it.

    I always ask myself though when I see these kind of patterns in history whether or not they really exist or if I’m just creating them. There’s no doubt Grant was hard working and determined, but you could make the same statement about R.E. Lee and other historical figures who didn’t enjoy the fame and success of Grant.

    Gladwell’s conclusion in Outliers still makes sense to me. You have to be brilliant, hardworking, and determined to give yourself a chance at “greatness,” but there will always be some role played by serendipity and circumstances.

  • One thing, Grant was considered one of the worst presidents of all time, worse than George Bush and Richard Nixon. It’s gets me thinking, did he just get lucky?


  • Bleh. I don’t find his story particularly inspiring.

  • mmodesti

    Love this. Nicely done.

  • If I had a quarter for every time binge drinking led to me being fired or dismissed, I would have enough money to binge drink again

  • Thank you for sharing this story. It’s always good to go back to the classics. Those who talk of luck will do well to remember that when we start saying successful people just got lucky, we run the risk of adopting a defeatist attitude. The harder you work, the luckier you get.

  • Dan

    It helps that I listened to it via audio book! The narrator has appeal.

  • Dan

    I’ve been reading up on his presidency as well… it’s interesting how important choosing the right playing field can be. His skills seemed great in some contexts (battle) and poor in others (business). I’ve noticed this in my own life as well.

  • Dan

    For sure! I’m curious to make a deeper dive into the stories.

    No question RE: luck. The fascinating opportunity once we recognize that is can we tap into ways to manipulate it more in our favor?

  • Dan

    Thanks Hunter!

  • Dan

    hahaha. I have no problem mounting a small Calvary brigade (ahem.. taxi) and attempting to take over your condo… assuming once I get there we can do some binge drinking.

  • Dan

    thanks !

  • Dan

    i hope so! there’s also the element here of sticking to your principles regardless of the outcomes. there’s a fine line between adapting your thinking to feedback and knowing which guns you should stick to.

  • If it is a month with more than 27 days and a day that ends in “y”, I am available for the aforementioned drinking binge

  • Dan

    Excellent. The men are marching and tickets are being booked.

  • I shall marshall the troops and rally the reserve. #tallyho and all that jazz

  • Great writing! I love these tidbits of history woven through inspirational blog posts.

  • Dan

    Thanks for that Janet !

  • Ron

    Awesome post. It’s easy (and useless) at 27 to compare myself with entrepreneurs the likes of The Zuck (et al.) and wonder why I haven’t made my first million yet. Helps remind me that I’ve started two businesses and still have 10 extra years on Mr. Grant to go from nobody to president of my domain. (With medical technology, I probably will get at least an extra 10 years on the back end of life as well.)

    No excuses for past failures, you either want it bad enough now or you don’t. Stay thirsty, mis amigos!

  • Dan

    Thanks Ron! I agree with this, especially nowadays we need to develop strategies to get a little zen about comparison. Here’s a quotable:

    “Chase after money and security and your heart will never unclench. Care about people’s approval and you will be their prisoner. Do your work, then step back. The only path to serenity.” – Lao-Tzu

  • I’ve been waiting for more blog posts to read over in this part of town.

    Stories like this remind me that a lot is to do with being in the right place, at the right time. Or in more positive terms, working with what you have. It’s less about comparing yourself to some child prodigy, and more about working hard until the opportunity arrives.

  • Dan


  • I’d rather be lucky than good…

    I wonder if Grant would agree with that.

  • Dan

    was listening to some training the other night and it emphasized “turning up.” agreed, it’s tough to be an entrepreneur if you don’t “turn up” to where they are.

  • brad

    I’m disappointed to hear the DC is closing for new members. Do you still suggest/ require that members have a business before joining?

  • Dan

    that’s correct. we’ll re-open sometime next year once we get our act together :)

  • is it closed or is it closing? Because I was planning on joining when I get home before the new year:(

  • encruste8

    sometimes its all about being at the right place at the right time in the most opportune circumstances….there are people who have searched forever and never found their true calling in life….and so they end up doing what dopeshit of a job they can find just to pay the bills.

  • Dan


  • Hey Dan are you familiar with “Message for Garcia”? Another winner of a story.

  • Dan

    No cheers appreciate the heads up.

  • 2 other things related to mistakes by Grant that happened after the time period discussed in this article:

    1.) Grant’s presidency was one of the most scandal-ridden in the nation’s history (maybe behind Harding, but no one remembers who the hell he was).

    2.) He barely saved his family from destitution by finishing his autobiography just a few days before his death.

    Goes to show that those we consider to be successful and admirable often actually lead lives of intense struggle and contrast.

  • Dan

    Great point. It’s one of the most interesting topics in business for me, how what ways our predilections impact our businesses. For example you hear a lot of entrepreneurs say they are attracted to the big risks and ups and downs of entrepreneurship— they lost it all and started again kinda thing– but those kind of speeches generally come from people who have the same patterns in other areas of their lives.

  • I love hearing stories like this! Sometimes I get really down on myself because I’m 28 and I don’t feel like I’ve accomplished as much as I would like to have accomplished by this age. We continually here stories of young Mark Zuckerberg’s who have made it big in their low to mid-20’s. It’s great to hear of people who have endured a lot of adversity and failure so that we who are still trying to figure things out don’t feel so bad that we haven’t quite made it yet :)

  • Dan

    Cheers Aaron thank you for reading!

  • J

    I have things in common with President Grant. Huh. Maybe all is not lost.

  • Dan


  • This (very long) discussion is continued so eloquently here:


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