Failing at your 20s? You are in Famous Company

Failing your 20s? ---You are in famous company

Your 20s not going as planned?

Perfect. You’re in great company.

And I’m not just talking about the two million 20-somethings currently blogging about their quarter-life crisis.

No, failing in your twenties is a historical rite of a passage. Like being sent out into the wilderness to kill a lion — naked, blindfolded, and wielding a dull stick.

But is experiencing a quarter-life crisis such a terrible thing? Here’s why our 20s detour into the wilderness puts us in the best company imaginable.

The Fabulous and Famous who Failed Their Twenties

Abraham Lincoln – 16th President

If you made it through 5th grade, you’ve heard of this guy. But if you would’ve known Honest Abe when he was thirty years old, you would’ve only known him as a lovable, gangly, unfortunate loser.

Let’s see… Failing your 20s? ---You are in famous company

23 years old — Abe runs for the Illinois General Assembly. He’s defeated. By a country mile.

24 — He opens a village store. Same year the store goes belly-up.

25 — He falls in love with Anne Rutledge. At 26, Anne dies.

27 years old — Begins serious pursuit of Mary Owens.

28 years old — Asks Mary Owens to be Mrs. Lincoln. She declines.

Abe enters his 30s struggling with depression along with relationship and political defeats.

Abraham Lincoln tragically exits this world too early in his 50s as the savior of the United States.

Morgan Freeman – Actor Extraordinaire

“Jobs were hard to come by and he continually went hungry, often starving for days before he’d ask his friends for help.” – Morgan Freeman Bio 

At 22 years old, Freeman moved to LA to become an actor and landed an amazing role — transcript clerk at LA city college.

I went to Hollywood straight away. I got a good running start but the wall was brick.” – Biography Channel, Morgan Freeman

Freeman moved back to New York, taking any role he could. The first time he received a leading role — the play closed in four nights.

Freeman entered his 30s playing bit parts on the Electric Company — a Sesame Street-esque TV show, with his marriage about to end in divorce.

Today he is one of the highest grossing actors around.

Parker Palmer – Best-selling author, activist, teacher

“As the darkness began to descend on me in my early twenties, I thought I had developed a unique and terminal case of failure. I did not realize that I had merely embarked on a journey toward joining the human race.” Parker Palmer, Let Your Life Speak

Parker Palmer left college assured he was to do God’s work, so he enrolled in a theological seminary. And after a year bathing in Bible, bad grades and a bruised ego, he left.

Most of us arrive at a sense of self and vocation only after a long journey through alien lands.” Parker Palmer

After struggling through his 20s filled with ought’s, should’s — searching for status and praise, Palmer found himself entering his 30s and a small Quaker community. A place that promised a personal reset.

“I was in my early thirties when I began, literally, to wake up to questions of about my vocation.” Parker Palmer

You are Right Where you Need to Be

Our 20s aren’t about sheer success. Our 20s about perseverance and preparation.

As I wrote in my book 101 Secrets For Your Twenties,

Failing means you’re simply finding a more profound way to be successful, if you’re willing to learn from it, and then have the courage to possibly fail again. And possibly more profoundly than before.

We can’t let failure be our death sentence instead of just one more sentence on the page before we turn it to the next. If we go for it, we will fail. We have to. That’s part of lifting a weight heavier than you. You tear your muscles so that they can become stronger.

The only real failure of our 20s would be if we never had any.”

Sure there will be the Mark Zuckerburg’s of the world who wipe their rear-ends with billion dollar bills.

But the heroes in the history books who kicked status quo in the ass, often failed the biggest in their 20s.

Failure can be the best clarifier in life.

Failure doesn’t ruin your story. Failure helps you write it. (click to tweet that)

Feel like you’re failing your 20s? You’re in famous company.

Do you feel like you’re failing more than you’re succeeding in your 20s? You’re not alone. Join the conversation and tell us your story within the comments on this article.

Photo Credit: DonkeyHotey – Creative Commons



  1. Emmy

    I needed this today. Thank you!

    • admin

      Thanks Emmy. I need to be reminded of this pretty. much. every. day.

  2. Dianne

    Wow. I needed every article here today. My business is clapping on the side lines while others parade through. The pearls of wisdom never were so true, I was lost at 6 years old in the San Diego zoo, I meet my ex husband whilst we were lifeguards and I was 19, never lived on my own. I’m rolling Pennies to buy gas to try and make a buck,.and those Facebook posts you say never to read while in turbulence? They scar my retinas. I’m a painter lost in a crowd, and i’m scraping by. I really need more articles like this, and about how to live as a free lancer, having friends with awesome jobs makes hanging out almost impossible.

  3. Ben

    Don’t forget Mark Zuckerberg!

    Stealing a great idea and leading those people on?
    Cheating out his roommate and friend?
    Manipulating Underwriters/investors to make billions?


  4. Catie

    These words are so comforting on a rough Sunday night thinking that the last few months have been far from what I planned. Thank you so much for this as well as your site!!

    • admin

      Thanks Catie! All Groan Up is here for you whenever you need a pick me up 🙂

  5. Ashley

    Wow-thanks so much for this. I feel so much better knowing I’m not alone with my mid-20’s struggle. I mean, I never really thought I was, but it can still feel that way. This is so reassuring and wonderful. So happy to have stumbled upon this site!! 🙂

    • admin

      Awesome Ashley! Thank you. Excited to welcome you as an official “Groan Up!”

  6. Amaranth

    Paul, most of your words come as such comfort in the gloomy days of my twenties… This post made me think a little about my failures and the perspective I look them through, especially when most of the time I wonder how come some people have it all together: a great job straight out of college, great relationships leading to engagement, great number of friends etc. (Classic Obsessive Comparison Disorder haha). While I constantly ponder on my twenties’ ups and downs and never find the right answer. Thanks again, knowing that we are not alone in this makes the days go by smoother. Cheers!

    • admin

      Thanks Amaranth for the kind words!

  7. James

    I believe that more famous/successful people than we think FAILED and STRUGGLED miserably in their 20’s just to succeed later. My partner’s uncle was one, Jim Carey, Dan Ludwig went from broke until his 40’s when he finally figured out how to build a gigantic shipping fleet and died a (B)illionaire. Zuckerberg is a very big outlier and should not necessarily be modeled after. One important thing to remember though, im guilty as charged and paying my dues, is keep your eyes on the prize (your ideal life). You might have to hustle here and there, take detours in your career while you work out the kinks but if you keep your eye on the end goal eventually you will get there.

    • admin

      Thanks James. Great wisdom there.

  8. Bola Hanson

    Again Paul you always seem to capture how I feel presently and inspire me at the same time. Like now I just turned 28, I have been home for a month after getting my masters and haven’t found a job yet. I don’t have my own car nor a relationship. Haven’t reached my health goals and I don’t even have ideas to start my own thing while waiting for interviews. To me it seems like failing. I just can’t seem to get to where I want to be.

    • Paul Angone - All Groan Up

      Thanks for sharing Bola! This part of your story is taking you where you need to go, even if it doesn’t feel like it at the moment. Keep warring for hope!

  9. Nicole

    I’m 22, going 23 in a few months now. Earned a bachelor’s, a licensed professional. But somewhere along the way, I realized this is not the profession I would like to be doing for the rest of my life. Thought I’ve clearly figured out back then what I wanted to do. Now I am so lost, so unmotivated, so dispassionate–just went from one job to another only ending up still unfulfilled. I’m thinking of a career change which is totally unrelated from my profession, though I don’t know where to start…I am sooo lost… Ugh, this sucks and I don’t want to disappoint my parents (moreso, myself). 🙁

  10. Jason Rafferty

    This is a fabulous article and I’ve recommended it to friends. Just discovered your site this evening after listening to a John Mayer song, (go figure!) Haha and I ordered your ‘101’ book on amazon. Thanks for the great insights!


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