Fail-Proof Your Twenties! One Simple Step to a Freaking Fail-Proof Life

Fail Proof Your 20's Picture


Fail-proofing your twenties might seem too good to be true, but I’ve got the secret sauce you’ll want to spread across the entire decade. I first mentioned this in the Top Five Things We Should Have Heard At Graduation, but let me elaborate further as it’s something I need to hear over and over and over and over. And over. And…

I don’t know about you but I can’t say my twenties have been a roaring success. There’s been sprinkles of achievement sure, but not the random-people-hoisting-me-up-on-their-shoulders-like-a-quarterback-who-just-won-the-Super-Bowl success – like I’d imagined.

That’s why when giving us the secret of how to completely avoid failure in this decade seemingly smothered in it, I’m not going to give us even five easy answers this time to a fail-proof life.

No, I’m going to give us just one.Fail Proof Your 20's Picture

So without further ado…. drum roll please……To fail-proof your twenties…..

Fail, but never define anything as a failure. BAM! Done! Where is my fee?



Whatever mistake. Whatever wrong turn. Whatever set back. The business that went belly-up. The relationship that died like a salmon on a summer sidewalk. The amazing investment opportunity that fell like a tree during a lumberjack competition. These events are only failures, if we make them such. If we let our story end right there, only then will it be a failure.

Sure the details haven’t turned out the way we planned. But honestly (and I say this as nicely as possible), our plans weren’t that good to begin with. If things lined up like the dominoes we envisioned, we wouldn’t have had one ounce of conflict, struggle, or growth for the next 20-30 years.

We need the hardships and trials to persevere through. Failure is a necessary part of success. We will not actually do any thing, if we first do not learn how to fail without labeling ourselves a failure. And believe you me, I’m the first to look in the mirror to start the name calling. Who needs the school bully to hold us down any longer – we have ourselves.


Make plans, have goals, dream dreams, yes and yes.

But get ready when the pick your own adventure, picks you instead.

Sure people are still not carrying you around like a war-hero coming back to the States.


Sure your bank account is not the Duck Tales gold coins swimming pool you envisioned.

Maybe someday.

But I realize now the only real failure of our 20’s, would be if we never had any.


Below is the video version of this post with some extra commentary on why us Millennial’s, Gen X, and Gen Y’ers might not do failure well. Do your eyes and heart a favor by watching it. Unless you don’t care about your eyes and heart. And if that’s the case, well, that’s just sad.

I’d love to hear your thoughts on this whole failure thing in the comments below. Do you think this fail-proof secret has merit? What’s failure been like in your 20’s? Any other secrets to fail-proofing you’d like to share…


  1. Joanna

    Pick your own adventure…”But get ready when the pick your own adventure, picks you instead.”

    This reminds me of those books growing up–I think Encyclopedia Brown was one of them, where at the end of a chapter you could pick the next twist and turn of the mystery, and there were several alternate endings. I think I thought life would be a bit like that–and in my version most of the twists and turns were assents to ever greater heights of success.

    But I am reminded that a good story always has set-back, and climax, it has a redemptive arc. God likes good stories, right? So why would he write anything less beautiful with our lives?


  2. Kate

    I think you’d like this quote, Paul. It’s one of my favorites:

    “Nothing in the world can take the place of persistence. Talent will not, nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent.” – Calvin Coolidge

    • admin

      Kate- Couldn’t be more true! Calvin Coolidge knew his stuff. Something I believe our generation really needs a crash course in…and it will probably be more crash than course. At least it has for me.

  3. Megan

    Yes, yes, and more yes! I totally agree that our generation was coddle in regards to achievement and it’s made this whole failure thing pretty tough to stomach at times.

    I’m not sure what the catalyst in my life was that shifted my perspective of failure, but somewhere along the line, I started embracing it. After enough failures to fill a book and then some, I realized that failure is essentially a fork in the road – get buried in it or make something amazing out of it. The latter has proven to be a) a hell of a lot less painful and b) the predecessor to almost every single one of my adult successes.

    • admin

      “Get buried in it or make something amazing out of it.” Love that line Megan. So true.

  4. Morgan

    TOTALLY agree! Luckily, I learned pretty early that it’s OKAY to fail, as long as I learn from my failure. That’s one reason I’m not afraid to try new things, because if I fail, then I’m sure as hell going to learn something from it.

    Great stuff! 🙂

    • admin

      Thanks Morgan. Great perspective and way to live life.

  5. NyssaJay

    I really enjoy reading your posts. They help me keep perspective on life.

    The part about instant gratification really hit home. We’re the generation of IMs and texts. But, as you wrote in your post about the 90s, we still had notes passed in class.
    Children now have cells phones or other messaging devices in elementary school.
    While we’re the generation of blue ribbons and honorary medals, they now encourage games that can’t be lost, or ending on tie (as I was told while working a day camp, once).

    I fear that they’ll be more lost than we are and I hope that they have someone around to help keep them in perspective too.

    • admin

      Thanks NyssaJay! Great points. Yep, everything has gotten so much faster and instant. It’s hard not to feel like a failure when things don’t work out right away. But it all takes time. We’re just not used to waiting

  6. Kate

    I just came across your blog and love what you’re sharing here. I am turning 31 this year and have found so much of it to be true of my twenties and beyond. I especially love your reference to the Duck Tales gold coin pit. I thought by now, I’d have one of those for sure!

  7. Ashleigh

    Yes, we are so used to having everything so instantaneously and correctly, when things happen unexpectedly, I am upset or disappointed. Even some unplanned events aren’t even always bad things, but because they are not the preconceived idea I have in my mind of how they should go, I end up getting upset. It’s just a frame of my mind that we all need to work on changing. Failing is okay, and it’s how we learn and figure out what we DO want.

    • admin

      Well said Ashleigh! Yep it’s often those pesky pre-conceived ideas that are the most ill-conceived.


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