Generate momentum toward your new path with my tips on living and working with purpose.

Fail Your Twenties Like a Pro


You make an enormous number of major life decisions in your twenties and early thirties that define the course of things. Even as you might grasp the inevitability of failing along the way, that pressure-fueled determination to get it right can be overwhelming. There’s this sense that you might just screw it all up, your whole life. That’s a heavy load.

Like anything, when I read books or posts about capitalizing on your twenties, I see the necessity for balance. I mean, in some ways, your twenties are just designed for going off the rails a bit, dating people who kind of embarrass you, quitting boring jobs and not maintaining references, binge eating junk and drinking too much, only to pledge a new commitment to health every Sunday night. We’re not robots, we’re humans, and, unfortunately, we’re designed to learn the hard way sometimes.

So how do you strike that sweet spot between the downward spiral of degradation and being the model over-achiever who maintains it all, but stresses even one misstep?

Fail Fantastically, Not Haphazardly

We’ve all heard the trite saying that if you don’t know what you’re looking for, you’ll never find it. While it really is ok if you don’t have your shit totally together, it’s tricky to harness the energy of your bad decisions so they work for you if you’re acting at random all the time. The magic is creating intentionality around your mistakes by giving some forethought to what you would have wanted to happen, let’s say, before you ate the whole box of Cinnamon Toast Crunch for dinner, had sex with that douchey guy again after he finally called, or ticked of the three year mark at a job that makes your eyeballs bleed.

How do you do that? Well, think about what you want and set some specific goals around it. You don’t need to have it all figured out in order to do this. Start small in one area of your life where you are currently feeling like the biggest, fattest loser. First, take a breath, stop being mean to yourself (i.e. referring to yourself as a big, fat loser), and then think about what you would like to see if you knew you couldn’t fail. Write it down in detail. What would it look and feel like to see yourself living out this ideal? Finally, choose one thing you could try to do differently to get yourself closer to that today. Next time you make some poor decisions in that arena, come back to what you wrote down, and use it as a guide to get back on track again.

Recognize How to Stop Mistakes Before They Become Bigger Mistakes

I remember dating a guy years ago who seemed like a dream. Then, we got a few months in and it all starting falling apart. We brought out the worst in each other; with him, I was the overbearing critic who couldn’t let anything go, and he would hunker down in the victim role self-righteously flinging up dramatic accusations. Despite that fact, we stuck it out for over six months, and actually signed a lease on a house, before it culminated in one hot mess of a vacation. Immediately upon landing back home, I made the call to cancel the lease, forgo the deposit, and proceeded to face the shame of explaining to everyone in my life what happened.

I may have been embarrassed then, but now when I look at this story, I think “THANK ALL THAT IS MERCIFUL that I did not move in with that man!” It saved us a both an enormous amount of grief to end it when we did.

So, quitting jobs after two weeks, ending bad relationships in messy ways, and usually anytime you have the good sense to jump ship—these aren’t times to lament your poor decision-making; they are times to give yourself props! Way to not let something get worse just to save face. I’m a firm believer that if you are sticking out a bad situation because you’re worried how it will look to everyone if you leave, you’re on a one-way road to supreme unhappiness. The benefit of life experience is that if you say no, quit, run screaming in the other direction, often enough when you sense something isn’t right for you, you’ll learn to flex that muscle early on and find yourself stuck a whole heck of lot less.

Find What Fits…at the Sake of All Else

Essentially the whole point of your failures and mistakes in your twenties is to figure out what fits. A lot of people spend inordinate amounts of time and energy forcing a fit. If you stay in that place for too long, complacency sinks in and it can start to feel ok, like Good & Plenty would be ok if you were stranded on a dessert island. Basically, you rationalize it, and then you hesitate rocking the boat.

I think of my dad sometimes on this topic. I had the benefit of growing up with a dad who showed me what it meant for a man to have character. He taught me a million valuable lessons, never let me of the hook when I wasn’t giving my best, and always came through. For all of that I’m so grateful, but my dad can be a real son of a bitch. He’s full of integrity, almost to a fault. I mean the man knows his mind. And if he thinks someone he’s interacting with isn’t in line with what it means in his book to be a stand-up, honest person, watch out, because he will not mince words about it. It’s made for many cringe-worthy moments, but you have to respect someone who sticks to his guns like that.

Maybe that’s an extreme, but it’s one I appreciate when I’m second-guessing myself because to me the most amazing thing about getting older is that you stop caring as much what people think of you. If you can start doing that early on, it’ll free you up to choose based on what you actually want instead of what your friends want, or your family wants for you, and then instead of settling for just good enough, your life will be filled with Reese’s Peanut Butter Cup-sized opportunities (or whatever your candy equivalent to awesomeness may be).



Purposeful Life Lessons

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