I Hope You Fail (The post wherein I quote Ashton Kutcher)

I was asked the other day in an interview to explain a time where I failed. So, apparently, it’s good to have failures if for no other reason than to be able to answer that question in an interview! And, of course, I tried to think of one that didn't make me look too incompetent, but instead just some example of how I’ve learned from something. I described the time a colleague recommended I look into the graduate program he did at Harvard.


I have to admit, for some reason, that is the Ivy League school I’ve always had on a pedestal in my mind. Not Princeton, or Yale, or even Cambridge where I spent a semester romantically riding my bike around that campus pretending I really was a full-time student there (of course I also spent time around that campus running hysterically down stairs in bookstores and wearing flame retardant suits while driving go-karts, but we can discuss that later).

So when this man (who incidentally had deployed himself to help with the response efforts I was involved with for Hurricane Katrina and was telling me about this Harvard idea while he was sleeping on the floor of an abandoned mall....) told me he thought I could succeed in this program, I was all about it.

Not about it enough, however, to put much time or thought into the three essays I was supposed to write for my application though.

I realized later that I went into that situation with arrogance. I thought my little work experience, and the fact that this guy was vouching for me, would be enough to get me in.

Fun fact: you actually need to try to impress Harvard. Shocking, I know.

So of course, I got rejected and then life kept going and I never really thought about reapplying, but I used that moment as a lesson to myself to never get cocky or entitled. It’s ignorant and it doesn't work out well.

So that’s the innocuous story I used for my interview, but that’s certainly not the worse failure I’ve had. But you know what? Failure is a really important part of growth. I find it really challenging to work with some of junior members of this new generation of “teacup kids” who are unfortunately known by the fact that they grew up never being told "No," never experiencing rejection (and ok, I'm actually technically part of that Teacup Generation due to my age, so I'm going to blame that for that whole entitlement moment with the Harvard thing...) But not only does that mentality often create some frustrating personalities,  it’s also really debilitating to the people who grow up with it. Because life can’t be totally controlled. And when something does become hard for them, they are going to panic and crumble.

Whereas if you’ve gone through something once, you fear it less the next time. 

I was sitting at my pool yesterday and this little boy was playing with his mother and she’d make him throw a floating ball as far as he could into the pool, and then he’d need to jump in and swim to that ball. It was a goal for him to get him swimming farther and farther. And I heard him say “I’ve done it before so I can do it now.” And I thought to myself how great and simple that was and how adults should keep reminding themselves that about a lot of situations. And the little boy jumped in and got almost to the ball –

and his mother plucked it up and threw it out farther.

Isn't that just like life? Always moving the goal post on your dreams...

But in the words of Ashton Kutcher (never thought I'd say that): "Opportunity ...looks a lot like hard work." You have to put forth effort and along with that, you have to be willing to take risks. 

I do think it’s important to not only work hard, but also to prove to yourself along the way that you can survive failure. It actually feels a lot like surviving embarrassment. For instance, I now know I will not, in fact, die of embarrassment if my pants split open during a run, or if the guy who just broke up with me joins an awkward date I’m on, or if I have an extremely embarrassing wardrobe malfunction at the gym then someone else puts their lock on my locker making it impossible for me to change clothes and escape - because all of those things have now happened to me.
Seriously, how do all these things happen to me?

Did I need that many examples? Not sure. But it does make me less fearful about embarrassment. And I've definitely tried out for things and applied for things that I just didn’t make the cut for – and I survived those too. But my – and apparently Ashton Kutcher’s – point is: you can’t stop trying. You can’t expect things to just happen. You really do need to put in effort and risk failure, embarrassment, and disappointment. 

My pastor (who also recently quoted Kutcher… seriously I feel like this is a sign of the end of the world or something) just said something to the effect of “think of those people who you’d most want to be, and I guarantee you, you would not want to travel the road they took to get there.” Everyone sees the “overnight successes” that actually took 20 years of working unnoticed to get to. 

And for anyone who wants Ashton's job, listen to the video below of some of the road he had to take to get there. And for anyone who thinks working in the government sounds great, take a look at some of the roads I've taken here... (ok, so maybe I also take ridiculous roads because I'm curious and can't help myself. You probably shouldn't necessarily seek out opportunities to glue Styrofoam together on your own journey to career-bliss....)

So, I recently applied for something that I really want (I won’t know if I got it for several more weeks so you are just going to have to wait for that news, sorry. It’ll build character.*) And as I was sitting with my friends, talking about the application process, my friend Sean interjects with “and she went after it like a Spider monkey!” And I had to laugh, because he’s right.  It became like my second full-time job to get in all the pieces I needed for this application and to network like crazy in the area where I’m trying to get to. I wanted to make sure I went above and beyond the criteria and get a buzz going about my motivation. But you know what might also be part of the reason for my spidermonkyness? 


Had I not experienced failure, I probably wouldn't fully appreciate the importance of hard work and going after what you want.

So in the end, I wish you all the gift of failure. Having failed at things will teach you what to change the next time. But it also just frees you up from worrying about failing. You’ve already been there and done that. Just wrap tape around your thigh and keep running. 

*This post was written a couple years ago and the thing I was applying for -- was to become a Public Affairs Officer in the U.S. Navy Reserve. I'm grateful to say that I and six other people were selected in the end so I'm very glad I applied Spider Monkey-levels of effort in pursuit of that goal