Failing Up and the Big Reveal

When I was a kid, I never imagined myself as a grown up with a grown up job. I did not have a vision of success. I understood that I was expected to “perform” and maybe even “excel” at certain things, but I was surrounded by ultra high performing, totally driven and excelling kids who seemed to know what they were doing, so I accepted they would probably be hoarding all the success for themselves. I was intimidated by their determination, and had only a vague notion of what an adult purpose might be, but I also had a hazy belief that I would land on my feet somehow and accomplish the requisite adulting things. I also possessed the inconsistent conviction that I was going to be famous at something, though I possessed no skills or abilities that made this conclusion logical.

As a teen, I kind of drifted along, doing the expected things and checking the expected boxes because I wanted to please my family; but I was mainly going through the motions. Luckily I made up for my lack of a plan by also lacking direction. I was a smart enough and a diligent enough student to get into a very good college. I arrived at my ivy tower certain only of one thing: I was certainly an imposter who didn’t belong there. I wasn’t a grind or even a particularly hard worker and I was not one of those exceptional kids other parents gush about admiringly in hushed, somewhat envious, tones.

However, despite not having the vision thing, and being generally adrift, I excelled at and was passionate about writing. From elementary school through law school, my teachers and peers consistently praised and encouraged my writing, so I can fairly state it was not just my parents who thought I had some skills. (Ok, it was mainly my parents--but there were a few others).

I became hooked on writing in third or fourth grade when I wrote my first deeply insightful short story about a butterfly named Juan who performed many heroic and kind feats while butterflying about.

While I have often drifted here and there, and never quite arrived at a predetermined destination, I have always been single-mindedly compelled to write, and I have kept writing ever since Juan emerged from my psyche to flutter about heroically when I was 8.

Despite my obsession with writing, I was cowardly about facing rejection, so instead, I chose a more traditional path as a lawyer. Not being a linear thinker, I had to train and restructure my brain to pursue this path. It felt unnatural, but I am glad I muscled through law school-- but not because I learned anything there. Anyone who has attended law school knows that law school is primarily three years spent climbing over the still warm corpses of your friends and classmates. It is basically an infested petrie dish of anxiety, fragile egos, insecurity and fear, with a dash of paranoia mixed in to make it fun. However, years of practicing law and learning from talented, gifted lawyers forced me to hone analytical skills that I might not have developed and helped me become a critical thinker. In the real world, I leveraged my writing skills and managed to "fail up" despite a career in which I am not naturally gifted. Also, I worked my ass off. Let me be clear: failing up did not come easily for me.

I know it is trendy to talk about “failing up.” I am lucky to live in a generation in which you can admit that failing consistently is how you accomplished things. It’s the ultimate humble brag. Except, I really believe I have achieved successes because I have the ability to process and learn from my mistakes. So I am not being humble: I am proud to say that coping with failure molded me into someone who was not just a character, but someone with character. I learned at least one thing from each mistake and stumble-- and I realized I had the fortitude to pick myself up and keep moving (even when I wasn’t sure what direction I was going, because it sure as hell wasn’t always forward). And keep moving I did. I stayed in motion, even when hiding in fetal position in the closet would have felt much more satisfying. (And by the way, for any teens out there who likely aren't reading an old lady's blog anyway-- so who really cares what you think-- I lied in the previous blog about not butchering teen slang any further: it’s possible I may just be flexin' about my mad failure skills). Old people: go look it up. This is a flex friendly zone.

I am nearly done bragging about my talent at failing and have nearly arrived at the Big Reveal.

But first I need to share the pinnacle of my failures. I failed so successfully throughout my career that I ended up failing into the C-Suite at a large company. Never in my wildest dreams had I imagined I would be so good at failing! After a short period of being impressed with myself, I realized that I hated my job. It doesn’t matter why I hated it, or whose fault it was (definitely other people though). What matters is the epiphany that I did not want an all consuming career where I was traveling all the time and never seeing my family. My daughter, a junior in high school at the time, said she didn’t want to spend her senior year with me never being home or always working even when I was at home. I was blatantly putting my career ahead of my family—I made no attempt to hide it-- and all of it felt shitty. So I quit. I walked away from the Biggest Opportunity of my career so far.

The somewhat anticlimactic Big Reveal is that I was never very ambitious in my career. I never wanted to "have it all" or be a Master of the Universe. I have no idea what drove me, beyond fear of failure and a need to please. I never cared much about traditional success or titles or achievements. Walking away from my Big Opportunity was a hard decision. It was a terrible decision financially and professionally. Perhaps it was another "failure." But if so, it was the best of my failures and the one of which I am most proud.

The Big Reveal moment is over, but I am feeling a bit panicky now because I am worried there may be more steps to this public admission and confession process. I hope I don’t have to apologize to everyone I ever met, or stop drinking Chardonnay. I think I can reasonably manage up to maybe 5 steps-- if they are easy and don’t interfere with my binge watching whatever is streaming lately.

Just in case, I'm gonna sneak out the side door now, before I have to commit to anything that might require effort. So, until next time, friends-- define success for yourself and pursue it your own way (I realize that failure doesn't work for everyone), stay woke and keep it 100!