[We haven’t done one of these in ages, and this one is apposite. This post was originally published on my old blog on April 13, 2009.]

Every now and then I get really discouraged about this writing gig. When I’m down in those familiar dumps, I amuse myself by looking up famous literary rejections. Did you know that, in 1944, T S Eliot, then a director of Faber and Faber, rejected George Orwell’s Animal Farm for publication on the grounds of its political subtext? Someone also once told Rudyard Kipling that he didn’t know how to use the English language, and informed Nabokov that Lolita was “overwhelmingly nauseating” and would be best buried under a rock for a thousand years. Writers have some of the best rejection stories out there, simply because rejection comes with the territory and the good zingers are captured for posterity.

That’s not to say that only writers feel the sting of rejection. Rejection is an equal opportunity pox: everyone gets it sometime. For my part, rejection is like failure: to be avoided at all times. I’ve been pretty successful in doing it most of my life. If that sounds like bragging, it’s not. I’m not particularly proud of this achievement because it represents a failure in itself – a failure to take chances, reach higher. It’s not to say that I’m a slacker or an under-achiever; but I’ll never be entirely sure whether I might have achieved more had I been more willing to face rejection, or failure. I’ve done well in everything I’ve chosen to do, but I’ve chosen to do those very things because I knew I could do them well. My victories were born of hard work and perseverance, not ingenuity or audacity; hardly the stuff for laurels and parades.

The world needs fearless gamblers. If people couldn’t face rejection, the whole species would be extinct by now. If people couldn’t countenance failure, we’d probably still be living in caves. The fact that we’re still around, and kicking around slightly fancier digs, speaks volumes about our inherent resilience in the face of (temporary) set-backs.

Rejection, I was once told by a young gentleman who (I can only assume) must have been something of an expert in the subject, is a numbers game. Getting rejected nine times out of ten still means you get one “yes”. After a while, you build a certain immunity to the sting of rejection. Failure is not entirely dissimilar. A friend of mine once told me that the reason why she didn’t ski was because she was afraid of falling. Having learned to ski the hard way (by being dumped by my parents at the top of the black diamond slope on my third day in skis*), I told her that the fear lasts only until your first fall. Falling on your butt, unpleasant as that is, is the best thing that can happen to a new skier. Now, if only I could take my own advice and apply it to my fear of failure, right?

Of course it’s not that easy. I’m nearing 30, and I’m still trying to ready myself for that first really big wipe-out. One of these days.

* I was about 7 years old. I made it down safely, mostly on my ass.

[Editor’s note: I was actually looking for another old post of mine when I came across this one, and went: “a-ha.” The fear of failure has been on my mind again lately, likely because this year is set to be a time of some significant changes in my life, mostly career-related. It’s a fear that was must have been ingrained in me so early on in life that, to this day, I have a very visceral reaction to the idea of failure. As I wrote almost 6 years ago (and even more so since then), to a lot of people, my accomplishments may seem like a pretty good definition of success (at least in the context of an average person’s life). And yet, the spectre that looms over it all for me is the fear of failure. I’ve still never really failed at anything – with the possible exception of baking – in 35 years and the thing that is hard to admit, even to myself, is that the reason is negative: I’ve just never really reached beyond what I knew, for certain, to be the limits of my abilities. The known limits of my abilities, if you will.

Perhaps there is more to it. This year, I’m determined to find out.

A friend of mine got me thinking about choosing a word to define my year. At first blush, it seems like such a kooky-Facebook-quiz thing to do. Exactly the sort of thing I hate. But I’ve been re-reading The Tibetan Book of Living and Dying, and thinking about the power of our intentions, and of the energy we put forth in the world. And that got me thinking that choosing a defining word – a theme – this year would be a lot like picking a mantra to help focus myself. And so, after some more thinking, I did. I chose a word that scared me with its implicit messages.

Soar.

Its grandiosity scares me. Its presumption does too. I keep thinking about the lessons of Icarus. And, yet, there is such a sense of freedom that comes out of it too. Of lightness. Of letting go of things that hold one back, and also of rising above the turbulence of our human sphere. Which reminds me of something else I want to focus on this year: learning to be more compassionate. Resting bitch face notwithstanding, I don’t think I’m a un-empathetic person. But reading about compassion (the wish fulfilling jewel) in The Tibetan Book of Living and Dying made me realize that I still have a very long way to go as far as practicing everyday loving kindness goes. “Soar” will hopefully remind me to rise above attachments to personal desires and frustrations, and channel my energies towards others’ well-being instead. Lofty goals all … but I’m ready to try and fail, rather than not try at all.

Holy TL;DR of a post, eh? If you’re still awake, tell me: have you conquered the fear of failure, and if so, how? Have you picked a word for 2015, or are you more of a specific-resolutions kind of person?

More style confessions this way … volume 1, 2, 3, and 4.

I’m Having a Style Crisis

Because I think I should dress like this:

But I always somehow seem to end up looking like (an infinitely less cool version of) this:

And, really, it all comes down to thoughts I’ve been having after reading this article. Go ahead and read it. I’ll wait.

OK, it’s a bit ridiculous. A lot ridiculous. I wasn’t sure at first if it was satire or not. I’m still not sure that the author isn’t trolling all of us; regardless, let me reiterate: don’t spend hundreds of thousands (or even tens of thousands) of dollars on your work wardrobe. Your career doesn’t require it and probably isn’t worth it, and that’s not an insult – neither is mine. I don’t make a million bucks a year, which is what I would have to earn in order to make a $162,000 wardrobe bill even remotely palatable (from a financial perspective at least).

[As an aside, last year I spend about 6% of my annual net income on clothes. This number is a little higher than I’d like it to be, but it’s not irresponsible given my overall financial picture and the fact that I count my clothes habit as a hobby more than a functional necessity. I don’t have a lot of other hobbies, and they tend to be inexpensive.]

Back to the clothes-as-an-investment thing. Once and for all: they’re not. An investment is something that appreciates (or has the potential to appreciate) in value, not something that depreciates. Clothes, bags, shoes: they all lose most of their value the minute that you take them out of the store. With that said, if you’re working in a client-oriented field, where personal presentation is key, clothes can be a sort of indirect investment vehicle. Looking the part of a competent, successful fill-in-the-blanks matters; maybe not as much as being a competent, successful fill-in-the-blanks, but enough. If you consider that your career is likely to be your biggest investment (i.e. money-making asset), spending money in furtherance of it can be a wise choice, provided you do it within reason and with an eye to your ROI.

But that’s not really what I want to talk about. [Holy freaking diversion.]

I’ve always been bothered by the phrase “dress for the job you want.” For a long time I thought it was silly, because I was convinced that ability would always trump presentation. The older I get, though, the more I realize that the world is (sadly) not as black and white, or fair, as I had assumed in my naïve youth. But I think what really bothers me is the implication that your job should dictate your style. As you guys know, I consider style a very personal form of self-expression. And I struggle with the idea of being defined by my career. I do what I do, but I am not what I do. It’s one thing to wear nylons, or knee-length skirts, or close-toed shoes, because of an office dress code. But style is another thing.

And yet.

After a few “wilderness years”, and then some family-building years, it’s now time for some career-making years. My career could still take any one of several different paths, but if I decide to stay on the current course, I’m probably going to have to take a hard look at my wardrobe. If I’m being honest with myself, it really should look more like that first picture. And it is a lovely outfit, don’t get me wrong. It just doesn’t feel like me. It feels like a some-day-I’ll-be-a-grownup version of me.

I’m not sure I’m ready for that, even if my career is.

I’m not sure I can afford to wait any longer to be ready.

The thing is, I’m dead serious about my career, and about what I want to accomplish. The work and personal sacrifices that will be required are also no joke. It’s probably time to stop fooling around with my style.