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Coming back home to New York and hearing about Brett Favre’s training made me wonder, when is it time to hang up your jersey?

Then, between Jets training highlights, I heard about David Foster Wallace, and my vacation took a turn for the brooding. Here’s what’s been rattling around upstairs as I walk the streets of the city that never sleeps.

Getting out of the game, to me, means one of two things. Assume you’re good at what you do. You can either pull out when you’re at the top – because I truly can’t wrap my head around what happened, I’ll cite David Foster Wallace as an example — or you can retire. But if you’re like most people who are blessed enough to be successful at something they enjoy, this is a bittersweet retreat. Just look at Mr. Favre, Lance Armstrong, or Jay-Z. If you want to be even more confused, take a peek at Michael Jordan, who made proverbial swings and misses literal.

For the sake of brevity I’m not even going to address the possibility of a quiet retirement, or fading out into oblivion, or even continuing to play, write, create until you’re no longer considered relevant, a la…oh, Michael Jackson. A legend when he was a legend for sure, but now he’s just legendarily creepy.

I want to know when I should give up. I know, it’s not retirement, because I haven’t achieved a modicum of success. But that’s just it. Mr. Wallace didn’t know if there’d be a doubly successful follow-up to Oblivion. He didn’t know if there would be more than one highly lauded and fiercely competitive college course with his work as the focus of debate, or if he would become a subject of a reality show on VH1, or if whatever it is that proves that you’ve “made it” would occur. No matter what level of international or personal success he achieved, he felt – in the most disastrous way – that he’d done as much as he could.

Suicide is a macabre and extreme example of putting on the brakes. But if you inspect the pressure, criticism, and trappings of selling out that flanked what I can only assume was the mental malaise and depression of one of our generation’s most spectacular literary celebrities, I suppose the volatile and sudden fall makes some sort of sense.

But not really. I honestly cannot fathom how this could have happened and I’m effected in a way that I can only assume I would be if, God forbid, a blood relative did the same thing.

To me, I’m trying to locate the bottom. I’ve figured out the top (book deal, sustainable income, literary notoriety, or maybe just some recognition…basically everything that Mr. Wallace had on the surface that still wasn’t enough) and now that I’ve dreamed big, it’s time for me to identify where the proverbial buck stops. When do I know that I’ve done all I could? When is it time throw in the towel? When does the end begin?

For me, retreat is the inevitable, may it be now or twenty years in the future.

There are a few key indicators for when your time trying something is up. One is financial ruin. The other is misery. You can be destitute and happy. You can be wealthy and be miserable. In the past year I’ve gone from having a life devoid of much other than a steady paycheck and little desk under cool office lights, to having an existence filled with creativity, dinners from a can, and adrenaline. It’s been a struggle, but it’s been fun.

So as I face another month of anxiety, the question becomes, does not being able to afford rent mean tucking my tail between my legs and throwing my resume – now with an oh-so-desirable year long gap between steady gigs – into the abysmal job market? Do I say “uncle,” pack my bags, and move back to New York to live with my mom?

God, I hope not.

I like to find solutions. I’m a big fan of untying knots. Maybe if I achieved all that I desire and still felt unaccomplished I would see the only way out being, well, the only way out. Or maybe I would decide to take a break, reassess, and go to school to become a registered nurse. Who knows. But I feel like I’ve still got some fight in me yet.

My hometown has always helped to combat my personal struggle with depression, even if it was in a way that those around me couldn’t see. I am happier living in New York than I am living anywhere else, this much I now know is true. I’ve long slammed Portland for being the bastion of vapid hipsters, kids with no follow-through, brainstorming joke after overdone joke about skinny jeans, ironic facial hair, bandannas, fixed gears, and privilege. But what it really comes down to is, I love it here out east, and I’m willing to do more to make myself less miserable when I’m in the town that I love. It makes me feel sane. If I had my apartment in Northeast Portland transplanted into Manhattan, well, I’d be finding a more creative way to keep it, other than whining about the pains of freelance writing on the Internet. I’d be stripping.

(Okay, maybe not stripping. I’m an A-cup on my biggest days and have the grace of a hippopotamus with an itch.) But certainly I’d be taking some shit job that meant nothing to pay the bills, at least part-time, while in my “off hours” I’d still be attacking my words full-throttle. I would have found a way in between all or nothing. Even if I had to taper my efforts writing full-time for a while, I would still go back to it, eventually, if I could swing it. The definition of success changes depending on your circumstances, and therefore so does your stamina.

My business partner is the key factor I’m not addressing here. Because, regardless of what I do to put food in my maw, his persistence in my life isn’t being debated. Our friendship, like eye-color, lineage, and playground scars, is unequivocally permanent. He is what keeps the sad out.

All of this leads me to wonder what it is we should sacrifice when we start sensing that our efforts might be fruitless. It all comes down to what is important. Is it a job, or a town? Is it a recreational pursuit, or a relationship? Again, I think that giving up on anything is simply a matter of perspective. I still have hope that I can make it, even if my bank account is hoarse from screaming the opposite. I believe that one day I’ll be able to better manage my internal struggles, as well as my professional ones. I’m still having fun, dammit, and I still believe I can do it, whatever “it” may be. As long as you’re still getting some enjoyment out of your struggle, it’s still worth going after, fuck what happens and fuck what other people think. Just ask Michael Jordan, even though his image was never associated with stickball, he’s still flying high on the training sneakers of most pro players in any sport. As for asking David Foster Wallace, well, he didn’t give us the option. And, unfortunately, that’s an epilogue whose footnote can never be written.

If you, or someone you know, needs to talk about depression, feelings of hopelessness, or thoughts of suicide, don’t sit around. Call 800-273-8255 or click on the National Suicide Prevention website. There’s always a better way.

I haven’t been able to find any specific and credible funds where you can donate to support Pomona in DFW’s name, or Mr. Wallace’s wife, Karen Green, but when I encounter one I’ll put the information up here. It’s necessary. Until then, here are some links where you can see a sliver of his work. A Supposedly Fun Thing I’ll Never Do Again was a book that changed my approach to writing when I was in college. He was one prolific and incredible writer and, from what I hear, a fantastic professor as well. He’ll be missed.

Reprint of the essay, Consider the Lobster.

Commencement speech from Kenyon College (2005)

The Howling Fantods! comprehensive site with DFW archive, resources, and merch info.



  1. Two things I’ll say.

    1. As Gil Grissom said once on an episode of CSI (bear with me here), when it came time for him to quit, there wouldn’t be a party or any cake in the break room. He’d just be gone. That, I think, is the best way to go out. That is, on your terms.

    2. I’m a big fan of “Inside the Actor’s Studio”. Dave Chappelle spoke of his decision to start doing stand-up full time and how he defind success. His parents were teachers. He told his father that if he could make the same money doing comedy as a teacher made teaching, he’d be successful. His father responded with some great advice. Set your price now. If it ever gets more expensive than that, walk away.

    In my mind, that is how and when you make your exit.

  2. I’ve been having similar thoughts in light of my mis-planned move. Not DFW thoughts. Quitting thoughts. Leaving thoughts too. Mostly just the crushing weight of a few new insights into the way the world works. For some reason reality has a hard time taking root in my brain. I don’t want to make a life in LA. I only moved here because I was in love. And I might have nowhere else to go where I can make money. Having no plan B really is the only way to stay in the industry.

    So I’m moving back to NYC for whatever reasons people feel they must retreat. Had plenty of thoughts of moving to Portland but it’s really just another idea with no grounds. I liked Portland when I visited. I’d have no place or job there either.

    But as much as I retreat I also know there’s no escaping myself. So I’m going to meetings, trying my best out here too before I leave. Stepping back from my writing (that would’ve surely killed me) and getting down to what’s left. Just feeling happy and comfortable. Whatever that means today.

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