Tell Me What Success Looks Like

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“Tell us what success looks like to you in five years,” the owners of Literati said to me in my three-month employee review, as casually as if they were asking for my weekend plans. “Write us a vision of what a day in your life looks like on June 25, 2021. You wake up, and do what? Tell us who’s there, where you are, what you’re doing. Does that make sense?”

“I can do that,” I replied, most likely nodding with enthusiasm. “When do you want it by?”

“Let’s meet back in a month,” they said. “And we’ll talk about your vision together. We know you won’t be with us for the rest of your life, and we want to know what we can do to help you get closer to success before you move on.”

I’d never been assigned this type of exercise before, and certainly never by my place of work. And yet, as you’re all no doubt tired of me saying, Literati is much more than a place of work. Still, with utter arrogance, I expected that this unorthodox vision board would be right up my alley. After all, I was raised to understand what success looked like.

Here is a not particularly flattering story about myself. If you ever find yourself in my parent’s house in Maryland, you might find a to-do list that I made in high school titled, “What I Have to Do To Get Into a Good College.” It is still taped behind the basement bookshelf, and I visit it every year or so, not only to laugh at how determined I was to succeed, but also to take just the tiniest bit of pleasure at how nearly every box on that list has been checked. Get a varsity letter in cross-country? Check. Get on the Cum Laude society? Check. Get an editor’s label at the school newspaper? Check. I run my finger down all those sloppy checks and I am proud of my younger self for knowing how to dream, and how to break down that dream into a workable reality.

Even after I decided I wanted to be a writer — a career path that everyone, especially my parents, agreed was nebulous at best — I eventually saw how one could become a “successful” writer. Get into an MFA program, get published in a literary journal, get an agent, sell a novel, win a prize maybe, and, obviously get writing. I don’t think I’m alone in this way of thinking. I think we all, generally, have some idea of the signifiers of success.

Yet in the time it took for me to walk out of Literati and in front of my computer, utter panic settled into my body and would not leave.

The vision was simultaneously too grand and too specific. I had to imagine a future five years in the distance without laying out the steps in between. Instead, like Jennifer Garner in 13 Going On 30, I would simply wake up one day in June, solidly embedded in my perfect life, with no memory of how I became my most successful self. At the same time, I had to come up with my entire schedule for that day, every errand I would have to run, task to complete, responsibility to take charge of, people to mentor, pasta to make from scratch. The scale was out of my reach in both directions, I who treaded the middle ground of concrete, but general steps; the utterly practical dreamer.

Sitting in front of my laptop, I tried to imagine myself actually on a panel, rather than just invited to speak at one. What would I say? What would it be like to spitball with other authors? My stomach began to hurt so badly that it was as if I were on that slightly raised stage already. Could I see myself lecturing an entire hall of college students? Editing articles by respected authors? Running a magazine? Suddenly my stomach felt like an angry snake lost in its own coils, intent on eating itself whole.

I backed away from my computer and procrastinated the panic away. Even imagining some far-off future where I might, maybe, possibly be responsible for anything slightly influential made me want to burrow myself into the present, to cling onto my current life. I wanted to live in my tiny apartment forever, drinking my stale, hazelnut flavored coffee and using my parents’ health insurance and their Costco card for the rest of my days.

But of course, once I start thinking about a thing, I can’t just not think about that thing. Even though I didn’t write a single word of my vision in the month that followed, I went over it in my head every day. I thought about how my employers, Mike and Hilary, learned the vision technique from a Zingerman’s small business seminar. How they wrote their visions in only an hour and then, three years later, unearthed these forgotten pages only to find that so much of their original vision had manifested itself in the Literati they’d built in that interim time. I wondered if just by writing their vision they had, a la The Secret, taken some invisible step towards achieving their goals.

And I thought also of the steps that I decided built up to success. In each step I either got a thing or was given a thing. I worked hard to get or be given those things, but in the end, that was the marker of success — not so much the work, but the check in the box. I wanted to get my novel published. I wanted to be given a National Pulitzer Booker prize (one created just for me by a committee of my peers and favorite celebrities). I wanted to be given a nice party thrown in my honor and then go home to my normal life. Wasn’t that success? A day out of the ordinary? So how was I possibly going to show my vision of success on some ordinary day?

On the day my vision was due I finally sat down and forced myself to write out the ideas that had trailed me for the past thirty days. Start small, I think, and unclench your stomach, please. So I started small. I thought not of what I wanted to get, but what I wanted to do and feel and be. I imagined what the perfect way to wake up would be. The answer was obvious: in a big bed, covered in books, sun streaming in as my only alarm. What would I be reading? ARCs (advance reader copies) I’d been asked to blurb, books for the new syllabus I was building, and pure pleasure reading. How long would I read for? An hour, until someone beloved came to bring me coffee. Against all odds, I, and my stomach, began to relax. I let myself be a little silly, a little arrogant, a little over-the-top. But I also asked myself and really thought about what would make me feel happy, connected, necessary, and, dare I say, successful.

I wrote for just about an hour, tracking my future self’s movements from eight in the morning until midnight. And at the end of the imagined night, I scrolled back up the page and reread what I’d written. So this was success, I thought.

I didn’t feel tied to the vision, as I thought I might, nor did I feel like I’d just drawn up an impossible measuring stick for myself. I felt only that I had written up a nice life for myself, one filled not just with acclaim and piles of cash, but also with good friends, tasty food, and general kindness. That was the point of writing out an entire day, for me at least. I could see the trends of my desire, what would fulfill me and what was just fun window dressing. Amidst all the obvious signifiers of professional success was my daily Skype date with my parents, a coffee shop that knew my order, hours to write every day, an invitation to a Fourth of July party, a student to mentor, respected writers and teachers to trade notes with, and old friends to beg me to stay out late singing karaoke. Mike and Hilary said that their vision set in motion much of how they made decisions for their business down the road. I didn’t understand at the time how that could be. I think that I do now.

At our meeting, I told Mike and Hilary that what I was about to read to them I’d never told another person, and that was the truth. Not my parents, not my friends, not my partners, not my dogs. In fact, the reverse is also true. I don’t know what success looks like to the people I very much hope will still be in my life in five years, the success that I may be witness to personally, or even, if I’m lucky, be a helping hand in. Of course, I know that success means drastically different things to different people, that our various life experiences draw borders around where we want ourselves to be in five years time and where we believe others should also be. In sharing our visions, we may face judgment, or disbelief, or the wrong kind of laughter. And when that reaction comes from someone who is close to us, who understands our strengths and our limitations and our history, their rejection, or their confusion, or even their slightest hesitation will feel much more painful. But, if they are supportive? If they are excited? If they at the very least accept our success, and entertain the possibility of it? If that’s the risk and that’s the reward, then I’m willing to give it a try. That’s the decision my vision set in motion. That’s what success looks like to me.


Image: Davey, Moyra. “The Coffee Shop, The Library.” 2001. The Museum of Modern Art, New York.

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