For the first couple of decades of my life, I didn’t have to try very hard. (Wait–don’t leave. This was actually a bad thing.) Success in school and my two main interests, art and writing, came pretty easily. Schoolwork was easy. Tests were easy. Everyone who read my writing loved it. Everyone who saw my drawings said I was soo talented.

But there’s a ceiling to succeeding without trying. That ceiling came somewhere between tenth grade and this morning. 

When I started to sometimes not get the things I wanted, I was bitter. In college, a series of “failures” (not really failures, but fairly mild rejections) shook my confidence pretty deeply. I wasn’t selected to be a section editor on my college paper. I didn’t win any of the college writing awards. I didn’t get on the staff of the literary magazine. And, finally, and perhaps hurting most, I wasn’t selected for English department “honors,” despite entering an ambitious novel as my honors project. I was devastated. If I “couldn’t even make it” at my small liberal arts college, what chance did I have in the real world? (Hopefully I didn’t say things like this too much out loud. If so, sorry, college friends!)

Somewhere in there, things had gotten mixed up in my mind. I thought that success was a benchmark of how smart I was or how much talent I had, instead of how hard I tried. Because I wasn’t trying, but I was succeeding, at least by my tiny, childlike markers of success.

I didn’t get it.

I thought filling out an application meant I was trying. But really trying, really pursuing what you want, is so much more than asking a small group of people to judge you based on a few pages of writing or how you filled out one application. Really trying means doing the hustle.

I guess hustling usually means making money in a shady way. I’m okay with that–whatever their (many!) other faults, drug dealers and criminals definitely have great hustle. Some of us polite, reserved, always-smile-at-everybody people could learn something from them.

Hustling to me means putting yourself out there. Following opportunities, seeking out opportunities, making your own opportunities. Emailing/calling/tweeting people you don’t know because you think they’re doing cool things. Going to events where you don’t know anyone. Letting people know what you want, what you’re looking for, and asking them if they can help you get it. 

If I wanted to win poetry awards (and I didn’t, really, I mostly just wanted the validation that I was a “good writer), I shouldn’t have stopped with the one at my college and then sat around feeling sorry for myself. I should have applied for other poetry awards, submitted my stuff to every place that accepted poetry in Writer’s Market (and I DID know about Writer’s Market). Or I could have started my own literary magazine, or my own literary website, or just freaking posted my stuff on writers’ forums and gotten it out to the world that way. That’s how the world grows and develops, people doing stuff like that and not just accepting what’s on offer.

I am not an expert at hustling. If, at 14, my hustling power was at 0%, it is now at 20 or 30%. But I know that most of the good things in my life wouldn’t have happened if I didn’t hustle, if I didn’t plant a bunch of seeds and hope that a few of them would grow. 

Hustling doesn’t always work out. Rejection is a fact of life. The less you let it beat you down and the sooner you learn to endure it, the better. Rejection should be a spur to further action.  

If you want to succeed in a competitive field—or, probably, in any field—you can’t just send out your resume a few times and say you tried. You’ve got to seek out opportunities and try for those, and then try to sniff out opportunities that aren’t being advertised, and let people know you’re interested, and then if you don’t see what you want or you aren’t getting it you’ve got make your own opportunities. Even if you want something pretty conventional this makes sense. The New York Times is probably going to be more impressed with someone who started her own underground newspaper than someone who wasn’t named editor of her college paper and so accepted the advertising position she didn’t want and dealt with it.

“Dealing with it” is for things like your best friend getting cancer or having to whatever the hell you can to support your family. Dealing with it is not for your dreams. Yes, you need to start at the bottom, but there is no point in starting at the bottom of a ladder that you already know you’re not interested in. If you think you need to put in your time, put in your time and ALSO do you own independent thing.

And if you’re not that ambitious or don’t care that much that’s cool. Ambition is kind of a sickness, one that’s pretty specific to our culture. The world needs people who are content with doing their nine to five, or loving their friends and family, or daydreaming. I’m serious about that. The world needs lots of those people, and if that is the kind of person you are, don’t apologize for it. You will probably be happier in the long run than seriously ambitious people. 

What the world doesn’t need is people who really, really wanted to be engineers but when they got rejected from Cal Tech resigned themselves to being accounting clerks because a friend knew about a place that was hiring accounting clerks. And who are then resentful, or spend vast amounts of time talking/thinking about how they could have been so much more.

What the world doesn’t need is people who try kind of half-assedly to become video game designers for a couple of months and then complain about how unfair the video game design industry is. Maybe it is. But be honest with yourself about how hard you tried to make that dream come true before you blame someone else for it. Once you’ve pursued your dream of being a video game designer as hard as you freakin’ can for five years then let’s talk about a biased industry.

This goes for things besides careers, too. If you want to learn to cook or type really fast, hustle. If you want to go to Ireland, hustle. If you want more friends, hustle. I’m not sure this 100% applies to love, but even with love there is a numbers game going on: if you meet 100 new people a year versus 10 you are probably more likely to find someone you really connect with.

Try to save regret and “dealing with it,” as much as possible, for things you can’t control: infertility when you always dreamed of having kids, the company you loved working for that went under. There will be enough regret of that type in life without adding on things you could have tried harder for.

Hustling doesn’t mean you’ll succeed. The world is all kinds of unfair, and nothing is guaranteed. What is guaranteed is that if you don’t try, you can’t succeed. And wouldn’t you rather be the person who really pursued their dreams and didn’t make it than the person who’s always been on the sidelines complaining? I guarantee you the first person is more fun to hang out with and has better stories to tell. 

NB. There are a few people are successful but who, like me at 14, don’t seem to have to hustle. Try to ignore them. First, there’s a chance they are hustling hard, in a way that isn’t obvious to you. There’s also a chance that their “success” is something they fell into but don’t really love. At any rate, you are not them. You are one of the hustlers. (I’m speaking mostly to myself here. :))

A while back I got an urge to go roller skating. Initially, I thought I would just to go to a roller rink, strap on some rented skates, and spend an hour or so messing around. But I quickly discovered that the only remaining roller rinks in the Chicago area are either WAY out in the suburbs, or WAY on the edge of the south side. There were a few Roller Derby classes available, but these were a) also in the suburbs b) cost money and c) cool as Roller Derby seems, I didn’t really want to take up a contact sport. I just wanted to roller skate.

I looked into roller skate rentals, but the only place I could find charged $20 to use inline skates for a few hours, which–well, at that point, you might as well buy a pair of skates. And I didn’t want inlines, either–I wanted old-school old-fashioned roller skates. I asked around to see if anyone had skates I could borrow, but finally I concluded that if I wanted to roller skate, I was going to have to buy some damn roller skates.

My new skates arrived on Monday. They’re cute, white sneakers with purple accents on top of purple wheels. I had them delivered to work, and tried them on in my office to make sure they fit. I felt tall and slick in my new skates, and was tempted to skate down the hall to show a coworker my new purchase, but I didn’t think my boss would appreciate the midday recreation break.

Since it’s already cold in Chicago, I thought it would be a while before I could try them out. But on Wednesday morning it was almost 50. So I put on my new skates, my purple leggings, a navy dress, and a cardigan. I thought maybe I would skate down to a nearby forest preserve, which is just a little too far too be a comfortable walk. But on skates it would be easy, right? I would have to skate down a busy street, which might make me look a little quirky–a 32-year-old woman roller skating alone in a dress on a weekday morning in December–but I thought I could handle a few shouts of “Hey, Roller Skate Girl!” or whatever other witticisms people trotted out.

Realization 1: I may have overestimated my skating skills

I had only taken a few steps when I found myself grabbing for the fence to keep my balance. Skating didn’t feel as easy as it had when I was a kid. I didn’t feel as steady on my feet. I guess it was going to take some practice.

After a few feet, I ran out of fence. Okay, I told myself. I can do this. I glided a few more feet and promptly fell on my butt.

I didn’t fall hard. And only a few people saw me–commuters heading for the rail station across the street from my house. I laughed it off and tried to look confident as I stood up and started skating again.

I made it past two or three houses before wiping out again, falling forward this time, my dress flipping up around my waist. My legging-covered knees were now covered in small smears of mud. The commuter closest to me had now seen me wipe out twice in the space of three minutes.

Realization 2: I may have underestimated my capacity for embarrassment

It quickly occurred to me that while I was okay with “Roller skate girl!” I was going to be less okay with kindly strangers trying to help me up or asking, “Ouch! Are you all right?” My cute, quirky dress suddenly seemed more “delusional middle-aged lady dressing too young.” And I became aware of how many people were actually on the street in my seemingly quiet neighborhood–a couple of commuters crossing the street, a lady walking two German shepherds. I’d have to get past all three of those obstacles before reaching the first bench.

Instead, I took my skates off and darted left into the alley, walking in my black socks. I affected a confident stance, hoping as long as no one came too close they would think I was wearing black flats, not walking in a wet alley in my stocking feet like a crazy person. I think I pulled it off.

A few houses from the park, I crouched on another curb and put my skates back on. I wobbled around the walking track that encircles the park, nodding greetings to the occasional jogger or dog walker. In my head, the track at the park was smooth. But on roller skates, every small bump becomes a hazard: berries, twigs, even maple tree helicopters.

I learned to use my skates to walk over anything bumpy looking, and I managed to keep my balance.  Barely. I was going so slowly and moving so deliberately that the birds became comfortable and began to hop nearer. I hoped perhaps I could turn this into a successful bird-watching expedition, but all I saw were robins, though one appeared to have partial albinism around his head. I made a mental note to look up albinism in robins when I got home. God, I was getting weirder by the moment.

By the time I completed one shaky rotation around the park, I was exhausted. But it had been a success, I decided. I was feeling more steady on my feet, like next time I really might be able to make it down to the forest preserve. By the time I got back to my block, I was feeling downright cocky. At least until I looked up. Dozens of guys in bright orange vests were working on the train tracks across from my house.

If I fell again, I didn’t want to do it in front of a bunch of maintenance guys. I cut right back into the alley, this time with my skates still on. I’d gotten pretty good at walking in them, and since the alley was gravelly and rough, I did that all the way home.

Well, almost all the way home.

Less than thirty feet from my house, I wiped out again–hard. I broke my fall with my hands, scraping my palms and landing hard on both my wrists. I got my tailbone pretty well, too. I sat there stunned for a moment before limping home, thoroughly chastened.

Realization 3: Roller Skating Is Not for Cowards

I spent the next two days with my wrists wrapped in splints and Ace bandages. I went to the doctor, and I hadn’t broken anything, but I was having trouble putting my hair back and even–ugh–flushing the toilet. As I struggled to tie my shoes, I felt even more ridiculous than I had when actually skating.

On Friday night, I went out to dinner with a much more athletic friend. “You have a sports injury!” she exclaimed.

And suddenly I felt kind of badass. I’ve never had a sports injury before. From the way the recovery was going, it was pretty clear I wasn’t going to have any permanent damage. And I had a story that had been making people laugh all week.

As soon as it gets warm out, I’m going roller skating again.

From age five to somewhere around my junior year of college, I was defined by my crushes.

I always had a crush. My crush was always my biggest secret. I thought about my crush every night as I was falling asleep. My  crushes dominated my diary, my disappointments, and my hopes for the future.

In elementary school, I crushed on your standard prepubescent cute boys–nice, cute, mildly popular kids in my classes at school. I had one crush for first and half of second grade, another crush from second through fourth grade, and a couple of different crushes in fifth grade. I was very loyal, and leaned towards the clean-cut, all-American type. My last crush in fifth grade was a boy with a great smile from my Sunday School class.

Then came sixth grade. In sixth grade, I had two major crushes. One was a freckled, blond, baseball-playing, joke-cracking kid. And the other one was a huge nerd.

I called him DOTE, a nickname with a complex background that I am too embarrassed to explain here. He was obsessed with video games, before that was cool. He wore too-short pants,  paced constantly, and had glasses that were honest to goodness taped together. He was the smartest kid in sixth grade, except for me. He was also the least popular kid in sixth grade, except for me. The mean kids liked to shove us into each other or write me fake notes supposedly from him. Everyone, even the nice kids, teased us, saying we should go out. So in public, I shunned him. But in private, I was in love.

DOTE taught me the words “demented” and “aphasia,” and made up a fake language he used while pretending to be aphasic. (Note: Yes, I now realize this is offensive to people actually dealing with this condition.) He carried a huge camouflage binder full of messy papers covered in his cramped handwriting. He lived on our block, and sometimes my brother and I would go over to his house after school. He had all the video games. He had countless Star Trek tapes taped from TV.

And when people teased him, he fought back. Usually verbally, but one day someone knocked DOTE’s binder out of his hands and DOTE attacked him, kicking and scratching at the other guy’s face. I think they both got suspended. But I admired DOTE for standing up for himself, something I could never seem to do when people made fun of my long nose or called me a suck-up. God, I loved him.

After that, I didn’t get crushes on the milk-fed nice boys anymore. I got crushes on the weird boys, the boys who played Magic: The Gathering, the boys who asked the teacher why we had to learn algebra–really, what was it good for?–the boys who had 103 averages and bad wardrobes. They were usually reasonably cute, but no one would ever call them cool. What attracted me was their passion.

Alas, it was never directed towards me. In college, I had a crush on a guy who reminded me a lot of DOTE. He was a math nerd. He played the clarinet, and he knew about classical music and theology and the Reichstag. We were friends, and for two years I hoped we’d be something more. But sophomore year he started dating someone else–a small, pale, quiet girl who skittered around campus like she was afraid. I watched them fall deeply, publicly in love–on my small college campus, it was not unusual for me to turn a corner and come upon them together, kissing deeply, or him on his knees making some passionate declaration. By graduation, they were engaged. And though I’d dated a few people, I was no closer to falling in love–really in love–then I ever had been.

R was the first nerd boy I ever dated. R was a computer nerd. In high school–back in the early nineties–he had run a file-sharing website. He burned me Smashing Pumpkins CDs and introduced me to Peaches. He knew what I meant when I talked about the categorical imperative. The first Christmas we were dating, he asked me for the book The Eternal Braid: Godel, Escher, and Bach.

And R wanted to hear about my nerdy things, too. When I started collecting The Baby-Sitters Club, he thought that was cool. When he found out I wanted to write a biography about my favorite author, he thought that was cool. When I wanted to stay up all night to watch the sun rise over the lake, when I wanted to kiss at the top of a Ferris wheel just because it was a romantic cliche, he did those things with me.

He stalked me on livejournal and wrote a computer program calculating how many days we’d been together.

The program’s still running.

The book I’m writing–and with any luck, will finish in the next few weeks–is about fashion. If you saw me, that would probably surprise you. I have a small, mostly nondescript wardrobe. I rarely go shopping. I wear the same pair of shoes almost every day. Every once in a while I’ll shake things up with a metallic top that makes me look like a flapper, or my floor-length MaxMara coat, but on an everyday basis, I look like someone who doesn’t give a toss about clothes.

Yet I used to worship VOGUE. In the nineties, when I was a teenager, I knew what was going on at all the major fashion houses. I loved Prada’s deliberately ugly shoes, Louis Vuitton’s padded raincoats. I followed the careers of the top high-fashion models of the time: Shalom Harlow, Amber Valletta, Stella Tennant, and Kirsty Hume. I plastered my room with ads from Calvin Klein and Versace.

Some people are armchair travelers. I was an armchair fashionista.

At the time, there were a lot of things that prevented me from wearing the clothes I saw. I didn’t have a lot of money. I lived in small towns that didn’t have branches of the stores those magazine clothes came from, or even trendy knockoff stores. There were school dress codes, parental rules, and my own body (short, short legs, not skinny) to contend with. But wearing the clothes wasn’t really the point.

What I loved were the stories. Every runway collection, every fashion editorial, every ad was a story. A model could be a story, too: the character she took on in a particular photo shoot, the overall character she took on throughout her career. A particularly beautiful shot of, say, John Galliano’s latest collection for Christian Dior could conjure up an entire world, satisfying as any novel.

And, of course, the clothes were beautiful, too. They introduced me to new worlds of color and shape and texture. Or, because it was the nineties, they taught me that beauty didn’t always have to be beautiful: sometimes it could be frumpy, or stark, or even deliberately frightening.

Part of me still wants to have a fabulous wardrobe someday. Someday, I’ll spend entire weekends combing thrift stores for gorgeous bargains. Someday, I’ll dress like a punk one week, like a Victorian doll the next.

But there are many parts of fashion I know I’ll always admire only from a distance: high heels, tiny skirts, pixie haircuts. Those things just aren’t my style. Even if I someday expand my horizons to include other pairs of shoes and donning more than one piece of jewelry at a time, wearing high fashion isn’t really my style, either. What I love about fashion is the fantasy. For some people, that fantasy becomes a creative, fabulous part of reality. But for me, it’s a place I’d rather visit in magazines–or in books.

If you look up the word “adult” in the dictionary, you’ll find a picture of my parents.

My parents have systems for everything. They keep Day-timers. They keep an inventory. They Dewey Decimalize their computer files.

They love routines and habits. And so I resist routines and habits like a stubborn toddler. Nothing strikes fear in my heart like the idea of doing something every day. “Just make it part of your routine!” well-meaning people will say about some desirable habit: flossing, eating vegetables, cleaning the tub. “Make it something you do without thinking, like brushing your teeth.” Even that doesn’t make it sound any easier to me. I mean, sometimes I brush my teeth before my shower, and sometimes after. If I’m running late, I’ll do it at work, and on the weekends, sometimes I don’t do it until noon. And sometimes, before bed (whispers) I’m too lazy to do it at all.

But somehow, in the last few years, I have finally developed a routine. And I like it. When it gets disturbed, I miss it. It’s my Saturday morning routine, the routine I follow any day when I’m not working.

On a typical Saturday, I wake up between 7 and 8. I don’t use an alarm on any day of the week, unless there is something Very Important (flight, doctor’s appointment) happening first thing in the morning. I think I have set an alarm maybe 5 times so far in 2013. I have the type of job where if I come in 15 minutes late, I can just stay an extra fifteen minutes in the evening.

So, I wake up. I make oatmeal with peanut butter and brown sugar (it’s really good, I swear) and eat it while either reading the Internet or reading a book. I don’t rush myself at this point in the day. I rush myself enough on weekdays. On weekends, I read until I feel ready to move on.

By 9 or 9:30 I’m usually ready to exercise. I put on my exercise clothes and dance for 30 minutes to one of my workout playlists, trying to work up a sweat and use as many muscles as I can.

Post-workout, I often read the Internet a little more until I cool off and am ready for a shower. Then I go to the library to feed my book addiction. I don’t spend much time at the library, just long enough to drop books off and pick up my holds.

By the time I get home, it’s usually 10:30 or 11. I put on water for a tea. I put on my around-the-house shoes, a pair of glittery Old Navy sneakers. I find it easier to be productive if I’m wearing shoes. I open Scrivener, the program I use to write.

If I’m feeling procrastinate-y, I might mess around on the Internet a little more. But it’s getting later, and it’s time to get serious.

My goal for a typical writing session is either 1,000 words or 2 hours of revision. I got this idea from Carolyn See’s Making a Literary Life, which is a book I recommend to anyone serious about writing.

Since I tend to write too much and then need to cut down, I usually end up doing 2 hours rather than having a word count goal. I get my cup of tea. I set an online stopwatch for two hours. And then I write.

Two hours feels like a good chunk of time to me. It’s satisfying. I feel like I’ve made progress. Sometimes, I’ll keep going after two hours, or come back to the book later in the day. But after I’ve done my two hours, the choice is up to me. I can write more. I can read one of the books I picked up at the library. I can take a nap. After the two hours, it doesn’t matter. I’ve earned the title “writer” for the day.

And I guess, if it helps me feel like a “real” writer, I can live with a little routine.