When Will You Know That You’ve Made It?

One Big Question is my baby. I’d been kicking around the idea since before I started at the Hairpin, and it was one of the first columns Haley and I created when we got here. It comes from my habit — — not sure if good or bad, really — — of getting stuck on one big question, whatever enters my brain and refuses to budge, and posing it to everyone I know. It masquerades as a desire to learn more about the insides of people’s brains — — which I genuinely want to do, please everyone give me your brains — — but it’s also been a clever way to take my fears and sneak them into conversation, float them around to see if anyone else identifies, then pull them back in, mostly unscathed. I’ve called it One Big Question, but a better name might be Please Let Me Not Be the Only One Who Feels This Way.

“When will you know that you have made it?” was the jumpoff. Last summer, I was consumed by the idea and polled all of my friends, and was confused when they listed states of being or intangible goals — — making it was about seeing it, about having real, definite things. Here’s my summer 2014 “Making It” list: to give a reading at Housing Works Bookstore, to be on a 30 under 30 list, sit on a panel, and to own a really nice chair. These were things, that I could point to or revisit or sit on to remind myself that, whatever happened next, I’ve already done what I wanted to do, and I wouldn’t feel better until I did. My “Making It” list wasn’t aspirational; it was just a to-do list.

A year later: I’m so fucking proud of myself, for maybe the first time. At this point, more than ever, I should feel like I’ve made it — — ten-year-old me would be ecstatic, albeit slightly confused (“what’s a blog?”) — — but I don’t, despite knocking almost everything out on my list and more. If I haven’t now, maybe I never will. Maybe the feeling of “making it” is just another term for complacency, the entryway to regret. Last year, I accomplished something I never thought I could; three days later, I said, “OK, now I need another dream.” Perhaps it’s better to stay hungry.

I don’t know if there is such a thing as “making it.” I think the act of doing it is the same thing as making it. There are certainly some mornings where I wake up at 10 and work naked from bed with a sleepy comedian beside me and I’m like “Oh okay I made it for sure” but then that same day I’ll look at my bank account and be like “Oh right” or I’ll get a rejection or something. It would be silly to assume I was working towards an individual, defining moment of success; that’s not how life works. I don’t think there will ever be a moment longer than a few minutes that feels like “I made it!!!” because there’s always something else to do.
Monica Heisey

I know I’ll have made it when I read every single book on this list:

[list of 1,000 books I’ve never read]
Silvia Killingsworth

I find the idea of “making it” to be very stressful because once you’ve made it…then what? There’s no place to go but down? I like constantly making new goals, constantly having new things to work towards. It’s a reason to get up in the morning, I guess. For the longest time my goal was to get a Shouts & Murmurs published, which seemed like this BIG and IMPOSSIBLE goal and then that happened just last week (here it is in case you wanted to link to it and then print it out and put in on your wall idk) and that was groovy and exciting but by the next day I was like, “Ok, I guess now I need to write another one. And how hard would it be to write a TV show? Maybe I should try to get a book deal.” Those goals feel, right now, BIG and IMPOSSIBLE but motivate me to sit and write. Right now my next immediate goal is to get published in the New York Times magazine. I know one of the editors there. I hear she’s very mean and impressive, but I will try to win her over.
Anna Fitzpatrick

I will know that I have “made it” when I can sustain a career without having to be on Twitter. For me, that website is a necessary administrative evil that comes with being a person who writes on the internet. I would love to someday be able to get work and have readers without regularly exposing myself online as totally thirsty for work. I don’t think Twitter is inherently bad, but it takes up a good deal of time and mental energy that I could put towards actual writing or other projects. I am really put off by the follower-count-as-credibility mindset, and people who have “made it” definitely don’t have to care about how many Twitter followers they have.
Jamie Keiles

Honestly? I feel like I’ve made it when I’m asked to do things like this. I have imaginary interviews with myself all the time so I’m ready to give my opinion or thoughts or advice on everything. Also, if and when I’m asked to do something I’ve never done before, based purely on the other type of work I’ve done before. Like if someone paid me to write the announcement for their presidential candidacy based on my witch jokes. And now I want a future where that happens, thanks.
Sulagna Misra

I will know I have made it when I have as Nancy Meyers movie kitchen and linen pants, so I’ll probably never make it.

I usually feel pretty A+++ about my relationships, so making it for me is all about career. This is hilarious because I am a freelance writer. I feel like “making it” would mean that I could create things only out of a desire to create things, and not from a money and/or inadequacy-based panic. But sometimes when it’s nice outside and I think of something funny that I really want to pursue and I realize I can, I feel like I have already made it. Other times, it’s raining.
Meredith Haggerty

I will know when I have made it when I stop worrying so much about whether I’ve made it.

This question has plagued and haunted and tormented me for as long as I can remember. Sometimes there was a defined sense of what it would be, and sometimes it was just a free-floating anxiety, a pulsing when-will-I-ever-get-there-and-feel-at-ease-ness. When I’ve worked toward something and reached a goal, I often move right into thinking about the next one. There has been a lot of making but not a lot of “it.”

In exactly two months I will be 40. I think about where my life is. I think a lot more about all the things I haven’t yet accomplished, rather than those I have. I think about how some things are harder to do when you’re older, and some things are much easier. Most things in my life are a million miles from where I imagined they’d be or how I expected they’d turn out. Plans and goals are wonderful tools to keep taking steps forward but a lot of times I forget to appreciate those steps because I’m always worried about what might happen, what could happen, what will or won’t happen. And when, as sometimes happens, life takes a massive dump on you, that plan can’t save you. Sometimes life feels unstoppably amazing and sometimes it feels like the terrible shit will never stop happening, and part of making it for me is being able to ride those cycles through with less worry.

It feels so cheesy to say it, but I’ll know I’ve made it when I be more present, enjoy more of the now and worry less about what may or may not happen. Not when I finally write that first book or the fifth one, or when I get that next job, or when a relationship will stop feeling hard, but when I can more regularly look at what I have in front of me and say “Ok, here’s what I can do right now with what I have and what I know. It’s related to the things I love to do and want to continue doing, and it connects to my goals, but let me focus and enjoy until the next step comes along.” I will have made it when I am proud of whoever I am right now, and ready to take on whatever comes next.
Leah Reich

I still cling to this secret idea of arrival: that one day you get all your true and perfect pillars of stability in place (your Job, your Home, your Person) and then…that’s it. You don’t have to want anymore. You get to rest.

And boy howdy do I know how dumb that is! Because I have HAD the pillars, had the dream job and the beautiful apartment and the maybe-not-forever-but-at-the-very-least-indefinite relationship, and still I ached and still there was so much further to go.

My best friend and I talk a lot about what we call the Pendulum Theory. When we get hurt or mess up or something just doesn’t work out, the thinking goes, we swing in one direction. The next time around we try to correct for that and usually swing too far in the other. We’re circling ever nearer (we hope) to this thing, this place, this arrival.

So your day-to-day work changes; so you lug a small lifetime of boxes down one set of stairs and up another, and so you say goodbye over spaghetti carbonara. You swing closer and closer and then one day, maybe, you forget to measure the pendulum’s arc. It’s not that you’ve reached the center, because there isn’t one and even if there is it shifted long ago, but that you’re okay with living in the space between.

What I am saying is: One day I will wake up and my entire wardrobe will be floor-length Eileen Fisher cardigans, and I will have arrived.
Alanna Okun

I’ve been trying to be more kind to myself, so I often find myself quietly congratulating myself for very small, everyday things. I moved to LA by myself last year while my old life may or may not be continuing on without me in Toronto. I managed to make a whole new life without emotionally crippling myself in the process. Yet, my idea of “making it” is the feeling I get when I walk over to my landlord’s mailbox and drop in my rent check, or when I quietly remind myself I need to buy more toilet paper when I’m sitting in a meeting at work. It’s mostly the general maintenance of my life that makes me feel like I have my shit together. Somewhere out there, my 10 year old self is in awe of all of the fancy-lady skin creams that I now use.
Nada Alic

Honestly, waking up every day and having a job to go to that I like with people I respect is enough to know that I’ve made it, because I’m grateful for being able to do something that I like every day for money. Money lets me know that I’ve made it. I know that I’ll have made it when I have my own apartment, a space big enough for my piles of unread books and a bathroom I don’t have to wait to use. Making it means that I can buy some new shoes and an eyebrow pencil without checking my bank account after I leave the store or close the tab. Making it means that I will no longer take a deep breath before opening the third letter from my student loans in as many days. Making it means that I’ll be able to say, “Dinner’s on me” and not feel a rush of panic, swirling into my anxiety pit that lives deep in my chest. Making it means being able to take a trip somewhere warm and sandy without feeling like I won’t have the scratch to take the cab I so desperately want home after I get back to Brooklyn. Making it means that money only worries me a little bit, instead of every single day.
Megan Reynolds

I’ve always been an ambitious person, but not to the point where I have a goal in mind. I know how to take advantage of opportunities as they come to me, and to work hard at what I love, but I’ve never been like “I want to be the editor of a well-known magazine by the time I’m 35.” That can make me anxious sometimes and wonder just what the hell everything I’m doing is for, but it also helps in just enjoying the moment. In the moment I’ve made it. I’m making a career out of what I love, I have good friends and family, I have a social life and other interests. I have my frustrations, but I never feel like I’m wasting energy on something I don’t care about. And similarly to you, I don’t know if I want to make it, because I want to stay open to things. I want to appreciate my accomplishments and be able to relax around them, but never to the point where I say “welp, I’ve done this thing, and that’s that.” I want to still be able to see new things I can accomplish.
Jaya Saxena

“Making it” always feels like such an abstract concept. I have a hard time imagining some future date where I’ll accomplish something so spectacular like cure herpes or split-ends or win an Oscar for best screenplay AND best actress in the same year — that I’ll be so self-actualized as to say “I’ve made it” and go lay on a beach somewhere and wait for my body to die. If there’s one thing I’ve learned from having the most obscure list of accomplishments in the history of ever is that the human condition is to always be striving. The moment I win those two Oscars and launch 500 think-pieces about Hollywood, diversity, natural hair, and the “power of new media,” I’m going to want to become an astronaut or some outlandish shit. Maybe I think I’ll have “made it” on my last day on earth when I’m too old and tired to imagine another mountain to climb.
Akilah Hughes

When I’m offered a cameo in a Muppet movie or an Illuminati conspiracy blog writes about me, whichever comes first.
Maddie Davies

As much as I obsess over every inch I’ve moved forward (or, often, backwards) in my career, making it has never been about my career. Insecurity is the world’s strongest paralytic, and while I’ve finally started to inch towards “making it” as a writer, it’s come at the cost of insecurity more rampant than I’ve ever felt before — which, to be fair, I think is what’s supposed to happen when you realize you’ve reached a stage in your career that isn’t just you being buoyed by youthful optimism alone. So for me, making it, is being able to deal with the insecurity better. Not freedom from insecurity (the other fun part of growing up is realizing that recognizing your feelings doesn’t instantly make the tough ones go away), but freedom from letting that paralysis rule me, rule my decisions, and moreover, rule my anxieties. Being the eye when everything feels like a hurricane — that’s making it.
Beejoli Shah

I’m almost officially Middle Aged, so hopefully I can offer an elder’s wisdom about what it means to know you’ve “made it.” I’ve had great professional success — first in a very business-y career in which, when I finally hit that 6-figure salary mark, I knew I had made it, or at least was well on the way to doing so. Then I left that behind to write, and can point to very specific achievements that in anyone’s book would count as having made it. Those are great things! But they’re not things that, once you get there, make you stop and say, “Yeah, I’m done now.” There are always new goals, fresh challenges, all that good stuff. It’s human to strive. The thing about having those NeNe Leakes moments when you can say, “I have arrived, and the spotlight is on me!” is that when you’re working on the next set of challenges and goals, you can go back to those “I made it!” moments and pull strength from them. Because you will always doubt. You will always fear. But you can still always say, “Damn, I did that thing. I’m hot shit.”
Jolie Kerr

I’m such a steak tartare capitalist that my fever dreams of making it all revolve around bill$ bill$ bill$. At 3 a.m. in our dorm room, I would tell my overworked friends our grand future. We were going to be boss Ladies Who Lunched and we would fight over who would pay, and we wouldn’t have to share dessert. That still makes me moan, but I have a longer list of debts now. I no longer worry about “auditioning for my family’s love,” as Junot Díaz’s scalpel put it, but hunger still worries the bones. Like, my résumé of major accomplishments have all been borne out of some seed of rejection? I know I will have made it when I accomplish more goals, not in reaction to some/thing/body, not for people-pleasing yoga, but for my own selfish agenda. I want to kiss, not be kissed. That sounds romantic, but I’m a conflict crybaby whose biggest breakthrough this year was telling a secret to a roomful of strangers without letting the hiccuping snot slow me down. I’ve never held so many people in my orbit. I was the star. When I say I want to be known, that’s what recognition means for me. “I see you.” That’s making it. Until then, we can split dessert.
Monica Torres

Never, really. As soon as I achieve a goal I start wanting another, and I can’t imagine it will stop anytime soon. So instead of quantifying success with achievements, I try to think of it in terms of my own happiness. If I can achieve a lasting happiness that doesn’t depend on career successes out of my control, I’ve already made it. Now, don’t get me wrong. There are things I want, and when I achieve them they will be milestones that help me relax and feel like a successful person. For example, I want to write and direct a feature film. And I’d like money, so I can live in an apartment building that doesn’t vaguely smell of cat pee. More than anything (ANYTHING IN THE WORLD!), I want to take vacations without stress. Without worrying about missing an improv practice, or getting behind on a project. I want the freedom and security to travel and to make my own schedule. My dream is to wrap on a movie and then say “I think I’ll go write in Bali for 3 weeks!” Have you seen Rihanna’s Instagram? She’s always traveling but always killing it. She’s in control of her time. That’s my dream. I’ll know I’ve made it when my life is more like Rihanna’s Instagram.
Ali Vingiano

I think… I won’t. That’s me trying to be realistic. Like, there are definitely things I hold in my brain as evidence of “making it.” For a long time those things were all tied to money: paying off my debt, being able to pay all my bills and rent and groceries and still having enough left over to buy a few dumb books and go out for drinks with friends without obsessively checking the banking app on my phone which would inevitably say “yep still poor.” Recognition is another thing I think is evidence of making it: when people notice you’re doing good work and tell you so. There are some personal career goals, like, certain publications, or certain milestones, that I would classify as “making it.” Moving to New York was something I considered “making it.” But “making it” is, I think, a state of mind, not a state of being; like, a lot of those things have happened. Or are currently happening. And in my mind it’s still always “what’s next, what’s next, what’s next,” not necessarily because I’m impatient or ungrateful — although I am certainly both of those things — but because right now I’m thinking a lot more about being realistic and less about being definitively satisfied with my own success.

I think that real, measurable change, the kind that denotes “making it,” is something we can’t really feel as it’s happening. We can know that it’s happening, and maybe we’ll feel a little lighter or a little more relaxed, but we’re still just ourselves, right? Just always like, “what’s next, what’s next, what’s next,” because in my experience being an ambitious person who cares about something like the concept of “making it” means that you will never be satisfied, that you will always be searching for that next thing, which is a good thing in a lot of ways — constant motivation! — and a bad thing in other ways — constant exhaustion! — but mostly a very human thing. I want to consider myself as having “made it,” sure, but if I ever really do get to a place where I’m like “well, that’s it, I’m done, I’ve accomplished literally everything I wanted to do and now I have MADE IT” I will probably be dead. That’s the only time I trust I won’t be thinking about next next next. Or maybe it’s more more more.

I always want more of “it”, no matter what “it” is, and I know that about myself, and that’s not going to change, I don’t think. Instead I want to be able to see a consistent timeline of aaallll the various “its” in my life, financial or professional or personal or whatever, and at least be able to be like, ok, maybe I wouldn’t say I’ve “made it”, but I’ve done a lot of shit that cumulatively creates the perception of a pretty cool life. That’s, for me, a more realistic expectation. If I’m ever like “nope I’m done forever” you have permission to slap me.
Haley Mlotek

One Big Question is a monthly series. Because I’m really nosy, I’ll pose a question to a bunch of our contributors and collect their responses. I figured a few of you might be really nosy too; together, we can find out everything about everyone. Got a question you’d like me to ask? Email me.