MR Round Table: How Do You Define Success?

Especially in the age of entrepreneurs, 27-year-old millionaires and start ups


Leandra Medine: This conversation started during one of our editorial meetings a couple of weeks ago when we were talking about what success looks like in 2016.

Amelia Diamond: One of our readers commented about how hard it can be to navigate the idea of success when you’re constantly comparing yourself to the seemingly endless stream of 21-year-old billionaires and 22-year-old entrepreneurs and app starters. And I totally know that feeling. You think you’re doing fine until you come across someone who who is doing so much better, and you wonder, “Should I be doing better?”

So this Round Table is to discuss the idea of success in general, and explore “normal success” — that like just because you haven’t founded your own company by the time you’re twelve doesn’t mean you’re not successful.

Leandra: The definition of success changes so vastly from person to person, and doesn’t have to be contingent on what you do work-wise, either. Somewhere along the way, happiness became conflated with fiscal wealth, but I think the layers of that mindset are shedding and people are doing things for their own self-worth, happiness. It’s not about the paycheck at the bottom line.

Haley NahmanI think many of the parents of our generation define success as a good salary and stable job. Which many of my friends and I internalized until we were a couple years in and then it was like “Ugh, okay, we’re making salaries, but this doesn’t feel right. We’re not actually doing what we want to do!” I know “passion” is a concept everyone’s obsessed with now and even I think it’s annoying! But I’ve experienced a total lack of it in my work in a role and it sucks. It felt to me like I was…unsuccessful. Even if my parents saw it completely differently.

Verena von PfettenI think there are a lot of things at play. One is that, yes, our parents’ generation is about security and having a job. It depends on which generation of parents you’re talking about, but it used to be that if you got a job and could keep until you retired, that “the dream.” That legacy actually still exists in a lot of countries, just not in the U.S.; like in Italy and France, you sign lifetime contracts when you get a job. But it’s also like, how mobile does that feel? How hard is it to take another job when you have another job that in theory, you could have for life? It sort of prevents you from pursuing passions in some ways.

But then we have the media. Because of the rise of start-ups, I think we get a skewed idea that every job has to be the “most fun” job on the planet. I read a very interesting N+1 article that talked about how, if everyone thinks success only means the best jobs or the most fun jobs, then the world doesn’t run. The author spoke about how the ability to do what you love is a privilege and why it shouldn’t be.

From a generational perspective and from a media or cultural perspective, we’re inundated by what a “dream job” looks like or what a “good job” looks like. There’s also the stratification of the types of success and jobs we’re talking about and the specific class world that we’re talking about when we talk about success or dream jobs.

Amelia: Yes, there’s definitely a level of privilege involved. I’ve seen memes that make fun of those aspirational life quotes that tell you to “quit your job, move to Bali, learn to surf!” Like, oh! Okay! That sounds fantastic and clearly a bunch of people are doing this and supporting this because they’re posting on Instagram about it, but how do I pay my rent?”

Amelia: Yeah. The idea is to ultimately fulfill your bliss, but what about college loans?

Verena: To this day, whenever I talk to my mom about what I’m doing or what my job is — because she never understands any of my jobs because she doesn’t understand what the internet is — her only question is, “So how much are they paying you?” That’s the measure by which she decides if I am successful or not, which is fine.

I don’t blame her from coming from that perspective because like she’s like, “Don’t you want to be able to buy a house? Support yourself? Think long-term?” All of those things.

I think there are micro-generations, and I definitely graduated like pre-recession and was probably one of the last to graduate where everybody got a job; it wasn’t a question. But I wonder if the recession had an affect on the way people view the quality of life at a job, because jobs were so hard to come by that I almost wonder if there was an extreme reaction to, “We’re all kind of fucked, so why not try to find something you love? None of us are making money anyway and we’re going to be paying off student loans for the rest of our lives. Might as well love our jobs.”

Leandra: I feel like that’s the really optimistic angle to come at it from. You touched upon a really important point earlier — which I think is worth reiterating and should be articulated and expounded upon — which is that you’re not supposed to love every element of every day of your job.

Amelia: It’s called work for a reason.

Leandra: Yeah! It’s called work for a reason. Just the same way that you could marry the love of your life but still wonder every now and then if you’d prefer to have that bed to yourself. That piece of it is really interesting to me because it seems like more and more, people’s response to their work — specifically when they’re working really hard — is like, “I should be happier, shouldn’t I?” And I don’t know, if the quality of your life is pretty good and you’re happy, like, five out of seven days, that’s pretty strong, you know?

Verena: And I think it varies a lot from person to person. I think that some people our age just want a job that is secure, that isn’t terrible, is doable and doesn’t cut into their social life, it’s is very compartmentalized: “This is my job, it pays me well, I don’t think about it when I’m not there and that’s great.” And then there are some people for whom that would be miserable. The compartmentalization is very difficult for them.

But I do think that there is — especially with people just graduating — this sense that if your first job isn’t fulfilling, if it isn’t your dream job, then you’re miserable and need to go find that dream. I have a hard time getting behind that. I want people to have careers that make them happy, but I really think there needs to be a reality check on what work is and what a job is. Do find something that is big-picture fulfilling, but work is literally work, which is why someone pays you to do it as opposed to you doing it for free.

Haley: I think the important thing you said there is “big-picture fulfilling,” and that’s what gets tricky. At least for my friends and I — we all went to business school because we had those parents, I think, who encouraged us to go on a path of stability — we all got stable jobs and we were constantly struggling with why we still felt unfilled. Like “Wait! I have good hours! I’m making good money! The job challenges me enough! It’s not always fun, but sometimes it is…this is how it should be! Right? Is my listlessness a result of unrealistic expectations?” I feel like we were constantly having that debate and it was so frustrating.

Then it switched for me. I realized the big picture of my job wasn’t fulfilling even if the small picture was enough in some ways, at the moment. It can be hard to parse that with the knowledge that you’re not always going to be happy in a job, because ultimately I was using that as an excuse to not push myself harder.

Also, I think with the internet there’s so much exposure to really interesting jobs now. It can make it hard to appreciate a more humble role, one that doesn’t have any visibility to the world.

Verena: It’s fascinating that you talk about visibility in regards to your job. Every company shows their inner workings now thanks to Snapchat, Twitter, Instagram, Facebook Live… When I was graduating, you didn’t see or know any of this stuff. There was no company or job visibility; that’s a very new phenomenon.

Amelia: It is! Something I find myself repeating lately when I talk to anyone who is looking for a job is that you cannot only hope for the “name brand” job or company. And I think that’s because of visibility. When I was in college, it was like, “Okay, who actually gets a job at Vogue or Chanel?” Now, thanks to Instagram, you can probably follow every single Vogue or Chanel employee. It seems much more within reach.

But what’s important now is to remember that the name brand — it’s almost like this is the new logo — isn’t what matters, it’s the people who work there that matter; it’s a setting yourself up a the path that sort of makes sense. It’s remember that you will have more jobs. No one likes their first job out of college! It sucks, you’re the bottom of the barrel, doing what no one wants to be doing, but can you look at your boss and kind of be into what she’s doing? That’s what counts.

Verena: I think it’s really important to hate your first job. I think it’s really important to set up a variable or something you can compare or contrast to because people who get their dream jobs — what they think is their dream job — right out of college struggle really hard with what work actually means and how to work harder and what a good job is and what a bad job is. There’s no context.

Leandra: It’s much easier to determine what you like based on what you don’t.

Verena: Exactly. I took a job at a jewelry designer because I had interned at a magazine and hated my experience. I probably could have worked for a jewelry designer and been relatively happily for the rest of my life and worked on the business and marketing sides of things. But I realized I missed writing, so I started doing that on the side, and that was the exact same time that Huffington Post launched and Fashionista launched. It was 2006 and all of a sudden I was like, “Wait! There’s a job in which you write things and people read them on the internet?” It was a brand new industry and I was like, “I want that.”

The feeling of fulfillment I got when I moved full time into digital, even though I worked seven thousand times harder than I have ever worked for those first two years at the Huffington Post was so worth it to me. It made me a) realize what it meant to work hard compared to my first job;what it meant to use my brain in a way I hadn’t used before, and b) see what different industries look like. You only do that by trying things out. Social media will skew your sense of what a “good job” is.

Leandra: What we’re not addressing is the comparative nature of the way in which we quantify success personally, right? Maybe you got a raise or a huge promotion, but your friend just appeared on the cover of Wired for selling her app. Comparing yourself to others is a cautionary tale as old as time, and its much harder to silence when it’s consistently showing itself to you. As far as I’m concerned, the only way to actually comparison is to be “mindful” about the fact that what you see is a very particular vantage point of someone else’s life that they are specifically showing to you, for a very particular reason.

Amelia: Of course. But that idea of quantifying your success based on someone else, it’s almost as if reconciling and dealing with that is important, too. Also a tale as old as time: parents being like, “you should have been a doctor or a lawyer!” Social media or not, there’s always going to be someone holding some shelf over your head, pressuring you, whether they mean to or not, into being better.

It’s up to each person to decide what’s right for them and to figure out what their personal success looks like.

Haley: Maybe people coming out of school won’t have their own definition of success initially because they can’t yet. There’s no context. Maybe that’s a version of self-realization: figuring out how to define success for yourself. I mean, when you hear people who have experienced success as it’s broadly defined talk about how they got there you’ll always here things like, “Oh, my twenties were a nightmare and I didn’t realize X, Y and Z,” because no one can figure it out without years of trying different things and understanding their own definition.

Verena: I wish we had someone who was closer the the retirement part of a career because I wonder if anyone ever feels truly successful. I’m 99% sure no one has ever reached the definition of success.

Leandra: People who feel successful are the people who are not self-actualizing or complacent, but are very comfortable in their own skin.

I was talking about success in the work place with recently. I was talking about how I care so much about what other people think, how it doesn’t feel like a job well done until I’m getting validation from the last person possible who could have given it to me. And Abie was like, “the most successful people are those who don’t care about what other people think.” Those are the people who are compassionate and respect themselves.

Amelia: This is taking us off track a little, but a traditional measure of success in some sense is retirement. That feels so far off, but it kind of means, “I’ve done enough. I did it. I’m satisfied.”

Verena: Where things get really interesting is the area in the middle, where big promotions start happening — especially as someone who, in the last few years, has managed a lot of people and learned what a promotion really is.

A lot of people want a promotion because that means they’ve done a good job and they get a bigger job. And, sure, when you’re at a junior level,  it’s a good thing that comes with a raise and a little more responsibility. But then there’s this middle tier where people want a promotion because they think the next step up means greater success — and that’s not always the case. I once promoted someone from features editor to a deputy editor, and I said, “I’m not sure that you want this, but let’s give it to you and you can try it, but it might not be the job you want.”

A year later, this person was like, “That was the best and worst thing that has ever happened to me because I do not want to be a deputy. I thought I wanted to be promoted because I want the success and I can tell my parents I’m in this more senior position, but I’m not happy in that position. I don’t want to be managing, I don’t want to be looking at numbers; I want the job where I actually just focus on content.”

That’s a really interesting point in people’s careers, especially in writing and editing when you have to decide do you want to be a writer or do you want to be an editor? Or how high up do you go? And success gets muddy with the idea of promotion and pay and especially, again, this is more recession talk, how you get paid, and in some ways you feel like you have to get promoted in order to get paid. But what if you could continue to do the thing you’re best at? You’re typically best at a job right before a promotion. Like, you’re really, really good at that one thing you do, and if there was a way to just reward people for continuing to be good at that thing….

Haley: At my old company we had that: senior designers always wanted to be promoted to managers but the actual managers would say that when they were senior designers it was the best years of their careers because they were producing so much. And we were talking about this, Leandra, about how you’re sometimes envious of Amelia’s role, right?

Leandra: Yeah, totally.

Amelia: It’s like your junior year of college or high school where you don’t have the pressure of graduating and you’re not a freshman or sophomore where you don’t know anything. You’re totally savvy, you’re good at what you’re good at, you have your friends, your lunch zone; life is set. But then you feel weird or crazy if you don’t want the next thing.

Leandra: But we’re constantly fed that you need to want the next thing.

Haley: I think that’s the point we keep returning to which is how do you measure your own success? Is it your own internal barometer or is it society’s version?

Leandra: Well, how do you define success right now? I think that’s an interesting question for all of us to answer.

Haley: Well, for me, I think that when I was considering a career change, I knew that in my current role there was no one’s job I wanted. I wasn’t motivated on a gut level. I liked helping people and found joy in my role, but I wasn’t passionate about what I was doing on a larger scale. At all. I was satisfied enough with the day-to-day, but I’d always return to this funk of not feeling like myself. I wanted to be feel more organically motivated by what my company was doing and what role I was playing in that.

Amelia: And now that you’re doing that — not to be presumptuous, but you took the risk, you changed the job — have you achieved success or are you more on the way to achieving it?

Haley: I would say yes and maybe swap in the word “fulfilled.”

Leandra: Well, I don’t feel like you need to swap in the word. I think we should not think of success as a destination, in the same way you can’t really think of happiness that way. And that it’s sort of a balance and a process that changes according to where you are in life. A successful person is psyched to get out of bed in the morning.

Haley: And they’re also psyched on hard, shitty days, because they still know that, big picture, they love what they’re doing.

Leandra: That’s definitely an important piece of it. The terms of success for me are defined by what my personal goals look like and whether or not I’m achieving those. Because I can be very clear and honest about my business goals and very straight forward about reaching them and achieving them, and for the most part I am, but I’ve been much more accommodative of mutating my personal goals to align with what’s happening business-wise for me, which is starting to wear me down. And so, in the last six months, probably in part because of the injections, the suppression, and the hormone-induced depression, any reason to laugh is what I call success.

Verena: Yesterday my personal trainer asked me about surfing and he asked me, “How good are you?” and I was like,“I’m not very good,” so he said, “Don’t you want to be good at it? Do you practice all the time?” and I was like, “No!” My only goal with surfing is to be good enough so that whenever there’s a small wave, I can just surf it and have fun. I have no interest in surfing big waves, no interest in learning to do tricks; I just want to be able to get on a board and stand up, have that one good feeling.

This exchange just came back to me during our Round Table which made me think, “Why don’t I have the same, clear sense of success with other areas of my life — including professional?”

Amelia: It’s really interesting you say that. This whole time I’ve been thinking about how my idea of success translates into every aspect of my life. I hate using the word “perfectionist” because I’m not, but I definitely have lofty, ambitious goals. For me, success is being, yes, happy. And when I think of success in regards to other people, when I’m speaking with my friends or to anyone who has asked for my advice, it’s all about happiness.

But I know, for me personally, my happiness is tied into steps of success. So I feel like successful, for me, is being recognized at being excellent in my field. The best. Even in regards to some of my hobbies. I ride horses, but I can’t “just” ride for fun, because for me, that hobby or sport is about the competition. It’s about setting goals, measuring success tangibly and beating other people. It’s really hard for me to track success without merit. But like you with surfing, Verena, since I’ve started taking tennis lessons, it’s the first activity in a long time where all I care about is being “good enough” — good enough to play with whoever who agreed to play against and not completely annoy them.

Verena: I feel the exact same way. It’s why I was so shocked. Why is this the one area that it’s okay to be “meh” about something?

Amelia: Well, okay, douche alert but I’ve always ridden horses, so I’m “supposed” to be good at that. And we’ve both always worked hard in school and in jobs — so we’re “supposed” to be the best by now. These new hobbies don’t have any pre-existing pressure.

Verena: Right, like there is not a world in which I am actually gonna be a competitive swimmer, so I don’t have to worry about trying to be there.

Haley: I think getting motivated and having goals and wanting to be better and being competitive are fun parts of life. But maybe it’s about striking a balance between working hard and still thinking it’s fun. Because a little competition is good. Otherwise you can become complacent right?

Leandra: That’s the other thing: we’re told that contentment is not good, or not the goal, you know what I mean? Like you should always be pushing yourself and forcing yourself to do better. I think in many ways that’s true, because that’s how you learn. If you are promoted and you hate the job, you’re like, “Oh, now I know this is not what I want to do.”

Haley: But there’s a difference between like contentment and complacency, right? Maybe you can be content but also internally motivated by your own set of goals. Whereas if you’re complacent you’re not caring enough about your goals.

Amelia: I think complacency is knowing you’re kind of C-minus-ing.

Leandra: It’s coasting.

Amelia: Knowing you’re coasting and feeling gross about coasting but not doing anything to change that — versus being happy and proud of where you are, regardless of where you are. There’s always gonna be someone better than you, smarter than you, everything more than you. And then, the reverse: there’s always gonna be someone not as good as you, not as smart as you…everyone just has to find comfort on their own shelf.

Haley: Verena, how do you define success?

Verena:  I think I’m still learning how I define success. I’m also currently in a place where I’m trying to cast out what other definitions of success look like, because you don’t really know until you try it. I think that I am someone who, very similar to how Amelia described it, wants to be best at a certain thing.

I feel very fortunate with my timing and how I started in like this particular career path. I fell into digital media when it didn’t really exist, and I got to be one of the first people doing it. That has brought me really really far, to a point where there are only a handful of people with my level of digital experience in this particular industry. I’m really friendly with these people, but we’re also competing against each other, which is a really weird thing to do. So is trying factor what success looks like among this small group of people since not a lot of precedent has been set.

Since I work in a freelance capacity now — and Leandra, you must experience this — there are plenty of pressures that come with being your own boss. But what you don’t necessarily have is someone else putting that pressure on you to compete with anyone — another company, a coworker. Still, it’s part of my job to compare myself to people and try and beat them. That’s how the web works. And that’s a hard thing to try and parse personal success versus professional success, when my professional success in digital media is predicated on beating other people. Like that’s literally what it’s about, to drive more traffic, and make more money than any other person in this competitive space. So that is a really hard thing to sort of parse what success looks like when that when it’s baked in.

How do you define success?

Photographed by Krista Anna Lewis.


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