Demystifying the “Dream Job”

Demystifying the “Dream Job”

Turns out, Hannah realizes, reaching career bliss isn’t about the title, but finding your flow. 

In my college years and certainly in my 20s I raced toward something of a “dream job.” I was in love with fashion and with writing; I wallpapered my childhood bedroom in fashion editorials, and becoming a fashion director at a digital publication felt like I had manifested exactly everything I had ever wanted from a career. Cut to my mid-thirties, two kids later, and, if I’m being honest, sometimes—often—work is a grind. I still feel lucky to do what I do—but the older I get, the more I find the notion of a “dream job” puzzling, if not problematic. 

How much of ourselves are we neglecting when we become fixated on the obsession with a dream work scenario? In tying all of our hopes up in one career, we might be missing the bigger picture, like the parts of our life that aren’t tied up in work—that require interest and nurturing, too. And, if it doesn’t feel like a dream—if it actually feels like a slog some days—are we just setting ourselves up to be disappointed? It’s something Leah and I have talked lots about—something you might remember from our past issue about the ways work and identity get all tied up together and how lots of us want—and maybe hope—what we do reflects who we are. And, even though I want to love what I do, I have to wonder: is the dream job actually just a hoax? 

I circled around that idea for a while, wondering if the women with careers I admired most—whether in my circle, or from afar—felt it too. Carly Cardellino is one of those women who I’ve watched in wonder, moving seamlessly from beauty director at Cosmopolitan to mom and creative, freelance writer, and beauty and wellness guru who I follow avidly on Instagram (because of her I’ve taken up a lymphatic drainage massage ritual!). When I called her up for this story, I wanted to know: Was the big job she had at Cosmo as glamorous as it appeared from the outside? “I think that it's all very glitzy,” she told me. “You're traveling, you're with celebrities, your friends are the top makeup artists or hairstylists. There's a lot of glamour to it, and that is very true, but there are also a lot of late nights that you're at the office or going in on the weekend or whatever the case is that you're not posting about on Instagram. I was at the office until 2 a.m. probably Monday through Friday when I worked at my first job, because you're an assistant, you're hustling and you're just trying to get everything done, and also, people can take advantage [of you]. So looking back now, maybe I would have said, ‘I can't stay that late’ because of [protecting] my mental health. It's a lot of hard work put in on the backend that people don't really see. There are tears that people don't see.” 
That feeling was shared by Andrea Campos, an illustrator and creator (with two new children’s books under her belt!), who left her full-time gig in marketing at the start of the pandemic. Now, it certainly appears that she’s got a “dream job” scenario, especially if you follow her on social media. Still, she confessed to the same grind behind the scenes when I asked her about it: “Online, it looks like I’m living the dream. Working remote, getting to work on fun projects and collaborating with big brands, but I don’t think most people realize just how much work starting something on your own is. Right now, I am my own illustrator, photographer, CMO, CEO, janitor and everything in between. It means many long nights and a hustle that is 24/7. At times, It feels like I am treading water and not moving forward, but I know I'm growing stronger and learning something new.” 
Regardless of what’s happening behind closed doors, we’re all enamored with the shiny parts—the titles and the prestige at big companies or the freedom that working for yourself might allow—but when we see only the dreamiest parts of someone else’s job or career path, we also fail to see the nuances of their work and their experience, the why’s and what got them there—why we end up in the jobs we do, and also, why we stay. 

Dr. Wendy Osefo, professor, author, and activist—and yes, Real Housewife of Potomac, had some of her career drama play out on Bravo, as she wrestled with continuing her professorship at Johns Hopkins. For her, the optics come with added pressure: “For me there are external pressures because as a woman, a woman of color, and a younger woman, I know that there is symbolism in the fact that I occupy spaces that so many people who look like me don’t. I feel as though I have to stay there so I can be that person who I didn't have growing up. I have so many students who tell me how just my presence inspires them.” 
The idea that a job is “special” and, most importantly, matters to us, can also matter to people from the outside looking in—and sometimes it matters so much that it starts to obscure our own thinking. For Wendy, the added weight for a woman of color is a lot to shoulder, and “when you think of it from that lens, you do struggle with walking away from something as if you were blessed to have it,” Wendy shared. “Sometimes I question myself and say, ‘Is this what I’m supposed to do? Am I just being a brat by saying I don’t want to do this anymore? Is this career my calling? What if I leave it and can't find anything else that's close to what I’ve accomplished here?’ The fear of flying almost.” 

What’s tethering us to the “dream job” or even the notion of it is rooted so much in the eyes of others—and since that seems to keep a lot of us there, so how do we get over it? Carly’s answer to this provided something of an “ah-ha!” moment for me: “I think when people struggle to make a leap, it's because their job defines them, and I never really let my job define me. It was just something that I did. I remember talking to somebody about this at Hearst and she was like, ‘Well, doesn't your job just define who you are?’ And I'm like, ‘No. And that's why I'm leaving.’” 

Carly has the kind of confidence about life and career that lots of us crave. But, it’s not a quick fix. It’s a true perspective shift, and doing that work seems to be the only way to really free ourselves from the expectations of others—and also reframe for ourselves what a dream job actually is or what it can be. Carly put it this way: “I care about people, but I don't care about what people think of me. And I think that that's the toughest hurdle. ‘Am I going to be good enough for other people to see me?’ I know a lot of people struggle with their work and everybody can. I'm not saying that I still don't here and there, I think it's just human to do so. But I think the more you build a person up from when they're young and instill that they're worthy of all the great things that come to them, you kind of just have an attitude of, ‘Alright, well, if this isn't working out, something else will.’ What is meant for you will not miss you. And I think that you just have to remember that.” 

I try to, even as I’m writing this. I try to remember that we are not our jobs—even when we love them, they’re not us; they’re just the stuff we do. They can be made into so much more than that—and it’s tempting when it all looks good to let that happen; then it’s crushing when there are failures and setbacks. The upshot is that we’ll likely be more at peace with ourselves if we try to create space. 

Wendy offered a way to acknowledge what the career is, without overstating what it means for us: “When it comes to career you have to look at it as ‘this too will end’ and you should be grateful for the experience. You're able to say, ‘Yes, I did that once in my lifetime.’” It’s unnerving to think that nothing lasts forever, but that kind of thinking can be liberating too, especially when you recognize your autonomy in that. That’s the piece that has ultimately given Wendy a stronger sense of self in her career, recognizing that it has been her decision to do what she does. “That was the moment I was liberated,” she said of her choice to continue working as a professor. “It was almost like you don’t have to feel stuck, and for so long I felt stuck—this is it, [this is] what I have to do—and for me I felt like the a-ha moment would be me leaving my job, but in reality it was finding out I could leave if I wanted to. That has liberated me in ways that I couldn’t even imagine.” In that way, maybe the career isn’t a dream scenario, but it fulfills a desire in us, or it motivates us. Maybe that should be enough.

For Andrea and Carly, leaving the corporate world may have come more easily. As Andrea put it, the decision to set out on her own was a chance to create the right opportunity for herself: “Today, I’m less focused on landing the dream job and instead am creating it.” For Carly, even if working at a magazine had been fulfilling, even if her departure from a high-profile title might inspire awe from others, that didn’t phase her. The choice to leave supported a life she wanted, as she welcomed a baby (then, another baby!) and wanted to spend more time at home. The freelance and influencer life afforded her that—a next-gen kind of dream job that’s more in line with the lifestyle you want.  

I asked Carly about her second act, how she’s navigating life and career now. “I think that's something that I'm actually still figuring out and maybe will never have figured out. I feel like balance is hard to achieve. I'm a Libra and I feel like, right now, I'm just looking at my life as the Libra scale. And it's just kind of going back and forth. It's never going to be an even level because sometimes, my kids need more attention or sometimes my work needs more attention. I think that's kind of how you have to let it be. You have to forgive yourself and just be like, ‘Okay, today, maybe I didn't check my email, but I really focused on my kids.’ It's always going to be fluid. I follow TyLynn Nguyen, and once she posted that her husband said to her, ‘TyLynn, just be like water.’ And it's just so true. You just need to flow.” 

Flowing, ahh. That’s the dream, isn’t it? Or more so, that’s the secret to making it all work. It’s the letting in and letting go—it’s knowing that the thing you thought would be the dream job might not turn out to be in a few years’ time, and that’s okay. It’s knowing that you can walk away when that happens, and being resolute in the fact that you are not leaving something too precious behind, or something that makes you you. You are you, regardless—and your jobs, even at their best, amount to experiences. That’s what I’ve come back to—that, and this gem from Wendy, who wondered, “Is there a dream job or are there just different pillars, different tiles in the mosaic of life that we are able to achieve, and once you achieve that thing it just adds to your mosaic and you move on. If I thought about it like that I wouldn’t struggle so hard.” She’s right, I think—with that mindset, we’d just flow. 

 

[This story first appeared in issue no. 3]