Founder of Career Contessa on the Non-Reality of Dream Jobs

While on the hunt for her "dream" job, Lauren McGoodwin became a career junkie, obsessed with finding her place in the working world. She tried on the idea of numerous careers, from event producer to teacher, before realizing that she didn't believe in a dream career. 

With this clarity, and loads of experience behind her, she left her job at Hulu to work on her brainchild, Career Contessa. Launched in 2013, it is an online platform dedicated to career and business advice for women, sharing inspiration, information, and direction-- the likes of which she's sharing with us.  

You can never have too many honest conversations about the real work, 

Did you have a dream career when you were young?

When I was a kid, I had many dream careers— I wanted to be everything from an interior designer to a dermatologist. In college, I decided to pursue a degree in education with the idea that I wanted to become a teacher. Somewhere around my junior year, I suddenly realized becoming a teacher wasn’t my dream. Instead I wanted to pursue a more “business-focused career.” I laugh looking back on that now because I really had no idea what that meant— or how to get started—I think mostly I just knew deep down a traditional 9-to-5 job wasn’t for me.

Was there a point when you realized just because it’s a dream doesn’t mean it’s always fun? And how did you handle that disconnect?

After stepping away from the teacher track, I asked myself what my “dream job” would be if I could pick anything. For me, event marketing sounded dynamic and exciting. I remember thinking: “How could it not be amazing?” 

I worked very hard to find a summer internship—in fact, that was my first real introduction to job-hunting, networking, etc. Ultimately it worked, and I wound up at an event stadium in Portland, Oregon. Initially, I felt on top of the world. I got cool bragging rights with my friends because I spent all summer at concerts, and I could hook them up with free tickets. But behind the scenes, I was shocked to find I was bored.

"Behind the scenes, I was shocked to find I was bored."

During the internship, I had this moment where I realized that everything I’d tried so far, I’d hated. That was terrifying. I handled the disconnect by going back to school on a mission to participate in everything and anything the Career Center hosted, whatever it took to find my way. I was like a career junkie. I went to workshops, information sessions, career fairs, etc. to figure out what career I should pursue— and how to land it. 

It was a period of experimentation, but letting go of the idea that there was one “right answer” ultimately saved me from myself. Actually, it was around this time that I realized I didn’t believe in the idea of a “dream job,” and I still don’t. Careers are so fluid these days, if you don’t leave yourself open to evolving, you’ll wind up unhappy—even if you’re sitting in the most gorgeous corner office or traveling the world and eating delicious meals on your per diem. 

Same goes for moments of fear. What’s your advice for taking risk?

The majority of my life I’ve been very risk-averse, honestly. But running a start-up, suddenly fear and the unknown becomes just part of the day job. 

For me, the secret is preparation. That might be writing something out, talking to a friend, or just giving myself plenty of time to think before I jump. I planned for over a year before I left my full-time job at Hulu to launch Career Contessa. I talked to other entrepreneurs, created a business plan, mapped out my expenses, etc. It was still scary to leave my stable career, but I felt more excited than anything because I’d spent the time to let the idea noodle. At some point, you’ve prepared so much, it just feels like you can’t turn back. 

"I want to prove my fear wrong.  Let your fear inspire you." 

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For the times when you can’t really prepare, I say “fake it till you make it.” I’m an introvert so public speaking makes my nerves go crazy. But I’m also competitive as hell so when I host a workshop or panel, I let the fear push me forward. It’s like competing with myself—I want to prove my fear wrong.  Let your fear inspire you.

Can you take us through the evolution of Career Contessa? Where is started and where it is today?

Career Contessa actually started as the project for my master’s thesis. After college I’d found myself struggling in yet another job, I was shocked by that because I’d been so proactive throughout college. After all those hours in the Career Center, I still felt poorly equipped. Even after I went back for my masters, I couldn’t let go of that frustration —so I decided to use it. 

We’re so lucky that there are so many different types of jobs and companies out there, but all those options can feel paralyzing. It’s no longer simple to answer “What do you want to do when you grow up?” you know? 

Career Contessa was my alternative approach to answering that question. In 2013, I started the site—although it was more like a blog really at that point. Back then, we only had our Contessa profiles, which are these great interviews with successful, professional women. I’d hoped that by reading about the career paths of successful women, our audience would find inspiration and direction for their own careers.  

Almost immediately, those profiles sparked endless dialogues and debates. Our readers sent us questions about informational interviews, networking, personal branding, etc. They needed so much more help than those profiles could provide. That’s when I started to realize that Career Contessa had the potential to be much more than a passion project or a weekly interview series. 

In 2014, I left Hulu to focus on building Career Contessa into a full-fledged site. 

I’ve always believed in trusting your audience—ultimately, they’ll make the right decisions for you. In 2015, we sent out a series of surveys, asking our readers what they wanted from us, what they loved about Career Contessa, what they hated. We realized they wanted two things: sophisticated advice and a direct connection to women like them who’d successfully advanced their careers. That’s what guided us to where we are now. 

Everything from there went really quickly. We hired a Managing Editor to shape our content and shift it towards the kind of smart advice our readers wanted. Then we launched our first paid service, Hire An Expert, which lets readers work 1:1 with a trusted career “mentor” of sorts, without the commitment of pricy coaching packages. 

As we evolve, we always try to stay close to our audience, and we know that a one-size-fits-all approach won’t work for them. Our goal is to continue the conversation as we go.

What parts of your professional history and personality did you leverage when starting Career Contessa?

All of it! I was a Recruiter at Hulu so I was very familiar with how the hiring process worked on both sides. I also leveraged many of my professional relationships to help me recruit career experts, launch a College Tour with corporate sponsors, and hire our first employees at Career Contessa.

My personality is also a big part of Career Contessa. I’m very ambitious, which helped me get out of a dead-end job and into my gig at Hulu. It also helped me leave there to start my own company. And although I’m an introvert, I love meeting new people and hearing their stories. This makes me a natural networker, which is really key to growing a company.

Was there a woman you looked up to that helped shape your career?

There have been many! From mentors to sponsors to colleagues, I’m constantly shaped by the hard-working women around me! The women that I’m particularly shaped by are women leaders. I’m trying to build a company and lead a team at the same time. Of course I want to be “good” at both so I look up to women that are successfully doing this like Alexa Von Tobel of LearnVest, Sheryl Sandberg of Facebook, and many of our own Contessas.

The culture of women in the workplace is shifting. It not every woman for herself, but rather, you scratch my back, I’ll scratch yours. Why do you think this shift toward empowerment is vital?

One of my favorites quotes is, “When women support each other, amazing things happen.” This is 110% true and I think women are catching on that supporting each other and rooting for another woman’s success won’t dampen your chances of succeeding.  I also think this shift is vital because empowered women help empower others and they serve as role models for everyone coming after them. 

"Rooting for another woman’s success won’t dampen your chances of succeeding."

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What does it mean to be a Career Contessa?

It means realizing that your job can and should be an integral part of your life. It’s part of what makes you feel fulfilled and, ultimately, happy and sane. A Career Contessa knows that thinking proactively about her professional growth is both necessary and empowering. She’s daring and she takes constant risks. She also makes mistakes—sometimes huge ones—but she knows how to evolve from them and she has a sense of humor about it. Honestly, she’s the sort of woman who’s way too smart for cheesy, traditional career advice or gross life coach retreats. but she’ll read all day about careers and professional growth when the information is clever and valuable. That’s who we’re trying to reach.

What about those WTF career moments? Where you think, I have no idea what I’m doing. How do you work through those?

Easy. I find other women to talk to. I’m not the first woman to launch and build a business and I wont be the last. Yes, we have Google to help but nothing replaces a great conversation with another women. The energy, momentum, and direction I get from a career conversation with another women is really vital to moving me out of me WTF freak out moment.

"The energy, momentum, and direction I get from a career conversation with another women is really vital to moving me out of me WTF freak out moment."

What’s next for you in 2016? 

2016 is going to be a big year for growth for Career Contessa and me. At Career Contessa we are focused on building our brand awareness and Hire An Expert service. We’re also focused on more engagement opportunities like our monthly webinars, college tour, and other workshops.  Navigating your career is tough— and pretty much never ending—but we’re doing our best to make it fun and personal.

Photos courtesy of Joe + Kathrina