Lauren is the Founder & CEO for Career Contessa, which facilitates honest conversations by real women about work and life—to help women achieve fulfillment and balance in both. 

How did you come up with the concept behind Career Contessa?

This is really a two-part story.

Part one: I graduated in 2009 and fell right into a dismal job market that led me to take the first full-time job I could get. The happiness didn’t last long since I hated the job and the company culture wasn’t a great fit. This really spurred my obsession with finding a job I would love. Eventually I got introduced to recruiting as a career and immediately knew that is was the career I wanted to pursue, but I had no idea where to start.

So, I started on LinkedIn and connected with any LA recruiters that would accept my request. Once they did, I would ask for an informational interview so I could learn everything about what it was like to be a recruiter. I ended up having more than 30 interviews over nine months and learned everything I could about the specific type of recruiting and company I wanted to focus on. When a job in university recruitment at Hulu opened, I very aggressively pursued it.

While working at Hulu I noticed the amazing impact having a job I loved, at a company I loved, had on me throughout my work life and my personal life. Even more amazing is that I landed the job not because I was the most experienced, but because of the information I had collected through listening to other recruiters tell their career story. The informational interviews provided me the education I needed to land a new job.

Part two: While I was working at Hulu I was finishing my master’s thesis on millennial women and career resources. As part of my thesis project I created a mock-up of Career Contessa which, featured written informational interviews with successful career women as a way to provide career direction, and presented it to focus groups. The response was overwhelming and it was the catalyst that convinced me to move forward and make Career Contessa a real career resource for women.


Once you knew you wanted to launch Career Contessa what steps did you take to make that a reality? 

Before I thought about the website I knew I needed to collect an inventory of interviews. I also knew that I wanted to have strong visuals to include with each feature. So I used Pinterest to teach myself about photography, borrowed a camera from my dad, and sent cold email pitches to career women I wanted to interview.

Next, I would go to the woman’s house and record the interview followed by taking photos. Then I transcribed the interviews and edited them. I only did interviews for about nine months before I brought on additional help and reached out to a professional web development company to design my website.

Having a professional website was always important to me and I selected a company that was in the same building as Hulu to create it for me. I paid for everything out of my own pocket. I would go down on my lunch break to discuss the site’s function and design. I absolutely loved the creative process.

Collecting interviews, editing photos, and designing the site tool about 18-months before we officially launched on October 21, 2013.

What lessons have you learned along the way?

There are so many! I wish I had thought about my site more as a business from day one. Specifically, I wish I had been more thoughtful about building my email list and spending the time to create a strategy for social media.

I’ve also learned a lot about how to build and work with a team. Running your own business is very personal, but I’ve had to really learn how to separate my emotions from the business.

What has surprised you about starting & running this business?

The amount of detail that gets poured into every decision. Also, the amount of uncertainty that you have to endure when you’re starting and running a business.

Do you have a daily routine or certain rituals you do?

I like to get up early and make time for myself. A ritual I have is going for a long walk each morning before my day gets started and trying not to look at email right when I wake up.

What hardships/obstacles have you had along the way?

Building a team has been an ongoing obstacle because I’ve mostly hired freelance employees. Freelancers are very talented however; they are always balancing multiple projects at once.

Another obstacle is content marketing. We publish content at least once a day and it’s my job to make sure as many see that content as possible. Marketing is a puzzle and there are times when you’re left to create the missing puzzle piece too. I spend a lot of my time Googling information and talking with others about marketing.

What do you wish you would have known going into this?

To be patient. No one is an overnight success and it can, and often does, take years of building a brand before anything happens. The Internet is crowded place so you have to be creating something valuable if you want your readers to give you their time and email address.

What have you found works for you as far as organizing your business and time?

I’m all about a notepad and pen to make my to-do list. I know there are fancy project management tools, but I like the physical act of writing it out. I also like to plan my day each morning and prioritize the day. There is something therapeutic about starting the day like that.

Highlight of your career so far? Low point?

It’s hard to nail down one career highlight! They are so many like our launch in 2013, when I left Hulu to work on Career Contessa full-time, hiring our first full-time employee, landing partnerships with brands like Refinery29, our first sponsored content, etc. It’s a nice thing to reflect back on where you’ve come. Each day is not filled with highlights, but I feel lucky and grateful for the ones we do have.

Looking back, what would you do differently?

I don’t have any regrets and I wouldn’t change anything. That doesn’t mean each day has been full of rainbows and high-fives either! I strongly believe that everything happens for a reason. A good example is when I had to switch my business plan mid-site development. It was very costly and it really made me second-guess if I should be pursuing Career Contessa, but I survived it. I picked myself (and Career Contessa) up and we moved on. Now I’m happy I made that mistake because it provided such a valuable learning experience that has helped with my decision-making skills going forward.

Best advice you’ve been given? Any advice that you’d give other entrepreneurs?

The best advice I’ve heard is that clarity comes from engagement. If you’ve got an idea for something, just get started. Talking about it and thinking really hard on it won’t build anything.

Also, a walk and some fresh air can cure almost anything!


Photos by Joe + Kathrina