Wednesday, December 23, 2015 Gabby Bill 0 Comments

One of the cool things about being a career coach is that once people hear you're in this line of work, they become really interested in talking to you about their jobs. And that's great, because I find that even people who think they've had boring careers inevitably have experienced something super cool and unique that makes for a compelling story.

I'm motivated to pass along what I hear not only because people are unbelievably fascinating, but also because I'm on a mission to convince you that dream jobs exist. I've been chanting this mantra consistently, but people still look at me like I'm an alien talking about unicorns and pots of gold at the end of the rainbow. Clearly, additional evidence is needed to support my claim.

And that takes us to today and the very exciting launch of a brand new series of posts on Career & The City. A few times a month, I'll bring you stories of people whose careers deserve some time in the spotlight. Sometimes we'll talk about their career path; other times, we'll laser in on a topic or experience that might teach you something. With each of them, I hope you find a kernel of inspiration and maybe start clapping your hands in rapturous belief that fairies exist (OK, I'll settle for the former). No matter what, I'd love to hear your feedback and ask that you please send me a note if you, or someone you know, would be a great candidate for this series.

The honor of being our very first Center Stage chica goes to my friend and former HBS colleague, Christina Appleton. I love Christina because she's like a living bubble laced with a disarming and wonderful undercurrent of sarcasm. From the moment you talk to her you can sense her effortless effervescence, but then just when you think she's an endless optimist, she'll throw in a barb that forces you into a state of eruptive laughter. It's a pleasure.

Why else do I love Christina? She's had an amazing, twisty-turny career.

It started off normal enough, as most careers do. Armed with a degree in psychology and sociology from Northwestern University, Christina marched straight into a prestigious brand management position at General Mills, worked there for three years, and right on schedule, went to business school. (In her words, "When you get into Harvard, you go to Harvard.")

Business school was fantastic, but her career plans didn't fall into place as expected. It started with an ill-fitting summer internship at Sony Corporate in New York where she learned that business development was not her thing. Thinking perhaps she should try the creative side of the entertainment industry, her story continued with a painful post-graduation job hunt in California where she spent most of her time in a tiring commute from San Diego to LA for interviews. As a Harvard Business School graduate with an impressive, classically-trained CPG background, this wasn't the happy ending Christina thought she was in for.

Things took a turn for the better when, after a year and a half, Christina snagged a job working with Fox Sports in LA. She was given the awesome opportunity to develop and grow a brand new program - Fox Creative University - that combined sports, marketing, business savvy and both on- and off-air campaigns. As expected, she ran with it -- until it starting running her.

The program grew rapidly, to the point where she could no longer manage it on her own. Rather than give up, Christina hung on, developing ideas to continue to grow the program, while simultaneously making it more manageable for her life. Her leadership team shut her out. It became clear that they didn't truly care about Christina's happiness or sanity, and this felt like a slap in the face after all she had dedicated to the work. When she couldn't take it anymore, she quit without another job to go to.

This was a turning point for Christina. She had spent the last three years searching for her "place" in the working world, and ultimately, wasn't finding the satisfaction she craved. But pinpointing what was missing was tough. Wisely, she took a much-needed break to reflect, and what she discovered surprised her.

Christina comes from three generations of familial entrepreneurs, but had always told herself that the small business world was the very last thing she wanted to experience. Her great-grandparents had started a family grocery store, which her parents ran while she was growing up, but as an adolescent Christina had noticed more challenges with the lifestyle than benefits.

"My parents never took a vacation, and anytime something happened, it was always their problem to solve," she says. "Working at General Mills, at the end of the day if you screw up, it's just cereal. But for them it seemed like a very difficult life."

It was funny, then, that as Christina reflected, she couldn't get start-ups off her mind. She realized one of the most important things in her work was the ability to truly make an impact, influence a business and "matter" to the company. She was tired of feeling like a replaceable cog in a giant wheel, constantly at the whim of decisions made for her by a faceless c-suite executive who would never know her name.

Of course, moving to a start-up or small business would solve for this problem, but would also mean facing some of her previous fears: things like not having work/life balance and being directly responsible for the consequences (or successes!) of her decisions. Scared or not, she leapt toward the challenge.

For her first role, she took a job doing marketing, sales and operations for a weight loss startup, mostly because they were able to pay their employees -- something not many early-stage companies can do. After a few months, she transitioned to an interior design company, and about 8 months ago (it's commonplace for start-up employees to change jobs frequently), she took a job at the rapidly growing online health retailer, Thrive Market, where she leads merchandising and purchasing. And she loves it.

For Christina, the start-up world has provided the symbiotic work environment that she craved. She's free to dig in deep, make a big difference and grow her skills as she tackles challenges for which the path is unpaved. In return, she brings to the table a stellar resume with experience dealing with big personalities, unwieldy corporations and massive cross-functional teams.

And her fears about decision making and work/life balance? Unfounded. Christina had developed "rules" for herself based on things she observed or from what was "en vogue" at the time, but had never actually put herself in situations in which she could test the validity of these thoughts. When confronted with the challenges head-on, she realized neither actually bothered her, and in fact, they excited her.

"I sit and look at our e-commerce back-end and I'm changing pricing and putting together categories," she says with glee in her voice. "Plus, I realized that I don't need work/life balance. I actually want work to be a big part of my life."

Christina doesn't pretend that start-up life is perfect and readily admits that it can be tumultuous, but in her mind the risks are worth the reward. She envisages herself as the operationally-minded businesswoman that comes into a team of creative dreamers and "creates order out of chaos." She's fired up by the chance to shape the foundational structure the company will need to support the growth they crave and loves seeing the immediate impact of her decisions.

These days at Thrive, Christina's role focuses on negotiating with warehouses, managing inventory levels and pricing, and ultimately aiming to create the best customer experience possible. Her aim is to stay in start-ups as long as the market allows, ultimately moving into a COO-type role where she can use her strong project management skills to focus on a business' operations. She feels challenged and excited by her work every day, and for the first time, can say she's one of those people that loves reporting to the office.

I asked Christina if she would share her advice for breaking into the start-up world, and she offered these five tips:

  1. "Throw out all of your expectations about who your coworkers are, who they should be and what work looks like. Going from an environment where everybody was an MBA or came from a top college program, we were all taught to approach or solve problems in a similar way. Going into start-ups maybe one or two other people have an MBA. You have to learn that just because you’re used to everyone approaching things the same way doesn’t mean it’s the best way."
  2. Recognize that "every single start-up founder is crazy. The thing you'll find is that they’re all crazy in their own way. Understand the kind of crazy you’re ok with. Talk to as many people as you can. Whatever seems less weird and not so bad to you is who you should work for."
  3. When you're negotiating your offer, you have to choose to negotiate for equity or for salary, not both. "If you don't have to worry about the cash flow as much, it’s most important to negotiate the equity side. If it was all about salary for me, I would have gone and worked for McKinsey like everyone else. On the other side, I have friends who are single and they focus more on the salary. [Figure out] what’s the bottom line that you need [cash-wise] to pay your bills and to save in case it goes under."
  4. "You can be a structured person in the start-up world. Maybe I just missed that page in business school, but it wasn't clear to me. People think there’s only a need for big dreamer, creative types, but every start-up is going to become an actual business. They need someone to focus the big dreamers and get them to think about economics and ROI; how to make this an actual business."
  5. "You have no data about what you’re getting into when you’re going to a start-up. When you join a corporation you can talk to people, you can research what it’s like to work there, but none of that information exists at a start=up. You have to just take a leap and sometimes it works out and sometimes it doesn’t. Know when it's [time to stay] and when to cut your losses."

If you'd like to connect with Christina directly or have additional questions about start-up life, you can reach out to her on LinkedIn or via email

Now it's your turn. If you've worked at a start-up, do you agree with Christina's advice? Has your experience been markedly different? If you want to work at a start-up, what are your biggest concerns or questions? Let me know in the comments section below!

Gabrielle "Gabby" Bill is a career coach and consultant who believes everyone should be working in a job that leaves them feeling fulfilled. She coaches groups and individuals through a reflection process, uncovering often hidden motivations, values, goals and skills as they relate to their career. These reflections are then parlayed into concrete action plans to guide clients through the process of finding, creating and landing their dream jobs. You can learn more about her services by visiting