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Tips from the Corner Office: A Silicon Valley Insider’s Take on Success

Tsai, Christine “It’s said that experience is what you get when you don’t get what you want,” says Christine Tsai, founding and managing partner of 500 Startups, a venture capital seed fund. “If that’s the case, then I’ve amassed heaps of experience over the years.” Tsai, who graduated from college “at the worst possible time—right after the dot com bust” and tried several times to get a transfer at Google before moving to the product marketing team, has learned that “perseverance is the most important trait you can have.” She considers it the secret to success. To tap more of her wisdom gained from succeeding in Silicon Valley, (which recent news has shown to be a boys’ club, no less), we asked her to play career coach for an hour.

How do you define success?

“Happiness is the best definition of success. I don’t believe money or position can hold a candle to that. Of course, some days are hard and you’re not going to love everything you do or be happy 100 percent of the time, but generally speaking, are you happy at work? In life? If you are, I would say you’re successful.”

What’s a career rule everyone should break?

“The traditional view is that you should map out your career, know what you want to achieve in a set time frame for the next five and 10 years. I say eschew that. You will severely limit your opportunities if you view your career as a linear trajectory where you’re constantly climbing a ladder. Instead, think of your career like a collection of stories or chapters. Or as Sheryl Sandberg puts it, a jungle gym.”

What’s your favorite mantra?

“‘An ounce of action is worth a ton of theory.’ I’m a big proponent of execution. Talking about doing things gets you nowhere. Actually doing stuff, even if you fail, is much more effective. Another quote that I equally love is, ‘Opportunity is missed by most people because it is dressed in overalls and looks like work.’ Many people, especially in Silicon Valley, have a sense of entitlement or want to be doing ‘strategic’ work versus things that are seemingly ‘beneath them.’ Or they’re quick to throw their weight with their title. Big turnoff. Even to this day, I still get my hands dirty and I firmly believe everyone should, regardless of their title or position.”

What would you tell someone feeling stuck in her career?

“Talk to as many people as you can to get a sense of what’s out there and what you’re worth. What helps even more is going into these conversations with the mindset that you’re going to leave your current role. It makes you committed to finding a new opportunity, and it also makes others more likely to help you than if you’re just ‘thinking about leaving’ or ‘exploring options.’ To commit to that decision is not easy, but remember that the sun doesn’t rise and set on any particular company or job.”

How do you get a mentor?

“I think it works out better the more casually and naturally it happens. I never approached anyone and formally asked, ‘Will you be my mentor?’  Rather, I interacted with a small number of coworkers and people outside the company who always had sound advice for me, and I viewed them as mentors. Depending on the relationship you have with a person, you can certainly make a point to meet semi-regularly for coffee.”

What career-advice book do you recommend?

Nice Girls Don’t Get The Corner Office, by Lois P. Frankel. It touches upon very specific, real-life situations of behaviors or actions women commonly do that may hold them back. I loved that it had actionable advice, all positioned from the perspective that women are in control. Oftentimes, the problem with unconscious bias or sexism is that they’re viewed as something women have no control over and we’re at the mercy of men, or it is up to men to ‘let’ women in. I fundamentally don’t believe that. The onus is on both genders, and I believe women should take matters into their own hands.”

How do you relieve stress?

“Sitting on the couch watching Netflix with my husband and sharing a pint of ice cream or boba tea is something I look forward to every night to let steam off. I also like to meet up with close girlfriends and catch up with them. Additionally, I enjoy baking. It’s relaxing to make something with your hands and it makes me feel productive. Finally, although I haven’t been able to make time for it recently, I love going to ballet class. Nothing like working up a sweat to get your mind off things and recharge your batteries.”