A Gentlewomen’s Guide to Making it in the Tech World

Maybe it’s something in the water (or on Newsweek magazine covers), but I have been getting asked a lot lately for advice from young women about how to succeed in business and overcome the significant anti-female bias that still exists in many quarters, but especially in Silicon Valley and finance. The question often sounds like this: “you have done so well and so few have made it as far; what did you do differently to make it?”

That’s a really flattering observation, I must say, and I appreciate the attention, but I also think that it is only in retrospect that I can look at my own experiences and actions, perfect or imperfect as they are (healthy helping of both), and think about how it has all transpired. It’s not as if I had some grand plan or even believe that one could be created, firm adherent as I am to the religion of luck and being in the right place at the right time with respect to how things typically go in a career. But that’s not to say that you can’t try and do more and be proactive if you are a young woman (or any age woman) seeking to move to the next space in the game of Life.

Last night I had the lucky lucky occasion to hang out with three of my sisters-in-arms, Jane Sarasohn-Kahn, Alexandra Drane, and Susannah Fox. All three are powerhouses, well recognized for their accomplishments in the healthcare field and highly sought-after business leaders and speakers. We spent an entire 6 hours together (9 if you count the fact that Jane and I first snuck out to see a Broadway matinee of A Gentlemen’s Guide to Love and Murder, which is about as great and funny a show as I have ever seen).  Much of our conversation, mostly inadvertently, led to a short manifesto of ideas for how women can better their situations in the workplace and generally in life. As a person who is never anywhere without a pen (though I am not so perfect that I didn’t have to borrow some paper), I was able to capture some of the really useful thoughts to pass along to those of you of the XX variety (although I know that some of you XY people are closet supporters of this endeavor and can also benefit from some of these same thoughts).

So here it goes: the collective wisdom of the Four Miss-keteers, as it were, informed by good food, good drink and a lot of experience in the trenches.

1. Be a lifelong learner; keep sucking up new knowledge and never stop because you think you are a so-called expert. Particularly in healthcare (and probably everywhere else too), change is fast and furious. If you stop seeking to understand the next trend, the newest technology, the lastest regulatory implications, the changing healthcare economy, you will rapidly go with the way of the dinosaurs. “Expert” is a title that goes stale faster than you think.

2. Be humble. This doesn’t mean you shouldn’t promote your own successes in a thoughtful, factual and obvious way, but it means you shouldn’t get arrogant about it. It’s often hard to find that fine line between self-promotion that leads to career advancement and self-love that makes everyone in the room want to get away from you, but keep looking to stay on the human side of that line. The minute you think you’re all that and a bag of chips, you will be reminded that God (or whomever) likes a good joke and particularly one that sets you on your posterior for all to see. Yes, in Silicon Valley we see the guys running around with a lot of brio and arrogance at times (not all of them, but enough that it has become a legendary joke about the place). Do you want to be part of the joke? I don’t think so.

3. Embrace your failures and don’t let it stop you from trying again. Too many people get so scared by their own mistakes that they stop seeking to move forward. They get wrapped up in their shame and embarrassment and forget that this happens to pretty much everybody in the business game. I am quite sure that if you go through the mental rolodex of people you know you will find that every successful person in it has been fired from a job, screwed up and lost money on an investment, made a total ass of themselves at one time or another. And yet there they are on the cover of Fast Company. I can assure you that every successful company I have seen close up has had a moment where the CEO made a bad choice that could have brought the company to ruin. Behind every successful person is a trail of bad decisions. It happens. Learn from it, get over it, don’t let it define you.

4. Have a small group of confidants who you can expose your weaknesses to and who will be there to catch you when number 3 happens. As Alex Drane told it last night, it is particularly great to have a group of people who will say, “Hey, you think that’s bad? Let me tell you how I did it worse…” It’s so essential to have a pit crew of like-minded people who are there to remind you that you are awesome and worthy of love and success in those moments when insecurity becomes your hoodie. And don’t for a minute think that anyone doesn’t have insecurity from time to time. The trick isn’t to never be insecure (that is impossible); the trick is to know how to pretend you aren’t when you are in front of a room of people you want to impress. I think it’s really important to remember this. Everyone, male and female, is insecure sometimes. Anyone who tells you they never ever feel insecure or down on themselves is a liar.

5. It’s ok to love and prioritize your family and not to pretend you are indifferent about them with your work colleagues. I will never understand why men are never asked about how their family obligations might affect their work lives but it’s perfectly fine to assume women’s careers must be complicated or compromised by the kids (not the men, but that too). Don’t men love their kids and want to take care of them? Weren’t they the guys that put the Y chromosome on the board? Seriously. It reminds me of that Chris Rock routine where he criticizes some men for being idiots because they say things like, “I take care of my kids!” like it’s a badge of honor. Sorry, boys, it’s your job to take care of your kids. If you made them, you own them.

And of course it’s the same for women and that should not be treated as an affliction. I am not saying that having a big career and a family will lead you never to feel guilty about how to balance them. Guilt appears to be one of the core values of women executives, as far as I can tell. It’s a shame, because guilt is pretty toxic, but it can also drive one to extraordinary levels of multi-tasking productivity. So that’s the silver-ish lining. Whatever you do, don’t pretend you don’t have a family or don’t need to worry about them in order to appear more advanceable in your career. That’s just wrong and any man who takes that path should be ashamed. In one of the episodes of the Tech Tonics Podcast, that I do with David Shaywitz, we interviewed Geoff Clapp, CEO of Better, Inc. It was so refreshing to hear him talk about the complexities of being a single dad and I am not sure I have ever heard that candidly discussed before. Shame on the others with kids who don’t make family a part of their lives that is equally important to work. As they saying goes, no one wants their tombstone to say, “I wish I’d spent more time at the office.” Be worried about what it will say if you neglect your family and leave them to choose your epitaph.

6. Just be who you are. Love the imperfect being who inhabits your clothes and don’t waste a lot of energy trying to pretend you are something you aren’t (except per number 4 above when you are pretending you are not insecure). Energy and time are the most precious resource of professional women, so using them up by trying to be something you’re not is like wasting water in a drought-ridden California. It’s bad form and bad for the community. The more you try to be whomever you aren’t to win over others, the less you will like yourself, so it’s a vicious cycle. This means saying what you feel and think and contributing to the conversation from your own perspective. It’s an amazingly refreshing feeling to give words to the truth and to say what’s on your mind, albeit in a professional way. I wrote a whole post about this once so I’ll just reference that HERE.

7. And the other not so little things: always have a pen and paper (or electronic means) of capturing your thoughts.  A good black dress can hid a lot of sins.  Prioritize sleep. Don’t say mean things to yourself (saw an article about that just today) because after a while you start to believe them. Get fresh air every day. Don’t ever give up your friends for a man or a job (you will need them to perform number 4 on this list). And once in a while, just buy the damn shoes or take the day off or eat the chocolate or have the extra glass of Prosecco (or bourbon in my case) or whatever it is that soothes your soul in times of need. Last night the four of us practiced this task liberally and I have it on good authority that we all felt better for it today. Trust us, we have enough miles on us to know.