What Entrepreneurs Can Learn From Taylor Swift And Other Game Changers

In a world where change is now a constant, what can we learn from a serial entrepreneur, a sports executive, and a Wall Street powerhouse about re-evaluating the status quo and changing the game?

Taylor Swift’s Tumblr post and Apple’s quick response has generated lots of articles about her influence and business savvy.  Similarly, the number of articles on women entrepreneurs and success of women-focused venture funds over the past few weeks have skyrocketed.

My takeaway? There has never been a better time to talk about female business prowess and the power of female consumers.  And the lessons we can learn from all of this regardless of our gender.

From the perspective of someone who is passionate about unleashing the human potential and eliminating the gender bias, these events are even more poignant. They mark a shift in mindset.   It’s shift to a mindset that’s taking full stock of one’s assets and testing existing assumptions of what is possible. Swift and successful  leaders see the wider realm of possibilities, and then, they got into the driver’s seat to create the type of change they wanted to see.  

They didn’t wait for things to happen. They had agency and acted on that to create value.

And yet, all too often, we (especially women) wait for the dream job to come into existence and then to hire us; wait for an organization to recognize our value, to be asked to join boards, for those in positions of power to ask us to join their club.

The reality is, we have more agency than we think.  In looking at the assets (our networks, our skill sets, our talents and experiences) and understanding what we truly have, we can create the types of things that have tremendous value and that generate value for others rather than waiting for them to acknowledge our value. We can create the thing that others would want to join instead of waiting for others to invite us to join.

One of my early memories of career advice came about when watching a Madonna biopic with my dad (my first mentor).  In one scene, she didn’t get a record deal she wanted.  But instead of wallowing in rejection, she assessed what she had, summoned up courage, and went on to create her own record.   My dad turned to me and said.

See, she didn’t let that one setback get her down.  She didn't wait for the record company to accept her.  She figured out a way to create her own opportunity and make it happen."

I remembered this advice again when years later, my friend, Kimberly Jenkins, shared a  story from an early phase in her career.  One of the most creative and entrepreneurial people I know, Kimberly had always been passionate about education, receiving a PhD degree in the field. As a doctoral student, she audited a business course where the professor had advised her to give up pursuing a PhD in education and instead, switch over to business where she can have a more lucrative career.

She disregarded his advice and ended up in Seattle at a new startup. While there, because of her background in education, she saw an opportunity for the company to partner with universities and apply the product to education. Though the founders were doubtful of the idea, she persuaded them to give her the bandwidth to test out the idea. Instead of waiting for that perfect education job, she created value and ended up creating the education division for the startup - Microsoft.

Madonna’s and Kimberly’s stories happened in the eighties and nineties during a time when the ability to create one’s own opportunity weren’t as accessible.  Today, there is more opportunity and more support to actualize ideas. 

I’m not talking about breaking the rules. I’m talking about reassessing the rules to see which ones no longer apply and then, changing the game.

Every person has a different set of assets and the opportunity has to be authentic to their assets and be responsive to the constraints of their individual circumstances.  In other words, there is no one size fits all.  Each one of us just needs to figure out what we can bring to the game, how to put everything together in play, and have the fearlessness to move forward.

Here are three pointers from three game changers as a start:

Find the work environment that allows you to be you. 

Carla Harris, a Wall Street powerhouse and vice chairman and managing director at Morgan Stanley, once shared this advice with me in one of my Center's LifeChat interviews. What I admire about Carla is her wide range of talents – from being a gifted banker to noted speaker and author of Expect to Win and Strategize to Win, to amazing gospel singer.  I love the incredible way she can energize others in a room by giving them the space to bring their full selves to the table. She once said:

Part of being authentic is choosing a working environment or a job that lets you be you. It may not be the natural part of you, but you need to pick a seat where you can bring all of who you are to the table.

She talks about Morgan Stanley as a place that does that.

“For example, I can come in to Morgan Stanley one day as ‘Carla the singer,’ and when it’s time to be social, I become ‘Carla the party person, and same for  ‘Carla the spiritual warrior’ when necessary. When there is a deal that is not going well, I will skip lunch and tell my team that I am going to Mass to pray about it. I think you enhance yourself in any environment by bringing all of yourself to the table."

"You can’t suppress all the unique things that make you," she continued, "Because that is your competitive advantage. Being you is something you do best; better than anyone else, as much as they might try."

Cultivate mentors and friends who can help you unearth what you love doing.

Melissa Bernstein and her husband Doug had started up their toy company, Melissa & Doug, without any formal business training, but with a vision for creating toys that had educational value, can spark the imagination, and a company with keen care for its customers.

When I asked her how she mustered up the gumption to enter into seemingly unknown territory, she shared the following with me.

Following your gut is hard for women because we're pleasers. Women know what they are passionate about, but are sometimes afraid to say it.

But if you have a mentor or a loved one who allows you to reflect, asks you what you love, and lets you think creatively, you will more easily be able to find your passion in life and discover what you love to do. Women often have to go against society’s idea of success and find our own passion, and pursue our own dreams. By using your passion to craft what you do, you will be able to create a career around what you love."

Today, their toys are in more than 80 countries and beloved by children all over the world, including my own.

Be what you can’t see.

Donna Orender is an innovator and pioneer in many domains from business to sports to digital and entertainment industries.  In one of our many conversations, she and I were talking about the need for examples of those who had done it.  I shared about my center’s Women’s Leadership Initiative and quoted Marie Wilson -You can’t be what you can’t see - as the need for more women examples.

Donna responded back –

It’s also about being what you can’t see. To disrupt the status quo, you need to imagine a wider realm of possibilities and sometimes go for the seemingly impossible."

What I admire about Donna is that she has always been unfettered by pre-existing notions of what is possible and can separate out the false assumptions.   She was the Commissioner of the WNBA who took the league to another level. As the mother of twins, she decided to step down to spend more time with her children and during that next phase of her career, she saw the power of getting people together and the ripple effects of individual positive change.

So, she created GenerationW, which has affected thousands of lives through helping people see their personal strengths, which then cascades to community, national, and global impact. Her career has been one in empowering others to do the seemingly impossible.

I reflected on her comments.

If someone had told my twenty-some year old self that today, I’d be able to create positive changes as the head of a leadership think-tank center at Duke University, as a member of boards,  a coach for entrepreneurs, working with military leaders and sports industry executives, and being a mom to 3 wonderful children, I would have thought it all a stretch from the realm of possibility.    

Looking back, I have no regrets because I love where and who I am now. I just wondered how much faster I might have arrived here had I also taken stock of my assets and strengths and created, instead of reflecting solely on my shortcoming and waited out of self-doubt, out of being in the comfort of a game in which the rules were familiar.... 

When have you been the game changer in your own career? Share your story in the comments below. 

Sanyin Siang is the Executive Director of the Coach K Center on Leadership & Ethics (COLE) at Duke University's Fuqua School of Business.  She also serves on the committee of Duke University's Women's Weekend.