National Women's Political Caucus of Washington

5 Questions with Tiffany Dufu

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We sat down with Tiffany Dufu, Founder and CEO of The Cru and New York Times best-selling author of the book, Drop the Ball. Dufu was a keynote speaker at Merrill and Bank of America’s 2019 #WomenInvested event in Bellevue. Tiffany lives in New York, but she was born and raised in Tacoma, Washington. 

When asked what she does, Dufu shares that she relentlessly pursues one goal: a world in which women’s gifts and voices are fully harnessed for the benefit of all of us.

Her good advice and personal revelations span gender and generation. 

Question: We love the concept of being OK with “dropping the ball” but what about the single mom who is working two full-time jobs just to get by. Is being able “drop the ball” only an option for some women as a result of their privilege? How can this concept apply to an individual who has never felt they had the option?

Dufu: I define dropping the ball as letting go of expectations that we have of perfection, and figuring out ways to engage people in our lives. So it’s called “drop the ball” not “get other people to pick up the ball” because for me, it starts with the self. 

In my research interviewing a lot of different women, some paid, some working moms, some not, a surprising lessons for me was how single moms are often much better ball droppers than women who are married, in the workforce, particularly those married to men. In fact, some research just came out and there was an article in the New York Times about a study done that said straight, married women in the workforce do more housework than single moms. It sounds very counter-intuitive but in my connections with single moms, it makes so much sense. 

Single moms are less seduced with this idea that your home has to be perfect. This is by virtue of their lived reality, and so they have kind of let go of the expectation that they are going to have a perfect home, that everything is supposed to happen neatly or perfectly. In part, because their lives don’t “measure up” to this unrealistic ideal standard. They have had to let that go. 

Secondly, single moms have more experience with getting support and asking for help by virtue of having to do that in order to function. Oftentimes, women who are not single and are married and working outside the home are able to mask and pretend and get by without getting the help they need. 

And third, I found that single moms tended to have children who were more self-sufficient. This is because their moms don’t have the bandwidth to do every little thing. They end up with kids that are more self-sufficient and better helpers around the house. I think there is a lot we can all learn from single moms about how to go about our lives in a way that’s not incessantly trying to meet the expectations of some third party, but really doing what is best and right for us and our kids.

Question: You spoke about pressure to succeed at work. For young professional women who are also the primary wage earners of their households, daily pressure can stifle risk taking because it can affect the household finances and family life. How does someone take that leap? 

Dufu: I started a company called “The Cru." I launched it last year, so I’m an entrepreneur. In the beginning, the business doesn’t necessarily make money because I was investing back into the business. I’m not the primary breadwinner, but I have economic responsibility. Our family couldn’t afford for me to not bring in income. 

I think this is the most exciting time to be in that position, in large part because the future of the world economy is much more democratized. Depending upon what your passion is or what your side project is, you can launch it with very minimal investment in some earlier version. I mean, if you happen to love flowers and you want to open a flower shop, you can start by making arrangements and picking great images of them and putting them on Instagram and developing a following. You can start by planning events on the weekends and doing the floral arrangements. I’m completely making this up, but there are so many ways for you to start with just a side hustle and build up a platform with the tools that we now have available. It is nothing to go onto one of these sites like Squarespace that pays to create a website and you don’t have to know how to code in order to do that. 

The biggest challenge for women is: what is that going to be? What is the business going to be? How can I monetize that in a way that demonstrates my values? For me, it was less how I was going to figure out how to cutback and rearrange my work schedule. It was more about getting the bravery, the courage, and the knowledge to know that I had something to offer the world that was so enormously valuable that people were going to pay me for it. 

I was used to getting direct deposits every two weeks. Which, by the way is not security. People feel that this is security, but in today’s world, all you need is a restructure and then that direct deposit that you thought was secure, is not. It’s actually much healthier to have a diversified portfolio – which I’m sure someone at Merrill would want us to stay – but thinking about that in terms of your income as well. I have a diversified work portfolio now. I earn income through public speaking, I’m an author, I’m an entrepreneur, I have other investments that I make that sustain me so that I have more flexibility.

Question: In your book and in your presentations, you share that the more you ask for help, the less you will need to do it. How do you think this plays out in many women’s daily lives? What do you think holds us back from being able to ask for help? How can we remind ourselves to ask?

Dufu: What happens fundamentally, is that we don’t believe that we are worthy of the help and the support. It’s hard for us to imagine why someone would want to help us and get nothing back in return, for free, ostensibly, when we perceive that we don’t have anything to offer in return. That’s part of what it is, we think: “Why would someone do that?” 

The crazy thing about that mindset is that as women we do this all the time for people. We would drop anything to support someone else. When I was in the air coming here today, I found out that someone close to me had lost their mom. She happened to be here in Seattle visiting her. I knew I was getting back on a flight after this event but we met, if only for a moment to hug and talk. As women are so willing to give help that we shouldn’t fear asking for it in return. 

Asking for someone for help is giving someone else an opportunity to learn and to grow. The first year after my book was released I traveled a lot. I was expressing gratitude to my husband at the end of the year for missing out on sleep. When one of us travels for work, the other has to do the double duty of getting the kids up, getting them ready and getting them to school. And he said to me, “Tiffany, thank you, but I didn’t lose any sleep this year.” And I was like, “How did you not lose any sleep? When I have to get the kids up, I get myself up an hour earlier. I get myself ready first, then I get the kids ready and then we leave out the door.” When he told me what he was doing in the mornings to get the kids out the door, my mouth dropped open. He basically said “Oh, I just get myself up at the same time I would normally get up, and then I go into the kids room and basically make a proclamation that I am going to set a timer for 45 minutes and I need them at the door, dressed, with their shoes, with their backpacks, and breakfast in their stomachs because mom isn’t here and I don’t have time to get you ready.” My first response was, “they can do that?” 

Whether it’s at home, or at the office, there may be something you’re working on that may be an amazing growth opportunity for someone on your team, for an associate. But you’re not letting go and you’re perceiving that it has to be done in a particular way. You’re actually robbing someone else of an opportunity to grow. I think it’s critical.


Question: All the things you mentioned in your Ted Talk – opening every piece mail every day, eating leftovers in a specific order, folding the towels a certain way – was your HCD (Home Control Disease). While I wouldn’t go as far as eating leftovers on a schedule, I feel a strong connection around having a clean and organized house and being able to be productive at work. How do you come to terms with dropping the things that real don’t matter, but tend make you feel better or more in control?

Dufu: One of the privileges I have is that I can connect with the stories of a lot of women. Women are honest and open in sharing their struggles. What you are experiencing, the next woman is also probably experiencing. One of the things I do sometimes is introduce a woman I met with at 9 a.m. to the woman I meet with at 10 a.m. and I say, “The same thing you’re having a problem with, she is about to talk to me about that exact same problem.” 

The behaviors, for example, making sure things are tidy at home and this feeling of productivity – you are the source of that, but it likely came from outside of you. You do have the power to recreate what behaviors you associate with what values. We know this because a man can be sitting in a very messy apartment and feel like he is being very productive. All we have to understand is that this socialization, particularly around women’s primary roles as a mother, causes us to quickly jump to, “Oh, my gosh! There are dishes in the sink, I’m not a good person”. That’s how that happens, and recognizing that is important.

And that’s why it matters to figure out what is important to you, so you can have some kind of framework for saying to yourself “actually, what I have determined is that my career trajectory, at this phase, is most important to me.” Or, in my case, it’s getting Cru off the ground. It’s a startup, it’s going to require an enormous amount of time and energy, and if that means that dishes are in the sink piling up and spilling over, that’s okay, because I’m building a multi-billion dollar company. One day I will be able to have a staff come and clean these dishes. Until now, a little mold is going to have to do. 


Question: What does a “Drop the Ball movement” truly look and feel like? 

Dufu: For me, it’s freedom. One of the tragedies of our modern world is that so many women who are smart and talented and creative and innovative and who, every single day, are just trying to do right by themselves, their families, their communities, and their organizations, feel as if in the process of doing so, they’re committing some kind of moral transgression. 

That’s what guilt is. Guilt is the feeling that you’ve done something terribly wrong, and I find it infuriating, actually, that so many women feel this way. I’ve never met a woman who was a slacker. I’ve never met a woman who was like “I was late because I was at the spa not doing anything.” 

Anytime a woman is late for anything she apologizes profusely. And she’s always late because she’s doing something for someone else. I just would like to obliterate guilt, obliterate this feeling that we’re not enough. I think that’s energy that is much better served in solving some of the biggest problems we have right now.

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