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Starr Sackstein of Mastery Portfolio: “Vision/Purpose ”

Vision/Purpose — you need to have clarity on what your vision is and you mustn’t waver in that vision. When you’re driven by a desire to help the greater good, you can’t go wrong. How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with […]

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Vision/Purpose — you need to have clarity on what your vision is and you mustn’t waver in that vision. When you’re driven by a desire to help the greater good, you can’t go wrong. How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love, and life as a powerful woman.

As a part of this series, I had the distinct pleasure of interviewing Starr Sackstein. Starr Sackstein is the Chief Operating Officer of Mastery Portfolio, an ed-tech start-up committed to helping schools transition away from traditional grading practices toward a more authentic, standards-aligned model. She is the author of more than 10 education books on assessment reform. Sackstein is the mother of teenager Logan and partner to Charlie, her co-adventurer.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”? I was always an eccentric, driven person. My parents knew at an early age I’d be a teacher, but I didn’t have that understanding until much later. I wanted to be a writer. For as long as I could remember I carried a notebook with me and captured my musings and observations in words and photos. Having grown up in a small, affluent suburban town on Long Island in NY, I often felt like an outsider. Since I played sports, sang in multiple groups, and was academically invested, I was that person who had friends in every group, fluidly moving from one to the next; I didn’t belong to any one of them and often struggled to fit in. Fortunately, I realized quickly that I didn’t have to. Once I accepted this reality, I comfortably marched to my own beat, taking advantage of whatever opportunities came my way. This has served me well in my adult life as it has solidified my ability to stay true to my own values despite not always aligning with the people around me. A strong sense of self has helped me transcend adversity.

Can you tell us the story about what led you to this particular career path? After working in IT for a few years, I felt frustrated and uninspired, so I decided to go back to school to get my master's in education. Since I have a degree in British and American literature with a minor in writing, being a high school English teacher seemed like the right move. Of course, I was idealistic about what it meant to be a teacher, and when I landed my first teaching job in NYC while I was still in my graduate program, I was shocked by how different teaching was than I expected. However, I always loved working with my students as they taught me as much as I taught them, maybe even more. Once I was in the classroom for a few years, I started taking more and more risks. When I didn’t get the guidance I wanted from my leaders, I took it upon myself to find learning opportunities that continued to push me and keep me engaged. Being just a good teacher was never good enough, I wanted to be the kind of educator students remembered long after they graduated and I also wanted to help change the educational landscape so more students had opportunities.

Can you share the most interesting story that happened to you since you began your career? I have been so fortunate to have a very interesting career so far and when you’re working with teenagers, they always keep you on your toes. So I’m not sure I’d be able to pinpoint a particular moment in my classrooms that may have been more interesting than another, but one moment that stands out as a career highlight was having the opportunity to present a TEDx Talk about giving up grades. I’m a natural introvert so every time I’m expected to be in front of a crowd or around new people, it takes a big effort. As I prepared for my Talk, I worked tirelessly to make sure I was super prepared. My students helped me practice and gave me feedback and when it came time to record it live, I was fortunate to have a friend and colleague there to cheer me on. I was really terrified and almost didn’t go through with it. Knowing my nerves were getting the better of me, the organizer gave me a nudge when it was my turn to go out onto the stage, and fortunately, the lights were bright enough to drown the audience out. For just under 12 minutes, I was completely in the moment, trying hard to just share my message. When it was over, I was proud of myself and already had reflected on how I would do it differently if I had another chance to present again. This was the first of many speaking engagements where I was building stamina and confidence as a speaker. I knew what I had to share had value and could help people and so I had to force myself out of my comfort zone to be able to continue doing work like this. The impact far outweighs my discomfort and I will continue to do it so long as I could help even just one person.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each? I’m a risk-taker — although they have been calculated risks, I’ve known there was a trade-off with every move I have made to get to where I am now. I was in a school for almost a decade and I loved being there, but I wasn’t growing as much as I wanted to be. It was a hard decision to leave the school, but if I didn’t leave it, I wouldn’t be where I am. In order to be able to make big gains, we have to move away from comfort and into the unknown. We take a leap of faith and then the opportunities happen. Every time I’ve decided to make a move, it has led to greater opportunity.

I learn quickly. Each time I have started something new, my learning curve was steep. Walking into the new opportunity, I fake it until I make it. Talking to anyone who will engage, asking a lot of questions, and humbling myself to know that I don’t know everything. Sometimes listening when you start instead of dominating offers an opportunity to observe and learn. During these shifts, I’ve built relationships quickly and wasn’t afraid to admit the gaps in my knowledge. My ability to ask and humbly learn has disarmed people and created more opportunities for growth.

I’m a collaborator. In order to be in a partnership in a company or in a school, you have to be open to other ideas and people. Although I’m passionate about what I believe, I want to work with people and lift them up in order for us to succeed as a team. Success is never mine alone and so developing good working relationships with colleagues is very important and welcoming other ideas and finding a way to work toward the greater good is essential for success. It’s because of my willingness to put my ego aside, that teammates are willing to partner with me.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so? Whenever a person breaks away from traditional stereotypes, the folks who like to exist in the status quo are uncomfortable. It has been my experience that powerful men are often threatened by powerful women. They try to silence us because we don’t conform and we are comfortable in our own skin. When intimidation efforts happen and we are unphased, they don’t know how to categorize us. Anyone who can’t be labeled easily seems to be a challenge. I’ve been in situations with powerful men in particular who sought to silence me because I didn’t fit the mold they expected me to and I’ve had to walk away in order to stick to my own values and ethics in some of those instances. Of course, there were times I stood my ground to give voice to those who weren’t in the room and didn’t have a voice themselves. I’m not afraid to be a loud voice when others are being silenced and I don’t care if people like me if it is a choice between that or getting an initiative through. My focus is always on the greater good and therefore sacrifices need to be made and sometimes that means being the unpopular voice.

Without saying any names, can you share a story from your own experience that illustrates this idea? I was often asked to do things that I didn’t necessarily agree with or didn’t align with what I knew to be right for my team or students. Rather than do as I was told, I’ve found ways to exploit loopholes and do what I know to be right, allowing the impact and outcomes to be drivers. Administration and/or other leaders weren’t happy with my blatant disregard for the rules when there was no way around it, but they couldn’t deny the outcomes. Because I’ve taken risks, I’ve put myself in situations that have sometimes gotten me in trouble and I believe that my gender and outspoken personality have unequally put me at risk for retribution. Sometimes I choose not to stay quiet and that has put me in situations where I’ve been publicly reprimanded or humiliated. They weren’t my finest moments, but I wouldn’t have changed what I did even if it still resulted in punishment.

What should a powerful woman do in a context where she feels that people are uneasy around her? I’m not sure it is our responsibility to acquiesce to make other people feel more comfortable. I try to stay empathetic and treat people the way I want to be treated, but not at the expense of my own self-worth. When I was younger I often shrank to make others feel more comfortable, but diminishing our own light doesn’t solve the problem, it exacerbates stereotypes. If we are to make the impact in the world that we know we can, we need to stand strong in our convictions and let those who feel uneasy work through their own personal discomforts.

What do we need to do as a society to change the unease around powerful women? We need to continue to do the work of breaking down and redefining gender stereotypes and roles. I’m eager to see a time when we don’t have to talk about the differences in people in power as it pertains to gender and we can just focus on impactful leadership and innovation. Being a woman doesn’t make me any less qualified for something than anyone else — it just means I have to work harder to show I am capable. As a society, we need to be cognizant of our own implicit biases and ensure that the right people are put in place to do the work. If the most qualified people are chosen, we must make sure that there is equity from the beginning with not just women but with all kinds of folks who currently aren’t in the same position as many powerful white men. We have a lot of work in our society to do to make this happen, though and we can’t simply wait for it to happen. More people in charge have to take risks and allow these valuable other perspectives to be heard.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us? I’ve fought just to have a seat at the table in my career. I’ve been fortunate to have mentors and people in influential places who have recognized what I have to offer who have brought me into the fold. Once I’ve been in these situations, I’ve been taunted and intimidated because I haven’t conformed. One time, for example, a person approached me at a conference, I was polite, answered questions, but ultimately, I didn’t behave the way the person expected me to. He publicly attacked me on social media just because he felt I didn’t pay him enough attention. Now, as a woman, I already have to contend with folks who are looking at me in unsavory or unwanted ways, but to also need to defend my behaviors as they pertain to my work because of how it puts me in the spotlight, is unfortunate. Rather than publicly fight a battle with him on social media, I had to force myself to let it go. People will call us names and say unprofessional things but when we engage with this behavior it only makes it worse. I’ve had to develop a thick skin and cling to my own beliefs. I know I can’t please everyone and that is okay.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts? Women have to fight to be heard by and listened to by the vocal majority and we have to expend a lot of energy making sure that what we say and how we say it doesn’t offend anyone. Too often a strong woman is labeled as a bitch if she is articulate and direct whereas men don’t have to worry about their tone as much. It’s unfortunate, but even as I have become more successful, there are some situations with powerful men where I still feel like I need to prove myself like I have to keep showing why I deserve a seat at the table. If I’m too passionate about what I care about, then I’m labeled as emotional and therefore can be assumed weak if I can’t manage my emotions appropriately. My sensitivity is a strength. My compassion helps me connect with others in meaningful ways. My ability to be empathetic helps me see and feel things deeply and most men don’t seem to connect with these feelings as readily. If was decide to hold my emotions at bay, then I’m aloof or cold and that too could be used against me.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was? It is a constant struggle for me to try to balance my career with my family. I love them both. Too often, I feel like something is always having to be traded off. I’ve missed my son’s school events which creates a lot of guilt. As a matter of fact, whenever I have to leave home to work I feel guilty. I don’t like having to choose between my family and my work. Men have to make this choice too but there seems to be less stigma around a working and traveling dad than there is about a mom doing the same thing.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium? I’m not sure I’ve really struck a balance yet — at least not as well as I would like to. Some days and weeks are better than others, but I’m still trying to figure it out. In the big picture, I say that I’m hustling now so that we can enjoy our lives more in the future, but sometimes I worry that that future won’t come. I enjoy my hustle, so it’s hard for me to slow down. Strong, smart women like Brene Brown have helped me understand the power of my vulnerability and how balancing my family with my work is essential if I don’t want to burn out prematurely. One way I have made a concerted effort to create more of a balance is by setting time boundaries as to when I stop working and what I prioritize. When my son has something special going on, I clear my calendar. When my husband has a race, it is all about him. The same way they let me be me and support me as a cheerleader, I try to do the same.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean? When I was a young person, the way I looked was a struggle for me. Challenged by stereotypes and expectations of what a girl is supposed to be physically, I’ve suffered with body dysmorphia and the range of emotions that go with that. I could ascertain that men and women found me attractive because I got a lot of attention, which wasn’t always comfortable. In some ways, it has opened doors but in others, I have struggled to be taken seriously because some people don’t expect an attractive woman to be intelligent. I’ve had men tell me to just focus on being pretty and someone will take care of me. These messages in society disgust me. As a young person, I often shied away from leaning on my femininity and covered myself up, but as an adult, I’ve learned to be comfortable and confident in my own skin. The simple reality is that being healthy and taking care of myself is an essential part of my well-being. When I feel good about the way I look, I feel like I can conquer anything.

How is this similar or different for men?

I don’t think men have to worry about their appearances as much. If you’re a homely woman, you’re often avoided and if you’re attractive, you’re treated like meat and your intelligence is questioned. I can’t say my brother, who is also an attractive man, has had to defend his intelligence because of his looks — for women, it is a double-edged sword. In fact, attractive men are assumed intelligent while attractive women are assumed not. And it is because of these mixed expectations that so many women have sadly had #metoo experiences because those powerful men feel like they could do whatever they want. Most women wouldn’t exploit someone else to get what they want, they’d find a way to do it that helped everyone feel they belong.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  1. Vision/Purpose — you need to have clarity on what your vision is and you mustn’t waver in that vision. When you’re driven by a desire to help the greater good, you can’t go wrong. For me, my vision to change assessment in education has been a driving force in every career move I have made. It is that clarity that has put me in the right places to enact more change along the way. It is also that vision that has made the decision to leave situations when they no longer aligned with my goals easier. Understanding who I am and assuring that all of my decisions align with that strong sense of self keeps me grounded. One example of this is when I left my leadership role because it didn’t align with my values and I was unable to make the kind of change I was hoping the position would afford me. In fact, when I was hired, I was sure it was because of the strong beliefs I had about reforming assessment and everything that goes with it which meant moving away from the status quo. Despite the financial loss, I took a risk and walked away in service of really wanting to focus on my passion with assessment in a place where I knew I could continue to move the dial away from the way we have always done things in education.

  2. Creative — you need to see the world in your own unique way and help others to see it that way too. This is where innovation happens, so you can’t be afraid to seek out solutions that haven’t been tried before. When I was in the classroom, I had to be creative in order to find loopholes I could exploit for the benefit of my students. That meant I had to find ways to adapt current practices to suit what I was trying to achieve. Since our online grading system required grades, but I didn’t want to use them, I found multiple workarounds in order to stay aligned to goals and give students the vocabulary to articulate their own progress.

  3. Humility — no matter how successful you are, there is always more to learn. We make mistakes and we need to know when to admit them. Women seem to be more comfortable being honest about their foibles whereas men seem to cover up their weaknesses to exude power. Frankly, I’ve never seen my being reflective and humble about my learning process as a weakness. In fact, I see that transparency as a strength. To that end, we need to know when to put our egos aside for the benefit of the whole and make choices that are going to further benefit the greater good. No matter how many books I’ve written or how many times I’ve been invited to speak in cool and different places, I am always looking for ways to learn without leading solely with personal successes. I don’t need to tell people I’ve been successful or that I’m a published author, the work will speak for itself and I will continue to fight the good fight.

  4. Perseverance — Being able to get back up again after you fail is a huge part of being a powerful woman. Doors will be slammed in your face, but you can’t let it deter you; you must push through those uncomfortable feelings of perceived failure and try again. In life, we will come against many hardships and struggles but we can’t allow them to get us down. As a child, I survived being around close members of my family struggling with addiction. Their struggles were family ones and understanding at a young age that I was predisposed to addictive or compulsive behaviors, I needed to find a way to channel that energy into something positive. This has been true throughout my entire life; I’ve found ways to make positives out of the challenges that have arisen and I would never let any obstacle stop me from achieving my goals.

  5. Reflective and transparent — If we want to thrive as powerful women, we need to be constantly reflecting on our choices and behaviors, honestly considering what is working and what isn’t. Do our actions promote the goals we are seeking? Do they hurt or keep others down? What are the tradeoffs? What strengths should we be building on? How long is too long to stay in one place without acceptable movement? And once we have taken the time to really see our circumstances for what they are, we need to communicate them openly. I believe that the reason why so many people have been moved by my work is the level of honesty I’ve been able to convey transparently. In the face of potential humiliation, I have admitted my mistakes, shared my regrets and engaged in dialogues of what I have learned from all of these things. It is not okay to acknowledge what you know to be unfair or not your best and then choose to do nothing about it. Hold yourself accountable to the standards you have and be honest with yourself about it. When I was still in the classroom, I often live-streamed my classes, not knowing if they would go well, but that was okay. Then I’d review the footage or the class after on my blog and write about what I learned from that time. I was able to grow from my own experiences and give other educators the permission to do so as well.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them. Oprah Winfrey because she is a powerful woman who has overcome a lot of obstacles to get where she is. She has then leveraged her platform to give voice to many who don’t have a voice. That is a big part of my mission in education. I’m completely invested in changing the way we assess in schools so that we can honor the dignity of all children. If we are going to have a world that is truly equitable it starts with the way we educate our youth. I’d love to partner with her to make sure children who haven’t had access to educational opportunities have them in the future.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this. — Published on October 4, 2021 Ming S. Zhao, CEO of PROVEN Ming Zhao is an entrepreneur, business strategist, investor, and podcast host. She is co-founder and CEO of PROVEN Skincare, a technology-powered personalized skincare company that won MIT’s AI Technology of the Year award and is backed by Y-Combinator and Stanford StartX. She is an immigrant, a third-generation entrepreneur, and a mother whose daughter is the same age as her startup. Prior to founding PROVEN, Ming was a private equity investor where she frequently worked 80-hour weeks, wreaking havoc on her skin and soul, leading her to pursue personalized skincare. She has an MBA from Harvard University and lives with her family in San Francisco, CA. Check out PROVEN’s Skin Genome Quiz at

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